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

The Birch Perch! Treehouse with spa and fire pit!
Romantic Honeymoon or fun family fantasy come true this treehouse has it all! Built by The DYI Network Treehouse Guys! Every detail custom crafted in this home in the tree tops makes your ultimate Vermont experience. All just 8 minutes to the lifts at Sugarbush. Kitchenette, cast iron stove, clawfoot tub, washer/dryer, AC, & outdoor shower all encased in a whimsical perch near skiing, waterfalls, biking and hiking. Incredible hillside views from your private deck! Romantic Hot tub in the trees!

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 VT Barn by Burlington-Firepit-BringUrDog-WiFi
Cozy barn, gas fireplace, fast WiFI in a peaceful wooded forest. Whether sipping coffee by the fire, spinning vinyl records or stargazing by the fire pit(wood provided), this is your space to disconnect or work remotely in comfort. Explore on-site hiking trails, snowshoe and spot wildlife. A short drive from breweries, restaurants, scenic hikes & towns. A perfect mix of seclusion & convenience, 35 mins to Burlington. Perfect for couples/solo travelers/anyone looking for a private nature escape.

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.

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.

The Guest House at Chandlery Farm
This classic Vermont farm estate has everything that description implies: end-of-the-road privacy with breathtaking views, where the only sound is the wind rustling through the leaves. The manicured gardens, stone walls and quaint but luxurious home seem plucked from classic American folklore. Guests can drink their morning coffee while soaking in views of rolling pastures and forested hills, and spend their days exploring the property's trails, and the beautiful towns and countryside nearby.

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 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!

Scandinavian design Chalet hiking trail + hot tub
This bright, well-designed Scandinavian-style chalet is the perfect cozy retreat. Nestled in the woods on a plot of 20+ acres, it offers scenic views and a private hiking trail leading to beautiful vistas, transforming into a winter wonderland for skiing adventures, a summer paradise for outdoor relaxation, and a vibrant canvas for leaf peeping during Vermont's stunning fall foliage season. Goodland wood burning hot tub is available 365 days a year.

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.

Treehut - Secluded Treehouse in the Forest
Discover the Treehut, a cozy off-grid escape nestled among four trees that we built by hand. This unique retreat features a tiny wood stove inside, an invigorating outdoor shower (with hot water), and a serene fire pit under the stars. Ideal for nature enthusiasts seeking peace and quiet, yet only 10 minutes from Randolph. Unplug and unwind in this magical hideaway.
Popular amenities for Stockbridge pet-friendly home rentals
Pet-friendly house rentals

Captain Tom's Cabin - Secluded Vermont Getaway

Mountain Getaway Pet friendly

Cozy Contemporary Downtown Texaco

Nature Lover's Paradise

Comfortable farmhouse with stunning views

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

The McKinley House

Charming, Cozy Cape
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

AC • Vermont Retreat • Dogs Welcome • Pool & Spa

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

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

Cozy/Private, close to hospital, i-89
Private, pet-friendly home rentals

1800s Farmhouse with River Access. Private w/ Land

Dog heavenly! Private, beautiful and relaxing.

The Looking Glass, a modernistic escape

5 miles from Woodstock-Dog Friendly w/FIOS

100 Acres Views & Creek near Woodstock/Killington

My house is your house!

Riverfront Retreat in Stockbridge

Rustic and Cozy Vermont Getaway at Sugarwood Cabin
When is the best time to visit Stockbridge?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | ﺩ.ﺇ1,451 | ﺩ.ﺇ1,462 | ﺩ.ﺇ1,186 | ﺩ.ﺇ1,028 | ﺩ.ﺇ848 | ﺩ.ﺇ874 | ﺩ.ﺇ1,014 | ﺩ.ﺇ1,010 | ﺩ.ﺇ1,010 | ﺩ.ﺇ1,149 | ﺩ.ﺇ1,076 | ﺩ.ﺇ1,388 |
| 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 30 vacation rentals in Stockbridge

Nightly prices starting at
Stockbridge vacation rentals start at ﺩ.ﺇ110 per night before taxes and fees

Verified guest reviews
Over 1,550 verified reviews to help you choose

Family-friendly vacation rentals
20 properties offer extra space & kid-friendly amenities

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





