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Vacation rentals in Stockbridge

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Top-rated vacation rentals in Stockbridge

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Home in Barnard

4.98 out of 5 average rating, 126 reviews

The Looking Glass, a modernistic escape

Welcome to The Looking Glass, a modernistic escape located in Barnard, Vermont! With floor to ceiling, south facing windows, you’ll be relaxing in comfort while taking in breathtaking views of the Green Mountains! You’ll love our commercial grade kitchen, boasting high-end cookware, a Wolf range and Subzero fridge. Take the spiral staircase upstairs to enjoy a long bath before calling it a night in the spacious king bed. Explore Silver Lake & Woodstock! Hike, bike or ski the neighboring trails

Chalet in Stockbridge

4.93 out of 5 average rating, 175 reviews

Killington ski house winter MTbike -new jacuzzi

Killington Ski Area with access to snowmobile and mountain biking trails. This is a 3 bedroom, 2 bath upper unit duplex. with outdoor Jacuzzi open year round with barbecue on very nice decks for those nicer days , snow mobile right from the house , on the tweed valley vast trails , in the summer mountain bike on the green mountain trail system right on our mountain keep us in mind for the summer event like the spartan race and the peak series Mt biking events too Fantastic unit check our review

Cabin in Royalton

4.99 out of 5 average rating, 203 reviews

Genuine Vermont Sugar House on 70 peaceful acres.

Stay in this genuine Vermont sugarhouse. Our family took great pride in making Maple Syrup and now we take that same pride in sharing this private piece of Vermont with you, our guests. There are trails that will take you through our 70-acre property including the sugar bush we used for the sugarhouse. Relax in the quiet beauty of rural Vermont. Located near the geographical center of VT. We do welcome friendly housebroken dogs. Please see other details under show more. Part of Three Maples LLC.

Guesthouse in Woodstock

4.98 out of 5 average rating, 233 reviews

Cozy Little Spot (Self Check-in)

Contactless check-in. Cozy guest house, cabin-studio-getaway; enjoy the sounds of a stream outside the window (next to the bed). Views of a larger brook below. The"Cabin"is nestled in the trees giving a feeling of floating above the brook below. The interior is decorated w/family heirlooms gathered from around the country. Nothing fancy, just a cozy simple getaway. 3.25 mi from town. Choose from a variety of activities in town or hop on nearby trails. NO PETS ALLOWED. ZERO CONTACT WITH OWNERS.

Treehouse in Stockbridge

4.94 out of 5 average rating, 107 reviews

Romantic Treehouse- Hot tub, FPLC, 20 Min to KLT

New treehouse was built by me with my own two hands during the pandemic. The architect styled design is one of a kind with huge windows. Radiant Heat, custom bathroom/kitchen. My grandparents once owned and operated a dairy farm in the area and I want to share this treehouse and surrounding area with my guests. Ski or Ride in only 20 min to Killington and resorts. My treehouse is located on the historic ski highway with Killington-20 min, Pico, Okemo, Sugarbush, Saskadena Six, and Stowe.

Chalet in Stockbridge

4.86 out of 5 average rating, 136 reviews

Vermont Chalet

Killington Skiing, Pico Peak, Sugar Bush, Mad River are all within distance. Killington is 14 miles away. Fall folliage is fabulous; kitchen well equipped; very light and lovingly cared for. Spring and summer are just as wonderful. I am walking distance to the White River where there is canoeing, tubing and swimming. Within walking distance is the Gaysville Campgrounds. Here you'll find river access to a fabulous swimming hole in the White River as well as trails to explore or walk your dog.

Home in Stockbridge

4.87 out of 5 average rating, 141 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.

Cabin in Stockbridge

4.95 out of 5 average rating, 107 reviews

1958 Classic "Hunting Cabin" w/ Breathtaking Views

Welcome to CAMP TREETOPS, located in the heart of the beautiful Vermont mountains. Our cabin is nestled at the top of a private mountain, surrounded by breathtaking views of Killington, Pico mountains, and the White River. Originally purchased from a Sears & Roebuck catalog as a hunting cabin owned by the same family until 2019. The cabin has since been transformed into its original vintage classic camp décor with antique furnishings and unique vintage finds that take you back in time.

Rental unit in Royalton

4.98 out of 5 average rating, 173 reviews

Quiet Vermont Get Away

This space is ideal for a family or friends. This is a dog-friendly apartment located above our garage with stairs. Just 5 min off Exit 3 on I89. Full kitchen to make family meals. Cozy living/dining space. Come and stay for skiing, snowmobiling, hiking, biking, golf, local breweries and so much more depending on the season. Close to Vt Law School. 35-40 minutes to Killington, Pico, Stowe, Bolton and Sugarbush. 20 minutes to Quechee and Woodstock. Sleeps 5/6 with using a bunk bed.

Cabin in Randolph

4.94 out of 5 average rating, 237 reviews

Secluded Log Home on 109 Acre Natural Wonderland!

Enjoy our remote, easily accessible, immaculate new log house, set in nature on 109 acres. Pond, woods, fields and trails; with high speed internet and smart TV! Sleeps 6, including a queen bed, 2 bunk beds, and a sleep sofa. Fully equipped kitchen, including a full-sized refrigerator, microwave, Keurig coffee maker and many other amenities. Screened in porch. Views from every room! In the heart of the ski corridor. Explore the trails, and the meditation yurt when available!

Guest suite in Bethel

4.97 out of 5 average rating, 153 reviews

Two bedroom. Separate entrance.

Please be advised that during winter months you may need to walk up Winterberry lane and our driveway if you do not have an AWD vehicle with good snow tires. Two bedroom apartment in the heart of Vermont. Snowmobile trail located off lane. Snowshoe, hike, or mountain bike from the door. Quiet private location with separate entrance and parking onsite. Ramp to access apartment, with stair free access. Pond, views and located in the center of the state, a great place to start!

Home in Rochester

4.97 out of 5 average rating, 197 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!

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Popular amenities for Stockbridge vacation rentals

Free parking on premises

Air conditioning

Stay near Stockbridge's top sights

Thundering Brook Falls Trail49 locals recommend

Green Mountain National Golf Course35 locals recommend

Clear River Tavern23 locals recommend

Gifford Woods State Park20 locals recommend

Original General Store20 locals recommend

Tozier's Restaurant17 locals recommend

Other great vacation rentals in Stockbridge

Home in Pittsfield

5 out of 5 average rating, 13 reviews

Skyeburst | Modern Mtn Home

Cabin in Stockbridge

4.98 out of 5 average rating, 46 reviews

RZEKA Cottage: Riverfront home in the Green mts.

Home in Stockbridge

4.89 out of 5 average rating, 18 reviews

Cozy Ski Farmhouse

Chalet in Stockbridge

4.86 out of 5 average rating, 76 reviews

Private House - Hot Tub, Steam Room, Fire pit

Cabin in Bethel

4.95 out of 5 average rating, 65 reviews

The Gourmet Cabin at Stitchdown Farm

Cottage in Barnard

5 out of 5 average rating, 17 reviews

Andas Hus: Little Luxury

Chalet in Stockbridge

4.95 out of 5 average rating, 42 reviews

BENT TREE Vermont, Mtn Chalet 25 min to Killington

Cabin in Stockbridge

4.86 out of 5 average rating, 14 reviews

T’s Hideaway

Quick stats about vacation rentals in Stockbridge

Total rentals
110 properties
Nightly prices starting at
$30 before taxes and fees
Total number of reviews
4.4K reviews
Family-friendly rentals
80 properties are a good fit for families
Pet-friendly rentals
50 properties allow pets
Rentals with dedicated workspaces
50 properties have a dedicated workspace

Frequently Asked Questions

Are there family-friendly vacation rentals in Stockbridge?
Stockbridge has more than 80 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.
Do cabin rentals in Stockbridge have wifi?
Absolutely! We offer over 10 cabin rentals with wifi in Stockbridge. Enjoy a tailored experience with all the comforts you desire.
Are there pet-friendly vacation rentals in Stockbridge?
Four-legged friends are welcome in Stockbridge. Choose from more than 50 vacation rentals for guests traveling with pets.
How much does it cost to stay in house rentals in Stockbridge?
Experience the best of Stockbridge with our house rentals, starting at about $130 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Are there vacation rentals with a dedicated workspace in Stockbridge?
Yes! Work meets play with ease at over 50 vacation rentals in Stockbridge featuring dedicated workspaces. Stay connected and productive in your home away from home.
Do house rentals in Stockbridge have air conditioning?
Absolutely! We offer over 10 house rentals with air conditioning in Stockbridge. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Stockbridge have free parking?
Absolutely! We offer over 40 house rentals with free parking in Stockbridge. Enjoy a tailored experience with all the comforts you desire.
Do cabin rentals in Stockbridge have a kitchen?
Absolutely! We offer over 10 cabin rentals with a kitchen in Stockbridge. Enjoy a tailored experience with all the comforts you desire.

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