Vacation rentals in Provincetown, MA with free parking

Explore 400 vacation rentals, homes, and villas with free parking in Provincetown, MA for your next getaway or business trip. With on-site parking included in your stay, enjoy the comfort and privacy of a home filled with premium amenities such as Air Condition Homes, Family-Friendly Homes and Best Affordable Homes. Throughout your stay, come and go with ease, knowing parking is always convenient and close at hand. With options starting as low as $90 per night and homes offering up to 11 bedrooms and 10 bathrooms, it's easy to book a personalized stay designed for your comfort. With 24/7 local support and high-speed Wi-Fi, you can also stay connected and protected throughout your trip. Plus, Marriott Bonvoy members earn points on every stay, making each trip more rewarding than the last. Book your next stay with ease and enjoy the convenience of free parking.

400 Homes with Free Parking in Provincetown

Beachfront with shared sundeck!

Provincetown, MA, US
2 Bedrooms 4 Guests
Sep 2 - 4
$186 night

11119 - Lounge All Day: Beachfront with shared sundeck! Nestled within the charming enclave of Provincetown, this inviting two-bedroom condo promises a retreat reminiscent of a private resort. Step into a haven offering all the comforts of home for your coastal getaway. Venture just 50 feet through a serene, shaded courtyard to discover an expansive sandy beach, where the gentle lapping of waves invites you to indulge in endless relaxation. On the beachfront, a shared sundeck beckons, offering a tranquil oasis adorned with lounge chairs and a grill, perfect for leisurely afternoons basking in the sun or enjoying a delightful alfresco meal. Here, amidst the picturesque backdrop of boats and the lively pier activity, find solace from the bustling energy of Provincetown. <br><br>Venture beyond the sands, and within mere footsteps, the renowned Commercial Street awaits, offering a myriad of enticing experiences. Explore quaint boutiques brimming with treasures, savor delectable culinary delights at local eateries, and embrace the vibrant nightlife that pulses through the town.<br><br>Begin your day with a tantalizing breakfast at Yolqueria, followed by a leisurely stroll along the bustling streets. For an evening of sophistication, indulge in cocktails or a sumptuous dinner at the chic Strangers & Saints, just moments away from your coastal retreat.<br><br>This idyllic location epitomizes the essence of Provincetown living—proximity to the vibrant pulse of Commercial Street, while nestled along the tranquil shores, providing a serene escape from the crowds. Embrace the perfect blend of relaxation and excitement in this seaside sanctuary, where every moment promises to be a cherished memory.<br><br>Home Details:<br>-No Dogs Allowed (fines remitted)<br>-Sleeps 4<br>Bedrooms<br>-Total 2<br>-2nd Floor Master Bedroom: 1 Queen Bed<br>-2nd Floor Bedroom #2: 1 Full Bed<br>Bathroom<br>Total 1<br>-Full bath w/ shower<br>Other Amenities<br>-Wall A/C Unit in Living Room<br>-Window A/C in Bedrooms<br>-Smart TV/Cable TV<br>-WiFi<br>-Large Communal Lounge Deck w/ Water Views<br>-Gas Grill<br>-please note outdoor amenities are seasonal<br>-1 Parking Space - No Oversized Vehicles--compact cars to small SUVs only<br>-50 Feet to Commercial Street<br>-50 Feet to Water<br>-Sheets and Bath Towels Provided with Beds Made Upon Arrival<br>-Cleaned with Hospital Grade Disinfectant<br>-Certificate #: BOH-23-77<br>-C0045212420

5 Min Walk to Town, Patio, Yard, AC!

Provincetown, MA, US
4 Bedrooms 8 Guests
Sep 10 - 12
$755 night

11143 - End of the Line: 5 Min Walk to Town, Patio, Yard, AC! Embark on a journey to the charming End of the Line with a summer retreat at our historic Provincetown home, originally crafted in the late 19th century to house the esteemed stationmaster for the Cape Rail Trail’s final stop. Nestled within its two-story standalone embrace, up to eight guests can revel in a sense of seclusion rarely found in Provincetown rentals, all while relishing the convenience of a mere five-minute stroll to town or the inviting bayside beaches. <br><br>Crossing the threshold through the inviting sky-blue front door, guests are greeted by a sanctuary where worries dissipate like morning fog. Unwind in the cozy embrace of our intimate abode, complete with a designated work-from-home station strategically positioned by a window overlooking the verdant garden. Savor the tranquility of mornings with a cup of freshly brewed coffee, perhaps from the nearby Wired Puppy, in the snug sitting area adorned with a gas fireplace to ward off any lingering chill.<br><br>Indulge your culinary aspirations in the remodeled kitchen, equipped with sleek stainless steel appliances and ample countertop space for culinary creations. Gather around the dining table for communal feasts or bask in the morning sun on the private patio while enjoying breakfast alfresco.<br><br>Ascend the stairs to discover four inviting bedrooms, each adorned with vaulted ceilings, ceiling fans, and the comfort of A/C. From the queen-sized sanctuaries to the spacious king-sized havens, every room offers a haven for rest and relaxation.<br><br>Revel in the modern comforts of our home, including WiFi, a Smart TV, and a gas grill for outdoor gatherings. Explore Provincetown’s vibrant offerings, from eclectic art galleries to sun-kissed beaches, before returning to the warmth of our abode for a memorable evening.<br><br>Make your final summer stop an unforgettable one at the End-of-the-Line—where history meets hospitality, and every moment is imbued with the essence of seaside serenity.<br><br>*There is a small Artist’s cottage with an additional parking space on the property that the owner will use throughout the summer. Renters do not have access to these spaces. <br><br>Home Details:<br>-No dogs (Fines remitted)<br>-Sleeps 8<br>Bedrooms<br>-Total: 4<br>-2nd Floor Master Bedroom: 1 King Bed<br>-2nd Floor Bedroom #2: 1 King Bed<br>-2nd Floor Bedroom #3: 1 Queen Bed<br>-2nd Floor Bedroom #4: 1 Queen Bed<br>Bathrooms<br>-Total: 2<br>-1st Floor: Bathroom 1: Full bath w/ shower<br>-2nd Floor: Bathroom 2: Full bath w/ shower<br>Other Amenities<br>-Split System (like Central Air in 3 Bedrooms) and Window Unit A/C (in 1 Queen Bedroom)<br>-WiFi<br>-Smart TV/Streaming<br>-Dishwasher<br>-Washer/Dryer <br>-Gas Fireplace<br>-Gas Grill<br>-Patio with Furniture<br>-Private Yard<br>-please note outdoor amenities are seasonal<br>-Walk to Water<br>-Walk to Town<br>-Sheets and Bath Towels Provided with Beds made Upon Arrival<br>-Cleaned with Hospital Grade Disinfectant<br>-2 Parking Spaces<br>-C0286382420

Stroll to Commercial St! Coastal Retreat w/ Patio

Provincetown, MA, US
2 Bedrooms 4 Guests
Sep 15 - 18
$334 night

Al Fresco Dining | Walk to MacMillan Pier | 2 Mi to Herring Cove Beach Provincetown style meets ultimate comfort at this well-appointed vacation rental. Fire up the gas grill for a sunset dinner on your private patio or sip coffee from the breezy balcony. From the condo, make the short walk to the vibrant Commercial Street galleries, shops, and world-class dining, or stroll MacMillan Beach. Your ideal Cape Cod escape starts here — secure your stay today! -- THE PROPERTY -- Lodging Certificate Number: C0011562420 SLEEPING ARRANGEMENTS - Bedroom 1: 1 queen bed - Bedroom 2: 1 queen bed MAIN FEATURES - Flat-screen cable TV, electric fireplace - Mahogany hardwood floors, spiral staircase - Coastal decor KITCHEN - Granite countertops, high-end stainless steel appliances - Bosch gas stove, oven - Drip coffee maker - Microwave, toaster - Cooking basics, spices, dishware & flatware GENERAL - Free WiFi - Washer, dryer - Central heating & A/C - Linens/towels, hair dryer ACCESSIBILITY - 2-story condo, 2 steps for entry - Bedrooms & full bathroom on 2nd floor PARKING - Designated spot (1 vehicle) -- THE LOCATION -- - Experience the eclectic soul of Provincetown just steps from your front door - Walk to Provincetown Art Association and Museum & Pilgrim Monument & Provincetown Museum - Walk to MacMillan Pier Ferry Terminal - 1 mile to Beech Forest Trailhead - 4 miles to Race Point Lighthouse - 47 miles to Cape Cod Gateway Airport -- REST EASY WITH US -- Evolve makes it easy to find and book properties you'll never want to leave. You can relax knowing that our properties will always be ready for you and that we'll answer the phone 24/7. Even better, if anything is off about your stay, we'll make it right. You can count on our homes and our people to make you feel welcome — because we know what vacation means to you. -- POLICIES -- - No smoking - No pets allowed - No events, parties, or large gatherings - Additional fees and taxes may apply - Photo ID may be required upon check-in ADDITIONAL INFORMATION - This 2-story condo requires 2 steps for entry. The bedrooms are on the 2nd floor Licence number: C0011562420

Renovated Oceanfront Penthouse!

Provincetown, MA, US
2 Bedrooms 4 Guests
Sep 15 - 17
night

11159 - Above Decks: Renovated Oceanfront Penthouse! Immerse yourself in the vibrant pulse of Provincetown’s Commercial Street with a stay at Above Decks—an exquisite penthouse offering unparalleled access to the heart of Cape Cod’s bustling downtown. <br><br>Ascend to your urban oasis, perched high above Kohi Coffee, where panoramic views of the waterfront greet you at the door. Natural light floods the spacious living room, illuminating the plush sectional and dining area—a perfect setting for indoor relaxation with a view.<br><br>Prepare cocktails and culinary delights in the well-appointed kitchen, complete with modern amenities and convenient washer/dryer facilities. A bonus room awaits, featuring a cozy Murphy bed and sweeping vistas of the iconic Pilgrim Monument.<br><br>Retreat to the comfort of two queen bedrooms at the rear of the home, each offering serene respite after a day of exploration. But the true highlight awaits outdoors—a sprawling porch boasting panoramic views of Provincetown’s bustling harbor, with Race Point Lighthouse on the horizon and the lively hum of Commercial Street below.<br><br>For moments of tranquility, descend to your private beach nestled beneath the vibrant streets of downtown Provincetown—an oasis of serenity in the heart of it all.<br><br>Above Decks offers more than just a place to stay—it’s a gateway to the eclectic charms of downtown Provincetown, where entertainment, culture, and endless adventure await just steps from your door. Experience the essence of Cape Cod living in this extraordinary urban retreat.<br><br>Home Details:<br>-No pets (fines remitted)<br>-Sleeps 4<br>Bedrooms<br>-Total: 2 <br>-Bedroom #1: 1 Queen Bed<br>-Bedroom #2: 1 Queen Bed<br>-Bonus room: 1 Queen Murphy Bed<br>Bathrooms<br>-Total: 2<br>-Bathroom #1: Full Bath w/ Shower<br>-Bathroom #2: Full Bath w/ Shower<br>Other Amenities<br>-Fully Equipped Kitchen w/ Dishwasher<br>-Central A/C<br>-WiFi<br>-Smart TV/Streaming<br>-Stacked Washer/Dryer<br>-Expansive Deck w/ Outdoor Dining & Lounging<br>-NO outdoor grilling allowed (Fire Hazard)<br>-Oceanfront w/ Views of Cape Cod Bay<br>-please note outdoor amenities are seasonal<br>-Access to Shared Private Beach<br>-Downtown Commercial St Location<br>-Sheets and Bath Towels Provided with Beds Made Upon Arrival<br>-Cleaned with Hospital Grade Disinfectant<br>-1 Designated Parking Space<br>-C0114342420

East End Condo Across from Assoc Beach!

Provincetown, MA, US
2 Bedrooms 4 Guests
Sep 14 - 16
$138 night

11160 - Harbor Breeze: East End Condo Across from Assoc Beach! Escape to the serene beauty of the Cape’s tip and immerse yourself in the Harbor Breeze—a tranquil retreat boasting mesmerizing water views, private outdoor space, and ample room to unwind. <br><br>As you step into this second-floor sanctuary, you’ll immediately be captivated by the views of Cape Cod Bay. Lounge on the couch and let the salty breeze caress your skin through the screen door, inviting you to savor cocktails or a leisurely breakfast on the deck—a secluded haven where the essence of Cape Cod air envelops you.<br><br>Prepare beachside delights in the well-appointed kitchen, a culinary haven ready to cater to your vacation cravings. Venture down the hallway to discover two inviting bedrooms, each offering queen beds and TVs for cozy evenings of relaxation.<br><br>Just a stroll away lies the bustling heart of Provincetown, where an array of shops, restaurants, and entertainment options beckon. Whether you’re seeking sun-soaked beach days or vibrant nightlife adventures, the Harbor Breeze ensures you’re perfectly positioned to enjoy the best of both worlds.<br><br>Soak in the tranquility of the Cape’s coastal charm and create unforgettable memories amidst the Harbor Breeze—a haven of relaxation and rejuvenation at the tip of the Cape.<br><br>Home Details:<br>-No Pets (fines remitted)<br>-Sleeps 4<br>Bedrooms<br>-Total 2<br>-Bedroom #1: 1 Queen Bed<br>-Bedroom #2: 1 Queen Bed<br>Bathrooms<br>-Total 1<br>-Bathroom: Shower<br>Other Amenities<br>-Window A/C Units in Bedrooms + Portable A/C Unit in Living Room<br>-Smart Lock/Self Check-In<br>-WiFi<br>-Smart TV/Streaming<br>-Deck w/ Outdoor Dining<br>-please note outdoor amenities are seasonal<br>-NO outdoor grilling (fire hazard)<br>-Water Views from the Deck<br>-Located Directly Across from Association Beach<br>-Walkable to Commercial St<br>-Sheets and Bath Towels Provided with Beds Made Upon Arrival<br>-Cleaned with Hospital Grade Disinfectant<br>-1 Designated Parking Space<br>-C0404402420

1 Min. Walk to Water/Town Patio and AC!

Provincetown, MA, US
1 Bedrooms 2 Guests
Oct 4 - 6
$172 night

11141 - Velvet Nation: 1 Min. Walk to Water/Town Patio and AC! Indulge in a week of seaside luxury at our newly constructed West End Condo, where opulence meets convenience in the heart of the action. Nestled between Bradford and Commercial Streets, this centrally located gem offers a haven for relaxation and adventure alike, accommodating two guests with utmost comfort. <br><br>Awaken to the coastal breeze and the promise of excitement mere steps away. Kickstart your day with an invigorating outdoor spin class at Muscle Beach Gym, just a brief stroll from your doorstep. Alternatively, relish a leisurely morning in the sleek confines of your abode before venturing out to the famed Afternoon Tea Party at Boatslip, conveniently a stone’s throw away.<br><br>Return to your modern retreat for a quick recharge or a wardrobe transition. The first-floor condo boasts a state-of-the-art kitchen adorned with stainless steel Samsung and LG appliances, marble countertops, and a chic subway tile backsplash. Savor seaside-inspired delights with a spiked seltzer in hand, then unwind on the plush couch in the spacious living room, indulging in entertainment on the Smart TV or simply basking in tranquility.<br><br>As night falls, retire to the comfort of the king-size bed in the inviting bedroom, complete with ample storage and split systems for optimal comfort. Refresh in the pristine full bathroom before stepping out onto your private garden patio, equipped with cozy seating and a propane grill—a serene escape amidst the bustling streets.<br><br>Additional amenities include a stackable LG washer/dryer, WiFi, and linens provided for your convenience. With grocery stores and charming eateries mere minutes away, every need is effortlessly met. Don’t miss the chance to experience the allure of Liz’s Cafe, Pop+Dutch, or Nor’ East Beer Garden—all within easy reach.<br><br>Secure your spot in this coveted retreat today, and embark on a getaway you won’t soon forget—where every moment is an invitation to indulge and unwind.<br><br>Home Details:<br>-No pets (fines remitted)<br>-Sleeps 2<br>Bedrooms<br>-Total: 1<br>-Bedroom: 1 King Bed<br>Bathrooms<br>Total: 1<br>-Bathroom: Full Bath w/ Shower<br>Other Amenities<br>-Mini-Split A/C System (like Central A/C)<br>-WiFi<br>-Smart Lock<br>-Smart TV<br>-Washer/Dryer <br>-Private Garden Patio<br>-Propane Grill<br>-Shared outdoor shower<br>-Please note outdoor amenities are seasonal<br>-Walk to Water<br>-Walk to Town<br>-1 Parking Space<br>-Sheets and Bath Towels Provided with Beds made Upon Arrival<br>-Cleaned with Hospital Grade Disinfectant<br>-C0409972420

Private Deck, Parking, Walk to Town!

Provincetown, MA, US
1 Bedrooms 2 Guests
Sep 27 - 29
$163 night

11117 - Little Treasure: Private Deck, Parking, Walk to Town! Discover the magic of Provincetown right from your front door at Little Treasure—a one-bedroom, one-bath sanctuary perfectly positioned on the edge of downtown. Imagine strolling just steps to the sun-kissed sands and sparkling surf, with the Atlantic Ocean unfolding before you. Begin your mornings with a fresh brew on your private patio, coastal air all around, before heading out to explore the vibrant galleries, boutique shops, and local cafés that line Commercial Street only a few minutes’ walk away. Inside, the home is designed with comfort and tranquility in mind. The inviting queen bedroom is a haven of rest, while the bathroom offers all modern essentials from plush towels to premium shower products. Prepare sunset-inspired dinners in the full kitchen—outfitted with cookware, baking sheets, a coffee maker, and wine glasses—then enjoy laid-back meals at your dining table or under the open sky with the gentle sea breeze. Beyond the front door, Provincetown’s iconic beaches beckon for swimming and sunbathing, while harbor-front restaurants and renowned art museums are a short stroll away. Secure off-street parking and high-speed wireless internet make your stay seamless and convenient, whether you’re planning a romantic retreat or a solo escape. Let Little Treasure be your serene Cape Cod destination where the rhythms of the ocean, the charm of town, and the comfort of home unite. Book your getaway today, and let Provincetown inspire your next unforgettable story. Home Details:<br>-No Dogs (Fines Remitted)<br>-Sleeps 2<br>Bedrooms<br>-Total 1<br>-2nd Floor Bedroom: 1 Queen Bed<br>Bathrooms<br>-Total 1<br>-2nd Floor: Shower<br>Other Amenities<br>-Central AC<br>- Central Heat<br>-WiFi<br>- Cable TV<br>-Smart TV<br>-Please note outdoor amenities are available seasonally<br>-Sheets and Bath Towels Provided with Beds made Upon Arrival<br>-Cleaned with Hospital Grade Disinfectant<br>-Parking for 1 car maximum<br>-CERT#: C0513302420 -BOH-24-962

1 Min. Walk to Water/Town Deck and A/C!

Provincetown, MA, US
1 Bedrooms 2 Guests
Sep 28 - 30
$207 night

11142 - The Roxy: 1 Min. Walk to Water/Town Deck and A/C! Immerse yourself in the vibrant pulse of Provincetown this summer at the Roxy—a chic and newly constructed West End Condo designed for indulgence and relaxation. Situated between Bradford and Commercial Streets, this centrally located haven offers an idyllic retreat just moments away from the sun-kissed shores of Cape Cod Bay, including the beloved Dog Beach, and the eclectic array of shops and eateries lining the coast. <br><br>Kickstart your day with a burst of energy at Muscle Beach Gym, conveniently a mere two-minute walk away, or savor a leisurely brunch before joining the festivities at the renowned Afternoon Tea Party at Boatslip, also just a stone’s throw away.<br><br>Retreat to the comfort of our A-Frame (2nd-Floor) Walk-Up, boasting a contemporary open layout adorned with high vaulted ceilings, rustic natural beams, and ample skylights flooding the space with sunlight. Unwind on the plush grey couch in the main living area, indulging in entertainment on the Smart TV or relishing a moment of tranquility.<br><br>Prepare a delectable Clams Casino dinner for two in the pristine, fully equipped kitchen featuring stainless steel appliances and a stylish marble-topped island, perfect for intimate culinary adventures.<br><br>As the day transitions into night, retire to the inviting king bedroom, complete with vaulted ceilings, a skylight, and ample storage for your belongings. Refresh in the luxurious full bathroom before stepping out onto your private deck to admire the enchanting views of Provincetown.<br><br>Indulge in al fresco dining and relaxation on your deck, equipped with a propane grill and dedicated parking space. Additional amenities include a stackable LG washer/dryer, WiFi, and linens provided for your comfort.<br><br>With convenient access to nearby grocery and liquor stores, as well as a plethora of dining options including Liz’s Cafe, Pop+Dutch, and Nor’ East Beer Garden, every need is effortlessly met. Don’t miss your chance to experience the allure of the Roxy—book now for an unforgettable summer getaway in Provincetown!<br><br>Home Details:<br>-No Pets (fines remitted)<br>-Sleeps 2<br>Bedrooms<br>-Total: 1<br>-Bedroom: 1 King Bed<br>Bathrooms-Total: 1<br>-Bathroom: Full Bath w/ Shower<br>Other Amenities<br>-Fully Equipped Kitchen<br>-Mini-Split A/C System (like Central A/C)<br>-WiFi<br>-Smart Lock<br>-Smart TV <br>-Washer/Dryer <br>-Private 2nd-Floor Deck <br>-Propane Grill<br>-Shared outdoor shower<br>-Please note outdoor amenities are seasonal<br>-Walk to Water<br>-Walk to Town<br>-1 Parking Space<br>-Sheets and Bath Towels Provided with Beds made Upon Arrival<br>-Cleaned with Hospital Grade Disinfectant<br>-C0409982420

Plunge Pool, Free Parking, Dogs Welcome!

Provincetown, MA, US
2 Bedrooms 4 Guests
Oct 18 - 20
$199 night

11161 - Coconut Cabana: Plunge Pool, Free Parking, Dogs Welcome! Immerse yourself in the vibrant atmosphere of Provincetown at the Coconut Cabana—a delightful retreat offering the perfect blend of comfort and convenience. <br><br>Step into this cozy ground floor unit and be greeted by the cheerful hues of the living room, where views of the inviting pool beckon from the back. Adjacent to the living area, a breakfast bar leads seamlessly into the well-equipped kitchen—a haven for brewing your morning coffee before embarking on your Provincetown adventures. After a day of exploring the wonders of the outer Cape, retreat to one of two inviting bedrooms, one adorned with a queen-size bed and the other with a full - both with ample storage for your vacation treasures.<br><br>Outside, the deck awaits, offering a private oasis for al fresco dining amidst tranquil surroundings. Take a refreshing dip in the plunge pool, shared only with the two units above—a serene escape where relaxation reigns supreme.<br><br>Just a short stroll away, an array of bars, restaurants, and entertainment options awaits, promising endless excitement and enjoyment.<br><br>Whether you seek a peaceful home to recharge or a vibrant vacation hub to immerse yourself in the spirit of Provincetown, the Coconut Cabana offers all you need for an unforgettable Cape Cod getaway.<br><br>Home Details:<br>-Dogs Welcomed (w/fee of $40/night per dog)<br>-Sleeps 4<br>Bedroom<br>-Total: 2<br>-Ground Floor Bedroom: 1 Queen Bed<br>-Ground Floor Bedroom: 1 Full Bed<br>Bathrooms<br>-Total: 1<br>-Ground Floor Bedroom: Full Bathroom w/ Shower<br>Other Amenities<br>-Private Access to Unheated Pool (Shared with 3 Units, Open Memorial Day and closed Oct 15th)<br>-Mini-Split A/C in Living Room<br>-Smart Lock/Self Check-In<br>-WiFi<br>-Smart TV w/ Streaming<br>-Propane Grill<br>-Please note outdoor amenities are seasonal<br>-3 Min. Walk to Provincetown Harbor<br>-Sheets and Bath Towels Provided with Beds Made Upon Arrival<br>-Cleaned with Hospital Grade Disinfectant<br>-1 assigned parking spot<br>C0402872420

Modern, Private Patio, Walk to Town!

Provincetown, MA, US
3 Bedrooms 6 Guests
Sep 8 - 10
$339 night

11102 - Montello Fellow: Modern, Private Patio, Walk to Town! Unveil the hidden gem of Provincetown where you’ll find our exclusive vacation rental. <br><br>Immerse yourself in the delight of coastal living as you step onto your private patio, with a convenient grill and inviting outdoor seating that beckon you to indulge in al fresco dining amidst the sublime surroundings. <br><br>Inside, embrace a sanctuary of comfort and convenience. A split system AC ensures an optimal temperature throughout, while a cozy gas fireplace sets the stage for intimate evenings. The open layout seamlessly connects the fully-equipped kitchen to the inviting living room, forging an ambiance that is both stylish and welcoming, providing the perfect retreat after a day of exploration. <br><br>Venture beyond the confines of the home and experience the vibrant energy of Commercial Street, a captivating thoroughfare brimming with vibrant shops, galleries, and culinary delights. Stroll through this bustling avenue, where every twist and turn reveals a treasure waiting to be discovered. Explore the natural wonders that surround Provincetown, take a leisurely stroll through Pilgrims’ First Landing Park, or revel in the serenity of the Hawthorne Wildlife Sanctuary. Nature lovers will revel in the treasures found just moments from your doorstep.<br><br>No adventure would be complete without indulging in the culinary treasures that grace Provincetown. Delight your senses at acclaimed establishments such as Mac’s Fish House, The Canteen, and Sal’s Place, where the freshest catches and flavorful creations await to tantalize your taste buds.<br><br>Embark on an extraordinary journey that blends coastal serenity, culinary delights, and captivating exploration. Book your stay today at our Provincetown vacation rental and unlock the secrets of Cape Cod with every breathtaking moment.<br><br>Home Details:<br>-No Dogs (Fines remitted)<br>-Sleeps 6<br>Bedrooms<br>-Total 3<br>-1st Floor Bedroom: Double bed w/ Ensuite Bathroom<br>-1st Floor Bedroom: 1 Double Bed<br>-1st Floor Bedroom: 1 Double Bed<br>Bathrooms<br>-Total 2<br>-1st Floor: Full Bathroom w/ Shower (en suite Double Bedroom)<br>-1st Floor: Full Bathroom w/ Shower<br>Other Amenities <br>-Split System AC <br>-Gas Fireplace<br>-WiFi<br>-TV<br>-Washer/Dryer <br>-Propane or Natural Gas Grill<br>-Please note outdoor amenities are available seasonally<br>-Sheets and Bath Towels Provided with Beds made Upon Arrival<br>-Cleaned with Hospital Grade Disinfectant<br>-Parking for 1 car maximum - space is small, best suited to compact cars<br>-C0429172420

Beachfront Condo! Couples Retreat on Commercial

Provincetown, MA, US
1 Bedrooms 2 Guests
Oct 1 - 8
$487 night

Beachfront Condo | Bring Your Pup | Breathtaking Beach & Water Views | Cookout Ready Kick back, relax, and enjoy effortless access to the sandy shoreline at this Provincetown vacation rental — ideal for your next Cape Cod getaway! Start your morning with a scenic stroll along the beach, then grab a local bite on Commercial Street or climb to the top of the Pilgrim Monument. Ready to recharge? Enjoy the salt air and a savory barbecue on the back deck. Book your beachfront escape today! -- THE PROPERTY -- C0558772420 OUTDOOR LIVING - Furnished deck w/ grill - Beach & water views INDOOR LIVING - Open-concept layout - Smart TV, fireplace - 6-person dining area - Mini-split A/C & heat units KITCHEN - Refrigerator, stove/oven, microwave, dishwasher - Cooking basics, dishware & flatware - Drip & pod coffee makers (bring your own coffee) ACCESSIBILITY - Single-story condo on 1st floor - 3 steps to enter PARKING - Designated spot (1 vehicle) -- THE LOCATION -- - Located on harbor side of Commercial Street and condo is on a the beach - steps to Provincetown Marina & MacMillan Pier - Close to Pilgrim Monument & Provincetown Museum - 2 miles to Herring Cove Beach - 4 miles to Race Point Beach -- REST EASY WITH US -- Evolve makes it easy to find and book properties you’ll never want to leave. You can relax knowing that our properties will always be ready for you and that we’ll answer the phone 24/7. Even better, if anything is off about your stay, we’ll make it right. You can count on our homes and our people to make you feel welcome — because we know what vacation means to you. -- POLICIES -- - No smoking - Pet friendly w/ $50 fee (+ fees & taxes, dogs only, 1 max) - No events, parties, or large gatherings - Additional fees and taxes may apply - Photo ID may be required upon check-in ADDITIONAL INFORMATION - This single-story condo on the 1st floor requires 3 steps to enter SECURITY CAMERA INFORMATION - 1 Ring exterior device - Location: front door - Coverage: front entrance Licence number: BOH-25-1027;C0558772420

Harbor Views + Private Deck: Waterfront P-Town Apt

Provincetown, MA, US
1 Bedrooms 2 Guests
Sep 29 - Oct 2
$263 night

Walk to Dining & Shopping | Beach Access On-Site | Towels/Linens Provided Soak up the best of Provincetown from this beachfront vacation rental in the heart of downtown. Head outside to buzzing restaurants, boutique shopping, nightlife, and sunny beach days just steps away! After spending the afternoon at Race Point Beach, return home to relax on the deck and soak in the bay breeze. From festivals to sunset strolls, the Cape’s most unforgettable experiences are right at your doorstep. -- THE PROPERTY -- C0045302420 SLEEPING ARRANGEMENTS Bedroom: 1 queen bed OUTDOOR LIVING - Furnished deck - Outdoor dining & seating - Beach & bay views  - Waterfront location INDOOR LIVING - 2 flat-screen TVs - Central heating, A/C - Dining table - Free WiFi KITCHEN - Stainless steel appliances - Convection oven, stovetop - Drip coffee maker, toaster - Cooking basics, dishes & flatware ACCESSIBILITY - 2-story home - Stairs & spiral staircase required PARKING - Designated space (1 vehicle) - No boats, large trucks, or commercial vehicles -- THE LOCATION -- - Waterfront condo located directly on Commercial Street in the heart of Provincetown - Walking distance to beaches, restaurants & shops - 1 mile to Whalers Wharf & Long Point Beach - 1 mile to Wood End Lighthouse - 1 mile to Pilgrim Monument - 2 miles to Herring Cove Beach - 4 miles to Race Point Beach & Lighthouse -- REST EASY WITH US -- Evolve makes it easy to find and book properties you'll never want to leave. You can relax knowing that our properties will always be ready for you and that we'll answer the phone 24/7. Even better, if anything is off about your stay, we'll make it right. You can count on our homes and our people to make you feel welcome — because we know what vacation means to you. -- POLICIES -- - No smoking - No pets allowed - No events, parties or large gatherings - Additional fees and taxes may apply - Photo ID may be required upon check-in ADDITIONAL INFORMATION - This 2-story home requires stairs for access and a spiral staircase to reach the living room and kitchen on the 2nd floor - No boats, large trucks, or commercial vehicles are allowed to park on-site Licence number: C0045302420

Stylish, Walk to Town and Beach!

Provincetown, MA, US
2 Bedrooms 4 Guests
Sep 13 - 15
$207 night

11174 - On the Prow: Stylish, Walk to Town and Beach! In the heart of Provincetown’s vibrant West End, this sun-dappled two-story cottage invites you to experience the Cape in effortless style. Just two blocks from Commercial Street and a short 0.3-mile stroll to Dog Beach, this idyllic retreat is the perfect base for exploring the town’s lively galleries, iconic landmarks, and celebrated restaurants like Liz’s Cafe, Sal’s Place, and Victor’s.&lt;br&gt;&lt;br&gt;Step inside to discover an elegant, coastal-inspired interior with white shiplap walls and a breezy, sunlit ambiance. The thoughtfully designed living room sets the stage for evenings of chess and movies, while the dedicated office nook ensures you can balance work and play. The fully equipped kitchen is a chef’s dream, featuring stainless steel appliances, a gas stove, a stand mixer, and a marble eat-in table. Upstairs, you’ll find two quaint, raftered bedrooms promising peaceful nights of rest. Please note the stairs are narrow and steep with a low ceiling to get to the bedrooms.&lt;br&gt;&lt;br&gt;Begin your days on the brick patio, savoring fresh coffee as the sunlight filters through the trees. After a leisurely breakfast alfresco, spend your day soaking up the sun at nearby beaches, cycling to Herring Cove, or venturing into the scenic Cape Cod National Seashore. When the sun sets, grill dinner on the gas barbecue, and toast to another perfect day.&lt;br&gt;&lt;br&gt;Whether you’re here for the beaches, the art scene, or the renowned nightlife, this home blends comfort and style in the perfect location. Your Provincetown adventure awaits—book today and let the magic begin&lt;br&gt;&lt;br&gt;Home Details:&lt;br&gt;-No Pets (Fines Remitted)&lt;br&gt;-Sleeps 4&lt;br&gt;Bedrooms&lt;br&gt;-Total 2&lt;br&gt;-2nd Floor Bedroom: 1 Queen Bed&lt;<br&gt;-2nd Floor Bedroom: 1 Queen Bed&lt;br&gt;Bathrooms&lt;br&gt;-Total 1&lt;br&gt;-1st Floor: Full bath w/ Shower&lt;<br&gt;Other Amenities &lt;br&gt;-Central AC&lt;br&gt;-WiFi&lt;br&gt;-Smart TV&lt;br&gt;-Streaming Service&lt;br&gt;-Washer/Dryer &lt;br&gt;-Gas Grill&lt;br&gt;-Sheets and Bath Towels Provided with Beds made Upon Arrival&lt;br&gt;-Cleaned with Hospital Grade Disinfectant&lt;br&gt;-Parking for 2 cars maximum - tandem parking on the LEFT side only&lt;br&gt;-C0407932420 Please note the stairs are narrow and steep to get to the bedrooms.

Private Garden, Central AC, Dog Friendly!

Provincetown, MA, US
3 Bedrooms 6 Guests
Oct 3 - 5
$520 night

11101 - Sailor’s Tea Time: Private Garden, Central AC, Dog Friendly! Welcome to Provincetown, a charming coastal town known for its vibrant art scene, picturesque harbor, and stunning beaches. Nestled in this idyllic setting, our vacation rental offers the perfect home base for your getaway. Located just two blocks away from the heart of Provincetown, you’ll have easy access to a plethora of dining options, art galleries, and exciting nightlife. Immerse yourself in the local culture as you explore the vibrant streets filled with unique shops and boutiques. &lt;br&gt;&lt;br&gt;For nature enthusiasts, Herring Cove Beach and the Dune Shack Trail are just a short distance away. Spend your days basking in the sun on the sandy shores or embark on a scenic hike through the dunes. Pilgrim First Landing Park and Beech Forest are also nearby, offering tranquil settings for a leisurely stroll or a picnic amidst nature’s beauty. After a day of adventure, retreat to our vacation home and unwind in the private yard with a charming patio. Enjoy the cool breeze as you relax and savor the peaceful ambiance. &lt;br&gt;&lt;br&gt;The rental spans two floors and boasts approximately 1,190 square feet of living space, providing ample room for up to six guests. Inside, you’ll find comfortable bedrooms with central AC provided via mini-splits throughout the home. The gas fireplace adds a touch of warmth and coziness, creating the perfect atmosphere for relaxation. We also welcome your furry friends, as dogs are allowed with an additional fee. For those who enjoy cooking outdoors, a gas grill is available for your use. Prepare a delicious meal and dine al fresco in the serene surroundings of the private yard. &lt;br&gt;&lt;br&gt;Experience the best of Provincetown from our vacation rental. Book your stay today and create unforgettable memories in this charming coastal town.&lt;br&gt;&lt;br&gt;Home Details:&lt;br&gt;-Dogs Welcomed (w/fee of $40/night per dog)&lt;br&gt;-Sleeps 6&lt;br&gt;-approx. 1,190 square ft&lt;br&gt;Bedrooms&lt;br&gt;-Total 3&lt;br&gt;-1st Floor Bedroom: Queen Bed w/ En suite bathroom&lt;br&gt;-2nd Floor Bedroom: Queen Bed&lt;br&gt;-2nd Floor Bedroom: Full bed (this is a small bedroom, best for kids)&lt;br&gt;Bathrooms&lt;br&gt;-Total 2&lt;br&gt;-1st Floor: Full Bathroom w/ shower (en suite Queen Bedroom)&lt;br&gt;-2nd Floor: Full Bathroom w/ shower/tub combo&lt;br&gt;Other Amenities &lt;br&gt;-Central AC via Mini-Splits&lt;br&gt;-WiFi&lt;br&gt;-Cable TV&lt;br&gt;-Washer/Dryer &lt;br&gt;-Propane Grill&lt;br&gt;-Gas fireplace&lt;br&gt;-Please note outdoor amenities are available seasonally&lt;br&gt;-Sheets and Bath Towels Provided with Beds made Upon Arrival&lt;br&gt;-Cleaned with Hospital Grade Disinfectant&lt;br&gt;-Parking for 2 cars maximum&lt;br&gt;-C0427232420

Quivett Compound 419-B Magnificent Mansion, Privacy, Pool, Water Views in Brewster

Brewster, MA, US
10 Bedrooms 20 Guests
Aug 30 - Sep 2
$2,413 night

This property is professionally managed by Pretty Picky Properties Magnificent Mansion, Privacy, Pool, Water Views in Brewster Come for July 4th! Arrive on Thursday July 2 or Friday July 3rd and enjoy the holiday! Sleeps 22 in 10 Bedrooms, 9.5 Baths Linens and Bed Making Included The newly constructed Quivett Compound is the perfect summer retreat for your discerning group of up to 22. The property is secluded on seven-plus acres and set far back from the historic Old King’s Highway in beautiful West Brewster by the bay, the property serves up sweeping views of Quivett Creek and Cape Cod Bay beyond. Launch an owner-provided kayak or canoe and explore the creek. Watch the kids frolic in the in-ground heated pool, which provides continuous entertainment when they come off the nearby bay side beaches in both Brewster and Dennis. You’ll spend a lot of time on the expansive shaded deck or outdoor patio with its built-in gas grill, fire pit and large dining table. Set up the net provided and organize a volley ball or badminton tournament. You certainly have plenty of space to do it! Inside, you’ll roam through 6,300 square feet of modern luxury, exquisitely designed and superbly furnished and appointed. The main level common living space includes an immense living room with two seating areas, one with a large flat screen, wall mounted TV. There is also a separate TV lounge with wet bar upstairs. The kitchen is big, bright and totally social. It is equipped with everything you could ask for, including two dishwashers, a beverage center and a Keurig coffee maker. The adjacent dining room offers a great place to gather inside, although you’ll likely choose to eat outside most summer days on the deck and patio. The lower level has a very cool game room, ready for action with a pool table, ping pong table, air hockey, video games and more. Then, it’s show time in the home theater, with its huge movie screen and comfy recliner chair seating. The laundry lives on this level, as well, with not one but two new washers and dryers. The ten bedrooms break down as follows: six kings, three queens, one full size double and two twins. The 9.5 baths sort out this way: one half bath on the main level, six bedrooms with en suite baths plus two full baths on the lower level. Finally, there is a room above the detached garage withe a King bed and a full bath. Of course, the home is centrally air conditioned and has high-speed Wi-Fi and Cable TV. **Please note that the bedroom and bathroom over the garage is fully winterized from 11/1 - 5/1 each year. As a result the property only has 9 bedrooms and 7.5 baths from November through April sleeping a maximum of 20 guests*** *** Pool is open and heated from Memorial Day (late May) through Columbus Day (early October)*** ****The Quivett Creek Compound does consider small events (with a maximum of 50 attendees including guests staying at the property) on site on a case by case basis in May, June, September and October. There are no events allowed in July and August. Please contact us for more details.**** Please enter your travel dates for up-to-date pricing. This property has a seven-night minimum during the peak season. As is customary in vacation rentals there are additional fees to the rates listed. Those fees include a reservation fee and a non-refundable Accidental Damage Protection (ADP) fee totaling $245.00 In addition, there are state and local taxes applied to all reservations less than 31 days in length that total 14.45%. Be sure to search the Pretty Picky site for your best selection of prime vacation homes available for summer rental on Cape Cod. It’s your vacation. Get Picky! ®

Close to Beach & P-Town! Cottage w/ Bay Views

Truro, MA, US
2 Bedrooms 6 Guests
Aug 26 - 28
night

The Outer Cape is your oyster at this 2-bed, 1-bath Truro vacation rental! Ideally situated in the High Head area of the Cape Cod National Seashore, this confection of a cottage puts you within a 5-mile drive of beaches and Provincetown. Perfect your tan along the nearby shores of High Head Beach during the day, then rinse off in the outdoor shower and enjoy an evening BBQ back at the property. Afterward, pile in the living room to cool down in the air conditioning and marathon movies. -- THE PROPERTY -- C0074893000 | Furnished Patio w/ Gas Grill (Propane Provided) | Outdoor Shower | 2 Beach Chairs | 1 Mi to High Head Beach | Located in Cape Cod National Seashore Bedroom 1: 2 Full Beds | Bedroom 2: Queen Bed MAIN FEATURES: Flat-screen TV, dining table, ceiling fans, Cape Cod Bay views KITCHEN: Dishwasher, Keurig coffee maker, toaster oven, fridge, stove, oven, microwave, dishware/flatware, trash bags/paper towels, cooking basics GENERAL: Free WiFi, window A/C unit, wall furnace for heat, washer &amp; dryer, towels/linens, complimentary toiletries, hair dryer ACCESSIBILITY: Single-story cottage, step-free entry FAQ: Pet fee (paid pre-trip) PARKING: Shared driveway (2 vehicles) ADDT’L ACCOMMODATIONS: An additional property is available on-site with a separate nightly rate. If you would like to reserve both rentals, please inquire for more information prior to booking -- THE LOCATION -- BEACHES: Cape Cod National Seashore (surrounding area), North Truro - High Head Beach (1 mile), Head of the Meadow Beach (4 miles), Herring Cove Beach (6 miles), Corn Hill Beach (6 miles), Ballston Beach (8 miles) THINGS TO DO: Truro Vineyards (3 miles), Highland Lighthouse (4 miles), Dolphin Fleet Whale Watch (5 miles) OUTDOORS: Dune Shacks Trail (4 miles), Pilgrims&#39; First Landing Park (7 miles), Great Island Trail (13 miles) AIRPORT: Provincetown Municipal Airport (7 miles) -- REST EASY WITH US -- Evolve makes it easy to find and book properties you’ll never want to leave. You can relax knowing that our properties will always be ready for you and that we’ll answer the phone 24/7. Even better, if anything is off about your stay, we’ll make it right. You can count on our homes and our people to make you feel welcome — because we know what vacation means to you. -- POLICIES -- - No smoking - Pet friendly with $100 fee (+ fees &amp; taxes, dogs only, 2 max) - No events, parties, or large gatherings - Additional fees and taxes may apply - Photo ID may be required upon check-in - NOTE: Your safety matters. This property features 3 exterior security cameras. Camera 1 is a doorbell device on the main house facing the main house&#39;s front outdoor entry and the shared driveway, camera 2 is on the north side of the main house, above the upper deck, facing the street and lawn, and camera 3 is on the west side of the main house, above a second-floor window, facing the water and lawn. The cameras do not look into any interior spaces. They record video and sound when activated by motion - NOTE: This single-story cottage offers step-free entry - NOTE: There is another bookable vacation rental on-site. Other travelers may be present during your stay Licence number: C0074893000

Breakwater Acres 164-B Luxurious Estate by the Bay in Brewster

Brewster, MA, US
8 Bedrooms 18 Guests
Aug 29 - Sep 1
$1,773 night

This property is professionally managed by Pretty Picky Properties Luxurious Estate by the Bay in Brewster: Sleeps 20 with Expansive New Pool, Walk to Beach, Walk to Town Rents Saturday to Saturday in Peak Summer Off-Season Weekends and Partial Weeks Available Choose this vacation headquarters and give your group of up to 20 the best of all options. A main house plus separate guest house on nearly an acre and a half of level yard for play space. A stunning new 20’ X 60’ heated saltwater pool with large stone patio. A three-minute walk to Brewster’s Breakwater Beach. And an eight-minute walk to the iconic Brewster Store and Main Street/Route 6A, where you’ll discover some excellent restaurant choices. The main house, just completed in 2020, offers elegance without pretense, centered on its spacious, thoughtfully outfitted chef’s kitchen. Here you’ll appreciate the large center island with high boy seating, beautiful granite and tile, as well as abundant counter space bathed in natural light. The kitchen opens to a TV lounge, which walks out to the expansive patio and pool. There is also a good-sized dining room here, as well as a handy half bath and laundry. The main house has sleeping for up to 12 in five bedrooms, two of which are king masters, one on the main level, the other upstairs. Each master has its own private full bath en suite. The separate guest house offers single level living and sleeps up to eight in three bedrooms with a full bath. You have a full eat-in kitchen here, as well as a TV lounge. Your outdoor summer living is optimized on the oversized patio which envelops the big pool. There’s also a hot tub, a large gas grill, a fire pit and an enclosed outdoor shower. Each house is centrally air conditioned, has cable TV, a SONOS Sound system and high speed Wi-Fi. Please enter your travel dates for up-to-date pricing. This property has a seven-night minimum during the peak season. As is customary in vacation rentals there are additional fees to the rates listed. Those fees include a reservation fee and a non-refundable Accidental Damage Protection (ADP) fee totaling $ 245.00 In addition, there are state and local taxes applied to all reservations less than 31 days in length that total 14.45%. Be sure to search this site for more Pretty Picky Properties - your best selection of prime vacation homes available for summer rental on Cape Cod. It’s your vacation. Get Picky! ®

Walk to Water, Dazzling Sunsets on the Bay!

Truro, MA, US
4 Bedrooms 9 Guests
Sep 3 - 5
$620 night

12211 - Sunset Dancer: Walk to Water, Dazzling Sunsets on the Bay! Tucked away in the serene landscape of Truro, just minutes from Provincetown, this charming water-view escape is your gateway to Cape Cod’s most beloved adventures. A short stroll (0.2 miles) brings you to the soft sands of Noon’s Landing Beach, while a quick drive places you in the heart of Provincetown’s vibrant energy.&lt;br&gt;&lt;br&gt;Wake up to gentle bay breezes and sip coffee from one of multiple decks overlooking the shimmering waters and dramatic dunes of Pilgrim Lake. Spend your day exploring—lounge on the beach, sip wine among the vines at Truro Vineyards, or savor fresh seafood and pasta at Montano’s, just three minutes away.&lt;br&gt;&lt;br&gt;Back at home, fire up the grill for an alfresco dinner as the sky turns golden, then sink into the hot tub under a blanket of stars. For a night in, gather in the ground-floor lounge, complete with a wet bar and daybed, perfect for cocktails and conversation.&lt;br&gt;&lt;br&gt;Inside, every detail is thoughtfully designed, from curated artwork to a layout that balances privacy and connection. The first floor features a fully equipped kitchen, living area, and a bedroom with a Queen and Twin bed. Upstairs, a King bedroom and a Queen bedroom await, along with a full bathroom.&lt;br&gt;&lt;br&gt;Whether you’re watching the sunset from the deck, rinsing off in the outdoor shower after a day in the surf, or strolling to the beach with your pup in tow, this home promises a stay filled with ease, beauty, and adventure.&lt;br&gt;&lt;br&gt;Don’t wait—book your unforgettable Cape Cod retreat today!&lt;br&gt;&lt;br&gt;Home Details:&lt;br&gt;-Dogs Welcomed (w/fee of $40/night per dog)&lt;br&gt;-Sleeps 9&lt;br&gt;Bedrooms&lt;br&gt;Total: 4&lt;br&gt;-1st Floor Bedroom: 1 Queen Bed and 1 Twin Bed&lt;br&gt;-2nd Floor Bedroom: 1 King Bed&lt;br&gt;-2nd Floor Bedroom: 1 Queen Bed&lt;br&gt;-Ground Floor: 2 Daybeds&lt;br&gt;Bathrooms&lt;br&gt;Total: 2&lt;br&gt;-1st Floor: Full Bathroom w/ Tub/Shower Combo&lt;br&gt;-2nd Floor: Full Bathroom w/ Shower&lt;br&gt;Other Amenities&lt;br&gt;-Split System A/C&lt;br&gt;-TV&lt;br&gt;-WiFi&lt;br&gt;-Washer/Dryer&lt;br&gt;-Gas Grill&lt;br&gt;-Outdoor Shower&lt;br&gt;-Hot Tub&lt;br&gt;-Electric Fireplace&lt;br&gt;-Ocean Views&lt;br&gt;-Walk to Water&lt;br&gt;-Sheets and Bath Towels Provided with Beds Made Upon Arrival&lt;br&gt;-Cleaned with Hospital Grade Disinfectant&lt;br&gt;-C0407773000

Brewster Barefoot Bliss: 3447-BMH Luxury Brewster Estate – Pool, Hot Tub, & Steps to Nature

Brewster, MA, US
6 Bedrooms 12 Guests
Aug 29 - Sep 1
$2,365 night

This home is professionally managed by Pretty Picky Properties Luxury Brewster Estate – Pool, Hot Tub, Steps to Bike Trail "Brewster Barefoot Bliss" 3447-BMH Rents Saturday to Saturday in Peak Season Linens Included, Beds Made Six bedrooms, Seven Full Baths Sleeps Twelve Pets Considered **Additional separate two bedroom cottage available to rent next door, total occupancy of sixteen possible** Discover the perfect blend of classic Cape Cod charm and modern luxury at this stunning six bedroom vacation home in Brewster. With four private bedroom suites and space to sleep 12 guests, this expansive retreat is designed for relaxation and adventure alike for groups of any size. Location Nature lovers will appreciate the home’s prime location—adjacent to the popular Cape Cod Rail Trail bike path and just across the street from Nickerson State Park. Spend your days exploring the park’s scenic trails or take a short stroll (under a mile) to Crosby Landing Beach, considered Brewster’s best by many. You can be in downtown in Orleans in about two miles via the bike path. Outside Living Space No doubt most of your lounging and living will be done out on the spacious pool patio with a covered cabana area, gorgeous outdoor kitchen, a large dining table and chairs, a full bathroom and, of course, the heated pool. There’s also a hot tub and gas fire pit, ideal for gathering under the stars. You can whip up a feast in the cabana’s completely outfitted outdoor kitchen. The large, manicured yard is bordered by a tasteful variety of flowering plantings and makes a perfect place to throw a Frisbee ® or whack a Whiffleball ® And here’s an unusual extra amenity: your own private hockey rink! The special synthetic surface accommodates both roller blades and ice skates. Inside Living Space This home seamlessly blends classic coastal elegance with modern finishes, offering stylish and comfortable living spaces. The main level consists of a spacious and elegant kitchen, complete with everything you’ll need to prepare any meal and entertain any group. There’s seating for 12+ at the main dining table and adjacent round table plus there’s additional counter seating at the immense kitchen island. This part of the main level includes a wet bar, pantry and parlor. Fitness enthusiasts will appreciate the fully equipped gym. Then there’s the “Great Room,” which is nothing short of awe inspiring. Original to the structure, this room with soaring ceilings exudes old world charm in stunning fashion. The wood paneled walls are from a French chateau, the circular stairs from a British ship. Sleeping Accommodations The main level rounds out with two bedrooms, one with a queen, the other with a pair of twins, plus a full bath and a half bath. There are three, count ’em, three sets of stairs to the second level bedrooms. The first is off the small parlor and features a vintage narrow staircase to a queen bedroom with a private full bath. The second, more modern staircase leads to a second level area with two queen-bedroom suites, each with a private full bath. The final upstairs area is the most recent renovation and is essentially a self-contained apartment with a living area, kitchenette, king bedroom and a luxurious bathroom with a step-in shower, soaking tub and dual vanity. For a summary of bedrooms and bed configurations, use the Room Details tab above. Amenities This home has high speed WiFi, a Sonos® Sound System and central air conditioning. For a complete list of amenities, please click on the Amenities tab above. The owners reside in a smaller home on the grounds. so you can be sure that any issues that may arise will be quickly addressed. But you won’t see them unless you need them. Book now and experience the best of Brewster in this extraordinary vacation retreat. Please enter your travel dates for up-to-date pricing. This property has a seven-night minimum during the peak season. As is customary in vacation rentals there are additional fees to the rates listed. Those fees include a reservation fee and a non-refundable Accidental Damage Protection (ADP) fee totaling $245.00 In addition, there are state and local taxes applied to all reservations less than 31 days in length that total 14.45%. Be sure to search this site for your best selection of prime vacation homes available for vacation rental on Cape Cod. It’s your vacation. Get Picky! ®

The Breakaway: 007-O Exquisite in East Orleans

Orleans, MA, US
5 Bedrooms 13 Guests
Oct 31 - Nov 3
$1,211 night

Exquisite in East Orleans, Heated Pool, Fire pit, Gym! Linens Included, Beds Made Pets Considered Rents Friday to Friday in Peak Summer Off-Season Weekends and Partial Weeks Available Pool & Hot Tub open from Memorial Day to Columbus Day Welcome to The Breakaway, a stunning vacation home nestled in the picturesque Tonset Area of Orleans, Massachusetts. This luxurious property offers a perfect blend of comfort and elegance, making it an ideal retreat for families or groups seeking a memorable getaway. With 5 spacious bedrooms and 5.5 bathrooms, this home comfortably accommodates up to 14 guests, ensuring everyone has their own space to relax and unwind. As you step inside, you’ll be greeted by a beautifully designed interior featuring a gas fireplace that adds warmth and charm to the living area. The central air conditioning throughout the home ensures a cool and comfortable atmosphere, even on the warmest summer days. The fully equipped kitchen is a chef’s dream, complete with modern appliances, ample counter space, and a dining area perfect for family meals. The outdoor space is truly a highlight, boasting a heated private pool and a hot tub, perfect for soaking up the sun or enjoying a relaxing evening under the stars. The fenced yard provides a safe space for children and pets to play, while the outdoor seating areas and fire pit create an inviting atmosphere for gatherings. For those looking to stay active, the property features a gym and a game room equipped with a pool table and entertainment options, ensuring fun for all ages. Each bedroom is thoughtfully appointed, with the master suites offering TVs and sound systems for added convenience. Located just a short walk from the beach and near various attractions, including local Breweries and outdoor adventures, The Breakaway is the perfect base for exploring all that Cape Cod has to offer. Don’t miss out on this exceptional property—book your stay today and create unforgettable memories! Please enter in your travel dates in top right corner of this page for up-to-date pricing. This property has a seven-night minimum during the peak season. As is customary in vacation rentals there are additional fees to the rates listed. Those fees include a reservation fee and a non-refundable Accidental Damage Protection (ADP) fee totaling $245.00 In addition, there are state and local taxes applied to all reservations less than 31 days in length that total 14.45%. Be sure to search this site for your best selection of prime vacation homes available for summer rental on Cape Cod. It’s your vacation. Get Picky! ®

Liberty: 030-O Brand New Luxury Home in Orleans, Heated Pool, Steps to Town and Bike Trail

Orleans, MA, US
4 Bedrooms 10 Guests
Nov 20 - 24
$1,064 night

This property is professionally managed by Pretty Picky Properties Brand New Luxury Home in Orleans, Heated Pool, Steps to Town and Bike Trail Sleeps 10 in 4 bedrooms plus a bonus room Rents from Friday to Friday in Peak Season Linens included, beds made Pool is open Memorial Day to Columbus Day Welcome to “Liberty” a newly constructed home near downtown Orleans and convenient to Skaket and Nauset Beaches. This luxurious home features all new furnishings and décor, a heated saltwater pool and over 4,000 square feet of living area over three levels. The main level features soaring paneled ceilings in the main living area. The state-of-the-art kitchen is adjacent with a sizable island. The dining room is also in this area for easy prep and service of meals. There’s a cozy sunroom off the back of the main level as well for additional lounging and relaxation space. The primary bedroom is just off the kitchen and features a king-size bed, TV and a luxurious private bath. Upstairs, there are two bedrooms, one with a king-size bed and one with 2 full beds. There’s a shared bath up here with a shower/tub combo. The 4th bedroom is up a separate flight of stairs and has a king-size bed plus a private bathroom. The Lower level is expansive and has a movie room area, wet bar, full bath and easy access to the pool deck. There is also a king bed on the lower level for additional sleeping. The pool area has ample lounging area and of course a warm saltwater pool for use. Head out on foot or by bike and in moments you’ll be in downtown Orleans for dining, coffee, and shopping. The bike trail intersection is 0.4 miles from the house. Or maybe it’s a beach day! Skaket Beach on the bay is 1.5 miles or maybe the rolling waves of Nauset Beach is your fancy! Head 4 miles east for the open Atlantic. Vacation at Liberty! This luxury home has high-speed Wi-Fi, multiple smart TVs, and central air conditioning. Please enter your travel dates for up-to-date pricing. This property has a seven-night minimum during the peak season. As is customary in vacation rentals there are additional fees to the rates listed. Those fees include a reservation fee and a non-refundable Accidental Damage Protection (ADP) fee totaling $ 245.00 In addition, there are state and local taxes applied to all reservations less than 31 days in length that total 14.45%. Be sure to search the Pretty Picky site for your best selection of prime vacation homes available for summer rental on Cape Cod. ​​​​​​​ It’s your vacation. Get Picky! ®

A Wave From It All: 227-O Overlooks Nauset Beach/Atlantic, Heated Pool, Hot Tub & Fire-pit

Orleans, MA, US
5 Bedrooms 14 Guests
Sep 12 - 15
$1,957 night

This home is professionally managed by Pretty Picky Properties Grand Villa Overlooks Nauset Beach & the Atlantic, Heated Pool, Hot Tub & Gas Fire-pit! Rents Friday to Friday Off-season partial weeks available. Sleeps 14 Linens Included/Beds Made Pool and hot tub are open Memorial Day - Columbus Day Your group of up to 14 will vacation in style at this superb ocean side manor house at famous Nauset Beach in East Orleans. The stunning location provides panoramic views of the beach and ocean from both levels of the house. And you have a very short walk to the beach. The property also features a 36’x18’ heated pool, hot tub and gas fire pit!! The spacious, social, fully loaded kitchen anchors the main level and includes a breakfast bar with high boy seating for four. A few steps away, the large dining room easily seats 10 and can accommodate more. Relax in the exquisite living room with lounge seating and a large flat screen TV. This home has Sonos sound system off the back deck and in the lower level living space. It is centrally air conditioned and has hi-speed Wi-Fi and cable TV. A large, covered patio is just off the living room, with a dining table and chairs, plenty of lounge seating and views of the Atlantic. A separate lounge/bar room offers a wet bar with fridge, another TV, and bar seating for three. Walk out from there to a beautiful, hexagonal screened porch which leads to the pool deck. There is one bedroom on the main level, a roomy primary suite with a King size bed and full bath en suite with a walk in shower. The main level also includes a half bath and quiet den/study to serve as your work station, if necessary. On the upper level, you’ll first encounter another lounge area, which walks out to the upper deck that presents 180-degree breathtaking views of Nauset Beach and ocean. Comfy lounge seating here too, including a king-size super comfy sleeper sofa. On this level, you’ll find four more bedrooms. There’s a second, oversized primary suite, with a king size bed plus twin day bed with a twin trundle below. There is a full bath en suite, of course. Another bedroom suite features a King size bed and private full bath. Bedrooms #4 and #5 can be closed off to create a two-bedroom suite. Both bedrooms feature a queen size bed with a standard twin bed and twin trundle bed. The two bedrooms share a full bath between, Jack & Jill style. The lower level of the home houses an extraordinary full home theater with a projector, 10-foot screen and luxurious lounge seats with cup holders for up to 12, plus giant bean bag seating for more. What an amazing place should the weather not cooperate or for your evening entertainment. Also on this level: a workout room, a ping pong table, and a half bath. There are four full and two half baths in all. The yard and grounds provide plenty of space for kids to play safely. There is also a gas grill and horseshoe pits to keep everyone entertained. Consider planning your summer vacation at this truly remarkable property in one of Cape Cod’s most coveted locations. Please enter in your travel dates in top right corner of this page for up-to-date pricing. This property has a seven-night minimum during the peak season. As is customary in vacation rentals there are additional fees to the rates listed. Those fees include a reservation fee and a non-refundable Accidental Damage Protection (ADP) fee totaling $245.00. In addition, there are state and local taxes applied to all reservations less than 31 days in length that total 17.45%. Be sure to search the Pretty Picky site for your best selection of prime vacation homes available for summer rental on Cape Cod. It’s your vacation. Get Picky! ®

Views of Bay Access to Private Beach!

Truro, MA, US
2 Bedrooms 4 Guests
Aug 27 - 29
$379 night

12218 - Spring Bluff: Views of Bay Access to Private Beach! Set atop a hill in Truro overlooking Cape Cod Bay, welcome to Spring Bluff! A walk up a flight of exterior stairs brings you to the home’’s entrance. Once inside, cook up a meal in the full kitchen and enjoy it in the cozy dining area. Watch a movie in the living room before heading to bed in one of two bedrooms in this sleeps 4 home. A set of twin beds in one bedroom and a queen bed in the other are the perfect places to count sheep after a day on the beach. &lt;br&gt;Boasting one of the most iconic views of the Cape, stare straight across Cape Cod Bay to the tip of Provincetown, with Pilgrim Monument clearly defined in the near distance. The breathtaking view is only one of the many perks of staying here. A private bayside beach is a short walk down a path at the edge of the property, while the shuttle to Provincetown center allows the opportunity to leave your vehicle parked at home for a carefree and car-less day. &lt;br&gt; &lt;br&gt;Spring Bluff is one of five two-bedroom cottages available for rent at this property; other cottages include Sunset Bluff (12215), Wind Bluff (12216), Bay Bluff (12217) and Summer Bluff (12219). &lt;br&gt; &lt;br&gt;Home Details: &lt;br&gt;-Sleeps 4 &lt;br&gt;-Single Floor &lt;br&gt;-2 Bedrooms &lt;br&gt;-Bedroom #1: 1 Queen Bed &lt;br&gt;-Bedroom #2: 2 Twin Beds &lt;br&gt;-1 Bathroom &lt;br&gt;-Bathroom #1- Full Bathroom with Shower &lt;br&gt;-AC via mini-split (please note, there is one AC unit that can cool the whole home, but you will need to leave the interior doors open) &lt;br&gt;-TV with Cable &lt;br&gt;-WIFI &lt;br&gt;-Smart Lock/ Self Check-In &lt;br&gt;-Deck with Outdoor Dining &lt;br&gt;-Propane Grill &lt;br&gt;-NO PETS (fines remitted) &lt;br&gt;-Waterfront &lt;br&gt;-Walk to Private Beach &lt;br&gt;-Walk to Shuttle Stop for Provincetown Center &lt;br&gt;-Sheets and Bath Towels Provided with Beds Made Upon Arrival &lt;br&gt;-Cleaned with Hospital Grade Disinfectant&lt;br&gt;C0425763000

The Meeting House: 023-O Private Orleans resort-style compound: heated pool/spa, fire pit & cabana

Orleans, MA, US
5 Bedrooms 14 Guests
Sep 7 - 10
$1,392 night

This property is professionally managed by Pretty Picky Properties. Private Orleans resort-style compound with heated pool & spa, fire pit and cabana Rents from Friday to Friday during summer weeks Linens included Pool & Hot Tub open from Memorial Day to Columbus Day Your multi-generational or multi-family summer vacation has found its home. Experience this stunning property with plenty of amenities for the entire family. The home features five bedrooms and sleeps up to 14 guests. The owners have added a heated salt water pool (18’x40’), hot tub and gas fire pit. There is also a cabana off the pool that features a sauna, full bar, half bath and comfy seating area with a big screen TV. In addition, there is a basketball hoop located off the back of the home. When you choose to venture out from your own private resort, world-famous Nauset Beach is less than a mile and a half down the road. Several restaurants, shops and an ice cream parlor are just a short walk away. Inside, on the main level, the open floor plan creates a wonderful space for the whole family to gather. You will find a chef inspired kitchen with high-end, stainless steel appliances including a gas range. The kitchen opens to a living area with large screen TV adjacent to a beautiful dining area. The main level provides two primary suites. Each is outfitted with a king size bed and en suite full bath. One of the primary suites has an enclosed deck with a commanding view of the magnificent patio and pool area. On the upper level, you’ll find three more bedrooms, each with a private bath. The first bedroom on the second floor features a queen size bed plus a day bed. Across the hall is another bedroom also with a queen size bed, a day bed plus en suite bath. The final bedroom upstairs is the perfect bunk room for the kids which is accessed from a separate stairway. It features two bunk beds (full size bed on the lower bunks) plus two twin beds, full bath and a private TV/game room. It’s a wonderful “clubhouse” where kids have their own space to play video games or watch their videos. This home is equipped with all the modern amenities you’d expect: high end furnishings, top quality bedding, central air conditioning, Wi-Fi, and cable TV. This property provides the accommodations you need for your group of up to 14 to enjoy your own private mini-resort. Whether it’s spending the day at the pool, relaxing in the sauna, or shooting hoops, the entire family can find something to enjoy. Once the day is done, marvel at the beautiful starry nights while dining al fresco on the deck. Or enjoy a beverage in the hot tub while discussing the plans for the next magical day on Cape Cod. Please note: pool and hot tub are open Memorial Day - Columbus Day. Please enter your travel dates in the top right corner of this page for up-to-date pricing. This property has a seven-night minimum during the peak season. As is customary in vacation rentals there are additional fees to the rates listed. Those fees include a reservation fee and a non-refundable Accidental Damage Protection (ADP) fee totaling $245.00. In addition, there are state and local taxes applied to all reservations less than 31 days in length that total 17.45%. This property offers a 3-night minimum stay during select weeks in May – June & September – November. Guests are charged a cleaning fee for all stays less than 7-nights. Stay 7-nights or more and the cleaning fee is waived. Be sure to search this site for your best selection of prime vacation homes available for summer rental on Cape Cod. It’s your vacation. Get Picky! ®

Vacation Rentals in Provincetown by Amenities & Features

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Vacation Rentals Near Provincetown

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