
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.
Vacation rentals for every style
Get the amount of space that is right for you.
Popular amenities for Stockbridge pet-friendly home rentals
Pet-friendly house rentals

Keys to Vermont
Our crew enjoyed their stay in Mary's home. She was very friendly and proactive with directions to her home.

Large New England Home w/ Gorgeous Mountain Views
This is a great house to stay in. There's a lot of space, places to sleep, sit and relax, eat, watch tv, play games, work, read, cook. Plenty of hot water.. Very private, although in a neighborhood. Nice back yard area when not covered in snow, looking up at the mountains behind. Sheri is top notch. Easy to reach, super friendly and helpful, easy going. We came at the tail end of a snow storm, but the driveway was cleared enough to get our car in and then Sheri worked with us to make sure everything was cleared before we had to go out the next day. Easy walk into the cute town of Bristol. Handful of nice shops (books, games, art, crafts, gifts, toys) and restaurants: Wokky's--ok Chinese/great staff; Minifactory--out of sight coffee/biscuits/sandwiches/fresh ingredients/lot of gluten free; Cubber's--locals' joint/excellent pizza/sandwiches; Farmhouse Chocolates--superb fresh organic truffles, bars, caramels/chocolatier is wonderful. Easy drive to Mad River Glen, Sugarbush for skiing.

Ranch at Mendon Mt Orchards
Perfect location for skiing, and cosy home that we all enjoyed (including our pup). We appreciated the thoughtful touches provided by the host, and the apple orchard was a beautiful setting. Would definitely stay again!

Mid century modern gem with views of Sugarbush
Place was as advertised. Beautiful, great location, great views, close to convenient grocery shopping and slopes. We'd love to come back some day.

Nature Lover's Paradise
We always love staying here. It’s so peaceful and the sound of the brook is so relaxing! Philip responds quickly and is an excellent host!!

Chic Farmhouse Decor | Deck w/view of Mt Sunapee
Thanks for a great stay and the clear communication! Spotless and in the perfect proximity to the mountain.

Sweet Blue Mint Ski House
This is our second stay here. The house is roomy and clean. We even had a visit from the neighborhood bear!!! Location is perfect and private. I highly recommend.

Cozy Home in Poultney, Vermont.
Kimberley's place was the perfect weekend getaway, with plenty of space, a very responsive host, and exactly as described on the website. Had we not brought our own boardgames to play, she even has a nice collection to stay busy now matter what the weather is outside. Would love to stay there again next time I am planning a board gaming trip!
Pet-friendly home rentals with a pool

Magical Farm Getaway - a must visit!
A fun winter break/birthday getaway! Sarah’s house had plenty of bedrooms for all guests. The game room, pool table, and wood stove/fireplace were great to have on these cold February days. Everyone enjoyed the sunroom and large dining table. The hot tub and outdoor sleds were used as well. The history of the house and beautiful views from the property were an interest to all. I bet this house is a lovely spot in the summer as well!

Secluded Paradise on the Connecticut River, VT
Keita's home was beautiful! right next to the river and very peaceful. The space was cozy and perfect for a getaway.

Relax in Recreation Paradise!
Chad was an incredible host! He was extremely accommodating with any requests we had. The views from his place are breath-taking! We enjoyed snowshoeing from the backyard onto trails in the woods. I fell in love with his cat who visited daily! He kept the driveway plowed and salted in a timely fashion. We enjoyed our stay and would highly recommend his place!

SugarBear Pool, Hot Tub, 2 En Suite BRs, FirePlace
Dan & Holly are amazing hosts. They provided everything needed to make our week great. They left dining recommendations and all of the information we needed for the property. It was the perfect space for our family. The on-site amenities were great. The pool space was super clean and the staff was amazing. The property is well maintained and we had everything we needed to feel at home. We would definitely recommend this property to friends and family. Downtown Rutland was a short drive, and there was so much to see just minutes from the property. Dan & Holly are extremely responsive and truly think of everything. We had no questions and checking in and out was a breeze because they are so thorough. It was a wonderful experience from start to finish.

Moon Valley Country Retreat no clean fee pets yes
There is not enough to say about the pristine beauty that is Loraine’s cabin. The instructions were helpful in navigating into the property and lights were turned on as it was dark to assure my comfortable arrival. The cabin feels like a nurturing home and is equipped with comforts and small touches. The bed was neatly made and felt like a picture walking in to see it. The stairs are cabin stairs and there is caution to take your time and step gently. Seemingly every question was answered with small notes around the cabin and a detailed welcome book. The care and attention to detail was perfection in a stay. I only wish I had been on a longer trip to fully enjoy the grounds and the surroundings. It was easy to feel at home and welcome with Loraine and Dean as hosts.

Hilltop View Lodge - White Mountains, NH
Our stay was wonderful at the cabin. The cabin was clean and centrally located to winter activities. Andrea was very responsive. Cant wait to go back again

2 Bedroom Condo & Loft- POOL + Wine Bar/Cafe!
Nice place for the 6 of us and dog for a long ski weekend in March. Condo was as described. The kitchen was very clean, nothing in fridge. New fridge and new oven. The bathrooms were very clean. The beds were comfortable. The upstairs space a bit tight for 4 adults, but we managed fine. Two of the twin beds are in an open loft area, which didn’t bother us as we were all going to bed at the same time and waking early to go skiing. Just mentioning this in case you were looking for a 3rd bedroom that was fully enclosed. The Spa and Cafe/ Wine Bar were a great addition to our ski weekend activities. The host was wonderful and very responsive. We highly recommend this condo.

Vermont Chalet w/ Indoor Hot Tub 10Min to Stratton
Peaceful, Serene location just 10 minutes from Stratton. We enjoyed the use of the new hot tub, and roomy kitchen. This space is surrounded by nature with plenty of space for you and your group. Would definitely stay here again!
Private, pet-friendly home rentals

Hubbard Park guest suite
A wonderful place to stay in Montpelier. The location was walkable to anywhere you wanted to go downtown. Jamie was responsive and friendly.

Cozy cottage in peaceful location
We had such a fun trip! Nikki’s cottage was absolutely gorgeous, nestled in the countryside. Would absolutely stay here again!

Breakaway House "B" Side: Renovated Ski Home
Beautiful relaxing property. Owners very responsive and accommodating. Great for small kids and dogs. Nice big open common area for group-lounging.

White Mountain Log Home Retreat
A very kind couple and a lovely home. We had a winter storm come through at the end of our stay and they were very accomodating of a late checkout if we needed some extra time to deal with the snow. Also their hommade Banana bread is a 10/10!

Charming getaway tucked away in the Green Mtns
We appreciated how pet friendly this place was! Fenced in yard. Blankets to cover the furniture to allow dogs on them. Close enough to many different ski mountains. Perfect to come home to the wood stove and hot tub.

Private cottage in the woods
We enjoyed our stay so much! The place was nice and clean and quiet, perfectly organised and thought through. Karen was a welcoming, friendly, and helpful host. I wish more AirBnBs were like this! Would be happy to return someday.

Holiday Retreat
Amazing place and Elaine was great host! Beautiful home with peaceful surroundings. Kids enjoyed the animals (Rosie and Felicia). This stay was key to a great trip. 😁

April/May special So Vt Cabin Mt Tabor Treasure
A great escape. We enjoy our stays here. We are booked again in June. Lori is so attentive. She is always one step ahead. Thank you! 😀
Quick stats about vacation rentals that are pet-friendly in Stockbridge
Total rentals
40 properties
Nightly prices starting at
$41 CAD before taxes and fees
Total number of reviews
1.8K reviews
Family-friendly rentals
30 properties are a good fit for families
Rentals with dedicated workspaces
10 properties have a dedicated workspace
Wifi availability
40 properties include access to wifi
Destinations to explore
- Montreal Vacation rentals
- Boston Vacation rentals
- Hudson Valley Vacation rentals
- Cape Cod Vacation rentals
- The Hamptons Vacation rentals
- Long Island Vacation rentals
- Plainview Vacation rentals
- East River Vacation rentals
- New York Vacation rentals
- Québec City Vacation rentals
- Pocono Mountains Vacation rentals
- Jersey Shore Vacation rentals
- Family-friendly rentals Stockbridge
- Rentals with a patio Stockbridge
- Rentals with a washer and dryer Stockbridge
- Rentals with a firepit Stockbridge
- House rentals Stockbridge
- Rentals with a hot tub Stockbridge
- Rentals with a fireplace Stockbridge
- Kid-friendly rentals Stockbridge
- Rentals with outdoor seating Stockbridge
- Pet-friendly rentals Windsor County
- Pet-friendly rentals Vermont
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom
- Stratton Mountain
- Okemo Mountain Resort
- Sugarbush Resort
- Stratton Mountain Resort
- Bolton Valley Resort
- Pico Mountain Ski Resort
- Magic Mountain Ski Resort
- Tenney Mountain Resort
- Fort Ticonderoga
- Cochran's Ski Area
- Northeast Slopes Ski Tow
- Ekwanok Country Club
- Country Club of Vermont
- Dartmouth Skiway
- Baker Hill Golf Club
- Dorset Field Club
- Hildene, The Lincoln Family Home
- Bromley Mountain Ski Resort
- Adirondack Extreme Adventure Course
- Cozy Cottages & Otter Valley Winery
- Lincoln Peak Vineyard
- Vermont National Country Club
- Autumn Mountain Winery
- Killington Adventure Center