Trailside Cottage, a pet-friendly self-catering property in Woodstock, Vermont, is located near the foothills of Mount Peg, a short walk from the Mt. Tom trailhead and 1.2km from the Woodstock Inn and village centre. This one-bedroom cottage sleeps four, boasting a king-size bed, sleeper sofa, full kitchen with stainless steel appliances, a workspace with monitor and keyboard, and an enclosed porch; nearby hiking trails and Mount Tom offer outdoor activities.
9.9 66 reviews
Woodstock, VT
25/07 – 01/08
SG$650/nighttotal: SG$4550 (7 )
Creekside: Contemporary Vt Retreat!
4 2
apartment , Woodstock
This four-bedroom property is located on a quiet private drive, just a few kilometres from the bustling centre of Woodstock, with its shops, galleries, and restaurants. The apartment has received excellent ratings for its location, cleanliness, and overall user experience. This spacious duplex can comfortably accommodate up to eight guests and features a well-equipped kitchen, a large garden with a patio and fire pit, and a mudroom with parking for three vehicles. Guests can enjoy the use of bikes, a fitness area, and a selection of amenities including a dishwasher, air conditioning, and a microwave oven.
9.4 64 reviews
Woodstock, VT
12/10 – 16/10
SG$297/nighttotal: SG$1188 (4 )
A Spacious 1 Bedroom Apartment
1 2
apartment , Pomfret
This one-bedroom flat is located in a private home in Pomfret, just a short three-minute drive from Woodstock Village and a 30-minute drive from Killington. The property has consistently received excellent ratings for cleanliness, location, and user experience. The flat has one bedroom and one bathroom, comfortably accommodating up to two guests. It comes equipped with modern amenities such as wireless internet, cable TV, a fully equipped kitchen, and on-site parking, making it ideal for a relaxing and convenient stay.
9.6 84 reviews
Woodstock, VT
02/09 – 08/09
SG$325/nighttotal: SG$1950 (6 )
Cozy Historic Hilltop Cottage With Mount Ascutney View
2 2
cottage , West Windsor
This charming cottage sits on a wooded hilltop just outside Brownsville, offering stunning views of Mt. Ascutney and a peaceful, secluded setting close to Woodstock and Windsor. It has received excellent reviews from previous guests, highlighting its unique character and comfortable amenities. The two-bedroom property, which can accommodate up to four guests, offers a fully equipped kitchen, a cosy living room with a fireplace, and a private terrace with a garden. Enjoy the peace and quiet of the surrounding nature, with easy access to hiking trails, local attractions, and the nearby Ascutney Mountain Resort.
9.9 51 reviews
Woodstock, VT
25/09 – 27/09
SG$748/nighttotal: SG$1496 (2 )
Cozy Vt Retreat Between Woodstock & Killington
1 2
apartment , Bridgewater
This Bridgewater apartment is conveniently located just off the main road, a short 10km drive from both Woodstock and Killington, offering easy access to the region’s attractions. It has received excellent ratings for location, cleanliness and user experience. The two-bedroom flat comfortably sleeps six guests and features a fully equipped kitchen, a living room with a 50-inch TV, and a shared outdoor space with Adirondack chairs and a fire pit. Amenities include high-speed Wi-Fi, linens, towels, toiletries, and laundry supplies, ensuring a comfortable stay.
10 118 reviews
Woodstock, VT
10/12 – 16/12
SG$490/nighttotal: SG$2940 (6 )
Falcon House: Vt Chalet W/sauna, Bike To Village
1 2
chalet , Woodstock
This modern chalet is situated on a 60-acre woodland just 5km from Woodstock village and 20km from Killington ski resort, offering a peaceful retreat close to local attractions. It has consistently received excellent ratings for location, cleanliness, and overall experience. The two-bedroom chalet comfortably accommodates up to five guests, featuring a master bedroom with a loft and a den with a double futon. Guests can enjoy a range of amenities, including a fully equipped kitchen, a private sauna, a hot tub, and access to hiking trails, bikes, snowshoes, and a snowmobile for exploring the surrounding area.
9.2 10 reviews
Woodstock, VT
30/08 – 06/09
SG$576/nighttotal: SG$4032 (7 )
Charming Ranch In The Woods - Woodstock Way
2 2
apartment , Woodstock
This 11-acre Woodstock farm, situated just over 1.6km from Woodstock Village Centre, offers easy access to local shops and restaurants. The self-catering property boasts two bedrooms, one bathroom, sleeps eight guests, and includes a gourmet kitchen with a Forno fridge and Zline range, plus a fireplace, enclosed porch, WiFi, smart TV, and detached garage with parking for three vehicles; nearby activities include a country club and golf course.
10 303 reviews
Woodstock, VT
02/09 – 08/09
SG$526/nighttotal: SG$3156 (6 )
The Loft, Stunning Views From A Timber Framed Barn
1 2
farm , Woodstock
This farmhouse is located just 3.5 miles from Woodstock Village and 3 miles from the Green Mountain Horse Association, offering a tranquil retreat on a quiet back road. It's highly rated for its location, cleanliness, and overall experience. The property can comfortably accommodate 5 guests in two bedrooms. Amenities include a fully equipped kitchen, outdoor recreational areas, and high-tech features like solar power and Wi-Fi, ensuring a comfortable and enjoyable stay.
9.9 95 reviews
Woodstock, VT
30/08 – 06/09
SG$533/nighttotal: SG$3731 (7 )
Elegant Village Apartment
2 2
apartment , Woodstock
This apartment is located in Woodstock, just a short walk from the village green and all amenities. It's situated in a peaceful setting, close to the shops, restaurants, and attractions of this charming village. The apartment consistently receives excellent ratings for location, cleanliness and user experience. The apartment has one bathroom and comfortably sleeps four guests, with a queen bed in one bedroom and a twin bed with trundle in the second. It comes equipped with a kitchen including a fridge, microwave oven, and dishwasher, as well as parking, internet access, and is family friendly.
10 62 reviews
Woodstock, VT
02/09 – 08/09
SG$352/nighttotal: SG$2112 (6 )
Green Mountain Retreat: The Skyland Duplex
2 2
farm , Bridgewater
This Bridgewater farm stay, a rustic-modern duplex apartment in a renovated barn, is situated in a rural area, its precise distance from nearby landmarks unspecified. The 50-acre property, boasting a spring-fed swimming pond, orchards, and trails ideal for cycling and hiking, offers two fully equipped kitchens, three bedrooms, two bathrooms, and sleeps 7-8 people.
9.7 6 reviews
Woodstock, VT
25/07 – 01/08
SG$669/nighttotal: SG$4683 (7 )
Historic, Walk To Town - South Woodstock Cottage
3 2
apartment , Woodstock
This beautifully restored 1807 farmhouse in South Woodstock, Vermont, is within walking distance of the General Store and Kedron Valley Inn, offering easy access to Woodstock's historic village centre. Sleeping up to six guests, this three-bedroom, three-bathroom property boasts an open-plan kitchen, paved patio, and access to the Inn's swimming pond; parking for three cars is available on-site.
This Woodstock, Vermont riverside apartment offers stunning Ottauquechee River and covered bridge views, a short walk (less than 2 km) from the village centre and 32 km from Killington Ski Resort. The 203 square metre property boasts three bedrooms, three bathrooms, sleeps six, and includes a kitchen with dishwasher, Wi-Fi, Smart TVs, fireplaces, a sauna, terrace, garden, parking, and keyless entry.
Best family friendly Woodstock, VT lodging
Among the 160 accommodations in Woodstock, VT, here are the 4 best for families
9.4 16 reviews
Woodstock, VT
12/10 – 16/10
SG$2399/nighttotal: SG$9596 (4 )
Luxury Estate 25 Gorgeous Acres Of Privacy Family Getawayswimming Pond
4 2
apartment , Woodstock
This family-friendly house is located in a rural area of Woodstock, just two miles from the Marsh-Billings-Rockefeller National Historical Park and Five Elm Arches. The house consistently receives excellent ratings for location, cleanliness, and user experience. The accommodation features four bedrooms and three bathrooms, spanning a spacious 372 square metres. Guests can enjoy a fully equipped kitchen, private spa tub, fireplace, game room, outdoor BBQ, and a tranquil garden.
10 60 reviews
Woodstock, VT
12/10 – 16/10
SG$749/nighttotal: SG$2996 (4 )
Woodstock Carriage House-280 Acres-views-gardens-skiing-farm-2.5 Miles From Town
2 2
apartment , Woodstock
This renovated carriage house, part of a 280-acre estate, is situated 3.2 kilometres from Woodstock town centre, near Killington, Pico, Okemo, and Suicide Six ski resorts. The 102-square-metre property sleeps four guests in two bedrooms and one bathroom, offering a kitchen with fridge and microwave, Wi-Fi, air conditioning, a garden, a spa, parking, and access to private hiking trails and fishing ponds on the estate.
9.9 151 reviews
Woodstock, VT
10/12 – 16/12
SG$679/nighttotal: SG$4074 (6 )
The Cottage On Westerdale Road
1 2
apartment , Woodstock
This charming cottage is just a short distance from the centre of Woodstock, placing you within easy reach of the town's restaurants, shops and attractions. The property has consistently received excellent ratings for its location, cleanliness and overall experience, ensuring a comfortable and enjoyable stay. This three-bedroom, two-bathroom home can comfortably accommodate up to six guests. Amenities include a fully equipped kitchen, air conditioning, a private garden and access to nearby fields, offering plenty of space for relaxation and outdoor activities.
9.6 109 reviews
Woodstock, VT
25/09 – 27/09
SG$616/nighttotal: SG$1232 (2 )
Woodstock Village Carriage House
1 2
cottage , Woodstock
This charming cottage is located on a peaceful cul-de-sac in Woodstock, just a short walk from the village centre and next to the Marsh-Billings-Rockefeller National Park and Mansion. It has received excellent user ratings, making it a popular choice for travellers seeking a relaxing and convenient stay. This one-bedroom property spans 84 square metres and comfortably accommodates up to four guests. It offers a fully equipped kitchen, a private garden, a spa, a tennis court, and internet access, ensuring a comfortable and enjoyable stay.
Best Woodstock, VT lodgings with a pool
Among the 160 accommodations in Woodstock, VT, here are the 4 best ones with a pool
10 2 reviews
Woodstock, VT
02/09 – 08/09
SG$539/nighttotal: SG$3234 (6 )
Highland Golf Course Getaway - Fairway Village 5b
3 2
apartment , Hartford
This three-bedroom condominium in Quechee, Vermont, offers direct access to the fairways of Highland Golf Course, just a short walk from the clubhouse and 24 kilometres from Woodstock. This property provides accommodation for up to seven guests, featuring two bathrooms, a fully equipped kitchen, air conditioning, a swimming pool, a terrace, and parking, with exclusive access to The Quechee Club's extensive amenities including tennis courts and a beach at Lake Pinneo.
Woodstock, VT
30/08 – 06/09
SG$551/nighttotal: SG$3857 (7 )
Quechee Club Access: Pool, Golf + Fireplace
3 2
apartment , Hartford
This rural mountain holiday home in Quechee is situated 3 kilometres from Simon Pearce Mill and 5 kilometres from Quechee State Park. This 124 square metre holiday home accommodates up to 8 guests across 3 bedrooms and 2 bathrooms, featuring air conditioning, a balcony, a fireplace, and a well-equipped kitchen, with access to a communal swimming pool, garden, and barbecue facilities.
9.4 676 reviews
Woodstock, VT
12/10 – 16/10
SG$1383/nighttotal: SG$5532 (4 )
Woodstock Inn & Resort
1 2
resort , Woodstock
The Woodstock Inn & Resort is located in the heart of Woodstock, Vermont, just a short drive from Marsh-Billings-Rockefeller National Historical Park and the Billings Farm Museum, offering easy access to attractions and the charming village atmosphere. The hotel enjoys excellent ratings for location, cleanliness, and overall experience. The resort features spacious rooms with modern amenities, including flat-screen TVs and refrigerators. Guests can enjoy a range of facilities, such as a full-service spa, a fitness centre, a tennis court, and a swimming pool, as well as dining options like the Red Rooster restaurant and the Main Dining Room.
Woodstock, VT
12/10 – 16/10
SG$493/nighttotal: SG$1972 (4 )
Walk To Lake Pinneo, Resort - Fairway Village 3c
3 2
apartment , Hartford
This non-smoking condominium in Quechee is a short 4-minute drive from Simon Pearce Mill and Quechee State Park, offering convenient access to fishing activities. This 101 square meter residence accommodates up to six guests with three bedrooms and two bathrooms, featuring a communal swimming pool, garden, private balcony, fire pit, Wi-Fi, air conditioning, and a fully equipped kitchen.
Frequently asked questions about accommodations in Woodstock, VT
What are the must-see sites in or near Woodstock, VT?
Woodstock is packed with charm! You definitely want to visit the quaint shops on the Woodstock Green, and the Marsh-Billings-Rockefeller National Historical Park is a must-see. If you're looking for a bit of a drive, the Quechee Gorge is a stunning natural wonder just a short distance away.
What are the best accommodations in Woodstock, VT?
The easiest way to get to Woodstock is by car, as it's about a 2-hour drive from both Boston and Albany. You can also fly into the Lebanon Municipal Airport (LEB) and rent a car, or take Amtrak to the White River Junction station, which is about a 20-minute drive from Woodstock.
What are the best accommodations with a pool in Woodstock, VT?
What outdoor activities can visitors enjoy in and around Woodstock, VT?
Woodstock is a haven for outdoor enthusiasts! You can hike the trails in the Green Mountain National Forest, go kayaking or canoeing on the Ottauquechee River, or hit the slopes at Suicide Six ski area in the winter. And don't forget to check out the beautiful Woodstock Farmers' Market in the summer.
What are the best accommodations with a jacuzzi in Woodstock, VT?
When is the ideal time to plan a trip to Woodstock, VT?
The best time to visit Woodstock depends on what you're looking for. Summer is great for hiking, biking, and enjoying the farmers' market, while autumn brings beautiful foliage and crisp air. Winter is perfect for skiing and snowboarding, and spring offers a chance to see the area come alive with wildflowers.
What are the best accommodations for families and kids in Woodstock, VT?
What are the best walking or cycling routes in Woodstock, VT?
For a leisurely stroll, try the Woodstock Green Loop, which takes you past the historic buildings and shops. For a longer bike ride, the Valley Rail Trail is a scenic paved path that follows the old railroad line. If you're feeling adventurous, you can tackle the challenging climb up to the summit of Mount Tom.
What are the best pet friendly accommodations in Woodstock, VT?
What nearby towns or cities can be explored from Woodstock, VT?
Just a short drive from Woodstock, you can visit the charming towns of Quechee, with its gorge and historic mill, and the vibrant city of Hanover, home to Dartmouth College. You can also explore the charming village of White River Junction, with its eclectic shops and restaurants.
What are the best accommodations with parking in Woodstock, VT?
What amenities can travelers expect from accommodations in Woodstock, VT?
Woodstock offers a range of accommodation options, from cozy bed and breakfasts to upscale hotels and resorts. Most accommodations offer amenities like Wi-Fi, breakfast, and parking. Many also have outdoor spaces, such as patios or gardens, where you can relax and enjoy the scenery.
Destinations nearby
Best Woodstock, VT accommodations with a garden
9.8 46 reviews
Woodstock, VT
02/09 – 08/09
SG$499/nighttotal: SG$2994 (6 )
Grange Hall, South Woodstock Historic Home
1 2
apartment , Woodstock
This charming home, located in the picturesque village of South Woodstock, is just a short distance from the Kedron Valley Inn, the Kedron Brook, and the South Woodstock Store. The apartment is highly rated for its excellent location, cleanliness, and user experience. The three-bedroom flat comfortably sleeps six guests and features an open-plan living, dining, and kitchen area. Amenities include a fully equipped kitchen, a patio with a grill, a garden, and parking, making it the perfect retreat for families or groups of friends.
Woodstock, VT
12/10 – 16/10
SG$690/nighttotal: SG$2760 (4 )
Sleep Woodstock - Deluxe Suite
2 2
apartment , Woodstock
This newly renovated 1200 sq ft Deluxe Suite is located within the Sleep Woodstock Motel, 6 kilometres from Woodstock village and conveniently situated near Killington Ski Resort and Quechee Gorge. This two-bedroom, two-bathroom apartment accommodates up to eight guests and features a fully equipped kitchen, a private deck with a gas grill, and access to an on-site family room with complimentary refreshments, offering a solar-powered and sustainable stay.
9.9 54 reviews
Woodstock, VT
25/09 – 27/09
SG$586/nighttotal: SG$1172 (2 )
Curtis Hollow School House
1 2
apartment , Woodstock
This renovated 1800s schoolhouse, near Woodstock, Vermont, is located 1.6km from Long Trail Brewery, 16km from Quechee Gorge, Killington, and Pico mountains, and a short walk from the Vast Trail System. This three-bedroom, one-bathroom property sleeps twelve, offering a finished basement, kitchen with dishwasher, air conditioning, garden, parking, and easy key access; ideal for families enjoying hiking, fishing, and exploring Vermont's natural beauty.
9.9 110 reviews
Woodstock, VT
25/09 – 27/09
SG$956/nighttotal: SG$1912 (2 )
Classic, Cozy Farmhouse In The 4 Season Playground Of Vt's Prettiest Town!
4 2
farm , Woodstock
This charming farmhouse is located in West Woodstock, just 5km from the Union Arena Community Center, the Ottaquechee River, and Five Elm Arches, offering a peaceful rural setting. It has received excellent ratings for location, cleanliness, and overall experience. This 4-bedroom, 2-bathroom property can accommodate up to 8 guests. The farmhouse features a fully equipped kitchen, a terrace, a garden, a fitness center, air conditioning, and parking, as well as internet access.
Best Woodstock, VT accommodations with a kitchen
9.1 30 reviews
Woodstock, VT
25/07 – 01/08
SG$407/nighttotal: SG$2849 (7 )
Kingswood Vista 10f
3 2
apartment , Hartford
Kingswood Vista 10F is a 3-bedroom apartment located in White River Junction, Vermont, 48 kilometres from Killington Peak, 11 kilometres from Mount Tom, 26 kilometres from Dartmouth College, and 45 kilometres from Gifford Woods State Park. This quiet and relaxing location offers a peaceful escape from the city bustle, with easy access to both natural beauty and cultural attractions. The apartment is rated excellent for cleanliness, location, and user experience, and offers 156 square metres of space, accommodating up to 8 guests. This well-equipped apartment features a kitchen, a private bathroom with a bath or shower, free toiletries, free WiFi, and a garden, allowing guests to enjoy a comfortable and convenient stay.
9.9 95 reviews
Woodstock, VT
10/12 – 16/12
SG$557/nighttotal: SG$3342 (6 )
Riverside Getaway! Minutes To Downtown Woodstock
1 2
apartment , Woodstock
This three-bedroom, two-bathroom apartment is situated near Woodstock, Vermont, a short drive from both Woodstock town centre and Killington Mountain. The riverside property, offering a fenced garden with a fire pit and barbecue, sleeps seven guests and includes a fully equipped kitchen, laundry facilities, and access to Wi-Fi.
9.9 88 reviews
Woodstock, VT
25/09 – 27/09
SG$327/nighttotal: SG$654 (2 )
Nana's House
1 2
apartment , Bridgewater
This Bridgewater apartment is situated just 10 kilometres from Woodstock, 30 kilometres from Ludlow, and 20 kilometres from Killington, offering easy access to popular attractions and outdoor activities. The property has received excellent ratings for cleanliness, location, and user experience. This self-contained flat is suitable for up to six guests and is completely independent with its own entrance and parking. Amenities include a fully equipped kitchen, air conditioning, internet access, and a pet-friendly policy for dogs under 30 pounds. Guests can enjoy nearby outdoor activities like hiking, biking, and skiing, as well as local attractions like breweries, farms, and museums.
9.2 42 reviews
Woodstock, VT
12/10 – 16/10
SG$438/nighttotal: SG$1752 (4 )
Golf Views! & Patio Dining - Windsor Village 3a
2 2
apartment , Hartford
This two-bedroom apartment is located in Quechee, Vermont, a short drive from the towns of Quechee and Woodstock, as well as Lake Pinneo, offering a peaceful escape from the hustle and bustle of Hartford. The property enjoys excellent user, location, and cleanliness ratings, ensuring a comfortable and enjoyable stay. The apartment spans 103 square metres and comfortably accommodates four guests. It boasts a range of amenities including a fully equipped kitchen, a private terrace, a shared swimming pool, and access to a gym, providing everything you need for a relaxing and enjoyable stay.