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.

0 of 0 items showing

1 of 3 pages

Guest favorite

Home in Killington

4.92 out of 5 average rating, 165 reviews

Cozy 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!

Jun 6 – 13

G$29,028 GYD per night

Guest favorite

Home in Tunbridge

4.98 out of 5 average rating, 316 reviews

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.

Mar 27 – Apr 3

G$62,587 GYD per night

Guest favorite

Home in Woodstock

5.0 out of 5 average rating, 110 reviews

Beautiful Woodstock Home-Perfect for entertaining

Newly renovated - 4 bedroom, 3 bath house, perfect for relaxing or entertaining. Close to all that the Woodstock Village and the Upper Valley has to offer. Amazing location! Only 1.5 mi to the Woodstock Green. Explore the property and feast on the blackberries in summer, raid the tomato garden in the late summer/early fall, and pick the wild fall apples for munching or baking. Bring your snowshoes or cross country skis (in winter) or hiking shoes in summer and explore the property and beyond!

Sep 17 – 24

G$125,899 GYD per night

Guest favorite

Home in Rutland

5.0 out of 5 average rating, 121 reviews

ONE ROOM SCHOOL HOUSE

Renovated one room school house. Spacious, open space. Music room has been converted into a bedroom. It is now a separate, private, room. New European style kitchen area. High ceilings with fans and air-conditioner. Propane fireplace/stove for heat and atmosphere. Storage for clothing, skis, snowboards. Exterior bicycle rack. Circular driveway for off-street parking. High speed internet and 65 inch Roku TV with surround sound. Everything brand new. We have added three season screened porch.

Aug 6 – 13

G$48,913 GYD per night

Superhost

Home in Stockbridge

4.87 out of 5 average rating, 134 reviews

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.

May 6 – 13

G$49,852 GYD per night

Guest favorite

Home in Barnard

4.92 out of 5 average rating, 141 reviews

Cozy 2bd, Tennis Court, Steps to Lake, on 6 acres

This 2nd floor space is great for small groups and couples. All wood interior space has been newly updated with modern appliances, handmade slab countertops, and cozy furniture. Directly across from Silver Lake and the Barnard General Store, with 6 parklike acres including a tennis court (with pickle ball)! Easy to find, minutes from Woodstock, VT. and award-winning dining, just 3 minutes to Silver Lake State Park, and just a few miles to multiple access points of the Appalachian Trail.

Mar 10 – 17

G$38,064 GYD per night

Guest favorite

Home in Rochester

4.95 out of 5 average rating, 144 reviews

Cottage in the Heart of the Green Mountains

Welcome to quintessential Vermont! Come stay at my cozy yet spacious, rustic yet modern, much-beloved Red Acre Cottage. Red Acre Cottage is nestled on a scenic ridge in the idyllic town of Rochester, just east of the Green Mountains and right off of Vermont Scenic Byway Route 100, one of the state's prettiest roads. Red Acre Cottage is an easy drive to Killington/Pico, Sugarbush, Mad River Glen, Rikert Nordic Center/Blueberry Hill XC skiing, Suicide Six, and Stowe Mountain.

Aug 22 – 29

G$34,465 GYD per night

Guest favorite

Home in Rochester

4.97 out of 5 average rating, 182 reviews

The Guest House at Sky Hollow

This quiet hilltop house on an 1800's farm turned homestead at the end of a dirt road 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!

Aug 22 – 29

G$33,721 GYD per night

Guest favorite

Home in Bethel

4.85 out of 5 average rating, 130 reviews

Hike, run, swim or cycle in beautiful Central VT

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.

Oct 22 – 29

G$26,396 GYD per night

Guest favorite

Home in Pittsfield

4.91 out of 5 average rating, 149 reviews

Beautiful Mountain Log Cabin with Scenic Views

A unique post and beam log cabin with beautiful scenic mountain views. 15 minutes from killington and pico ski areas. This one of a kind house offers an open floor plan with a great room and fireplace. Master suite has its own fireplace, jacuzzi tub and balcony. A loft area with pool table and tv . Outside hot tub with mountain views. Two car garage to park in on cold snowy nights. Large basement off garage makes getting out of your ski gear easy.

Jul 14 – 21

G$76,120 GYD per night

Superhost

Home in Pittsfield

4.83 out of 5 average rating, 221 reviews

Killington area home - 4-seasons & hot tub

Set on a private road in the hills of Pittsfield, our house welcomes you year-round. Right in the heart of the Northeast’s best winter-sports, convenient to Killington ski resort, VAST snowmobile trails, Mountain Meadows cross country skiing and Green Mountain National Golf course. Furthermore, there are wonderful hikes and mountain biking to be done on the property and beyond - particularly beautiful in the fall.

Nov 5 – 12

G$52,601 GYD per night

Superhost

Home in Rochester

4.9 out of 5 average rating, 282 reviews

Mountain Home ready for you!

Get away from it all in a secluded home atop a mountain in the VT National Forest. Home with large 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 lovely town of Rochester. Tubing and swimming holes nearby, tons of hiking and biking trails and berry picking nearby.

Sep 17 – 24

G$59,971 GYD per night