
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 G$18,821 GYD per night before taxes and fees

Verified guest reviews
Over 1,050 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.

Stylish Vermont Cabin | Views · Trails · Luxe
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.

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.

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!

New Firepit, Great Location, Dog Friendly, Kitchen
Welcome to @MendonMtGetaway - my warm & cozy VT retreat! With 3 bedrooms, comfy living room, full kitchen, washer/dryer, AND office space - I hope you'll feel at home right away. You are in a wonderful location here. Turn left & you are just minutes down the road from ski heaven - Killington and Pico Mountains! Turn right, and you're just minutes from cute & historic Rutland. Either way you’ll find tons of great outdoor activities & hiking, and lots of local shops and restaurants.

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!

Steps to Golf and Mountain Biking

Ranch at Mendon Mt Orchards

Classic VT Ski Chalet - Walkable to Okemo Ski Lift

Charming Sugarbush Standalone Condo

Dana Road House Sunlit VT Country Home w/HotTub

Luxurious family retreat home in the mountains
Weekly house rentals

Charming Vermont Schoolhouse

Private Oasis Under 10 Mins from Woodstock

1800s Farmhouse with River Access. Private w/ Land

Cozy Private House on Killington Mtn - Hottub

Mountain Getaway Pet friendly

The Looking Glass, a modernistic escape

cozy home for a relaxing fall getaway

Dawnside - Green Mtns Home with White Mtns View
Private house rentals

19th Century Bohemian Barn House

Skyeburst | Modern Mtn Home

Stunning 3 br Timber Frame ski retreat on 6 Acres

Mountain Home with Scenic Views

Sky Zen - Ridgeline Retreat

Fred Eddy Farmhouse

Skye Ridge Lodge: Private Hot Tub, Open Concept

The Old Home Place!
When is the best time to visit Stockbridge?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | G$88,456 GYD | G$85,738 GYD | G$78,001 GYD | G$60,853 GYD | G$56,671 GYD | G$62,944 GYD | G$62,735 GYD | G$62,735 GYD | G$64,408 GYD | G$77,791 GYD | G$73,191 GYD | G$80,510 GYD |
| 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 |
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- Pet-friendly rentals Stockbridge
- Rentals with a fire pit Stockbridge
- Rentals with a washer and dryer Stockbridge
- Rentals with outdoor seating Stockbridge
- Rentals with a patio Stockbridge
- Rentals with a hot tub Stockbridge
- Family-friendly rentals Stockbridge
- Rentals with a fireplace Stockbridge
- House rentals Windsor County
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- House rentals United States
- Lake George
- Okemo Mountain Resort
- Stratton Mountain
- Sugarbush Resort
- Stratton Mountain Resort
- Magic Mountain Ski Resort
- Pico Mountain Ski Resort
- Bolton Valley Resort
- Killington Resort
- Dartmouth College
- Tenney Mountain Resort
- Fort Ticonderoga
- Hildene, The Lincoln Family Home
- Fox Run Golf Club
- Middlebury College
- Bromley Mountain Ski Resort
- Adirondack Extreme Adventure Course
- Montshire Museum of Science
- Mount Sunapee Resort
- Stinson Lake
- Emerald Lake State Park
- Shelburne Vineyard
- Warren Falls
- Shelburne Museum





