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Best Vacation rentals and Airbnb offers in Woodstock, VT
Woodstock, VT
08/21 – 08/23
$2379/nighttotal: $4758 (2 )
Casita Alta \Nluxury House With Heated Pool In Woodstock, Vt
3 2
apartment , Woodstock
This private ultra-luxury retreat, an apartment in Woodstock, is situated just outside the village, offering an easy walk to shops, restaurants, Quechee Gorge Village, and King Arthur Baking Company. This 3-bedroom, 6-guest capacity residence features 4.5 bathrooms, air conditioning, a swimming pool, and concierge service, with nearby access to Billings Park and Trail, Quechee State Park, Red Wagon Toy Company, and Billings Farm and Museum.
9.7 20 reviews
Woodstock, VT
07/25 – 08/01
$315/nighttotal: $2205 (7 )
Modern Village, Community Pool - Newton Village 1c
2 2
apartment , Hartford
This 2-bedroom townhouse is located in the peaceful Newton Village of Quechee Lakes, Vermont, just a short walk from Lake Pinneo and the Quechee Club. The property has received excellent ratings for its cleanliness, location, and overall user experience. The 1550 square foot home comfortably accommodates up to 6 guests with a king bed in the master bedroom, two twin beds and a futon in the second bedroom, and a queen-sized pull-out sofa in the living room. Guests can enjoy amenities including a private garden, a terrace, a swimming pool, and a fully equipped kitchen with a fridge, freezer, microwave oven, and dishwasher.
9.6 5 reviews
Woodstock, VT
10/14 – 10/15
$586/nightfor 1 night
New Skye Ridge Carriage House With Hot Tub
2 8
house , Killington
Skye Ridge Carriage House, near Killington, Vermont, is conveniently located 5.1 miles from Gifford Woods State Park, 4.4 miles from Killington Peak, and 7.6 miles from Pico Peak. This 2000-square-foot vacation home boasts two bedrooms, two bathrooms (one with a hot tub), two living rooms, a fully equipped kitchen, and can comfortably accommodate up to 15 guests, featuring amenities such as a private hot tub, free Wi-Fi, and on-site parking.
9.3 117 reviews
Woodstock, VT
09/25 – 09/27
$310/nighttotal: $620 (2 )
Ludlow's Gem
2 2
house , Ludlow
Ludlow's Gem is a 2-bedroom house located in Ludlow, Vermont, just a short drive from Okemo Mountain and Jackson Gore Ski Area. The house has received excellent ratings for location, cleanliness, and overall user experience. This 960 square foot house can comfortably accommodate up to 6 guests. The house offers a fully equipped kitchen, a terrace, a garden, parking, and internet access. Guests can enjoy a peaceful stay with access to nearby ski resorts, satellite TV, and the convenience of self-catering.
9.9 51 reviews
Woodstock, VT
07/25 – 08/01
$317/nighttotal: $2219 (7 )
Cozy Vt Retreat Between Woodstock & Killington
1 2
apartment , Bridgewater
This Bridgewater apartment is conveniently located between Woodstock and Killington, offering easy access to both towns and their attractions. It boasts excellent user, location, and cleanliness ratings, ensuring a comfortable and enjoyable stay. This two-bedroom, two-bathroom rental comfortably sleeps six guests. The apartment includes a fully equipped kitchen, laundry facilities, a shared outdoor space with a fire pit, and high-speed Wi-Fi, making it perfect for families or groups looking for a relaxing getaway.
9.3 3 reviews
Woodstock, VT
10/14 – 10/15
$651/nightfor 1 night
Vt Lake House Minutes From Okemo
2 8
house , Ludlow
This Ludlow lake house is minutes from Okemo Mountain Resort, 20 miles from Gifford Woods State Park, and within 20-30 miles of Killington, Stratton, and Pico Peaks. This 1000-square-foot vacation rental boasts two bedrooms, three bathrooms, sleeps 15 guests, and includes a fully equipped kitchen, free Wi-Fi, a fireplace, and private parking.
10 293 reviews
Woodstock, VT
12/10 – 12/16
$170/nighttotal: $1020 (6 )
Cozy Little Spot (Self Check-in)
1 2
house , Woodstock
This cozy cabin-studio getaway is located just 3.25 miles outside of Woodstock, nestled in the trees near a stream and brook. The studio features a private garden, a fire pit, and a kitchenette with a mini-refrigerator, a propane camp stove, and a toaster oven, perfect for a couple seeking a secluded nature escape.
9.8 8 reviews
Woodstock, VT
12/10 – 12/16
$452/nighttotal: $2712 (6 )
Designer-restored 1870 Hideaway On Kedron Brook
2 2
apartment , Woodstock
This historic 1870 property in Kedron Valley, Woodstock, offers direct trail access and is a short walk to the country store and Kedron Valley Inn, with Woodstock village 5 miles away. This restored apartment sleeps four, features two bedrooms, a full kitchen with a dishwasher, and a private deck, providing immediate access to hiking, biking, and ski trails, plus a firepit for stargazing.
9.8 145 reviews
Woodstock, VT
07/25 – 08/01
$218/nighttotal: $1526 (7 )
New Modern Apartment - Woodstock Village On Mt Peg
1 2
apartment , Woodstock
This one-bedroom apartment is located in Woodstock, Vermont, just steps from the village center and at the edge of the Mt. Peg Town Forest, offering a peaceful escape from the village bustle. It has received excellent ratings for location, cleanliness, and user experience. The apartment features a private entrance, a full kitchen and bathroom, and tasteful mid-century modern design. It can accommodate up to two guests and offers convenient on-site parking, making it ideal for families or couples looking for a comfortable and stylish stay in Woodstock.
10 57 reviews
Woodstock, VT
09/02 – 09/08
$300/nighttotal: $1800 (6 )
Nana's House
3 2
apartment , Bridgewater
This Bridgewater, Vermont apartment boasts a tranquil riverfront location, just 10 minutes from Woodstock, Vermont and its attractions, and a short drive from Killington and Okemo ski resorts. This 1500-square-foot rental features three bedrooms, one bathroom, and accommodates six guests, offering amenities such as a full kitchen with dishwasher, air conditioning, parking, internet access, and proximity to Billings Farm & Museum, Long Trail Brewery, and numerous outdoor recreational activities.
Woodstock, VT
10/14 – 10/15
$771/nightfor 1 night
New! Spacious 4 Bedroom Condo In Quechee
1 8
apartment , Hartford
This 4-bedroom, 3-bathroom townhouse in Hartford offers 3,000 sq ft of living space, featuring a main-floor master suite, multiple living areas with a gas fireplace and downstairs den, and a well-equipped kitchen with an adjacent dining area. Located in a residential district, this rental is a short 1.5-mile drive from downtown Hartford's attractions, including the Wadsworth Atheneum Museum of Art and the Old State House.
Woodstock, VT
08/21 – 08/23
$824/nighttotal: $1648 (2 )
Woodstock Inn & Resort
1 2
resort , Woodstock
The Woodstock Inn & Resort is located in West Woodstock, Vermont, about 1.2 miles from downtown Woodstock, near the Woodstock Town Hall Theatre, Red Wagon Toy Company, and the Dana Museum. This pet-friendly hotel offers amenities including a restaurant, bar, outdoor pool, fitness center, spa, sauna, and business/family-friendly features like a conference room and game room.
Compare Vacation Rentals for Families in Woodstock, VT
Booking a family-oriented vacation rental in Woodstock, VT keeps you close to top city attractions for a stress-free getaway.
10 21 reviews
Woodstock, VT
07/25 – 08/01
$987/nighttotal: $6909 (7 )
Historic Riverfront House: 5 Bedrooms 3.5 Baths On 5 Acres
6 2
farm , Bridgewater
This six-bedroom farmhouse is situated in Bridgewater, Vermont, just ten minutes from both Killington Ski Resort and the historic town of Woodstock. The property features a fully equipped kitchen, a spacious terrace, a fitness center, and a private garden, offering a comfortable and relaxing stay for groups of up to twelve guests.
9.8 234 reviews
Woodstock, VT
09/02 – 09/08
$472/nighttotal: $2832 (6 )
Private & Affordable Charming Custom Ranch In S. Woodstock. Wifi And Ac.
4 2
apartment , Woodstock
This Woodstock, Vermont farmhouse sits on four private acres, three miles from Woodstock village, offering easy access to Billings Farm & Museum and Suicide Six ski area. The 1500-square-foot single-story house sleeps seven, boasts a fully equipped kitchen with dishwasher, features high-speed internet, and provides access to numerous outdoor activities including hiking Mount Tom and Mount Peg, and skiing at Killington, Pico, and Okemo.
10 2 reviews
Woodstock, VT
09/02 – 09/08
$453/nighttotal: $2718 (6 )
Community Pool, Cozy Fireplace - Coach Road 7a
3 2
apartment , Hartford
This luxurious Quechee, Vermont condo offers exclusive access to The Quechee Club, including golf courses, pools, and a ski hill, and is a short drive from Woodstock and other Upper Valley attractions. The 4-bedroom, 4-bathroom rental boasts a spacious layout, sleeps up to 8 guests, includes a private patio overlooking the Highland Golf Course, and features high-end furnishings, a game room, and an attached garage.
10 89 reviews
Woodstock, VT
12/10 – 12/16
$458/nighttotal: $2748 (6 )
Vermont Get-away End Unit Townhouse Nestled In The Trees
3 2
apartment , Hartford
This two-bedroom apartment in Quechee is conveniently located a short 15-minute walk from Simon Pearce Mill, Route 4 Glassblowing Studio, and The Strong House Spa. The apartment is highly rated by guests, with excellent scores for location, cleanliness, and overall experience. This spacious 1070 square foot condo features a fully equipped kitchen, two bathrooms, and a private patio. Guests can enjoy amenities like a fitness center, indoor and outdoor pools, and a spa, as well as a garden and parking.
Best Woodstock, VT vacation rentals with parking
8.0 1 review
Woodstock, VT
07/25 – 08/01
$748/nighttotal: $5236 (7 )
Historic, Walk To Town - South Woodstock Cottage
3 2
apartment , Woodstock
This meticulously restored 1807 farmhouse in South Woodstock, Vermont, is a short walk from the General Store and Kedron Valley Inn, and within 15 miles of numerous attractions including championship golf courses. This 1960-square-foot vacation home features three bedrooms, three bathrooms, and can accommodate up to eight guests, boasting a top-of-the-line kitchen, a paved patio, keyless entry, and access to a guest manual detailing local amenities.
9.1 25 reviews
Woodstock, VT
09/02 – 09/08
$441/nighttotal: $2646 (6 )
200ac, Views! 10min To Town - Scenic Ridge Retreat
4 2
apartment , Pomfret
This four-bedroom, three-bathroom cabin is located in Woodstock, Vermont, offering direct access to the Appalachian Trail and proximity to both Okemo Mountain Resort and Killington Ski Resort. The cabin features a fully equipped kitchen, a cozy wood-burning fireplace, and can accommodate up to eight guests.
9.2 42 reviews
Woodstock, VT
12/10 – 12/16
$254/nighttotal: $1524 (6 )
Golf Views! & Patio Dining - Windsor Village 3a
2 2
apartment , Hartford
This peaceful Vermont condo is a short drive from the charming towns of Quechee and Woodstock, offering easy access to local shops, restaurants, and attractions. It has earned excellent ratings for its location, cleanliness, and overall user experience. The 1110 square foot condo features two bedrooms and comfortably accommodates four guests. Enjoy access to a shared pool, gym, and a private patio and balcony, along with other amenities like a fully equipped kitchen, internet access, and parking.
9.8 9 reviews
Woodstock, VT
07/25 – 08/01
$374/nighttotal: $2618 (7 )
Cozy Fireplace, Pets, Club Access! - Saltbox 9a
2 2
apartment , Hartford
This Quechee, Vermont condo, a short drive from Woodstock and Killington/Pico ski resorts, offers a scenic mountain location with access to The Quechee Club amenities. The two-bedroom, two-bathroom rental sleeps six, features a well-equipped kitchen, fireplace, deck, and allows one dog under 50 pounds.
Frequently Asked Questions about vacation rentals in Woodstock, VT
What are some interesting places to visit in or near Woodstock, VT?
Woodstock is known for its charming historic downtown, with shops and restaurants along the main street. The Marsh-Billings-Rockefeller National Historical Park is a must-see, showcasing the history of the area's forests and the family who owned the land. If you're looking for a scenic drive, the scenic Route 100 offers stunning views of the Green Mountains.
What are the best Airbnb and vacation rentals in Woodstock, VT?
Which walking or cycling routes are the best in Woodstock, VT?
The Woodstock Village Green is a great place to start a walk or bike ride. The Vermont Rail Trail follows a former rail line and offers a flat, easy route for all skill levels. For a more challenging ride, try the climb up to Suicide Six ski area for stunning views.
What are the most popular Airbnbs in Woodstock, VT?
What sports or outdoor activites can visitors enjoy in and around Woodstock, VT?
Woodstock is a great place for outdoor recreation. In the winter, you can ski at Suicide Six or cross-country ski on the many trails in the area. In the summer, hiking, biking, swimming, and fishing are all popular activities. There are also several golf courses nearby.
What are the best vacation rentals with a pool in Woodstock, VT?
What amenities are commonly available in vacation rentals in Woodstock, VT?
Vacation rentals in Woodstock typically offer a variety of amenities, including fully equipped kitchens, laundry facilities, and comfortable living spaces. Many rentals also have decks or patios with views of the mountains or the village. Some rentals may also offer additional amenities like fireplaces, hot tubs, or swimming pools.
What are the best rentals for families and kids in Woodstock, VT?
What time of year is best to rent a vacation rental Woodstock, VT?
The best time to visit Woodstock depends on your interests. If you enjoy skiing, the winter months are ideal. For hiking and biking, the summer and fall are the best times to go. Spring is also a beautiful time to visit, with the leaves starting to turn green.
What are the best rentals or Airbnbs with a jacuzzi in Woodstock, VT?
Choose the Right Vacation Rentals with a Terrace in Woodstock, VT
Wake up to breathtaking views at these Woodstock, VT vacation rentals with balconies, perfect for your morning coffee.
9.4 676 reviews
Woodstock, VT
09/02 – 09/08
$677/nighttotal: $4062 (6 )
Woodstock Inn & Resort
1 2
resort , Woodstock
The Woodstock Inn & Resort is located in the heart of the Village Green, a short drive from Marsh-Billings-Rockefeller National Historical Park and the Billings Farm Museum. The inn boasts excellent ratings for user experience, location, and cleanliness. The hotel offers a variety of rooms and suites, all featuring modern amenities. Enjoy a range of amenities including a spa, a fitness center, a restaurant, and a bar, as well as activities like tennis and swimming.
10 1 review
Woodstock, VT
09/02 – 09/08
$333/nighttotal: $1998 (6 )
Newton Village 1a
2 2
apartment , Hartford
This Quechee condo, located at Newton Village 1A, offers a Vermont escape 25 miles from Killington Peak and 6.5 miles from Mount Tom, with convenient access to Dartmouth College and Gifford Woods State Park. This 1690 sq ft apartment features 2 bedrooms and 2 bathrooms, accommodating up to 11 guests with a fully equipped kitchen, swimming pool, on-site restaurant, and a terrace.
9.8 7 reviews
Woodstock, VT
09/25 – 09/27
$1409/nighttotal: $2818 (2 )
Premier Woodstock Village Riverfront Home
3 2
apartment , Woodstock
This historic riverfront estate in Woodstock offers a private, 3-bedroom, 2.5-bath apartment with exclusive garden access, located a 5-minute walk from Woodstock village's shops, restaurants, and the Woodstock Inn. This family-friendly rental features air conditioning, a full kitchen with a dishwasher, a fire pit, and is conveniently situated near Billings Farm and Museum, Marsh-Billings-Rockefeller National Historical Park, and ski resorts like Saskadena Six, just 7 miles away.
Woodstock, VT
07/25 – 08/01
$455/nighttotal: $3185 (7 )
Ski Oasis W/ Hot Tub Near Killington & Woodstock
1 2
apartment , Bridgewater
This Bridgewater Corners apartment is a 12-minute drive from Killington and a 15-minute drive from Woodstock and Quechee, with Long Trail Brewery within walking distance. This pet-friendly residence accommodates up to six guests and offers a shared backyard with a hot tub, wood-fire pit, and grills, along with a fully stocked kitchen and a dedicated workspace.
Discover Pet-Friendly Vacation Rentals in Woodstock, VT
Traveling with pets? These dog-friendly vacation rentals and Airbnbs in Woodstock, VT are steps away from dog parks and city walks.
8.8 3 reviews
Woodstock, VT
09/02 – 09/08
$489/nighttotal: $2934 (6 )
Charming Ranch In The Woods - Woodstock Way
2 2
apartment , Woodstock
This 11-acre Woodstock, Vermont farm sits just over a mile from the village center, near a country club and golf course, offering easy access to Upper Valley attractions. The 1400-square-foot ranch house features two bedrooms, one bathroom, and accommodates up to eight guests, boasting a gourmet kitchen, Wi-Fi, a fireplace, and a detached three-car garage.
10 6 reviews
Woodstock, VT
12/10 – 12/16
$335/nighttotal: $2010 (6 )
Highland Golf, Walk To Club - Lakeland Village 2d
4 2
apartment , Hartford
This lakeside Hartford, Vermont apartment, near the Vermont Institute of Natural Science and Sugarbush Farm, offers easy access to Quechee Gorge Village, King Arthur Baking Company, Red Wagon Toy Company, and Billings Farm & Museum. This 1,350-square-foot rental boasts four bedrooms, two bathrooms, sleeps seven, and includes a fully equipped kitchen, laundry facilities, a balcony with lake views, a garden, and on-site grills and fireplace.
Woodstock, VT
09/02 – 09/08
$565/nighttotal: $3390 (6 )
Great Pond Retreat
5 2
house , Barnard
Great Pond Retreat, a five-bedroom house near Killington, Vermont, is conveniently located approximately 9.4 miles from Mount Tom, 26 miles from Gifford Woods State Park, and 28 miles from both Pico Peak and Dartmouth College. This 5200-square-foot vacation home boasts a fully equipped kitchen, three bathrooms, a spacious living room, and can comfortably accommodate up to 23 guests, offering lake views, a terrace, a garden, parking, and free Wi-Fi.
Woodstock, VT
08/14 – 08/15
$2863/nightfor 1 night
Lux Chalet 4 Bd Fireplace Hottub Ac Pet Friendly
1 2
house , Killington
This Killington vacation home is conveniently located 4.3 miles from Killington Peak, 5.3 miles from Gifford Woods State Park, and 7.7 miles from Pico Peak, offering easy access to Killington's premier ski areas and attractions. This pet-friendly property boasts two bathrooms, one bedroom, sleeps up to 19 guests, and includes a full kitchen, air conditioning, a hot tub, free Wi-Fi, and private parking.