
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.

Remote, pond view log home, fully loaded, sleeps 6
Enjoy our remote, easily accessible, immaculate, pond-side cabin, 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, pots and pans, utensils and many other amenities. Screened in porch. In the heart of the Vermont ski corridor. Explore the trails, and our meditation yurt when available!

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.

Spacious 1-Bedroom Apartment at Log Heaven
1-bedroom walkout basement apartment with French doors that open onto a private patio. It is located at Log Heaven, a full scribe Log Home on 10 beautiful acres in Royalton Vermont. We are close to I-89, the White River, Silver Lake , Saskadena Ski Area, and Marsh-Billings-Rockefeller National Park . You need to travel on a gravel road which by VT standards is well maintained for 1.5-3 miles depending which direction you travel. We are 45 min to Killington Ski Resort, 1 hr to Okemo Ski area.

Secluded tiny house resort - DOG FRIENDLY
New tiny house, never lived in, but made to be comfortable. All amenities included: Air-condition, heat, WiFi, TV with cable, shower, tub, dry toilet, small full loft bed and full size couch futon, fire pit, river for swimming or fishing right out the door, small refrigerator, microwave, hot plate, toaster.ear three ski resorts (Killington, Okemo, Pico), Appalachian Long Trail two miles away, swinging bridge on trail beginning, White Rock hiking, lakes near for paddle boarding. Hot tub shared.

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.

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.

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.

Peaceful Log Cabin in the Woods
This log cabin is set in the woods in a rural part of northeastern Vermont. Escape the hustle and bustle, clear your mind, and enjoy nature. A great place to get some fresh air or to stay in and take a nap. Beautiful summers for easy hikes and refreshing swims in the lakes of our local Groton State Forest, unbelievable foliage to view from small dirt roads, and tons of outdoor winter activities. Great for a couples getaway, friends weekend, or some quality time with the family.

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 w/ private hiking trail
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.

"Swiss Charm"- A Beautiful Riverfront Chalet
Nestled comfortably on the banks of the Tweed River just 9 miles North of the Killington Access Road just off Rt. 100, "The Skiers Highway" with Direct Access to VAST Trails. A 2BR 1 BA A-Frame Chalet is the perfect Pet Friendly weekend getaway. Quaintly decorated and well stocked...This is truly a "Home Away From Home".
Popular amenities for Stockbridge pet-friendly home rentals
Pet-friendly house rentals

Captain Tom's Cabin - Secluded Vermont Getaway

The Oaks - secluded rural estate w/ amazing views

Modern Farmhouse on 25 Acres - Superb Views

Comfortable farmhouse with stunning views

Wright’s Mountain Retreat

Fresh Snow- Luxury Cabin near Ski Areas

Vermont Highland

Meadow View. 35 acres outside your door!
Pet-friendly home rentals with a pool

Upper Yurt Stay on VT Homestead

Epic Views of the Green Mountains

Ranch at Mendon Mt Orchards

Moon Valley Country Retreat no clean fee pets yes

Dog Friendly Mountain Condo w/Spa, Pool, Sauna

SnowCub Pets Indoor Pool Hot Tub Sauna, FirePlace

Dog-Friendly/Spa Onsite/Pool/Wine Bar

SKI ON/OFF Spruce Glen C | Sauna| Fireplace | AC
Private, pet-friendly home rentals

Skip's Place

Adorable Dog Friendly Cottage w/FIOS

Private Hilltop farm apartment

Private Cabin/PetsOK/Minutes to Okemo/Fast Wifi

Hancock hideaway

My house is your house!

Gatsby's Getaway

Spacious Country Guesthouse
When is the best time to visit Stockbridge?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | ﺩ.ﺇ1,469 | ﺩ.ﺇ1,469 | ﺩ.ﺇ1,186 | ﺩ.ﺇ1,028 | ﺩ.ﺇ848 | ﺩ.ﺇ874 | ﺩ.ﺇ1,014 | ﺩ.ﺇ1,010 | ﺩ.ﺇ1,010 | ﺩ.ﺇ1,069 | ﺩ.ﺇ1,054 | ﺩ.ﺇ1,484 |
| 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 ﺩ.ﺇ110 per night before taxes and fees

Verified guest reviews
Over 1,560 verified reviews to help you choose

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

Rentals with dedicated workspaces
10 properties have a dedicated workspace

Wi-Fi availability
40 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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- Pet-friendly rentals Windsor County
- Pet-friendly rentals Vermont
- Pet-friendly rentals United States
- Okemo Mountain Resort
- Stratton Mountain
- Sugarbush Resort
- Stratton Mountain Resort
- Magic Mountain Ski Resort
- Bolton Valley Resort
- Pico Mountain Ski Resort
- Tenney Mountain Resort
- Fort Ticonderoga
- Cochran's Ski Area
- Bromley Mountain Ski Resort
- Dartmouth Skiway
- Whaleback Mountain
- Hildene, The Lincoln Family Home
- Dorset Field Club
- Fox Run Golf Club
- Lucky Bugger Vineyard & Winery
- Autumn Mountain Winery
- Northeast Slopes Ski Tow
- Country Club of Vermont
- Ekwanok Country Club
- Montshire Museum of Science
- Mount Sunapee Resort
- Storrs Hill Ski Area




