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

Cozy Bow House Perched in Trees w/ Hot Tub & View
The Bow house was a beautiful place and Jen was incredibly hospitable and responsive. This is an amazing place to come and get away from the noise. Everything was so clean and cozy. Would definitely come again!

Captain Tom's Cabin - Secluded Vermont Getaway
Claire was an amazing host-beautiful location and she treated us like VIP guests with homemade soup and cookies! My parents loved it. Thanks for the stay!

Epic Views of the Green Mountains
We had a great stay at William’s. The location was beautiful and the house was comfortable. We had a great mix of day-tripping and relaxing with a view. We also ran into William and he was very helpful and friendly.

Modern Farmhouse on 25 Acres - Superb Views
We had a quiet stay at the Farmhouse. Very peaceful and quiet location. Lots of space for our dog to roam. The house is very nice and clean. We enjoyed having coffee and looking out across the fields, reading, and cooking. It’s near the small village of Rochester with a few restaurants and otherwise we explored neighboring towns like Middlebury, Waitsfield, Stowe, and Montpelier.

Modern 3-bedroom A-frame in Londonderry w/ Pond
We loved our stay here!! It was the perfect getaway for a long weekend. The property is beautiful and private but close to anything that you might need. The kitchen was super well stocked, beds were comfy, and we really appreciated the firewood supply. Nikki & Topher were great hosts - extremely responsive to all questions we had and proactive about check in/check out instructions. Would definitely come back!

Comfortable farmhouse with stunning views
Such a cool house. We loved the charm of the older section of the house. So many private spaces to cozy up and read a book. Then there is the more modern portion of the house. It was perfect for the folks to watch tv and enjoy the VT scenery out of the large windows. The road is quiet and the area is lovely. We easily drove into Manchester for groceries and dinner. Really loved it!!

Wright’s Mountain Retreat with Sauna
We loved spending our time in Vermont at Bonnie’s place! The house had everything we needed and Bonnie was a great and responsive host. The horses next door were such a treat for our kids to see and the views were beautiful.

Nature Lover's Paradise
Philips place was literally perfect! The location, the awesome house filled with super cool art, the cozy feel of the house, the amazing outdoor area we had available to us all made this a perfect experience! Philip was great with communications and I would recommend this place to anyone looking for a perfect place to stay in this area of VT. My dad and I were up there for a quick 2 day stay. We'll both be returning with our significant others to vacation there and will absolutely be coming here in the future whenever we travel to this area!!!
Pet-friendly home rentals with a pool

Upper Yurt Stay on VT Homestead
Jonathan communicated well and the place was beautiful - would definitely come back again !

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!

Ranch at Mendon Mt Orchards
We enjoyed our stay. we felt at home. very spacious and cozy. this house has everything you need for your stay. Very close to Rutland. The fresh baked apple pie was a bonus. It was so delicious. Everything was perfect for us! Thank you! We will definitely be back again!

AC/Dog-Friendly/Spa Onsite/Pool/Wine Bar
The Woods complex is a peaceful retreat style community. The condo is cozy with fresh, on point decor. The kitchen was a bit tighter than expected but has generous countertop space. The hosts are friendly and responsive. The stairs to get to the condo could be difficult to navigate for people with mobility restrictions.

A Sweet Suite! Modern. Pool. 2RM/2BA. Shuttle. 532
The place was great, clean, nice bathrooms. The oven seemed like it wouldn't go up to temperature at one point so I messaged the host and they responded right away to get the maintenance folks over. But it turned out that it was just set to Celsius and I was able to look up how to change it online (Hold down the broil button!). There were PLENTY of towels/linens which was nice.

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!

Cozy/Private, close to hospital, i-89
Laurie was a wonderful host — very friendly and attentive. Her home is in a beautiful setting and the unit is clean and comfortable. Pet-friendly too, which was a bonus for us. We enjoyed staying in Laurie's home and would return.
Private, pet-friendly home rentals

Picturesque Cabin on the Mettowee
Back to nature, tightly placed directly upon the river, such a lovely place. Totally off the grid, no phones, tv, I loved it. Bev is the perfect hostess. I highly recommend for those wanting a quiet get away.

Hillside Cottage @ The Mettawee Retreat
Our stay was fantastic! The cabin was clean, comfortable and cozy. There was obvious attention paid to the little details that make a trip extra relaxing. I don't think that there was anything that we wanted that wasn't thought of and ready for us. We booked our stay with the intention of disconnecting and unwinding& we were able to do exactly that. The property is absolutely magical! There was an endless amount of beautiful flowers and wildlife with a winding river. Our favorite part was relaxing on the deck watching the deer and birds. The customer service couldn't have been better. They went out of their way to be helpful and friendly. we definitely recommend & plan to return for a longer stay!

Vermont Hill Top Studio
The location is peaceful and private with a beautiful mountain view - maybe the most stunning view of any Air BNB we’ve stayed in!! Comfortable bed with cozy linens and very clean bathroom with all amenities (soaps, shampoo, conditioner, hair dryer). Our dog was at home and welcomed with his own water bowl, dog bed and mats for his food bowls. He met the hosts dogs and they had a ball running around the grounds together. Coffee/tea station and seltzer water was a nice touch! I highly recommend Xtine’s place for your Castleton stay!

Pine Cabin, Galusha Hill Farm, incredible view!
We loved our stay and hope to come back again!

The SugarMaple Treehouse @ Vermont ReTREEt
Loved staying here! So peaceful with great views. Very private and comfortable! Derek was very friendly and did an amazing job on the treehouse, two thumbs up!

The Cluck House
I really loved staying at the Cluckhouse. It was truly so beautiful and peaceful, a tranquil space that honestly was almost fairytale beautiful (even in the quiet rain of one of the days), while also being only 10 mins from the town Woodstock. Tina was an amazing host; she reached out well before I arrived with directions and suggestions, she was extremely thoughtful once I arrived, and, most importantly, a wonderful person with a calm peaceful energy; I really enjoyed talking to Tina whenever I’d come thru the kitchen. I’d love to stay here again

Outside Inn - Hot Tub/Killington/MtnTop Inn/VAST
Such a beautiful and comfortable place for our group to stay at. The beds were super comfortable, it was very relaxing. We spent time enjoying the hot tub and fire pit as well. Came in for a wedding at the Mountaintop Resort, with that being a 6 minute drive, we had nothing to worry about with time. There is a cute general store a couple mins up the road and Rutland isn't far for bigger needs. Nicole was very proactive on giving us all the instructions we needed to check in and plenty of recommendations for the area. There are little gems in the house that were hidden in plain site which added to the charm. Overall, this was a fantastic experience and I absolutely would stay at their property again!!

Yurt In The Woods - Private Refuge
I stayed at Angela’s yurt for Memorial Day weekend. It was exactly as described. My boyfriend and I had a very peaceful long weekend. The space was cozy and adorable and we especially loved the wood burning stove. Was a great stay, would definitely return and highly recommend.
Quick stats about holiday rentals that are pet-friendly in Stockbridge
Total rentals
40 properties
Nightly prices starting at
$39 SGD 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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- Stratton Mountain
- Sugarbush Resort
- Okemo Mountain Resort
- Bolton Valley Resort
- Pico Mountain Ski Resort
- Stratton Mountain Resort
- Dartmouth Skiway
- Magic Mountain Ski Resort
- Cochran's Ski Area
- Fort Ticonderoga
- Autumn Mountain Winery
- Dorset Field Club
- Tenney Mountain Resort
- Hildene, The Lincoln Family Home
- Bromley Mountain Ski Resort
- Country Club of Vermont
- Baker Hill Golf Club
- Northeast Slopes Ski Tow
- Ekwanok Country Club
- Vermont National Country Club
- Fox Run Golf Club
- Lincoln Peak Vineyard
- Adirondack Extreme Adventure Course
- Killington Adventure Center