
House vacation rentals in Stockbridge
Find and book unique houses on Airbnb
Top-rated house rentals in Stockbridge
Guests agree: these houses are highly rated for location, cleanliness, and more.

Luxury Condo Tucked in the Heart of Killington
Welcome to our ❄newly renovated❄ Cozy Condo Located right off the "loop" walking trail on river road. Our end unit condo sits just 5 min from the base of Killington with easy access to night life/restaurants and much more. Whether you are skiing, hiking, biking, kayaking or just enjoying the fresh Vermont air, you'll love the comfort of our condo. Enjoy a space that is truly convenient, comfortable, child-friendly and fun for you to enjoy during your hard-earned vacation time in Killington!

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.

The Willow House: a Modern Vermont Retreat
Just 7 miles (12 minutes ) to the Dartmouth Campus, this newly re-built little house sits beside its own pond on the edge of a sheep pasture. All the comforts of a modern home in 600sqft. Enjoy access to hiking trails and State Forest lands as well as an easy drive to world-class skiing an hour away and all that the Dartmouth College community offers just minutes away. This is the best of pastoral Vermont, with outside living-dining space ( south facing deck and north facing screen porch).

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.

Mountain Home ready for you!
Get away from it all in a secluded home atop a mountain in the National Forest. Home with deck and panoramic view of the Green Mountains. Idyllic in all seasons. Summer is lusciously green; fall colors seen from our deck; the magic of winter. Tons of privacy, but minutes from town. 35 min to Killington or Sugarbush; snowshoe outside your door, and x-country nearby. Snow tires or chains needed from Dec.-March. Please note that we cannot help you if your car gets stuck en route to the house.

The Spring Hill House
Escape to a haven of natural beauty and tranquility at The Spring Hill House. Our unique bow roof home offers breathtaking views of Camel’s Hump and the majestic Green Mountains, the perfect setting for a rejuvenating getaway. Despite being removed from the hustle and bustle of city life, The Spring Hill House is still centrally located, providing easy access to some of Vermont's most popular destinations. Please note: We have a firm no kids policy due to the open loft and stairs.

Cozy Home in Poultney, Vermont.
If you are looking for a cozy spot to relax in a small town, with fast internet and easy access to lots of fun activities, this house is it! On the main floor of the house, there is an open layout that includes a library, a small bar, a dining room, a kitchen, a bathroom, and two bedrooms. Downstairs, there is a finished basement that includes a large family area with a huge couch (perfect for movies), a workspace, and a laundry space. Private parking and lots of outdoor space.

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.

Affordable, private, surrounded by flower gardens
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. Go up to Silver Lake for a swim, head out on any of the back roads for a run or a ride.

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!

Killington Retreat | Deck-Fire Pit-Mountain Views!
Welcome to your new Vermont escape! This custom-built 2BR/1BA pet and smoke free home is nestled in the foothills of the green mountains. Our home sits on a 14 acre lot and is close to hiking, skiing, a horse farm, lakes and Rutland (10 mins). You will love the woodwork, luxury white bedding, floor-to-ceiling windows, massive sunny deck, and peace and quiet. There is plenty of space for family memory making, your peaceful mountain retreat awaits!

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

Magical Farm Getaway - a must visit!

Fish, Bike, Golf, or Hike!

Epic Views of the Green Mountains

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

Historic Home on 17 acres of land. Go escape!
Weekly house rentals

Charming Vermont Schoolhouse

Private Oasis Under 10 Mins from Woodstock

A million-dollar view near Killington on 60 acres.

Killington/Okemo, 7p Hot tub, Spacious, Mtn.views!

Stunning Okemo Views - 3BD 3BA on 10 Private Acres

Beautiful Woodstock Home-Perfect for entertaining

Fred Eddy Farmhouse

Ski, snow mobile, hiking, fun on slopes & trails!
Private house rentals

Unique Mountain Retreat

Skyeburst | Modern Mtn Home

Charming Modern Cabin Retreat

Secluded Private Farmhouse close to Ski Mountains

Cozy VT Getaway - Fully Furnished for Longer Stays

Hideaway Mountain at Killington

Cottage in the middle of family horse farm

Convenient Vermont Getaway
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 $126 CAD per night before taxes and fees
Verified guest reviews
Over 880 verified reviews to help you choose
Family-friendly vacation rentals
30 properties offer extra space and kid-friendly amenities
Pet-friendly vacation rentals
Find 20 rentals that welcome pets
Rentals with dedicated workspaces
10 properties have a dedicated workspace
Wifi availability
30 of Stockbridge vacation rentals include wifi 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!
Destinations to explore
- Plainview Vacation rentals
- New York City Vacation rentals
- Long Island Vacation rentals
- Boston Vacation rentals
- East River Vacation rentals
- Hudson Valley Vacation rentals
- Jersey Shore Vacation rentals
- Philadelphia Vacation rentals
- Mount Pocono Vacation rentals
- Quebec City Vacation rentals
- The Hamptons Vacation rentals
- Capital District, New York Vacation rentals
- Pet-friendly rentals Stockbridge
- Rentals with a washer and dryer Stockbridge
- Rentals with a patio Stockbridge
- Family-friendly rentals Stockbridge
- Rentals with a hot tub Stockbridge
- Rentals with a firepit Stockbridge
- Rentals with a fireplace Stockbridge
- Rentals with outdoor seating Stockbridge
- House rentals Windsor County
- House rentals Vermont
- House rentals United States
- Stratton Mountain
- Okemo Mountain Resort
- Sugarbush Resort
- Stratton Mountain Resort
- Bolton Valley Resort
- Magic Mountain Ski Resort
- Tenney Mountain Resort
- Fort Ticonderoga
- Cochran's Ski Area
- Dartmouth Skiway
- Pico Mountain Ski Resort
- Dorset Field Club
- Hildene, The Lincoln Family Home
- Bromley Mountain Ski Resort
- Lucky Bugger Vineyard & Winery
- Autumn Mountain Winery
- Northeast Slopes Ski Tow
- Ekwanok Country Club
- Fox Run Golf Club
- Whaleback Mountain
- Montshire Museum of Science
- Baker Hill Golf Club
- Mount Sunapee Resort
- Cozy Cottages & Otter Valley Winery