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Woodstock, VT vacation rentals
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Best Vacation rentals and Airbnb offers in Woodstock, VT

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.

Historic Riverfront House: 5 Bedrooms 3.5 Baths On 5 Acres - Woodstock, VT
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.
Private & Affordable Charming Custom Ranch In S. Woodstock. Wifi And Ac. - Woodstock, VT
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.
Community Pool, Cozy Fireplace - Coach Road 7a - Woodstock, VT
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.
Vermont Get-away End Unit Townhouse Nestled In The Trees - Woodstock, VT
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

Historic, Walk To Town - South Woodstock Cottage - Woodstock, VT
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.
200ac, Views! 10min To Town - Scenic Ridge Retreat - Woodstock, VT
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.
Golf Views! & Patio Dining - Windsor Village 3a - Woodstock, VT
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.
Cozy Fireplace, Pets, Club Access! - Saltbox 9a - Woodstock, VT
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

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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.

Woodstock Inn & Resort - Woodstock, VT
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.
Newton Village 1a - Woodstock, VT
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.
Premier Woodstock Village Riverfront Home - Woodstock, VT
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.
Ski Oasis W/ Hot Tub Near Killington & Woodstock - Woodstock, VT
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.

Charming Ranch In The Woods - Woodstock Way - Woodstock, VT
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.
Highland Golf, Walk To Club - Lakeland Village 2d - Woodstock, VT
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.
Great Pond Retreat - Woodstock, VT
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.
Lux Chalet 4 Bd Fireplace Hottub Ac Pet Friendly - Woodstock, VT
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.
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