Vacation rentals in Chittenden, VT with free parking

Explore 19 vacation rentals, homes, and villas with free parking in Chittenden, VT 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 Best Affordable Homes and Great for Groups. Throughout your stay, come and go with ease, knowing parking is always convenient and close at hand. With options starting as low as $87 per night and homes offering up to 4 bedrooms and 3 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.

19 Homes with Free Parking in Chittenden

Duplex Unit, 2 Mi to Chittenden Reservoir!

Pittsford, VT, US
2 Bedrooms 6 Guests
Aug 20 - 22
$381 night

Whether you’re looking to ski, hike, or boat in the beauty of Vermont, this 2-bedroom, 1-bath Chittenden vacation rental has it all. You'll feel truly immersed in nature on the wooded mountains. You can experience the beauty of Green Mountain National Forest or hit the slopes at Pico Mountain nearby. Then, return to enjoy the rec room’s pool table and wood-burning fireplace or unwind by the Smart TVs of your own private space. This home’s unique set up keeps your days versatile. -- THE PROPERTY -- Meals & Rooms Tax License No. MRT-11153470-001 | Front Porch w/ Cushioned Seating | Washer & Dryer | Free WiFi (Shared) | 6 Mi From Green Mountain National Forest | On-Site River Bedroom 1: Queen Bed | Bedroom 2: Queen Bed, Full Bed PROPERTY FEATURES: Smart TV, ceiling fans, screened-in deck w/ dining area (seasonal), grill, spacious yard REC ROOM: Smart TV, pool table, wood-burning fireplace, wet bar w/ bar top seating KITCHEN: Fridge, stove & oven, dishwasher, microwave, drip coffee maker, cooking basics, dishware & flatware, trash bags, paper towels GENERAL: Iron & board, complimentary toiletries, hair dryer, towels & linens, hangers, baseboard heating, 2 window A/C units (in bedrooms), wall A/C unit (in bar room) FAQ: 1 Ring exterior security camera (facing out) ACCESSIBILITY: 2 stories, step-free entry, 1st-floor bedroom & bath PARKING: Circular gravel driveway (6 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 -- HIKE, BOAT & SKI: Chittenden Reservoir (2 miles), Mountain Top Resort (2 miles), Green Mountain National Forest (6 miles), Pine Hill Park (9 miles), Pico Mountain Ski Resort (10 miles), Killington Resort (15 miles) LOCAL STOPS: New England Maple Museum (7 miles), Wilson Castle (12 miles) FUN FOR ALL AGES: Wonderfeet Kid's Museum (9 miles), Killington Adventure Center (15 miles) AIRPORTS: Rutland Southern Vermont Regional Airport (15 miles), Manchester-Boston Regional Airport (126 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 - No events, parties, or large gatherings - Additional fees and taxes may apply - Photo ID may be required upon check-in - NOTE: While this 2-story home offers step-free entry and a bedroom and full bathroom on the 1st floor, interior stairs are required to access the bedroom on the 2nd floor - NOTE: There's another bookable rental on-site; other travelers may be present and share WiFi connection and parking - NOTE: Your safety matters. This property features 1 Ring exterior security camera located on the front of the house, facing outward toward the driveway. It does not look into any interior spaces. The camera records video and sound when activated by motion - NOTE: The screened-in deck is not heated and is only available in warmer months, from May to October

Inviting Chittenden Apartment Near Pico Mountain!

Pittsford, VT, US
2 Bedrooms 4 Guests
Aug 20 - 22
$334 night

Hike, boat, and ski from this wooded retreat. Nestled in nature's embrace, this serene 2-bed, 1-bath vacation rental is the perfect gem for outdoor lovers. Spend your days hiking the picturesque trails of Green Mountain National Forest, taking a scenic drive to Chittenden Reservoir, and skiing the carefree slopes of Pico Mountain. After a day of adventure, cozy up for a movie on the Smart TV or cook a delicious dinner in the well-equipped kitchen. -- THE PROPERTY -- Meals & Rooms Tax License No. MRT-11153470-001 | 2 Mini-Split A/C Units | Front Porch w/ Cushioned Seating | 2 Mi to Chittenden Reservoir | On-Site River Bedroom 1: Queen Bed | Bedroom 2: Full Bed INDOOR LIVING: Smart TV, board games, ceiling fans KITCHEN: Fridge, stove & oven, microwave, drip coffee maker, cooking basics, dishware & flatware, trash bags, paper towels GENERAL: Free WiFi (shared), baseboard heat, washer & dryer, laundry detergent, iron & board, complimentary toiletries, hair dryer, towels & linens FAQ: 1 Ring exterior security camera (facing out) ACCESSIBILITY: Single story, 2nd-floor unit, stairs to access, internal step to 2nd bedroom PARKING: Circular gravel driveway (6 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 -- HIKE, BOAT & SKI: Chittenden Reservoir (2 miles), Mountain Top Resort (2 miles), Green Mountain National Forest (6 miles), Pine Hill Park (9 miles), Pico Mountain Ski Resort (10 miles), Killington Resort (15 miles) LOCAL STOPS: New England Maple Museum (7 miles), Wilson Castle (12 miles) FUN FOR ALL AGES: Wonderfeet Kid's Museum (9 miles), Killington Adventure Center (15 miles) AIRPORTS: Rutland Southern Vermont Regional Airport (15 miles), Manchester-Boston Regional Airport (126 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 - No events, parties, or large gatherings - Additional fees and taxes may apply - Photo ID may be required upon check-in - NOTE: This single-story, 2nd-floor unit requires stairs to access and an additional internal step to reach the 2nd bedroom - NOTE: There's another bookable rental on-site; other travelers may be present and share WiFi connection and parking - NOTE: Your safety matters. This property features 1 Ring exterior security camera located on the front of the house, facing outward toward the driveway. It does not look into any interior spaces. The camera records video and sound when activated by motion

Killington A-Frame

Killington, VT, US
2 Bedrooms 6 Guests
Aug 23 - 25
$314 night

The Killington A-Frame is a stylish two-bedroom, two-bathroom mountain home tucked into a quiet hillside neighborhood in Killington. Surrounded by trees and backed by the vast Green Mountain National Forest, this is your peaceful escape while still being minutes from all the action. Step inside to a bright open-concept main floor featuring a newly renovated kitchen with soapstone countertops, premium appliances including a Bertazzoni range, and a functional pantry. The cozy living area is centered around a wood stove, perfect for unwinding after a day on the slopes or trails. Both bedrooms are located upstairs, one with a queen bed and the other with two twin beds, along with a second bathroom. Designer touches like shiplap walls, curated lighting, and custom built-ins elevate the entire space. Outside, enjoy a large deck surrounded by nature, ideal for summer stargazing or year-round hot tub soaks after a day on Superstar. The hot tub is available year round with a required $195 setup fee to cover filling, balancing, and maintaining the water. Located just 12 minutes to Killington Resort, 7 minutes to Pico Mountain, and close to hiking, golf, mountain biking, and Kent Pond, this home offers the perfect balance of adventure and relaxation. • The hot tub is available year round and requires a $195 setup fee, which covers filling, balancing, and preparation prior to your stay. You understand that use of the hot tub and sauna is at your own risk and that special risks may be involved. You accept full responsibility for any bodily injury arising from use of the hot tub and agree to hold the owner and property manager harmless. • Our minimum rental age is 25. • We will provide you with access codes for our smart locks to come and go as you please. • We have some flexibility around our standard check in and check out times depending on other bookings. Guaranteed early check in or late check out may be available for an additional charge. • You must e-sign and return our written rental agreement after you complete your booking. • Winter weather is unpredictable. We do not offer weather-related refunds and recommend purchasing travel insurance for any unforeseen events. All wheel drive and winter tires are also recommended.

Pico Mountain Condo F106 (Pico Mountain Getaway)

Killington, VT, US
3 Bedrooms 8 Guests
Oct 31 - Nov 2
$488 night

Located right at the base of Pico Mountain, this condo gives you unbeatable ski on/off access and the relaxed, family-friendly vibe Pico is known for. You’re also just 10 minutes from Killington Resort, making it easy to enjoy the best of both mountains. (Local tip: Pico is an amazing choice on peak weekends and holidays when Killington gets busier, and it’s always a favorite for families.) This comfortable three-bedroom, two-bath condo has everything you need for a great mountain getaway. After a day on the slopes, unwind by the gas fireplace or cook dinner in the fully equipped kitchen. There’s plenty of room for everyone to spread out and relax. The layout works perfectly for families or two couples traveling with kids. You’ll find two bedrooms with queen beds and a third bedroom with two single beds. The open kitchen and living area make it easy to gather, eat, and relax after your day outside. Ski right from the condo to Pico or hop in the car for a quick drive to Killington for even more terrain and restaurants. We look forward to hosting you and think you’ll love staying here. • We have some flexibility around standard check-in and check-out depending on other bookings. Guaranteed early check-in or late check-out may be available for an additional fee. • Renters must be at least 26 years old per the condo association. • Smart lock entry allows for easy, contactless check-in. Your unique code will be sent the week of arrival. • Pack ’n play and high chair available upon request. • The entire property is non-smoking and non-vaping. Smoking is allowed only outside and 75 feet from the building. • Quiet hours are 9pm to 8am. We may use Minut smart home technology to monitor volume levels only. It is 100% privacy compliant. • For safety, a camera is located at the entryway of the condo (not inside any living areas). • No pets allowed. Unauthorized pets will result in a $450 fine. • A signed rental agreement is required. • Winter weather can be unpredictable. We do not offer weather-related refunds and recommend travel insurance. All-wheel drive and winter tires are also recommended. The Village Square at Pico Condo Association is a family-oriented community primarily used by owners and committed to the peaceful, safe and quiet enjoyment of their residences. While the Association allows rentals and encourages guests to enjoy their visit, they have implemented certain rules related to the use and enjoyment of the units. These rules allow the Association to issue fines and take other actions particularly as it relates to the enforcement of the minimum age requirement of 25, "Quiet Hours" from 9pm until 8am and their no pet policy. The Association will try to resolve issues through the owner or rental agency in the first instance but reserves the right to take action in real time as circumstances require. In short, please respect your neighbors while you are a guest in these condos. SKI RESORTS: Pico Mountain (0.1 miles), Killington Snowshed Base (6.3 miles), Killington K1 Base (7.0 miles), Mountain Meadows Cross Country (2.4 miles) SHUTTLE: Runs every 15 minutes from Thanksgiving to mid-March right outside the condo GOLF: Green Mountain National (5.4 miles), Killington Golf Course (6.3 miles) NIGHTLIFE: McGrath’s Irish Pub (0.8 miles), Flannels (2.2 miles), Pickle Barrel (4.2 miles), Wobbly Barn (4.7 miles), Nitespot (5.3 miles), The Foundry (3.7 miles) WEDDINGS: Killington Grand Resort (6.3 miles), Mountain Top Inn (11.4 miles) AIRPORTS: Rutland Regional (15.2 miles), Burlington International (71.2 miles), Albany International (108 miles), Manchester-Boston Regional (119 miles)

Cortina Mountain Chalet

Mendon, VT, US
3 Bedrooms 8 Guests
Aug 20 - 25
$405 night

Spend your mountain holiday in the heart of Vermont’s ski country at the Cortina Mountain Chalet private residence! Located on a hillside with southern exposure, you’ll be greeted by a morning sunrise with amazing views of Pico Mountain. In the evenings, you can watch the sunset from the hot tub, deck or around the outdoor fire pit. This modern and spacious home features three bedrooms, living room, family room, a loft and three bathrooms on three floors with fully equipped open kitchen, garage, high-speed Internet, streaming services, gas fireplace, work area and much more. (Hot tub fee applies mid- March to mid-December. Pet fee may apply. Please read below.) Love to ski or ride? We’re less than 4 miles west of Killington Road - a short 13 minute drive gets you to the Rams Head base of Killington Mountain, the "Beast of the East" with 155 trails over 1,509 skiable acres. Pico Mountain is only a 4 minute drive and a great family mountain with 58 trails over 468 skiable acres. You’re also close to the world famous apres-ski and nightlife in the area. In the off-season, you can enjoy hiking the Long Trail, mountain biking, beautiful golf courses, pristine lakes for swimming, fishing, & boating, fall foliage, sugaring, and much, much more. There is something for everyone in Vermont! Back at the house after a day out, you’ll enjoy the private outdoor hot tub, can sit back and relax by the fire pit and enjoy s’mores with loved ones. When you’re ready to come in from the outdoors, you are welcomed into a cozy yet spacious living room with ample seating, gas fireplace, many large windows and high ceilings offering lots of natural light and superb mountain views. Warm up with a cup of hot cocoa from the well-appointed country kitchen, then enjoy a family meal at the dining room table. Our home is well furnished to accommodate comfortable sleeping for your group and plenty of space to spread out. We’ve been happy to host family reunions, ski trips and summertime "work from the mountains" retreats! We look forward to welcoming your group! The house layout is as follows: Main Floor (1 bed) \- Primary Bedroom: 1 king bed, walk-in closet \- Living Room: sofa, futon and oversized comfy chair \- Well-appointed kitchen including pots & pans, utensils, refrigerator, microwave, coffee maker, gas range and electric oven, granite countertops, kitchen island with 2 barstools \- Dining room table seating 8 \- Gas fireplace \- Two outside decks, with a Weber propane grill \- Full bathroom \- Large flat screen TV with streaming services Upper Level (10 beds) \- First Bedroom: two full over full bunk beds \- Second Bedroom: two twin bunk beds \- Loft: full bed and queen bed \- Additional loft space with office area and direct views of Pico Peak \- Full bathroom Lower Level \- Sofa \- Full bathroom \- Large flat screen TV with streaming services \- Treadmill \- Walkout to the yard, hot tub, fire pit Cable, streaming services and high-speed Wi-Fi are provided. We are dog- friendly, subject to owner approval. Special 30+ day rates are available. Please inquire. This is a well cared for private residence and retreat. Not a party house. Quiet hours are from 10pm to 8am to respect our neighbors. SKI RESORTS: Pico Mountain (1.8 miles), Killington Snowshed Base (7.6 miles), Killington K1 Base (8.3 miles), Mountain Meadows Cross Country Ski and Snowshoe (2.9 miles) GOLF: Green Mountain National Golf Course (6.8 miles), Killington Golf Course (7.6 miles) NIGHTLIFE: McGrath’s Irish Pub (2.1 miles), Flannels Bar & Grill (0.5 miles), Pickle Barrel (5.5 miles), Wobbly Barn (6.0 miles), Mary Lou’s (6.6 miles), The Foundry at Summit Pond (5.0 miles) WEDDINGS: Killington Grand Resort (7.6 miles), Mountain Top Inn & Resort (9.7 miles) AIRPORT: Rutland Regional Airport (13.5 miles), Burlington International Airport (70.6 miles), Albany International Airport (106 miles), Manchester- Boston Regional Airport (120 miles) • Cell service at the house may be spotty depending on your carrier. • Our home is in a small homeowner’s association and all rules of the association must be followed. You agree not to trespass on neighbor’s properties which include any other driveways on the private road we are on. You may only use our land and the road itself. We have a $1000 fine for trespassing. • The hot tub is included for the peak ski season (late-December to mid- March). For other periods, there is an optional $195 set up fee. You understand use of hot tub and sauna is at your own risk and that special risks may be involved in using the hot tub. You accept full responsibility for any bodily injury arising from use of the hot tub, and hold owner and property manager harmless. • We have some flexibility around our standard check in and check out times depending on other bookings. Guaranteed early check in or late check out may be available for an additional charge. • We will provide you with door codes for our smart locks to come and go as you please. No one will meet you at the property. • Pack ’n play and high chair available upon request. (Please let us know in advance.) • Our entire property is non-smoking. You may only smoke outside. Please properly dispose of all butts. • Events and parties are not permitted. • Quiet hours are from 10pm - 8am. • A dog is permitted with the payment of our non-refundable $155 pet fee. • You must sign and return our written rental agreement. • Please be advised that this property utilizes a ladder to access the bunk beds. By renting this property, you are agreeing to hold the owner and property manager harmless for any injury or death that is resulting from the use of the ladder. • We partner with Killington and offer discounted lift tickets for our guests. We also offer discounts on rentals! • Winter weather is unpredictable. We do not offer weather-related refunds and recommend purchasing travel insurance for any unforeseen events. All wheel drive and winter tires are also recommended.

The Burrow- Near Pico, Hiking, Spacious!

Mendon, VT, US
3 Bedrooms 8 Guests
Aug 20 - 22
$197 night

The Burrow- Bright and spacious 3-bedroom home with a large loft, full kitchen, open living area, and floor-to-ceiling windows that fill the space with natural light. Two full baths, great ski storage at the entry, and plenty of room for families or groups. The loft offers an extra lounge space plus two queen beds. Enjoy the large deck with a grill—perfect for relaxing after a day on the mountain. This three-bedroom home is the perfect place to settle in, spread out, and enjoy your time in Killington. When you first walk in, you’ll notice the roomy entryway with plenty of space to stash skis, boots, and all your gear — super convenient after a day on the mountain. Head upstairs to the main level and you’ll find an open, easy-going layout designed for relaxing together. There’s a full bathroom on this floor, a comfortable living area with a dining space, and a fully stocked kitchen that’s ready for anything from quick breakfasts to full dinners. The floor-to-ceiling windows bring in a ton of natural light and keep the whole space bright and welcoming. This level also has two bedrooms: • Bedroom 1: Queen bed • Bedroom 2: One twin bed + a twin trundle (great for kids or friends traveling together) Up in the loft — accessed by stairs from the living room — you’ll find a second hangout space, another full bathroom, and two more queen beds. The loft feels open and spacious while still giving everyone a bit of privacy. Off the living and dining area, step out onto the large deck. It’s a great spot to get some fresh air, unwind, or fire up the grill. Overall, this home is comfy, bright, and easy to settle into — plenty of space for families or groups who want a relaxed, convenient home base for their Killington trip.

Alpine Chalet Grill, Fire pit, Pool, Gym, CornHole

Killington, VT, US
4 Bedrooms 8 Guests
Aug 25 - 27
$176 night

Welcome to Alpine Chalet at Pico Mountain, Killington, VT. This 4-bedroom retreat is perfect for mountain getaways, located just across from the slopes. It features a King bedroom with en suite, two Queen rooms, and a fourth room with a Queen and twin bunk. Enjoy the fully stocked kitchen, dining for 8, a cozy living room with a wood-burning fireplace, a bonus room, and an in-unit washer/dryer. Outside, relax on the deck, use the Weber grill, enjoy the fire pit, corn hole, and unique tree house. Welcome to Alpine Chalet, a stunning vacation retreat located at Pico Mountain in Killington, VT. Set along a beautiful drive with breathtaking mountain views, this charming chalet is just across from the slopes, making it a perfect home base for your alpine adventures. Inside, you’ll find four cozy bedrooms: a King suite with an en suite bathroom, two Queen rooms, and a fourth room with a Queen bed and a twin bunkbed. A second full bathroom serves the remaining bedrooms. The renovated kitchen is fully stocked and opens to a dining area with seating for 8, ideal for shared meals after a day on the slopes. Unwind in the living room by the wood-burning fireplace or spread out in the bonus room, perfect for kids or extra entertainment space. The chalet also offers the convenience of an in-unit washer and dryer. Step outside to enjoy a large deck with Adirondack chairs, a Weber grill, a fire pit, and a corn hole setup for outdoor fun. Don’t miss the unique tree house, offering stunning views of the surrounding mountains. You will have the entire home, driveway and yard to enjoy. The pool, sauna, and gym are all resort amenities provided by the Pico Fitness Center, which is a short drive down the road and through the Pico parking lot! They are open 6:00 a.m.- 8:00 p.m. Monday to Friday and 8:00 a.m. to 6:00 p.m Saturday and Sunday. They provide showers, lockers and a changing room, remember to bring a towel! The pool is by reservation only. We are local if you need us.

Near Hiking Trails & Ski Resorts: Killington Home!

Killington, VT, US
3 Bedrooms 8 Guests
Aug 20 - 23
$334 night

Pets Welcome w/ Fee | In-Unit Washer + Dryer | Seasonal Deck & Fire Pit Tucked away in Killington, this 3-bedroom, 2.5-bath home provides a cozy atmosphere and convenient location! Venture out in the winter to hit the slopes at Pico Mountain Ski Resort. In the warmer months, enjoy fishing, hiking, and biking in Green Mountain National Forest and Gifford Woods State Park. After, curl up by the wood-burning stove for a cozy night in or fire up the grill and dine on the deck. -- THE PROPERTY -- MRT-11153470-001 SLEEPING ARRANGEMENTS - Bedroom 1: 1 king bed - Bedroom 2: 1 king bed - Bedroom 3: 2 twin bunk beds HOME FEATURES - 4 Smart TVs - Wood-burning stove (firewood provided) - 8-person dining table - 4-person breakfast bar - Seasonal deck w/ seating - Seasonal backyard w/ fire pit - Gas grill (propane provided) - Dog bed & dishes KITCHEN - Dishwasher, stove/oven, fridge, stainless steel appliances - Drip coffee maker (starter coffee provided) - Crockpot, microwave, toaster, blender, ice maker, water filter - Dishware/flatware, spices, basic cooking essentials GENERAL - Free WiFi - Central A/C & heating, ceiling fans - Washer & dryer, laundry detergent - Towels/linens, hair dryer - Trash bags/paper towels FAQ - Pet fee (paid pre-trip) - 1 exterior security camera (facing out) ACCESSIBILITY - 2-story home, 2 steps to enter PARKING - Gravel driveway (3 vehicles) -- THE LOCATION -- - 0.7 miles to Pico Mountain Ski Resort - 1 mile to Appalachian Trail Crossing - 3 miles to Green Mountain National Forest & Gifford Woods State Park - 23 miles to Marsh-Billings-Rockefeller National Historical Park - 28 miles to Silver Lake State Park -15 miles to Rutland Southern Vermont Regional 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/ $125 fee per stay (+ fees & taxes, 2 max) - 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 on a tree in the front of the property, facing the front entrance. It does not look into any interior spaces. The camera records video and sound when activated by motion - This 2-story home requires 2 steps to enter - The deck, backyard, and additional outdoor amenities are available seasonally

Pico C103

Killington, VT, US
1 Bedrooms 4 Guests
Aug 20 - 22
$147 night

Pico C103 Cozy Condo Steps from the Lifts at Family Friendly Pico Mountain Pico C103 is perfectly located right at the base of Pico Mountain the ultimate family friendly ski destination. The chairlifts are just a short walk from your door, making it easy to ski out in the morning, come back for lunch, and hit the slopes again for the perfect ski day. This warm and welcoming one bedroom condo is ideal for a weekend getaway. Relax by the fireplace after a day of outdoor adventure or take the short drive to Killington Mountain, just minutes away, to experience even more skiing and the area’s vibrant nightlife. Guests also have access to a coin operated laundry conveniently located on the ground floor, and the shuttle bus to Killington runs right from Pico, so you can enjoy the best of both mountains without the hassle of driving. During your stay, enjoy access to the Pico Fitness Center, where you can work out in the gym, unwind in the sauna, swim laps in the pool, or join a spin or yoga class. The Village Square at Pico Condo Association is a family-oriented community primarily used by owners and committed to the peaceful, safe and quiet enjoyment of their residences. While the Association allows rentals and encourages guests to enjoy their visit, they have implemented certain rules related to the use and enjoyment of the units. These rules allow the Association to issue fines and take other actions particularly as it relates to the enforcement of the minimum age requirement of 25, "Quiet Hours" from 9pm until 8am and their no pet policy. The Association will try to resolve issues through the owner or rental agency in the first instance but reserves the right to take action in real time as circumstances require. In short, please respect your neighbors while you are a guest in these condos. Come experience the best of both worlds the cozy charm of Pico and the excitement of Killington right from Pico C103. Killington Resort extensive system of mountain biking trails. Killington Adventure Center Zip Lines, Mountain Coaster, Free Fall Jump Tower and more. Hiking Vermont’s Long Trail, Appalachian Trail. Kayaking Kent Pond, Woodward Reservoir and Chittenden Pond and more. Coolidge Homestead Vermont’s #1 visited site in Plymouth VT only 20 minutes away. Woodstock VT filled with wonderful shops and art galleries. Marsh Billings Rockefeller National Historical Park in Woodstock VT. Billings Farm Museum a wonder family activity. Green Mountain Golf Course the # 1 public course in the state. Killington Golf Course owned by the resort. VINS Vermont Institute of Natural Science a rescue and birth sanctuary.

Winter Brook

Killington, VT, US
3 Bedrooms 8 Guests
Aug 20 - 22
$294 night

Renovated Winter Brook Retreat | AC | Peaceful Brookside Setting Your stay includes two complimentary day passes to the Killington Rec Center pool, complete with a diving board. Nestled on a quiet knoll beside a babbling brook, this fully renovated Winter Brook retreat offers a peaceful setting close to all of Killington’s year-round adventure. The home features a beautiful new kitchen, wood floors, luxurious updated bathrooms, and stylish new furnishings. The open-concept living area is ideal for gathering with family and friends, especially around the wood-burning stove after a day on the slopes. On the main floor, one bedroom includes a bunk bed with a full bed below and twin bed above, while the second offers a queen bed; both share a remodeled full bath. Upstairs, the spacious loft features a king bed and a well-appointed primary bath with a garden tub and separate shower. A heat-pump system provides reliable comfort year-round, keeping the home warm in winter and cool in summer. Killington Golf Course and Green Mountain National Golf Course are both just minutes away. Please note: A caretaker resides in the lower-level apartment. Killington offers outstanding skiing and riding for every ability, plus snowmobile tours, tubing, ice skating, and a lively après-ski scene with favorites such as the Wobbly Barn, Pickle Barrel, and Jax’s. Come enjoy a relaxing Vermont getaway and create memories that will last a lifetime. • Killington Resort extensive system of mountain biking trails. • Killington Adventure Center – Zip Lines, Mountain Coaster, Free Fall Jump Tower and more • Hiking – Vermont’s Long Trail, Appalachian Trail • Kayaking – Kent Pond, Woodward Reservoir and Chittenden Pond and more • Coolidge Homestead – Vermont’s #1 visited site in Plymouth VT only 20 minutes away • Woodstock VT filled with wonderful shops and art galleries • Marsh Billings Rockefeller National Historical Park in Woodstock VT • Billings Farm Museum – a wonder family activity • Green Mountain Golf Course – the # 1 public course in the state • Killington Golf Course owned by the resort • VINS – Vermont Institute of Natural Science – a rescue and bird sanctuary.

CubsCorner - Pool, Sauna, Gym, Close to Mountain!

Killington, VT, US
1 Bedrooms 4 Guests
Aug 20 - 22
$180 night

Welcome to CubsCorner, a 1-bed short-term rental in Killington’s RobinWood neighborhood, minutes from Pico Mountain and 7 from the Killington base. Fully renovated, it features a fireplace, quartz counters, and a stylish bathroom. The queen bed with premium linens ensures a restful stay. The kitchen is fully stocked, and a murphy bed for additional guests. Relax in the spacious living room with a 55-inch Roku TV. Book now for a Vermont retreat! Welcome to CubsCorner, your charming 1-bedroom vacation rental nestled in the heart of the picturesque RobinWood neighborhood in Killington, Vermont. This cozy retreat is strategically located, providing you with easy access to both Pico Mountain, just across the street, and the Killington base, a mere 7-minute drive away. CubsCorner is a haven for outdoor enthusiasts, as it’s just a 3-minute walk from the famed Long Trail and Appalachian Trail, offering breathtaking hiking opportunities right at your doorstep. After a day of adventure, return to the comfort of this fully renovated home that seamlessly combines modern amenities with the warmth of a mountain retreat. Step inside to discover a beautifully redesigned space featuring quartz countertops, a welcoming fireplace, and a bathroom adorned with elegant tiled finishes and a sleek glass shower. The bedroom beckons with a sumptuous queen bed dressed in luxury linens, ensuring a restful night’s sleep. For those who enjoy culinary endeavors, the fully stocked kitchen awaits your culinary creations. Whether you’re preparing a hearty breakfast before hitting the slopes or whipping up a cozy dinner after a day of exploration, you’ll find everything you need at your fingertips. CubsCorner is designed to accommodate additional guests with a murphy bed in the living room. The spacious living area invites relaxation, boasting a 55-inch TV equipped with Roku guest mode streaming. Unwind in style as you catch up on your favorite shows or plan your next day’s adventures. Whether you’re seeking a romantic getaway or a solo mountain retreat, CubsCorner in Killington, VT, provides a perfect blend of comfort, convenience, and natural beauty. Make your short-term stay memorable in this thoughtfully curated home away from home. This is the lower level apartment of a stand alone home. The owner occasionally uses the home as a vacation home. There is a separate entrance to the unit and the driveway is shared, but parking is on one side for this unit. We are local if you need us. The pool, sauna, and gym are all resort amenities provided by the Pico Fitness Center, which is a short drive across the road. They are open 6:00 a.m.- 8:00 p.m. Monday to Friday and 8:00 a.m. to 6:00 p.m. Saturday and Sunday. They provide showers, lockers and a changing room, remember to bring a towel! The pool is by reservation only.

Snowarts- Game room, Fireplace, Close to golf!

Killington, VT, US
3 Bedrooms 8 Guests
Aug 20 - 22
$171 night

Welcome to "SnowArts," a Killington, VT retreat in the woods, 10 mins from base lodges. Well-equipped kitchen, wood stove, foosball, 4 bedrooms including a king with an updated en suite, 2 cozy queen rooms, and a room with 4 twin beds. Perfect for nature lovers and outdoor enthusiasts. Welcome to "SnowArts," an enchanting short-term rental home in Killington, Vermont, where the serenity of the woods meets the thrill of the slopes. Nestled amidst the whispering pines, this woodland retreat offers the perfect balance of seclusion and convenience, located just 10 minutes away from the base lodges of the renowned Killington Mountain Resort. "SnowArts" invites you to step into a world of warm and inviting ambiance. At its heart is a well-stocked kitchen, a hub for culinary creativity and a gathering point for family and friends. With modern appliances and ample counter space, it’s a haven for food enthusiasts who love to cook together or prepare a hearty breakfast before embarking on your mountain adventures. One of the standout features of "SnowArts" is the wood-burning stove, where you can curl up with a book or share stories of your outdoor escapades as the flames dance in the background, creating an ambiance of rustic comfort. It’s the perfect place to warm up after a day of skiing or hiking. "SnowArts" features four charming bedrooms, each thoughtfully designed for comfort and relaxation. The master bedroom boasts a king-size bed and a newly updated en-suite bathroom, offering a private oasis for those seeking a touch of luxury. Two additional queen bedrooms provide a snug and intimate retreat, perfect for couples or individuals seeking a peaceful night’s rest. For larger groups or families, the fourth bedroom offers four twin beds, creating a fun and comfortable space for children or friends. Entertainment abounds at "SnowArts," with a foosball table offering hours of friendly competition and bonding. It’s the ideal way to unwind after a day of outdoor activities and create lasting memories. Outside, "SnowArts" is surrounded by the beauty of Vermont’s woodlands, and a spacious deck beckons you to relax and take in the fresh mountain air. In winter, you can gaze at the snow-covered trees, and in the warmer months, it’s the perfect spot for alfresco dining or simply savoring your morning coffee in the serene surroundings. Whether you’re visiting for the thrill of skiing, the allure of hiking, or simply to escape the hustle and bustle of everyday life, "SnowArts" offers a serene sanctuary where you can immerse yourself in the natural beauty of the region while enjoying all the modern comforts and conveniences you desire. Your perfect mountain getaway awaits at "SnowArts." There is a key code to access the home. We are local if you need us. This home is a side by side duplex, so there may be guests at the other side of the duplex.

Jack S’Bearo- AC, Pool, Mountain Views, Hiking, Gym

Killington, VT, US
1 Bedrooms 4 Guests
Aug 22 - 24
$127 night

Ahoy, ski enthusiasts! "Jack S’Bearo" - a renovated 1-bed, 1-bath on Pico Mountain, VT, offers an exhilarating ski experience steps from the lift and a shuttle to Killington Resort. The new kitchen, wood-burning fireplace, and balcony make it a haven for relaxation. This ski on/ski off treasure boasts a cool design for easy access to the slopes. Grab your gear from the ski locker, step outside, and set sail to the lifts. Make "Jack S’Bearo" your pirate’s cove, where adventure meets comfort! Ahoy, ski enthusiasts! Welcome to "Jack S’Bearo," your swashbuckling sanctuary on Pico Mountain in Killington, VT. This fully renovated one-bedroom, one-bathroom condominium offers an exhilarating ski experience just steps from the lift, with a shuttle service to boot, ensuring a seamless journey to the legendary Killington Resort. Embark on a treasure trove of delights as you enter this meticulously updated unit. A newly minted kitchen, equipped with top-notch appliances designed specifically for this space, awaits to be the galley where you prepare hearty feasts fit for a pirate crew. The wood-burning fireplace adds a touch of nautical warmth, perfect for recounting the day’s adventures on the slopes. "Jack S’Bearo" isn’t just a condo; it’s a fully furnished haven with a bright and welcoming atmosphere from the moment you set foot on board. This ski on/ski off vessel allows you to navigate the slopes effortlessly. Take the elevator or climb the stairs to the first deck, grab your gear from the dedicated ski locker, and step outside—just a pirate’s walk away from the lifts. The sleeping quarters are fit for a captain! The king size bed is made with 600 thread count cotton sheets and there is a desk in the living room that is a murphy bed with a full size bed with a real mattress - so much better than a pull out couch or below deck hammock! Picture yourself on the balcony, raising a tankard to the breathtaking mountain views, surrounded by the crisp Vermont air. This condo promises an unforgettable experience, where the spirit of adventure meets the comfort of home. So, weigh anchor and set your course for "Jack S’Bearo," where every stay is a tale of mountainous excitement and cozy retreats. Arrr, don’t miss the chance to make this pirate’s cove your temporary abode! You will have full access to the condo. We are local if you need us. The Village Square at Pico Condo Association is a family-oriented community primarily used by owners and committed to the peaceful, safe and quiet enjoyment of their residences. While the Association allows rentals and encourages guests to enjoy their visit, they have implemented certain rules related to the use and enjoyment of the units. These rules allow the Association to issue fines and take other actions particularly as it relates to the enforcement of the minimum age requirement of 25, "Quiet Hours" from 9pm until 8am and their no pet policy. The Association will try to resolve issues through the owner or rental agency in the first instance but reserves the right to take action in real time as circumstances require. In short, please respect your neighbors while you are a guest in these condos. The pool, sauna, and gym are all resort amenities provided by the Pico Fitness Center, which is a short walk or drive across the parking lot. They are open 6:00 a.m.- 8:00 p.m. Monday to Friday and 8:00 a.m. to 6:00 p.m. Saturday and Sunday. They provide showers, lockers and a changing room, remember to bring a towel! The pool is by reservation only.

Pico D305

Killington, VT, US
1 Bedrooms 4 Guests
Aug 20 - 22
$147 night

Pico D305 – Ski-In Convenience and Cozy Comfort at the Base of Pico Mountain Welcome to Pico D305, a beautiful one-bedroom condo perfectly located right at the base of family-friendly Pico Mountain. Step outside and hit the slopes — you can ski all day and return to your warm and welcoming condo to relax by the fireplace and unwind. This cozy home features a queen-sized bed in the bedroom and a comfortable living area designed for relaxation after a fun day outdoors. A coin-operated laundry is conveniently located on the ground floor of the building for guest use. Getting around is easy — take the shuttle bus on weekends and holidays directly to Killington’s Snowshed Base Lodge, or drive just a couple of miles to experience Killington’s lively nightlife, restaurants, and entertainment. During your stay, enjoy access to the Pico Fitness Center, offering a gym, sauna, lap pool, and a variety of fitness classes including spin and yoga — perfect for both relaxation and staying active. Please note: This unit does not have air conditioning. The Village Square at Pico Condo Association is a family-oriented community primarily used by owners and committed to the peaceful, safe and quiet enjoyment of their residences. While the Association allows rentals and encourages guests to enjoy their visit, they have implemented certain rules related to the use and enjoyment of the units. These rules allow the Association to issue fines and take other actions particularly as it relates to the enforcement of the minimum age requirement of 25, "Quiet Hours" from 9pm until 8am and their no pet policy. The Association will try to resolve issues through the owner or rental agency in the first instance but reserves the right to take action in real time as circumstances require. In short, please respect your neighbors while you are a guest in these condos. Experience the perfect blend of big mountain skiing and small mountain charm at Pico D305 — your ideal Vermont getaway. • Killington Resort extensive system of mountain biking trails. • Killington Adventure Center – Zip Lines, Mountain Coaster, Free Fall Jump Tower and more • Hiking – Vermont’s Long Trail, Appalachian Trail • Kayaking – Kent Pond, Woodward Reservoir and Chittenden Pond and more • Coolidge Homestead – Vermont’s #1 visited site in Plymouth VT only 20 minutes away • Woodstock VT filled with wonderful shops and art galleries • Marsh Billings Rockefeller National Historical Park in Woodstock VT • Billings Farm Museum – a wonder family activity • Green Mountain Golf Course – the # 1 public course in the state • Killington Golf Course owned by the resort • VINS – Vermont Institute of Natural Science – a rescue and birth sanctuary.

Fox Hollow Village C4

Mendon, VT, US
2 Bedrooms 6 Guests
Aug 20 - 22
$173 night

Our Fox Hollow two bedroom, two bathroom condo is the perfect place for your Killington holiday. Located just across from Pico Mountain, the Fox Hollow complex is only ten minutes to Killington Resort. As you walk into this single-floor condo, you’ll find a spacious entryway/mudroom leading to two bedrooms, fully equipped kitchen with counter and stools, dining area with seating for six, living room, laundry room, and two bedrooms with dated ensuite bathrooms. The primary bedroom features a king bed and the second bedroom features two twin beds. The living room has a pull out sofa, smart TV and wood-burning fireplace (firewood provided). In the warmer months, you have access to the outdoor deck, tennis court, and shared heated outdoor pool (June to September), plus can store your mountain bikes indoors in the mudroom. In addition to the ski season, you’ll find tons of great outdoor activities, including the Appalachian Trail directly across the street. Plan to stay with us any season to experience the best of the Green Mountains! • We have some flexibility around our standard check in and check out times depending on other bookings. Guaranteed early check in or late check out may be available for an additional charge. • We have smart locks for contactless check in. Your unique access code will be sent the week of your arrival. • Pack ’n play and high chair available upon request. (Please let us know in advance.) • Our entire property is non-smoking and non-vaping. You may only smoke or vape outside and 75 feet away from the building. Please properly dispose of all butts. • Quiet hours are from 10pm - 8am. We may use Minut, smart home technology that measures volume levels throughout the property and allows us to respond to noise nuisances without disrupting your stay. Minut is 100% privacy compliant and is required on this property. If you have any questions, please ask. We are committed to your comfort so please let us know if we can do anything during your stay to make it more enjoyable. • For your safety & ours, we have a camera in the entryway to the condo. This is not in any of the living areas. • Pets are not allowed. There will be a $450 fine for any unauthorized pets. • You must sign and return our written rental agreement. • Winter weather is unpredictable. We do not offer weather-related refunds and recommend purchasing travel insurance for any unforeseen events. All wheel drive and winter tires are also recommended. SKI RESORTS: Pico Mountain (0.5 miles), Killington Snowshed Base (6.4 miles), Killington K1 Base (7.1 miles), Mountain Meadows Cross Country Ski and Snowshoe (2.5 miles) GOLF: Green Mountain National Golf Course (5.5 miles), Killington Golf Course (6.4 miles) NIGHTLIFE: McGrath’s Irish Pub (0.9 miles), Flannels Bar & Grill (1.7 miles), Pickle Barrel (4.2 miles), Wobbly Barn (4.7 miles), Mary Lou’s (5.3 miles), The Foundry at Summit Pond (3.7 miles) WEDDINGS: Killington Grand Resort (6.4 miles), Mountain Top Inn & Resort (11.4 miles) AIRPORT: Rutland Regional Airport (15.1 miles), Burlington International Airport (71.2 miles), Albany International Airport (108 miles), Manchester- Boston Regional Airport (119 miles)

Pico E205

Killington, VT, US
2 Bedrooms 6 Guests
Aug 20 - 22
$175 night

Pico Village – 2-Bedroom Condo Steps from the Lifts | Fireplace • Pool & Fitness Center Access Stay just steps from the chairlifts at Pico Mountain in this lovely 2-bedroom, 2-bath condo, perfectly located for your getaway to Vermont’s beautiful Green Mountains. The primary bedroom features a queen-sized bed, while the second bedroom offers two twin beds — ideal for families or friends traveling together. The open living area is warm and inviting, featuring a wood-burning fireplace where you can relax after a great day on the slopes. (Please note: This unit does not have air conditioning.) During your stay, take advantage of access to the Pico Fitness Center and Pool. Swim laps in the pool, work out in the gym, join a spin or yoga class, or unwind in the sauna — perfect for recharging after an active day. The Village Square at Pico Condo Association is a family-oriented community primarily used by owners and committed to the peaceful, safe and quiet enjoyment of their residences. While the Association allows rentals and encourages guests to enjoy their visit, they have implemented certain rules related to the use and enjoyment of the units. These rules allow the Association to issue fines and take other actions particularly as it relates to the enforcement of the minimum age requirement of 25, "Quiet Hours" from 9pm until 8am and their no pet policy. The Association will try to resolve issues through the owner or rental agency in the first instance but reserves the right to take action in real time as circumstances require. In short, please respect your neighbors while you are a guest in these condos. Pico Mountain offers “Big Mountain Skiing with Small Mountain Charm” — featuring terrain for every skill level, from beginners to advanced skiers, and instruction from world-class trainers, including past Olympians. Just a few minutes away, Killington Resort awaits with a lively après-ski scene, fantastic restaurants, and vibrant nightlife at spots like the Wobbly Barn, Pickle Barrel, and Jax’s. Beyond skiing, the region offers winter adventures for everyone — from snowmobiling through the Green Mountains to tubing parks and ice skating on Foundry Pond. Come to Killington and create memories that will last a lifetime — all from the comfort of your slopeside home at Pico. • Killington Resort extensive system of mountain biking trails. • Killington Adventure Center – Zip Lines, Mountain Coaster, Free Fall Jump Tower and more • Hiking – Vermont’s Long Trail, Appalachian Trail • Kayaking – Kent Pond, Woodward Reservoir and Chittenden Pond and more • Coolidge Homestead – Vermont’s #1 visited site in Plymouth VT only 20 minutes away • Woodstock VT filled with wonderful shops and art galleries • Marsh Billings Rockefeller National Historical Park in Woodstock VT • Billings Farm Museum – a wonder family activity • Green Mountain Golf Course – the # 1 public course in the state • Killington Golf Course owned by the resort • VINS – Vermont Institute of Natural Science – a rescue and birth sanctuary.

The Pico Family Getaway H103

Killington, VT, US
3 Bedrooms 8 Guests
Aug 20 - 22
$662 night

Wow! Located at the base of Pico Mountain, you have ski on/off access to this great family-friendly mountain resort and you’re only 10 minutes to Killington Resort as well. (Secret local’s tip: Pico is a great place to ski on peak weekends and holidays when Killington is much busier, and it’s always perfect for families.) Our renovated 3 bedroom, 2 bathroom condo is the perfect place to call home while you’re in Killington. Featuring new furnishings and appliances along with some great local artwork, you’ll relax by the gas fireplace after a day on the slopes and can cook a meal in the fully equipped kitchen. Lots of room to spread out and close to it all - what more could you want? Our renovated condo is the perfect getaway for families. Featuring two large bedrooms with queen beds for the grown ups and a third bedroom with bunk beds for the kids, everyone will have plenty of space. The open kitchen and living room with dining table and counter stools is the perfect place to relax together after a day on the slopes. Ski on/off to Pico Mountain which is just out your door or drive a short 10 minutes to Killington to experience the best skiing and riding on the east coast. We look forward to hosting you and are sure you’ll love your holiday here! • We have some flexibility around our standard check in and check out times depending on other bookings. Guaranteed early check in or late check out may be available for an additional charge. • We have smart locks for contactless check in. Your unique access code will be sent the week of your arrival. • Pack ’n play and high chair available upon request. (Please let us know in advance.) • Our entire property is non-smoking and non-vaping. You may only smoke or vape outside and 75 feet away from the building. Please properly dispose of all butts. • Quiet hours are from 10pm - 8am. We may use Minut, smart home technology that measures volume levels throughout the property and allows us to respond to noise nuisances without disrupting your stay. Minut is 100% privacy compliant and is required on this property. If you have any questions, please ask. We are committed to your comfort so please let us know if we can do anything during your stay to make it more enjoyable. • For your safety & ours, we have a camera in the entryway to the condo. This is not in any of the living areas. • Pets are not allowed. There will be a $450 fine for any unauthorized pets. • You must sign and return our written rental agreement. • Please be advised that this property utilizes a ladder to access the bunk beds. By renting this property, you are agreeing to hold the owner and property manager harmless for any injury or death that is resulting from the use of the ladder. • Winter weather is unpredictable. We do not offer weather-related refunds and recommend purchasing travel insurance for any unforeseen events. All wheel drive and winter tires are also recommended. The Village Square at Pico Condo Association is a family-oriented community primarily used by owners and committed to the peaceful, safe and quiet enjoyment of their residences. While the Association allows rentals and encourages guests to enjoy their visit, they have implemented certain rules related to the use and enjoyment of the units. These rules allow the Association to issue fines and take other actions particularly as it relates to the enforcement of the minimum age requirement of 25, "Quiet Hours" from 9pm until 8am and their no pet policy. The Association will try to resolve issues through the owner or rental agency in the first instance but reserves the right to take action in real time as circumstances require. In short, please respect your neighbors while you are a guest in these condos. SKI RESORTS: Pico Mountain (0.1 miles), Killington Snowshed Base (6.3 miles), Killington K1 Base (7.0 miles), Mountain Meadows Cross Country Ski and Snowshoe (2.4 miles) SHUTTLE: Every 15 minutes outside the condo from Thanksgiving to mid-March. GOLF: Green Mountain National Golf Course (5.4 miles), Killington Golf Course (6.3 miles) NIGHTLIFE: McGrath’s Irish Pub (0.8 miles), Flannels Bar & Grill (2.2 miles), Pickle Barrel (4.2 miles), Wobbly Barn (4.7 miles), Nitespot (5.3 miles), The Foundry at Summit Pond (3.7 miles) WEDDINGS: Killington Grand Resort (6.3 miles), Mountain Top Inn & Resort (11.4 miles) AIRPORT: Rutland Regional Airport (15.2 miles), Burlington International Airport (71.2 miles), Albany International Airport (108 miles), Manchester- Boston Regional Airport (119 miles)

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Vacation Rentals Near Chittenden

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