Winthrop, MA Vacation Rentals

Explore 10 vacation rentals, homes, and villas in Winthrop, MA for your next getaway or business trip. Experience the privacy of a home with premium amenities such as Air Condition Homes and Best Affordable Homes, designed for a more comfortable and convenient stay. Every home is curated and professionally managed, with 24/7 local support, high-speed Wi-Fi, and premium linens included. With homes starting as low as $97 per night and featuring up to 4 bedrooms and 2 bathrooms, there's an option for every trip, from family vacations and group getaways to extended stays. However you're looking to experience your stay, Homes & Villas by Marriott has your next vacation home waiting. Marriott Bonvoy members can also earn and redeem points on every booking.

10 Vacation Rentals in Winthrop

Steps to Short Beach: Ocean-View Apt w/ Deck!

Winthrop, MA, US
2 Bedrooms 4 Guests
Sep 20 - 22
$242 night

Recently Renovated | Day Trip to Boston Harbor Islands | Walk to Public Beach Skyline views and salty breezes set the scene at this Winthrop vacation rental! With 2 bedrooms, 2 baths, and easy access to the beach and Downtown Boston, it’s made for relaxed coastal days and city adventures. Start with coffee and a shoreline stroll, then catch the ferry for museums and cannoli. Back at the apartment, relax on the rooftop and take in the view — the ocean in one direction, the city in the other. -- THE PROPERTY -- C0462263460 SLEEPING ARRANGEMENTS - Bedroom 1: 1 queen bed - Bedroom 2: 1 queen bed APARTMENT HIGHLIGHTS - Smart TVs - 2 gas fireplaces - Designated workspace - In-unit laundry, large dining table - Furnished patio & porch - Fenced yard KITCHEN - Refrigerator, stove/oven, dishwasher - Drip coffee maker, toaster, microwave - Cooking basics, dishware & flatware GENERAL - Free WiFi - Mini-split A/C, baseboard heating - Linens & towels FAQ - 3 exterior security cameras (facing out) - Pet fee (paid pre-trip) - Long-term rental on-site (upper unit) - Quiet hours (after 10:00 PM) - Deck not childproofed ACCESSIBILITY - 2-story home, 3 steps to enter - Bedroom & bathroom on 1st floor - Interior stairs required to access kitchen & living area PARKING - Parking area (1 vehicle) - No street parking -- THE LOCATION -- - Across from Halford Beach & community park - 1 mile to Beachmont Station & Winthrop Beach - 1 mile to Revere Beach & 2 miles to Yirrell Beach & Winthrop Ferry Terminal - 6 miles to downtown Boston - 7 miles to Boston's North End - 7 miles to Boston Logan Int'l 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 - Pet friendly w/ $100 fee (+ fees & taxes) - No events, parties, or large gatherings - Additional fees and taxes may apply - Photo ID may be required upon check-in - Please observe the quiet hours starting at 10:00 PM ADDITIONAL INFORMATION - The rooftop deck is not childproofed and may not be suitable for young children - There is a long-term renter on-site, in the upper unit, and may be present during your stay - This 2-story home requires 3 steps to enter through the lower-level door. The kitchen and living room require interior stairs to access. There is a bedroom and a bathroom on the lower floor - Your safety matters. This property features 3 exterior security cameras located on the outside of the house facing the driveway, back patio, and front door. The cameras do not look into any interior spaces. The cameras record video and sound when activated by motion Licence number: C0462263460

Pet-Friendly Revere Getaway, Steps from the T!

Winthrop, MA, US
2 Bedrooms 4 Guests
Aug 30 - Sep 1
$224 night

Walk to Revere Beach | Remote Work Friendly | Easy Access to Downtown & Airport | On MBTA Blue Line Check off everything on your Boston bucket list from this primely located 2-bed, 1.5-bath home in Revere. Whether it's a Red Sox game at Fenway Park, a sightseeing stroll through Boston Common, or a pasta dinner in the North End, this vacation rental has got you covered with easy access to downtown Boston. Enjoy walks on Revere Beach, or stream the Pats game at this stylish and cozy abode! -- THE PROPERTY -- MassTaxConnectID C0330442480 SLEEPING ARRANGEMENTS - Bedroom 1: 1 queen bed - Bedroom 2: 1 full bed - Additional Sleeping: 1 portable crib HOME FEATURES - 2 Smart TVs (YouTube TV w/ NFL Sunday ticket) - Laptop-friendly workspace - Dining table w/ chandelier - Books, board games - Ceiling fans, skylights - Clothing storage (closets) OUTDOOR HANGOUT - Fenced-in yard (turf, sprayed weekly w/ Simple Green Outdoor Odor Eliminator for Pets), furnished patio - Bocce toys, gas grill - Beach gear provided (chairs, umbrella, 6 towels, small folding table, blanket, beach bag & games) KITCHEN - All major appliances, including dishwasher - Breakfast bar w/ seating, stainless steel appliances - Cooking basics, spices, dishware & flatware - Knife set, drip coffee maker, hot water kettle, toaster, air fryer, blender GENERAL - Free WiFi - Washer/dryer - Towels/linens - Complimentary toiletries, hair dryers - Central heating & air conditioning ACCESSIBILTY - 2-story home, stairs required FAQ - Exterior security camera (1, front door & main gate, facing out) - Pet fee (paid pre-trip) PARKING - Free street parking (1 vehicle max, digital parking pass provided, 8-day maximum) -- THE LOCATION -- - Easy access to South Station - 0.9 miles to Revere Beach - 5 miles to TD Garden - 6 miles to Faneuil Hall Marketplace - 6 miles to Boston Common - 8 miles to Fenway Park - 34 miles to Gillette Stadium - Less than 4 miles to Boston Logan International 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 - Pet friendly with a $25 fee (+ fees & taxes) - No events, parties or large gatherings - Additional fees and taxes may apply - Photo ID may be required upon check-in ADDITIONAL INFORMATION - Your safety matters. This property features 1 exterior security camera located above the front door, facing outward toward the entryway and the main gate. It does not look into any interior spaces or capture the patio or grill area. The camera records video and sound when activated by motion. It will record when it first senses motion, and 30 seconds after the last motion is detected - This 2-story home requires stairs to access Licence number: C0330442480;STR21-0034;C0330442480

Walk to Constitution Beach: Mid-Century Boston Gem

Revere, MA, US
3 Bedrooms 6 Guests
Sep 15 - 17
$177 night

Steps to Subway Station | Private Parking | Family Friendly | Easy Access to Downtown Blending historic charm with modern flair, this 3-bed, 1-bath apartment will have you feeling like a Bostonian in no time. Visit all the sights — from the cobblestone streets of Beacon Hill to the mouthwatering stalls of Faneuil Hall — or settle into the neighborhood, home to Italian eateries and the East Boston Greenway. Either way, this quiet yet convenient vacation rental puts you close to it all! -- THE PROPERTY -- C0506840351 | STR-575903 SLEEPING ARRANGEMENTS - Bedroom 1: 1 king bed - Bedroom 2: 1 full bed - Bedroom 3: 1 full bed - Additional Sleeping: 1 portable crib HOME FEATURES - 2 Smart TVs w/ cable - Dining table, remote workspace - Books, board games - Mid-century modern decor KITCHEN - All major appliances, including dishwasher - Cooking basics, dishware/flatware - Coffee bar w/ Keurig & espresso coffee makers - Coffee & sugar provided, trash bags/paper towels - Blender, kettle, spices, high chair GENERAL - Free WiFi - Washer/dryer, linens/towels - Complimentary toiletries - Hair dryer, iron/board - Central heating & air conditioning FAQ - Quiet hours (10:00 PM-8:00 AM) - Homeowner on-site (1st-floor unit) ACCESSIBILITY - Single-story apartment, interior stairs required to access PARKING - Driveway (shared, 1 vehicle) - Street parking (first-come, first-served) -- THE LOCATION -- - 0.5 miles to Orient Heights T Station & local restaurants - 0.8 miles to East Boston Greenway & Constitution Beach - 5 miles to Downtown Boston - Boston Common, Public Garden, New England Aquarium, The Paul Revere House, Boston Tea Party Ships & Museum, Museum of Science, Faneuil Hall Marketplace, TD Garden - 7 miles to Fenway Park - 9 miles to Harvard Square - 2 miles to Boston Logan International 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 - Please observe quiet hours from 10:00 PM to 8:00 AM - Additional fees and taxes may apply - Photo ID may be required upon check-in ADDITIONAL INFORMATION - When entering through the vestibule, this single-story apartment requires interior stairs to access - The homeowner lives on-site, in a completely separate unit on the 1st floor, and may be present during your stay

Revere Vacation Rental Near MBTA ~ 7 Mi to Boston!

Revere, MA, US
3 Bedrooms 6 Guests
Oct 13 - 15
$271 night

Discover the best of the Boston area with ease when you book this conveniently located apartment in Revere, MA — just a half-mile from the subway and 3 miles from the airport! The 3-bedroom, 1-bathroom vacation rental features a well-stocked kitchen, a flat-screen TV, and proximity to shops and restaurants. Take the 7-mile trip to Boston to visit Fenway Park, shop at the Faneuil Hall Marketplace, and explore Boston Common! In the summer, relax on the shores of Massachusetts Bay at Revere Beach. -- THE PROPERTY -- MassTaxConnectID C0419872480 | 3 Mi to Airport | 1/2 Mi to Subway | Wireless Internet Bedroom 1: Full Bed | Bedroom 2: Full Bed | Bedroom 3: Full Bed APARTMENT FEATURES: Flat-screen TV, dining table KITCHEN: Stove/oven, refrigerator, microwave, cooking basics, dishware & flatware, Keurig, toaster, tea kettle, trash bags & paper towels GENERAL: Free WiFi, electric heating, ceiling fans, linens & towels, hangers, keyless entry FAQ: Stairs required for access, 2nd-floor unit, no air conditioning, 1 exterior security camera (facing street) PARKING: Free street parking ADDT’L ACCOMMODATIONS: An additional 2-bedroom property for 3 guests 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 -- DOWNTOWN BOSTON (~7 miles): Boston Common, Fenway Park, Faneuil Hall Marketplace, New England Aquarium, TD Garden, The Paul Revere House, Public Garden ON THE COAST: Revere Beach (0.8 miles), Winthrop Beach (3 miles), Donovan Beach (3 miles), Nahant (9 miles) AREA ATTRACTIONS: Square One Mall (5 miles), Tufts University (7 miles), Middlesex Fells Reservation (9 miles), Harvard Square (10 miles) AIRPORT: Boston Logan International Airport (3 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 - No pets allowed due to the homeowner’s severe allergies. Please include any questions/requests regarding ADA-certified service animals prior to booking - No events, parties, or large gatherings - Additional fees and taxes may apply - Photo ID may be required upon check-in - NOTE: This property requires steep stairs for access, which may not be suitable for children - NOTE: This property does not offer air conditioning - NOTE: There is another bookable vacation rental on-site; other travelers may be present during your stay - NOTE: Your safety matters. This property features 1 exterior security camera located on the entrance, facing outward toward the street. It does not look into any interior spaces. The camera records video and sound when activated by motion Licence number: C0419872480

2 Mi to Dtwn: Boston Apartment Near Beaches!

Boston, MA, US
1 Bedrooms 2 Guests
Aug 30 - Sep 2
$153 night

Walk to Public Transportation | Beach Gear Provided | 2 Mi to Convention & Exhibition Center Just 3 blocks from the beach and 2 miles from the heart of downtown, this Boston vacation rental apartment invites you to slow down, explore the city, and savor seaside moments with your person. Head to the Prudential Center for shopping, dive into ocean wonders at the New England Aquarium, or grab a lobster roll along the Harborwalk and watch the boats drift by. The fun never ends in Beantown! -- THE PROPERTY -- C0120960351 SLEEPING ARRANGEMENTS - Bedroom: 1 queen bed MAIN FEATURES - Smart TV - Dining table - Dedicated workspace - Beach chairs, towels & umbrella - Walkable neighborhood KITCHEN - Refrigerator, microwave, stove/oven, Crockpot, toaster - Nespresso & French press coffee maker (coffee provided), tea kettle - Cooking basics, dishware/flatware - Spices GENERAL - Free WiFi - Central A/C & heating - Linens & towels, trash bags & paper towels - Washer/dryer, hangers - Complimentary toiletries, hair dryer FAQ - Homeowner on-site (upstairs unit) ACCESSIBILITY - Single-story apartment, 5 steps required to enter PARKING - Public lot (~1 mile) - No on-site parking -- THE LOCATION -- - Near the Thomas M. Menino Convention & Exhibition Center - Walk to M Street Beach & Pleasure Bay - 2 blocks from MBTA bus stop: Number 9 to Copley Square, South End, Back Bay, Red Line/Green Line Subway; Number 7 to Seaport, South Station, Downtown Crossing, Red Line/Orange Line Subway; Number 11 to Downtown Crossing, Chinatown, Red Line/Orange Line Subway - 1 mile to Fort Independence - 3 miles to Boston Common - 3 miles to Prudential Center - 3 miles to Faneuil Hall Marketplace, 4 miles to Quincy Market & Boston Public Market - 3 miles to New England Aquarium & 5 miles to Franklin Park Zoo - 4 miles to Museum of Fine Arts & Isabella Stewart Gardner Museum, 5 miles to Museum of Science - 5 miles to TD Garden, 7 miles to Fenway Park & 26 miles to Gillette Stadium - 4 miles to Boston Logan International 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 single-story apartment requires 5 steps to enter - The homeowner lives on-site in the upstairs unit with a separate entrance; they may be present during your stay Licence number: C0120960351;STR-472278

5 Mi to Boston & Airport! Townhome w/ Skyline View

Everett, MA, US
4 Bedrooms 7 Guests
Sep 1 - 3
$148 night

111 Bus & Dining Options Nearby | Easy Highway Access | Soaking Tub | In-Unit Laundry Visiting for a business trip or a classic city getaway? This Everett vacation rental lets you skip the downtown chaos and commute easily into the heart of Boston. Kick off the morning with a homemade breakfast, then try your luck at the Encore Casino or spend a sunny afternoon at Revere Beach. For a quiet night in, cozy up on the sofa and stream your favorite movie picks. Secure your New England escape! -- THE PROPERTY -- C0586480930 MAIN FEATURES - Open-concept layout, modern interior - 3 Smart TVs - Soaking tub - 6-person dining area - Washer & dryer - Boston skyline views - Central A/C & heating KITCHEN - Microwave, refrigerator, stove/oven, dishwasher - Cooking basics, dishware & flatware ACCESSIBILITY - 2-story townhome, steps to enter - 1 bedroom & full bathroom on 1st floor PARKING - 1 vehicle can be parked on the street on a first-come, first-served basis - 1 parking pass is located inside the unit - Additional vehicles parked on the street without a pass will be ticketed - Additional parking is available in the CHA Hospital Parking off of Garland Street (paid overnight parking) -- THE LOCATION -- - Urban-residential pocket near major highways into Boston - 3 miles to Encore Boston Harbor & Revere Beach - 5 miles to The North End, Boston & TD Garden - 6 miles to New England Aquarium - 7 miles to Boston Harbor - 5 miles to Logan Int’l 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 - 2-story townhome, steps to enter - 1 bedroom & full bathroom on 1st floor SECURITY CAMERA INFORMATION - 2 exterior devices - Location: Ring doorball at front door, doorbell camera at back door - Coverage: entry points Licence number: C0586480930

Charming Boston Area Home < 1 Mi to Revere Beach!

Revere, MA, US
1 Bedrooms 2 Guests
Nov 10 - Dec 10
$97 night

Venture off to the East Coast with a stay at this cozy Revere home, nestled less than a mile from the beach! Coming with all the fixings for an easy-going getaway, the 1-bedroom, 1-bath vacation rental is ideally located for exploring all the area has to offer, with Faneuil Hall and Boston Common all with a short drive or bus ride away. Whether you want to cheer on the Red Sox at Fenway or simply spend all day reading along Revere Beach, this coastal getaway will serve as the perfect home base! -- THE PROPERTY -- Walk to Bus Stop | Free WiFi | Laundry Machines Come and experience the coast of New England from this charming Revere home, perfect for a pair of two looking to relax on the beach by day, and explore the city by night! Bedroom: Queen Bed KITCHEN: Well-equipped, stainless steel appliances, kitchen island, ice maker, microwave, toaster, full knife set, blender, cooking basics, coffee maker, spices, ample cabinet space, dishware &amp; flatware INDOOR LIVING: Open layout, sofa, formal dining table, lofted ceilings, 2 flat-screen cable TVs GENERAL: Linens/towels, complimentary toiletries, first aid kit, hairdryer, keyless entry, window air conditioning, trash bags, paper towels, washer/dryer FAQ: Lack of child-friendly amenities PARKING: Street parking * Massachusetts Tax ID Number: C0239342480 * -- THE LOCATION -- BEACHES: Revere Beach (0.6 miles), Lynn Beach (4.3 miles), Red Rock Park (4.7 miles), Nahant Beach (5.3 miles), Fishermans Beach (5.9 miles), Nahant Short Beach (6.2 miles), Preston Beach (7.7 miles) OUTDOOR RECREATION: Sea Plane Basin (2.4 miles), Belle Isle Marsh Reservation (2.9 miles), Lynn Woods (5.4 miles), Middlesex Fells Reservation (7.3 miles), Horn Pond Recreation Area (12.9 miles) BOSTON: Faneuil Hall Marketplace (7.2 miles), The Paul Revere House (7.3 miles), TD Garden (7.3 miles), Boston Common (7.4 miles), New England Aquarium (7.5 miles), Museum of Science (7.6 miles), Boston Public Garden (7.8 miles), Boston Tea Party Ships &amp; Museum (8.2 miles), Fenway Park (9.5 miles), Museum of Fine Arts (9.9 miles) UNIVERSITIES: Suffolk University (7.3 miles), Massachusetts Institute of Technology (8.7 miles), Tufts University (8.8 miles), Northeastern University (10.2 miles), University of Massachusetts Boston (10.8 miles), Harvard University (12.5 miles), Boston University (13.2 miles), Boston College (16.8 miles) AIRPORT: Boston Logan International Airport (6.1 miles) -- REST EASY WITH US -- Evolve makes it easy to find and book properties you&#39;ll never want to leave. You can relax knowing that our properties will always be ready for you and that we&#39;ll answer the phone 24/7. Even better, if anything is off about your stay, we&#39;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 - NOTE: The property lacks child-friendly amenities and may not be suitable for young children - NOTE: Your safety matters. This property features multiple exterior security cameras, around the sides, front door and back door, all facing outward. They do not look into interior spaces Licence number: C0239342480

Vacation Rentals in Winthrop by Amenities & Features

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Vacation Rentals Near Winthrop

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