
House vacation rentals in Woodstock
Find and book unique houses on Airbnb
Quick stats about house rentals in Woodstock

Total vacation rentals
Explore 80 vacation rentals in Woodstock

Nightly prices starting at
Woodstock vacation rentals start at ﺩ.ﺇ 441 per night before taxes and fees

Verified guest reviews
Over 1,960 verified reviews to help you choose

Family-friendly vacation rentals
70 properties offer extra space & kid-friendly amenities

Pet-friendly vacation rentals
Find 40 rentals that welcome pets

Rentals with dedicated workspaces
40 properties have a dedicated workspace

Wi-Fi availability
80 of Woodstock vacation rentals include wi-fi access

Popular amenities for guests
Guests love Kitchen, Wifi, and Pool across Woodstock rentals

4.9 Average rating
Woodstock stays are highly rated by guests—averaging 4.9 out of 5!
Top-rated house rentals in Woodstock
Guests agree: these houses are highly rated for location, cleanliness, and more.

Cape Cod Home in Woodstock, Pet-Friendly & Wooded
Welcome to this charming 4-bedroom Cape Cod-style retreat in Woodstock, Vermont, a picture-perfect New England getaway set on a wooded hillside lot. With original wide-plank hardwood floors, a fully equipped chef's kitchen, and a spacious back deck with a 6-burner propane grill, this home offers the perfect blend of rustic character and modern comfort. Explore the covered bridges and artisan shops of Woodstock Village, or simply unwind in the peaceful garden setting. Please SEE: Other Things to

Custom cabin on Mt Ascutney, sweeping Hill Views
Combining sweeping views of distant hills with complete privacy and wraparound porches on two sides, the Red House is a custom cabin built for couples and smaller families. Surrounded by working farms and within easy reach of trailheads to hike or bike Mt Ascutney, or to visit Woodstock, Hanover, Ludlow and the Upper Valley, the Red House sits among some of the best restaurants in Vermont and awaits the discerning traveler who has earned the right to do absolutely nothing and experience it all.

Breathtaking Riverfront Retreat w/Mountain Views
Thoughtfully designed to elevate every moment of your Vermont getaway, our home offers a comfortable & uniquely historic experience, along with panoramic views of the beautiful Ottauquechee River. Perfectly nestled between the vibrant towns of Woodstock and Killington, guests have incredible hiking, skiing, golfing, shopping, leaf peeping, delicious dining, and so much more right at your finger tips. Wonderful for families, couples, or small groups looking to explore all that VT has to offer!

Cozy Bow House Perched in Trees w/ Hot Tub & View
The cozy Bow House is perched up above a lovely valley and boasts large south facing windows, a unique bowed loft and a warm, inviting space to relax. Up a charming dirt road past Brushwood & Fairlee Forests with hiking, biking and ATV trails nearby. Lake Fairlee is a scenic 10 min drive; 15 min to Lake Morey & I-91 and 30 min to Dartmouth College. Enjoy the glow of the rising sun and beautiful views above the fog, unwind in the hot tub surrounded by the magical woods and wildlife of Vermont.

Private Oasis Under 10 Mins from Woodstock
Less than ten minutes from Woodstock Village, this bright, 3 bedroom home is nestled on ten private acres with spectacular views of Pomfret's rolling hills. The open living area features a large picture window, cozy fireplace and fully equipped kitchen. Relax on the spacious deck with dramatic views of Pomfret’s hills. Please read reviews to see what our guests love about staying here: - Beautiful location - Squeaky clean - Fully equipped kitchen - Comfortable beds - Thoughtful amenities

Charming, Cozy Cape
Enjoy the warmth, style, and privacy of this lovely home, located on a hillside above the picturesque White River. Just minutes from restaurants, shopping, cocktail bars, and galleries in downtown White River Junction, and a 10-minute drive to Hanover, NH, and the Dartmouth College campus. Set on an acre of open land with beautiful views and sunsets from the back deck. Central heating to keep you cozy during the fall and winter months. Perfect for couples and families ... and pet-friendly!

Relaxing Countryside Oasis!
Welcome to our cozy 2BR/1BA cabin, ideal for 6 guests. Relax by the indoor fireplace or outside by the fire pit and hot tub. Listen to the stream from the patio. Fully equipped kitchen and washer/dryer for convenience. Only 10 mins from Dartmouth College and 5 mins to downtown Norwich, VT. Multiple ski resorts within 30-minutes. Perfect for a serene getaway, this cabin offers a blend of comfort, nature, and convenience, ensuring a memorable stay for family, friends, or a romantic retreat!

Birdie's Nest Guesthouse
Welcome to our newly renovated studio apartment, nestled among the trees in the serene hills of West Windsor, Vermont. Elevated on the second floor, this separate structure offers a tranquil escape with breathtaking views of Mount Ascutney and our own private pond. Immerse yourself in the comforts of this thoughtfully designed studio apartment, surrounded by the natural beauty of the Vermont landscape. Every detail has been curated to ensure your utmost comfort and enjoyment.

Meadow View. 35 acres outside your door!
Meadow View - pet friendly home away from home. 35 acres- including 2 trout ponds and 25 acres of wooded trails (perfect for hiking, cross country skiing/snow shoeing!). Featuring a newly remodeled kitchen and bathroom. Minutes from Mt. Ascutney (trails galore, rope tow in the winter). The unit is perfect spot for couples craving time in rural Vermont or for families/outdoor enthusiasts who want to go mountain biking, skiing, hiking. (Okemo 30 min Killington 45 min)

The Guest House at Sky Hollow
This quiet 120 acre hilltop house on an 1800's farm turned homestead offers high speed internet, hiking and mountain bike trails, a swimming pond, X-C ski, and sauna. Only miles from renowned New England ski resorts, and featuring 2 bedrooms, 1.5 baths, a full kitchen, an open floor plan, and a small backyard right beside a brook, the guest house is quiet and private, the perfect retreat for a cozy weekend with outdoor adventures and creature comforts!

Beautiful Historic 1909 Library with a Fireplace
An intimate experience with history! Quechee’s first Library (1909) original hardwood floors and shelves with treasures. Romantic Gas Fireplace, Claw foot tub (with NO shower) in the bedroom, Living area, Kitchenette, AC, WIFI, Comfy Queen bed, Window Seat, unique art, many amenities. Across the street, Covered Bridge, Waterfall, Simon Pearce Restaurant w/ Glass Blowing. Parker House with WhistlePig whiskey tasting and more. Hope you love it!

19th Century Bohemian Barn House
This 19th century barn-house has a welcoming, cosy, bright vibe and a funky bohemian flair. It's artsy, comfortable with touch of sophistication. Lots of sitting areas for reading, conversation and chilling out. Great view and backyard stream; perfect for nature lovers. Decks and wonderful outside space for a cook out or enjoying the brook & gardens on a nice day.
Popular amenities for Woodstock house rentals
House rentals with a pool

SugarBear- Pool, AC, Sauna, Gym, Tennis!

Ranch at Mendon Mt Orchards

Golf and Mountain Biking outside the door!

Luxury Condo Tucked in the Heart of Killington

Ski Mountain View Estate

Gorgeous Dog Friendly 2BR 2.5 Bath w/ Pool Sauna

Classic VT Ski Chalet - Walkable to Okemo Ski Lift

Magical Farm Getaway - a must visit!
Weekly house rentals

Architectural House Prickly Mountain

Charming Vermont Schoolhouse

The Willow House: a Modern Vermont Retreat

Quechee Getaway See the Vermont MTNs

The Barnbrook House

The Looking Glass, a modernistic escape

Eclectic Woodstock Retreat | Views, Deck & Firepit

Historic House near Woodstock Inn with Porch
Private house rentals

Woodstock Village Retreat

VT Farmhouse w/ Pond, Stream, Firepit & 20+ Acres

Quechee Retreat. Close to Everything!

Sky Zen - Ridgeline Retreat

Hot Tub + Gorgeous Views - Green Mountain Getaway

Dana Road House Sunlit VT Country Home w/HotTub

8-Acre Retreat with Trails, 7 Min to Killington

Secluded/Hot Tub/views! Minutes to Everything!
When is the best time to visit Woodstock?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | ﺩ.ﺇ 1,509 | ﺩ.ﺇ 1,480 | ﺩ.ﺇ 1,260 | ﺩ.ﺇ 1,744 | ﺩ.ﺇ 1,689 | ﺩ.ﺇ 1,513 | ﺩ.ﺇ 1,285 | ﺩ.ﺇ 1,212 | ﺩ.ﺇ 1,318 | ﺩ.ﺇ 1,451 | ﺩ.ﺇ 1,282 | ﺩ.ﺇ 1,609 |
| Avg. temp | -7°C | -6°C | 0°C | 7°C | 14°C | 18°C | 21°C | 20°C | 15°C | 9°C | 3°C | -3°C |
Destinations to explore
- New York Vacation rentals
- Montreal Vacation rentals
- Philadelphia Vacation rentals
- Boston Vacation rentals
- Quebec City Vacation rentals
- Jersey City Vacation rentals
- Newark Vacation rentals
- Portland Vacation rentals
- Mont-Tremblant Vacation rentals
- Providence Vacation rentals
- Newport Vacation rentals
- York County Vacation rentals
- Rentals with pools Woodstock
- Cottage rentals Woodstock
- Fitness-friendly rentals Woodstock
- Cabin rentals Woodstock
- Waterfront rentals Woodstock
- Family-friendly rentals Woodstock
- Rentals with a washer and dryer Woodstock
- Apartment rentals Woodstock
- Hotel rooms Woodstock
- Bed and breakfasts Woodstock
- Condo rentals Woodstock
- Rentals with a patio Woodstock
- Chalet rentals Woodstock
- Rentals with breakfast Woodstock
- Rentals with a fireplace Woodstock
- Villa rentals Woodstock
- Rentals with a fire pit Woodstock
- Rentals with an EV charger Woodstock
- Rentals with outdoor seating Woodstock
- Rentals with a hot tub Woodstock
- Pet-friendly rentals Woodstock
- House rentals Windsor County
- House rentals Vermont
- House rentals United States
- Okemo Mountain Resort
- Squam Lake
- Stratton Mountain
- Sugarbush Resort
- Pats Peak Ski Area
- Magic Mountain Ski Resort
- Pico Mountain Ski Resort
- Stratton Mountain Resort
- Dartmouth College
- Tenney Mountain Resort
- Ragged Mountain Resort
- Fort Ticonderoga
- Hildene, The Lincoln Family Home
- Killington Resort
- Middlebury College
- Fox Run Golf Club
- Bromley Mountain Ski Resort
- Squam Lakes Natural Science Center
- Mount Sunapee Resort
- Montshire Museum of Science
- Emerald Lake State Park
- Ice Castles
- Stinson Lake
- Camp Plymouth State Park





