
Pet-friendly vacation rentals in Stockbridge
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Top-rated pet-friendly home rentals in Stockbridge
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Pet-friendly house rentals

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.

Breakaway House "B" Side: Renovated Ski Home
Well located, close to the Killington ski area and nearby restaurants etc. Nicely kept. Place was very warm on the inside, even though temp was in the teens outside. Host was very responsive, flexible and informative. Even though the bunk bed in one of the rooms was a bit wobbly, all the other beds in other rooms were very comfortable. All in all, we had a great stay!

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
Had a fantastic time. Went backcountry skiing before work and then worked from his place with multiple people doing zoom calls without issues. Perfect place for us

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.

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!

Rand’s Retreat
We had a great stay! Loved playing board games in front of the fireplace. The house is minutes to Brandon (an adorable town) but still feels away from it all.
Pet-friendly home rentals with a pool

Upper Yurt Stay on VT Homestead
I needed a little break from my every day Vermont life. This was the perfect spot to get away from everything, but still not be far from home. I would definitely go back! Thank you so much!

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.

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

Cute Cool Cabin! Plymouth, Vermont.
Alecia and John were meticulous hosts from the well curated guide book to their responsiveness when we had questions. All made for a wonderful family fourth of july! We look forward to returning.

Hubbard Park guest suite
This was my second time staying here, and this time I stayed with my family in the bigger apartment, which was perfect for a family of four! The kids loved the huge bathtub and bunk beds!

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!

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.

Powder Park Place: Lower Unit. Cozy 2BR/1BA. Ski.
great stay!

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.

Hilltop Cabin on Barrows Road
Thank you Carol for a wonderful stay at your home in Northfield Vermont. The home is beautifully maintained, comfortable and perfectly located for exploring the area, hiking and skiing. We especially enjoyed the well equipped kitchen and the beautiful property. The home is extremely well furnished and cozy, welcoming and relaxing. We would definitely recommend your home for anyone looking for a great stay in Vermont! I received a bonus service-Carol helped me remove all the snow from my car! What a great host!

Beautiful Log Cabin with views near Lake
Exceeded our expectations. Kristine was super responsive and extremely helpful. The cabin is so spacious and peaceful. Easy drive from Burlington and other surrounding towns. Planning our next stay already!
Quick stats about vacation rentals that are pet-friendly in Stockbridge
Total rentals
40 properties
Nightly prices starting at
ﺩ.ﺇ110 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
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- Okemo Mountain Resort
- Sugarbush Resort
- Stratton Mountain Resort
- Bolton Valley Resort
- Pico Mountain Ski Resort
- Magic Mountain Ski Resort
- Tenney Mountain Resort
- Cochran's Ski Area
- Baker Hill Golf Club
- Fort Ticonderoga
- Dartmouth Skiway
- Northeast Slopes Ski Tow
- Country Club of Vermont
- Mount Sunapee Resort
- Adirondack Extreme Adventure Course
- Dorset Field Club
- Hildene, The Lincoln Family Home
- Bromley Mountain Ski Resort
- Ekwanok Country Club
- Killington Adventure Center
- Whaleback Mountain
- Storrs Hill Ski Area
- Fox Run Golf Club
- Lake Sunapee Country Club