Best Holiday rentals and Airbnb offers in Woodstock, VT
9.4 49 reviews
Woodstock, VT
10/12 – 16/12
SG$320/nightTotal: SG$1920 (6 )
Saltbox 12f
2 2
house , Hartford
Saltbox 12F, a two-bedroom house in White River Junction, Vermont, is conveniently located 49.9 kilometres from Killington Peak, 14.5 kilometres from Mount Tom, and 24.1 kilometres from Dartmouth College, offering easy access to Vermont's renowned ski areas and outdoor recreation. This 122-square-metre property features two bathrooms, a fully equipped kitchen with modern appliances, a terrace, a garden, a spa, a fitness centre, parking, and accommodates up to four guests, perfect for those seeking a comfortable base for exploring the White River Junction area.
9.5 6 reviews
Woodstock, VT
02/09 – 08/09
SG$283/nightTotal: SG$1698 (6 )
Steps To Ski Trail Fireplace - Kingswood 1b
3 2
house , Hartford
This three-bedroom house in Quechee, Vermont, is ideally located 49km from Killington Ski Resort and 13km from Mount Tom, offering easy access to outdoor activities near Hartford. The 97 square metre property boasts a swimming pool, garden, free Wi-Fi, and parking, comfortably accommodating up to 14 guests with three bathrooms and a fully equipped kitchen.
9.8 24 reviews
Woodstock, VT
14/08 – 15/08
SG$864/nightfor 1 night
Ledges 19 At Hawk Mountain
3 2
apartment , Plymouth
Ledges 19 at Hawk Mountain is a Plymouth, Vermont apartment, conveniently located approximately 29km from Pico Peak ski resort and within easy reach of Gifford Woods State Park (27km) and Dorsey Park (16km). This 167 square metre self-catering property boasts three bedrooms, two bathrooms, a fully equipped kitchen with dishwasher, private terrace, garden, spa, parking, and free Wi-Fi; ideal for families or groups of up to six, with access to nearby skiing.
9.9 23 reviews
Woodstock, VT
02/09 – 08/09
SG$628/nightTotal: SG$3768 (6 )
Charming Cottage In S Woodstock
3 2
apartment , Woodstock
This charming 3-bedroom cottage is situated in South Woodstock, a picturesque village in the Green Mountains, just a short distance from the Green Mountain Horse Association. The surrounding area offers stunning views and a tranquil atmosphere, perfect for a relaxing getaway. The cottage is ideal for families or groups of up to four guests. It features a cosy kitchen, comfortable living spaces, and a private bathroom. Guests can enjoy a range of on-site activities, including hiking, swimming, tennis, and a games room with ping pong, darts, and giant Jenga.
This Woodstock, Vermont apartment enjoys a riverside location two blocks from the historic downtown area, offering easy access to the Woodstock Inn and the Rockefeller estate. Sleeping six, the three-bedroom, two-bathroom property features a sauna, charcoal grill, Wi-Fi, and parking for two cars, plus access to nearby Green Mountain recreational trails and championship golf courses within 24 kilometres.
Woodstock, VT
21/08 – 23/08
SG$3058/nightTotal: SG$6116 (2 )
Casita Alta \Nluxury House With Heated Pool In Woodstock, Vt
3 2
apartment , Woodstock
This private, ultra-luxury flat is located just outside Woodstock village, offering a 500-meter walk to local shops and restaurants, with convenient access to attractions such as Quechee Gorge Village and King Arthur Baking Company. This 3-bedroom, 3-bathroom residence accommodates up to 6 guests and features a kitchen with a fridge, microwave, and dishwasher, air conditioning, a swimming pool, concierge service, and parking, making it an ideal retreat for those seeking comfort and ample space.
9.4 16 reviews
Woodstock, VT
25/09 – 27/09
SG$2775/nightTotal: SG$5550 (2 )
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
10/12 – 16/12
SG$572/nightTotal: SG$3432 (6 )
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.
10 57 reviews
Woodstock, VT
02/09 – 08/09
SG$385/nightTotal: SG$2310 (6 )
Nana's House
3 2
apartment , Bridgewater
This Bridgewater apartment, situated in a rural riverside location 16km from Woodstock, Vermont, offers easy access to Billings Farm & Museum, Suicide Six ski area, and Killington ski resort. The 139 square metre property sleeps six, boasting three bedrooms, one bathroom, a fully equipped kitchen (fridge, microwave, dishwasher), air conditioning, parking, and excellent guest reviews; nearby attractions include the Long Trail and Harpoon breweries, plus abundant opportunities for hiking, skiing, and other outdoor pursuits.
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.
8.5 14 reviews
Woodstock, VT
02/09 – 08/09
SG$554/nightTotal: SG$3324 (6 )
Walk To The Lakes
5 2
house , Ludlow
This five-bedroom Ludlow house, perfect for large groups, is situated 6km from Dorsey Park and within a 32-50km radius of Killington, Pico Peak, and Stratton Mountain ski resorts. The 189 square metre property boasts a spacious layout, two bathrooms, a fully equipped kitchen including a dishwasher, free Wi-Fi, a fireplace, and parking, making it ideal for self-catering ski holidays.
9.9 38 reviews
Woodstock, VT
10/12 – 16/12
SG$342/nightTotal: SG$2052 (6 )
Cozy, Clean Studio With Picturesque Vermont Views!
1 2
house , Pomfret
This one-bedroom loft is situated in Pomfret, Vermont, just 3.2 kilometres from Woodstock Village and 1.6 kilometres from the Saskadena Six ski resort. The self-catering property offers a fully equipped kitchenette, a modern bathroom, and parking facilities, making it ideal for couples or solo travellers seeking a peaceful retreat in the scenic Vermont mountains.
Best family friendly Woodstock, VT holiday rentals
Among the 113 accommodations in Woodstock, VT, here are the 4 best family friendly rentals
10 66 reviews
Woodstock, VT
02/09 – 08/09
SG$394/nightTotal: SG$2364 (6 )
Cottage In Barnard
1 2
apartment , Barnard
This charming lakeside property is situated just 1.2 miles from Silver Lake State Park, offering a tranquil escape in the heart of Barnard, within easy reach of other natural attractions. It has consistently received excellent ratings for location, cleanliness, and user experience, ensuring a comfortable and enjoyable stay. The cottage provides one bedroom and two bathrooms, comfortably accommodating up to four guests. Enjoy modern amenities such as free Wi-Fi, a Smart TV, and a fully equipped kitchen, along with a private yard, fireplace, and washer and dryer for added convenience.
Woodstock, VT
25/09 – 27/09
SG$1038/nightTotal: SG$2076 (2 )
Ski Home W/ Hot Tub Near Killington & Woodstock
1 2
apartment , Bridgewater
This rustic farmhouse in Bridgewater Corners, a 13-20 minute drive from Killington Mountain and a 15 minute drive from Woodstock and Quechee, offers a dog-friendly stay with a shared garden featuring a hot tub and fire pit. This apartment sleeps six guests and includes a fully equipped kitchen, air conditioning, a Jacuzzi, a terrace, and parking, with a check-out time of 10:00 AM.
10 99 reviews
Woodstock, VT
25/07 – 01/08
SG$468/nightTotal: SG$3276 (7 )
Breathtaking Riverfront Retreat W/mountain Views
2 2
apartment , Bridgewater
This Vermont carriage house, a unique historic property in Bridgewater, is situated 16km from Woodstock and 24km from Killington ski resort. The two-bedroom, two-bathroom property sleeps six guests and features a fully equipped kitchen, dining area, patio with fire pit and grill, high-speed Wi-Fi, and a washer/dryer; pets are welcome (fee applies).
Woodstock, VT
02/09 – 08/09
SG$324/nightTotal: SG$1944 (6 )
Villa ∙ 2 Bedrooms ∙ 6 Guests
2 2
house , West Windsor
This West Windsor holiday villa, located within the Holiday Inn Club Vacations Mount Ascutney Resort, offers easy access to Mount Ascutney State Park and is a short drive from the towns of Queechee and Woodstock. The two-bedroom, two-bathroom property sleeps six guests and boasts a fully equipped kitchen, swimming pool, fitness centre, and panoramic views of Mount Ascutney State Park; nearby activities include hiking trails and winter sports at Mount Sunapee and Killington.
Best Woodstock, VT holiday rentals with parking
9.2 42 reviews
Woodstock, VT
10/12 – 16/12
SG$327/nightTotal: SG$1962 (6 )
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.
10 215 reviews
Woodstock, VT
25/07 – 01/08
SG$376/nightTotal: SG$2632 (7 )
Cozy Log Cabin, Relaxing Retreat With 1pm Checkout
1 2
cabin , Woodstock
This charming log cabin is situated just 7.6 kilometres from Woodstock village and 15 kilometres from Killington ski resort, offering a tranquil escape in the heart of the Vermont countryside. It has consistently received excellent ratings for its cleanliness, location, and overall guest experience. The cabin comfortably accommodates up to four guests in two bedrooms and one bathroom. It boasts a well-equipped kitchen, a cosy living space, a dedicated rec room with a pool table, darts, and a gym, and a private garden with a brook, providing ample opportunities for relaxation and entertainment.
9.8 70 reviews
Woodstock, VT
02/09 – 08/09
SG$389/nightTotal: SG$2334 (6 )
Custom-built Tiny House On Forested Lot Near Quechee
2 2
apartment , Hartland
This one-bedroom house is located near Hartland, Vermont, within a 5km radius of the Vermont Institute of Natural Science, Simon Pearce Mill, and Route 4 Glassblowing Studio, making it ideal for exploring the area's attractions. The property has received excellent user ratings, indicating a high level of satisfaction from previous guests. The 30 square metre house can accommodate up to four guests and features a fully equipped kitchen, a relaxing spa tub, a peaceful garden, and a patio for outdoor dining. Enjoy the convenience of free Wi-Fi, a washer and dryer, and a sofa bed for added comfort.
9.1 25 reviews
Woodstock, VT
02/09 – 08/09
SG$566/nightTotal: SG$3396 (6 )
200ac, Views! 10min To Town - Scenic Ridge Retreat
4 2
apartment , Pomfret
This four-bedroom lodge is situated in Woodstock, Vermont, just a short distance from the Appalachian Trail and within easy reach of both Okemo Mountain Resort and Killington Ski Resort. The property boasts a fully equipped kitchen, three bathrooms, and a spacious living area with a wood-burning fireplace, comfortably accommodating up to eight guests.
Frequently asked questions about holiday rentals in Woodstock, VT
What are some interesting places to visit in or near Woodstock, VT?
Woodstock is a charming town with plenty to see. The Marsh-Billings-Rockefeller National Historical Park showcases the history of the region, while the Vermont Institute of Natural Science has fascinating exhibits. For a scenic drive, take Route 100 north to the Quechee Gorge, a dramatic natural wonder.
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 lovely spot for a stroll, and the nearby Ottauquechee River Trail offers a scenic bike ride. For a longer cycle, try the 100-mile Vermont Country Roads Scenic Byway, passing through charming towns and rolling hills.
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 paradise for outdoor enthusiasts. You can go hiking in the Green Mountain National Forest, skiing at Suicide Six, or fishing in the Ottauquechee River. In the summer, there's also kayaking, swimming, and golfing.
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 range of amenities, including fully equipped kitchens, comfortable living spaces, and laundry facilities. Many also have fireplaces, decks, and hot tubs, perfect for relaxing after a day of exploring.
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 preferences. The peak season is from June to October, when the weather is warm and the foliage is vibrant. For a quieter experience, consider visiting in the shoulder seasons, spring or autumn, when the crowds are smaller.
What are the best rentals or Airbnbs with a jacuzzi in Woodstock, VT?
What are the local dishes in Woodstock, VT region?
Vermont is known for its maple syrup, so you'll find it in many local dishes. Try the maple-glazed salmon at the Woodstock Inn & Resort, or the maple-pecan pancakes at the Red Rooster. The region also has a strong tradition of dairy farming, so you'll find delicious cheese and ice cream.
Destinations nearby
Best Woodstock, VT holiday rentals with a balcony
10 7 reviews
Woodstock, VT
25/07 – 01/08
SG$1507/nightTotal: SG$10549 (7 )
Country House Minutes From Killington And Okemo
4 2
farm , Plymouth
This chalet is situated in Vermont, just a short drive from popular ski resorts like Killington and Okemo, as well as the charming town of Woodstock. It has consistently received excellent ratings for its location, cleanliness, and overall experience. This spacious five-bedroom property spans over 500 square metres and offers ample room for families and groups. It boasts a well-equipped kitchen, multiple entertainment areas, a hot tub, and a fitness centre, ensuring a comfortable and enjoyable stay for all.
9.4 8 reviews
Woodstock, VT
02/09 – 08/09
SG$484/nightTotal: SG$2904 (6 )
Golf Views, Walk To Club - Lakeland Village 4b
3 2
apartment , Hartford
This Quechee Lakes Resort condo, a three-bedroom, two-bathroom apartment sleeping six, is located in a rural mountain area of Quechee, Vermont, near Quechee State Park and offering easy access to Green Mountain National Forest. The self-catering property boasts a fully equipped kitchen, including a fridge, microwave, and dishwasher, plus free Wi-Fi, cable TV, and access to resort amenities such as pools and golf courses.
8.8 3 reviews
Woodstock, VT
25/07 – 01/08
SG$621/nightTotal: SG$4347 (7 )
Peaceful Cavendish Retreat W/ Hot Tub & Fireplace!
3 2
apartment , Cavendish
This Cavendish holiday home, located within 9.6km of Camp Plymouth State Park and Echo Lake, and under 14.5km from Okemo Mountain Resort, offers easy access to Cavendish's natural attractions. This 208 square metre property sleeps eight guests and boasts four bedrooms, three bathrooms, a fully equipped kitchen with dishwasher, a jacuzzi, terrace, garden, parking, and internet access.
9.8 7 reviews
Woodstock, VT
25/09 – 27/09
SG$1811/nightTotal: SG$3622 (2 )
Premier Woodstock Village Riverfront Home
3 2
apartment , Woodstock
This private, self-contained three-bedroom, two-and-a-half-bathroom wing of a historic estate offers a peaceful riverfront setting in Woodstock, just a five-minute walk from the village's shops, restaurants, and the Woodstock Inn, with the Billings Farm and Museum and Marsh-Billings-Rockefeller National Historical Park located directly across the street. This family-friendly accommodation, ideal for six guests, features air conditioning, Wi-Fi, a kitchen equipped with a fridge, microwave, and dishwasher, a terrace, garden with a fire pit, and parking, providing convenient access to outdoor activities and winter sports, with the Saskadena Six ski area 7 kilometres away and Killington Skyeship Base Lodge a 20-kilometre drive.
Best pet friendly Woodstock, VT holiday rentals
Among the 113 accommodations in Woodstock, VT, here are the 4 best pet friendly rentals
9.9 110 reviews
Woodstock, VT
25/09 – 27/09
SG$938/nightTotal: SG$1876 (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.
Woodstock, VT
25/07 – 01/08
SG$269/nightTotal: SG$1883 (7 )
Rustic Vermont Carraige House
1 2
apartment , Bridgewater
This historic carriage house, offering 18th-century character and modern comfort, is situated in a picturesque setting less than 10 minutes from downtown Woodstock and a 10-minute drive to Killington Skyeship, placing you conveniently for both town amenities and outdoor adventures. This two-bedroom, two-bathroom flat accommodates up to four guests and features a kitchen with a fridge and microwave, air conditioning, and is pet-friendly, with internet access provided.
Woodstock, VT
02/09 – 08/09
SG$595/nightTotal: SG$3570 (6 )
High-end Loft - Cozy Firepit, Hiking And Biking Trails, Near Okemo
2 2
cabin , West Windsor
This newly built Ascutney Lofts lodge is located in Brownsville, a short stroll from local amenities and a 20-minute drive from the Upper Valley and Woodstock. This modern, serene 48 square meter, 2-bedroom, 1-bathroom cabin accommodates up to four guests and features a contemporary open layout, a kitchen with a fridge, microwave oven, and dishwasher, air conditioning, a terrace, garden, parking, a grill, and a Solo fire pit, with exclusive guest access to the entire house, patio, and laundry area.
10 10 reviews
Woodstock, VT
25/07 – 01/08
SG$304/nightTotal: SG$2128 (7 )
The Owl’s Nest
1 2
apartment , Bridgewater
This studio apartment in Bridgewater offers a secluded woodland setting in Central Vermont, providing a peaceful base for exploring the region's natural beauty. This second-floor accommodation, accessible via steep stairs, accommodates two guests with one bedroom and one bathroom, featuring keyless entry, internet, air conditioning, a kitchen, and parking, ideal for weekend getaways or longer stays.