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

Total vacation rentals
Explore 30 vacation rentals in Stockbridge

Nightly prices starting at
Stockbridge vacation rentals start at ﺩ.ﺇ 331 per night before taxes and fees

Verified guest reviews
Over 1,070 verified reviews to help you choose

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

Pet-friendly vacation rentals
Find 10 rentals that welcome pets

Rentals with dedicated workspaces
10 properties have a dedicated workspace

Wi-Fi availability
30 of Stockbridge vacation rentals include wi-fi access

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

4.9 Average rating
Stockbridge stays are highly rated by guests—averaging 4.9 out of 5!
Top-rated house rentals in Stockbridge
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

The Barnbrook House
Come relax in the serenity of the quiet countryside. This home boasts beautiful views, a large stone fireplace, and stained glass windows throughout the home. Enjoy the comforts of home with a full kitchen, amenities, and beds with 1500 thread count sheets while exploring the interesting features of this one of a kind house. Sit by the spring fed pond overlooking the property laced with apple trees. The home has direct access to short walking trails and is close to VAST trails for snowmobiling.

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.

Comfortable 3 Bedroom King size Master w/ En suite
This is a 3-bedroom rural home with a King size plush mattress in the master bedroom with En Suite bathroom which features a modern single vanity sink and a stall shower. The second bedroom located next to the master bedroom has a twin xl size bunk bed, the third bedroom has a queen-size bed. A unique feature is the pool table and big screen TV in the living room area which is open to the kitchen which has granite countertops and stainless farmhouse style sink. New GE front load Washer+Dryer.

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

Escape to Vermont
Welcome to the Red House at Stony Brook! This remodeled 1800's farmhouse offers peace, solitude and comfort in Vermont's national forest. Gaze at stars from the bedroom window and decompress in the mountains. Or, set out for a day of cycling, hiking, skiing and exploring all Vermont has to offer. A chance to experience wildlife, such as moose, birds, bears, turkeys and more. Nearby are Killington Mtn, Sugarbush, famous cycling roads, and several of VTs world renowned eateries and breweries.

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.

Hike, run, swim, cycle in green central Vermont
Enjoy the summer in beautiful Vermont. The guest area is the entire main floor of a large house with my quiet second home above. Private entrance, 2 bedrooms, full bathroom with washer and dryer, speedy fiber optic internet. The open kitchen has full sized stove and fridge with good cookware and appliances, adjacent to a large open living area. On a paved scenic road. Swim or paddle up at Silver Lake, or run or ride on the many tree-lined dirt roads.

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!

One Room School House. No Cleaning Fees!
Renovated one room school house. Spacious, open space. Music room has been converted into a bedroom. European style kitchen area. High ceilings with fans and air-conditioner. Propane fireplace. Off-street parking. High speed internet and 65 inch Roku TV with surround sound. Three season screened porch. Also, we have recently introduced a NO CLEANING FEE policy as our way of saying "Thank You" for respecting our property and guidelines.
Popular amenities for Stockbridge house rentals
House rentals with a pool

Luxury Condo Tucked in the Heart of Killington

Magical Farm Getaway - a must visit!

Golf and Mountain Biking outside the door!

Ranch at Mendon Mt Orchards

Classic VT Ski Chalet - Walkable to Okemo Ski Lift

Charming Sugarbush Standalone Condo

Luxurious family retreat home in the mountains

4 bedroom home w/mountain views & outdoor pool
Weekly house rentals

Charming Vermont Schoolhouse

1800s Farmhouse with River Access. Private w/ Land

The Looking Glass, a modernistic escape

Ski, snow mobile, hiking, fun on slopes & trails!

Custom cabin on Mt Ascutney, sweeping Hill Views

The Quechee Haus: VT Retreat with Outdoor Hot Tub

Romantic Retreat, Hot Tub, near Killington Mtn

Architectural House Prickly Mountain
Private house rentals

Skyeburst | Modern Mtn Home

Sky Zen - Ridgeline Retreat

Mountain Home with Scenic Views

Lull’s Brook Cottage

Green Mountain/Killington Getaway

Mountain Home with Epic Views

Skye Ridge Lodge: Private Hot Tub, Open Concept

Barn Hollow Farm
When is the best time to visit Stockbridge?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | ﺩ.ﺇ 1,553 | ﺩ.ﺇ 1,506 | ﺩ.ﺇ 1,370 | ﺩ.ﺇ 1,069 | ﺩ.ﺇ 995 | ﺩ.ﺇ 1,105 | ﺩ.ﺇ 1,102 | ﺩ.ﺇ 1,102 | ﺩ.ﺇ 1,131 | ﺩ.ﺇ 1,366 | ﺩ.ﺇ 1,285 | ﺩ.ﺇ 1,414 |
| Avg. temp | -6°C | -5°C | 0°C | 8°C | 15°C | 20°C | 22°C | 21°C | 17°C | 10°C | 4°C | -2°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
- Family-friendly rentals Stockbridge
- Rentals with a fireplace Stockbridge
- Pet-friendly rentals Stockbridge
- Rentals with a washer and dryer Stockbridge
- Rentals with a fire pit Stockbridge
- Rentals with outdoor seating Stockbridge
- Rentals with a patio Stockbridge
- Rentals with a hot tub Stockbridge
- House rentals Windsor County
- House rentals Vermont
- House rentals United States
- Lake George
- Okemo Mountain Resort
- Stratton Mountain
- Sugarbush Resort
- Magic Mountain Ski Resort
- Pico Mountain Ski Resort
- Stratton Mountain Resort
- Dartmouth College
- Bolton Valley Resort
- Tenney Mountain Resort
- Fort Ticonderoga
- Hildene, The Lincoln Family Home
- Killington Resort
- Middlebury College
- Fox Run Golf Club
- Bromley Mountain Ski Resort
- Adirondack Extreme Adventure Course
- Mount Sunapee Resort
- Montshire Museum of Science
- Emerald Lake State Park
- Stinson Lake
- Camp Plymouth State Park
- Shelburne Museum
- Warren Falls





