
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

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!

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!!!

The McKinley House
We had a great stay, lovely welcoming home and great location - short walking distance to nice places in town and 30min drive to either Sugarbush or Killington/Pico. Thank you!
Pet-friendly home rentals with a pool

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!

Secluded Paradise on the Connecticut River, VT
beautiful property. very private. our dog really enjoyed. the patio had swings with the river view it was gorgeous.

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.

Bunny Hill Cabin -Pets, Shared Hot Tub & Lap Pool
Excellent value, private, relaxing, tons of wildlife

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

Picturesque Cabin on the Mettowee
Very nice stay- Beverly was really friendly and helpful. The river nearby is lovely and the place has every amenity you could need. I wish I was a bit more prepared - I have Verizon and didn’t get service at the place or in the small town. I had to drive 10-15 mins towards Manchester. She communicated that there is WiFi at the library and a store which are super close but I didn’t try to access. It made directions or looking up restaurants a bit tricky

Private Farmhouse w/ River Access Fly Fishing Hole
We checked in to Kalyn’s house just before a storm gave us 15” of fresh snow. What a great place to get cozy in the winter! The house is remarkably clean given its rustic charm. The beds and bedding were all amazing. The record collection and fireplace set the mood for cooking and enjoying a meal. Our two sons and sheepdog Denver loved it too!

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!

Stunning Artist Retreat Cabin
Such a cute, unique cabin! It has inspired me to maybe build one back at home! We especially loved the tiny fireplace, seeing the stars from the loft, and the frog music. Only note for future guests is to make sure to read the full description as she notes that the Internet is spotty and didn't work the entire stay for us.

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

Ski, snow mobile, hiking, fun on slopes & trails!
Great spot, it was perfect for what we needed! I love how secluded the house feels, I wish we had better weather so we could have enjoyed the outdoor firepit and the front porch more. The house had everything we needed and everything was clean and comfortable!

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.

Private Barn On a Hilltop in Fairlee, Vermont
Heaven on Earth does not come close to describing this property. Perfect place for city goers to escape into nature and be reminded of what serenity and peace are. We were able to see the stars at night like we never have before. My partner and I kayaked, visited Glen Falls and had a blast at Dog Mountain. Highly recommend all these activities! Visiting Chapman’s General Store (5 minutes from the property) is a must! Amy and Reg were very accommodating and communicative when we needed anything. Reg was nice enough to point out a short trail in the back of the property where our pup could play in the water a little. We were grateful for every minute spent here and the clean, respectful and inviting environment they have created for their guests.
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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- Stratton Mountain
- Sugarbush Resort
- Okemo Mountain Resort
- Bolton Valley Resort
- Pico Mountain Ski Resort
- Stratton Mountain Resort
- Magic Mountain Ski Resort
- Cochran's Ski Area
- Dartmouth Skiway
- Fort Ticonderoga
- Dorset Field Club
- Tenney Mountain Resort
- Hildene, The Lincoln Family Home
- Autumn Mountain Winery
- Bromley Mountain Ski Resort
- Fox Run Golf Club
- Northeast Slopes Ski Tow
- Baker Hill Golf Club
- Ekwanok Country Club
- Vermont National Country Club
- Cozy Cottages & Otter Valley Winery
- Country Club of Vermont
- Montshire Museum of Science
- Adirondack Extreme Adventure Course