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Best Vacation rentals and Airbnb offers in Woodstock, VT
10 44 reviews
Woodstock, VT
07/25 – 08/01
$212/nighttotal: $1484 (7 )
Hilltop Hideaway Retreat In Woodstock
1 2
apartment , Woodstock
This Woodstock, Vermont apartment rental boasts a secluded setting, a five-minute drive from both Woodstock and South Woodstock's commercial centers, offering easy access to shops and restaurants. The one-bedroom, one-bathroom unit sleeps three guests and features a fully equipped kitchen (fridge, freezer, microwave), private garden, parking, and excellent guest reviews; enjoy tranquil surroundings and dramatic long-range views.
10 142 reviews
Woodstock, VT
09/02 – 09/08
$235/nighttotal: $1410 (6 )
Vermont Retreat
1 2
apartment , Bridgewater
This Bridgewater apartment is located just 2.5 miles from Long Trail Brewing Company and within 9 miles of both Killington Resort and Union Arena Community Center, making it a great base for exploring the area's attractions. The apartment has received excellent ratings for its cleanliness, location, and overall experience. This 1-bedroom, 1-bathroom apartment is 600 square feet and can accommodate up to 2 guests. The apartment features a fully equipped kitchen, a washing machine, free WiFi, a Smart TV, and parking on-site. Guests can enjoy the nearby Five Elm Arches and Ottaquechee River for hiking, fishing, and scenic walks, as well as the playground on the property.
9.4 49 reviews
Woodstock, VT
12/10 – 12/16
$249/nighttotal: $1494 (6 )
Saltbox 12f
2 2
house , Hartford
Saltbox 12F, a two-bedroom house rental in White River Junction, Vermont, is conveniently located near Killington Peak (31 miles), Mount Tom (9 miles), and Dartmouth College (15 miles), offering easy access to Vermont's attractions. This 1310-square-foot vacation home features two bathrooms, a fully equipped kitchen with a fridge, microwave, and dishwasher, plus amenities including a terrace, garden, spa, fitness center, and parking; it comfortably accommodates up to four guests and provides access to nearby skiing and Gifford Woods State Park (29 miles).
Woodstock, VT
08/14 – 08/15
$913/nightfor 1 night
50-acre Woodstock Estate | Views & Chef's Kitchen
9 2
apartment , Woodstock
This historic estate, a private Vermont retreat, sits on nearly 50 acres of rolling countryside just minutes from Woodstock. This 8,000+ sq ft luxury country house offers 9 bedrooms, 8 bathrooms, and accommodates 16 guests with a chef's kitchen, private pond, and sweeping mountain views, ideal for wellness retreats or luxury countryside escapes.
Woodstock, VT
09/02 – 09/08
$278/nighttotal: $1668 (6 )
Steps To Ski Trail, Fireplace - Kingswood 1b
3 2
apartment , Hartford
This three-bedroom, three-bathroom condo is located in Quechee, Vermont, a short drive from Quechee Gorge and Quechee Ski Area. The 1,040-square-foot rental boasts a fully equipped kitchen, in-unit laundry, a terrace, and a swimming pool, comfortably accommodating up to eight guests with access to nearby golf, tennis, and other recreational activities at The Quechee Club.
9.0 12 reviews
Woodstock, VT
07/25 – 08/01
$234/nighttotal: $1638 (7 )
Renovated Condo, Heart Of Quechee - Mill Run 3e
2 2
apartment , Hartford
Overlooking the Ottauquechee River, this two-bedroom condo in Quechee, Vermont, offers a serene ambiance and convenient access to Simon Pearce, Woodstock, and Hanover, NH. With an excellent user rating, this property provides a comfortable and inviting atmosphere for up to four guests. The open-concept living area with a wood-burning stove creates a warm and welcoming ambiance. The 1070 square feet of floor space includes two bedrooms, two bathrooms, and a fully equipped kitchen with modern appliances. Guests can enjoy access to a private deck, indoor and outdoor pools, a fitness facility, and tennis courts through The Quechee Club membership.
10 74 reviews
Woodstock, VT
12/10 – 12/16
$437/nighttotal: $2622 (6 )
Falcon House: Vt Modern Chalet W/sauna On 25 Acres - Hike - Bike To Village
3 2
chalet , Woodstock
This architect-designed chalet is located in West Woodstock, just 2.5 miles from the charming village and 15 minutes from Killington ski resort. It has received excellent user ratings, making it a popular choice for travelers seeking a comfortable and luxurious escape. The chalet offers 1400 square feet of space, accommodating up to 6 guests in its 2 bedrooms and 3 bathrooms. Amenities include a Finnish sauna, a chef's kitchen with stainless steel appliances, a cozy gas fireplace, and access to private hiking, biking, and snowshoeing trails.
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.
Woodstock, VT
12/23 – 12/27
$412/nighttotal: $1648 (4 )
Fireplace, Library - 21 Mountain Ave, Woodstock*
4 4
apartment , Woodstock
This spacious 4-bedroom, 3-bathroom apartment is located in the historic district of Woodstock, Vermont, on a quiet street within walking distance to the town's attractions. This pet-friendly rental accommodates up to 8 guests and features a gourmet kitchen, a formal dining room with a fireplace, a dedicated office, a lounge area, a living room/library, and a primary suite with a jacuzzi tub.
10 11 reviews
Woodstock, VT
07/25 – 08/01
$236/nighttotal: $1652 (7 )
The Owl’s Nest
1 2
apartment , Bridgewater
This secluded studio apartment is located in the woods of Central Vermont, offering a quiet escape within 10 miles of Bridgewater. This pet-friendly studio accommodates two guests and features a full kitchen, air conditioning, and internet access, with parking available.
8.5 14 reviews
Woodstock, VT
09/02 – 09/08
$431/nighttotal: $2586 (6 )
Walk To The Lakes
5 2
house , Ludlow
This Ludlow vacation home is situated 3.7 miles from Dorsey Park and within a 20-30 mile radius of Stratton Mountain, Gifford Woods State Park, Pico Peak, Mount Tom, Killington Peak, and Mount Ascutney. This spacious five-bedroom house, boasting 2,030 square feet, offers two bathrooms, a fully equipped kitchen with a fridge, microwave, and dishwasher, a fireplace, free Wi-Fi, and parking; it comfortably accommodates large groups or families and is near excellent skiing opportunities.
9.9 363 reviews
Woodstock, VT
12/23 – 12/27
$311/nighttotal: $1244 (4 )
Charming Log Cabin Apartment In Woodstock Village
1 4
apartment , Woodstock
This Woodstock apartment is located near Mount Tom and a flower garden, offering a peaceful setting just outside the town center. It has excellent user, location, and cleanliness ratings, making it a top choice for travelers. This one-bedroom apartment, spanning 900 square feet, comfortably accommodates up to four guests. Amenities include a full kitchen, laundry facilities, a private entrance, a mudroom, a garden, a spa, parking, and internet access, ensuring a relaxing and enjoyable stay.
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.
9.9 196 reviews
Woodstock, VT
12/23 – 12/27
$882/nighttotal: $3528 (4 )
The Quechee Haus: Vt Retreat With Outdoor Hot Tub
3 4
apartment , Hartford
This vacation home is located in White River Junction, just a short drive from The Strong House Spa, Route 4 Glassblowing Studio, and Simon Pearce Mill, offering easy access to local attractions. The home has received excellent ratings for user experience, location, and cleanliness. This 3-bedroom home spans 1650 square feet and comfortably accommodates up to 8 guests. It features modern amenities like a fully equipped kitchen, a fireplace, a patio, and free WiFi, along with a jacuzzi, a garden, a spa, and a tennis court for relaxation and recreation.
10 118 reviews
Woodstock, VT
12/10 – 12/16
$382/nighttotal: $2292 (6 )
Falcon House: Vt Chalet W/sauna, Bike To Village
1 2
chalet , Woodstock
This modern chalet is situated in a quiet, wooded area on the outskirts of Woodstock, Vermont, just a 5-minute drive from the village center and 20 minutes from Killington ski resort. The chalet consistently receives excellent ratings for location, cleanliness, and overall user experience. The chalet has two bedrooms and two bathrooms, comfortably accommodating up to five guests. Enjoy a variety of amenities, including a private 60-acre forest with hiking trails, a Finnish sauna, a chef's kitchen, a lofted master suite, a deck with a BBQ, and four mountain bikes.
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.
9.4 16 reviews
Woodstock, VT
09/02 – 09/08
$1571/nighttotal: $9426 (6 )
Luxury Estate 25 Gorgeous Acres Of Privacy Family Getawayswimming Pond
4 2
apartment , Woodstock
This family-friendly vacation home is located in a rural area of Woodstock, just a short drive from Marsh-Billings-Rockefeller National Historical Park and Five Elm Arches. The house has consistently received excellent ratings for user experience, location, and cleanliness. This 4,000 square foot house features 4 bedrooms and 3 bathrooms, providing ample space for families and groups. Enjoy a range of amenities, including a private spa tub, a fireplace, a game room, a garden, a fully equipped kitchen, a washing machine, and barbecue grills.
Best Woodstock, VT vacation rentals with parking
10 3 reviews
Woodstock, VT
09/02 – 09/08
$301/nighttotal: $1806 (6 )
Luxury Living In Heart Of Quechee - Mill Run 6c
2 2
apartment , Hartford
This 2-bedroom, 2-bathroom condo is located in Quechee, Vermont, a picturesque town situated on the Ottauquechee River, just a short drive from the Quechee Gorge and the historic village of Woodstock. The condo features a fully equipped kitchen, a spacious deck, and access to the amenities of The Quechee Club, including tennis courts, a golf course, and a fitness center.
10 217 reviews
Woodstock, VT
08/21 – 08/23
$325/nighttotal: $650 (2 )
Cozy Log Cabin, Relaxing Retreat With 1pm Checkout
1 2
cabin , Woodstock
Cozy Cabin is a secluded, 2-bedroom cabin with a private deck and stunning sunset views of Mount Baldy, located between Woodstock Village (7.6 miles) and Killington Ski Resort (15 miles). The cabin has an excellent user, location, and cleanliness rating. Cozy Cabin accommodates up to four guests and features a kitchen with a fridge, freezer, and microwave oven, as well as a garden, fitness center, and air conditioning. The cabin also has amenities like a pool table, darts, lounge, gym, and dedicated office space with Wi-Fi for remote work.
10 2 reviews
Woodstock, VT
09/25 – 09/27
$517/nighttotal: $1034 (2 )
Birch Landing #1
3 2
apartment , Plymouth
Birch Landing #1, a Plymouth apartment rental, is located approximately 6.3 miles from Dorsey Park and within a 19-22 mile radius of attractions like Gifford Woods State Park, Pico Peak, and Killington Pico Adventure Center. This 2,130-square-foot vacation rental boasts three bedrooms, three bathrooms, and accommodates up to 15 guests, featuring amenities such as a swimming pool, tennis court, and free Wi-Fi, plus a fully equipped kitchen with a dishwasher.
10 1 review
Woodstock, VT
08/21 – 08/23
$680/nighttotal: $1360 (2 )
Pet-friendly 2br Getaway Near Killington & Woodstock
1 2
apartment , Bridgewater
This Bridgewater condo rental is ideally situated between Woodstock and Killington, offering easy access to Killington Resort and Pico Mountain, as well as the Union Arena Community Center and Red Wagon Toy Company. This two-bedroom, two-bathroom apartment sleeps six and features a fully equipped kitchen with a refrigerator, microwave, and dishwasher, plus air conditioning, a terrace, a garden, parking, and internet access; guests can enjoy nearby hiking, skiing, golfing, shopping, and dining.
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.
10 1 review
Woodstock, VT
09/02 – 09/08
$392/nighttotal: $2352 (6 )
Views, Ac, And Family Fun - Kingswood 12e
3 2
apartment , Hartford
This three-bedroom, three-bathroom condo is located in Quechee, Vermont, a five-minute drive from The Quechee Club and offering ski-in/ski-out access to Ski Quechee. The 3-bedroom, 2.5-bathroom rental sleeps seven guests, features a kitchen with a fridge, microwave, and dishwasher, a terrace, parking, and includes baby gear; nearby attractions include Woodstock.
8.8 3 reviews
Woodstock, VT
07/25 – 08/01
$483/nighttotal: $3381 (7 )
Peaceful Cavendish Retreat W/ Hot Tub & Fireplace!
3 2
apartment , Cavendish
This Cavendish vacation home, located within six miles of Camp Plymouth State Park and Echo Lake, and under nine miles from Okemo Mountain Resort, offers easy access to outdoor recreation. This 2,240-square-foot house features four bedrooms, three bathrooms, and accommodates eight guests, boasting a fully equipped kitchen, jacuzzi, and outdoor amenities including a terrace, garden, and barbecue grills.
Woodstock, VT
12/23 – 12/27
$469/nighttotal: $1876 (4 )
Cozy Quechee Retreat/walk To Village | Mill Run 4a
2 4
apartment , Hartford
This 2-bedroom, 1-bathroom condo in Quechee is situated in a rural mountain setting, a short walk from Simon Pearce Mill and 7 minutes from Route 4 Glassblowing Studio. This 580 sq ft accommodation accommodates up to 4 guests and features a full kitchen, Wi-Fi, on-site parking, and access to a communal swimming pool and garden, with proximity to outdoor activities and attractions like Vermont Institute of Natural Science and King Arthur Baking Company.
10 1 review
Woodstock, VT
07/25 – 08/01
$443/nighttotal: $3101 (7 )
Steps To Ski Hill, Game Room, Club | Kingswood 6f
4 2
apartment , Hartford
This Quechee condo offers direct ski hill access, just 150 yards away, and exclusive Quechee Club amenities in the Upper Valley region, approximately a 15-minute drive from Woodstock. This 1890 sq ft condominium features 4 bedrooms and 3 bathrooms, accommodating up to 8 guests with a game room, private balcony, and full kitchen, while providing ski-in/ski-out convenience and access to year-round Quechee Club activities.
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.
9.6 5 reviews
Woodstock, VT
12/23 – 12/27
$684/nighttotal: $2736 (4 )
Converted Carriage Barn - The Carriage House Unit2
2 4
apartment , Hartford
This Vermont cottage rental near Quechee and Woodstock offers easy access to attractions like Sugarbush Farm and the Quechee Gorge. The two-bedroom, two-bathroom house sleeps four, includes a full kitchen with microwave and fridge, a private garden, a spa, and parking; guests can enjoy the nearby Quechee River Loop trail and seasonal hot air balloon views.
Woodstock, VT
07/25 – 08/01
$2120/nighttotal: $14840 (7 )
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.
10 377 reviews
Woodstock, VT
12/23 – 12/27
$352/nighttotal: $1408 (4 )
Fat Sheep Farm & Cabins
1 4
farm , Hartland
Fat Sheep Farm & Cabins is located in Windsor, Vermont, just a short drive from Killington Peak, Mount Tom, and Dartmouth College. This farm is highly rated by travelers, with excellent scores for location, cleanliness, and overall experience. The farm offers comfortable cabins with private bathrooms and fully equipped kitchens. Enjoy breathtaking mountain views, relax on the sun terrace, or gather around the outdoor fireplace for a cozy evening.
This Bridgewater, Vermont vacation home boasts a waterfront location, 1.7 miles from the Long Trail Brewing Company and within 6 miles of the Union Arena Community Center and Five Elm Arches. The two-bedroom house, featuring a sofa bed, sleeps six, includes a fully equipped kitchen with appliances, a private balcony, and parking, and offers proximity to Killington Resort and the Ottaquechee River (within 9 miles).