
Pet-friendly vacation rentals in Stockbridge
Find and book unique pet-friendly homes on Airbnb
Top-rated pet-friendly home rentals in Stockbridge
Guests agree: these pet-friendly homes are highly rated for location, cleanliness, and more.

Summit View Cottage:Ski | Hot tub|Fireplace3bd 2ba
Summit view cottage boasts 3 acres in the beautiful green mountains, we are 1,700 feet up in elevation . At this brand newly built PET FRIENDLY cabin you will have 3 bedrooms and 2 full bathrooms, which will sleep 7 comfortably. We have a brand new 6 person HOT TUB! You will find yourself within 15 minutes to the world famous Stratton mtn, 15 minutes from Bromley mtn and a close 4 minutes to the local Magic mtn.Very close proximity to the town of Manchester, which has great shops and restaurants

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.

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.

Pine Cabin, Galusha Hill Farm, incredible view!
Gorgeous view from your super private and charming cabin on Galusha Hill. This spot is beyond special and has been described as breathtaking by guests and locals alike. Pine Cabin has a sweeping view of the White and Green Mts, located on 1000+ acres of conservation land. The cabin itself has a fully equipped kitchen, newly renovated bathroom, two bedrooms, and a cozy living room with fireplace. The Front Porch, looking out at the view,is the best place to be with a cup of coffee or cocktail.

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.

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.

The SugarMaple Treehouse @ Vermont ReTREEt
This glamping style treehouse is cradled by three maple trees and stands as a haven above the ground nestled amidst the Green Mountain National Forest. It was hand crafted by us to offer a reTREEt in the heart of central Vermont. Do you want to hangout in a treehouse and get a chance to feel connected with nature? then book already and start looking forward to your trip Have a question? ask Any hesitation? reach out Want to discuss treehouses? send a message check out our listings

Hancock hideaway
Skiing, snow biking 10 minutes away at Middlebury Snow Bowl and Rikert crosscountry. Sugarbush and Killington half hour drive. Snowshoeing and hiking right behind house in the Green Mountain National Forest. Easy drive to river swimming holes and lakes. Excellent restaurants in Waitsfield and Middlebury - about half hour. Good restaurant, cafe, small grocery store, in Rochester, 4 miles. Great location, beautiful views, lovely little house, totally private, romantic.

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!

Cozy 4-season Cabin on Pond - "East Cabin"
Take refuge in a cozy log cabin with abundant access to Vermont's Green Mountains and rolling foothills. A quick drive to Woodstock and Quechee, the cabin is located on quiet dirt road with beautiful south-facing views overlooking the town of South Royalton, just a mile away. Spring-fed pond is steps from the cabin, take a dip! Follow the trails through the woods and fields and enjoy this pristine piece of Vermont.

Scandinavian design Cabin hiking trail + hot tub
Welcome to our charming cabin nestled in the heart of the woods, where comfort meets tranquility. This 400 sq. ft retreat is bathed in natural light, boasting high-quality appliances, strong WiFi and thoughtfully curated design furniture to ensure a cozy and memorable stay. Relax in our private Goodland wood burning hot tub. Goodland wood burning hot tub is available 365 days a year. EV charger level 2 available.

5 miles from Woodstock-Dog Friendly w/FIOS
Just 5 miles from Woodstock, the Cottage at StillwoodVT is a bright and cozy two-story home set on a peaceful 20-acre oasis of woods, pasture, and hill views. Two bedrooms (queen upstairs, full downstairs), one bath with shower, and open kitchen/living/dining area. Private, quiet, and surrounded by nature. One-bedroom use receives 10% back after checkout (not combinable with other discounts).
Popular amenities for Stockbridge pet-friendly home rentals
Pet-friendly house rentals

Captain Tom's Cabin - Secluded Vermont Getaway

Mountain Getaway Pet friendly

The Post Haus: one-of-a-kind modern VT experience

SugarBear- Pool, Hot Tub, 2 En Suites BR

Comfortable farmhouse with stunning views

Killington area home - 4 seasons - hot tub and A/C

Stylish Vermont Cabin | Views · Trails · Luxe

Architectural House Prickly Mountain
Pet-friendly home rentals with a pool

Ranch at Mendon Mt Orchards

Dog Friendly Mountain Condo w/Spa, Pool, Sauna

Moon Valley Country Retreat no clean fee pets yes

Lower Yurt Stay on VT Homestead

Dog-Friendly/Spa Onsite/Pool/Wine Bar

SKI ON/OFF Spruce Glen B | Sauna | Fireplace | AC

A Sweet Suite! Modern. Pool. 2RM/2BA. Shuttle. 532

Historic Home on 17 acres of land. Go escape!
Private, pet-friendly home rentals

The Looking Glass, a modernistic escape

Adorable one bedroom studio in 1844 farmhouse.

Fairytale cabin at The Wild Farm

Sunday Mountain Surprise

Fairlee Log Cabin

Apple Blossom Cottage: A Tiny House

Stylish factory-farmhouse deluxe loft

A frame cabin with Hot tub near Stratton, VT
When is the best time to visit Stockbridge?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $556 CAD | $556 CAD | $449 CAD | $390 CAD | $321 CAD | $331 CAD | $384 CAD | $383 CAD | $383 CAD | $435 CAD | $408 CAD | $526 CAD |
| 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 |
Quick stats about vacation rentals that are pet-friendly in Stockbridge

Total vacation rentals
Explore 40 vacation rentals in Stockbridge

Nightly prices starting at
Stockbridge vacation rentals start at $42 CAD per night before taxes and fees

Verified guest reviews
Over 1,460 verified reviews to help you choose

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

Rentals with dedicated workspaces
10 properties have a dedicated workspace

Wifi availability
40 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!
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- Lake George
- Okemo Mountain Resort
- Stratton Mountain
- Sugarbush Resort
- Killington Resort
- Magic Mountain Ski Resort
- Stratton Mountain Resort
- Pico Mountain Ski Resort
- Bolton Valley Resort
- Tenney Mountain Resort
- Fort Ticonderoga
- Fox Run Golf Club
- Bromley Mountain Ski Resort
- Hildene, The Lincoln Family Home
- Dartmouth College
- Montshire Museum of Science
- Emerald Lake State Park
- Adirondack Extreme Adventure Course
- Mount Sunapee Resort
- Middlebury College
- Shelburne Museum
- Stinson Lake
- Southern Vermont Arts Center
- Warren Falls




