Pet-friendly vacation rentals in Stockbridge

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Popular amenities for Stockbridge pet-friendly home rentals

Pet-friendly house rentals

Guest favorite
The uniquely shaped house, adorned with shingles, is surrounded by lush greenery. Large windows reflect the vibrant foliage, allowing natural light to illuminate the structure. The natural stone wall complements the rustic aesthetic, creating a harmonious blend with the wooded landscape.
Home in Fairlee
4.96 out of 5 average rating, 505 reviews

Cozy Bow House Perched in Trees w/ Hot Tub & View

DianaRating, 5 starstoday
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!
Top guest favorite
A two-story log house is set among trees with snow covering the ground. A wide wooden deck features multiple chairs, and a door is visible on the base level. The structure showcases earthy tones and has a circular window above the entrance, enhancing its rustic appearance.
Home in Roxbury
4.92 out of 5 average rating, 202 reviews

Captain Tom's Cabin - Secluded Vermont Getaway

RahulRating, 5 stars2 weeks ago
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!
Guest favorite
The exterior of the cottage features a warm wood facade with red accents. Large windows allow natural light to fill the interior. A spacious deck is visible, equipped with a grill and outdoor seating, providing a comfortable area to enjoy nature.
Home in Granville
4.96 out of 5 average rating, 145 reviews

Epic Views of the Green Mountains

ColbyRating, 5 stars1 week ago
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.
Guest favorite
A vast green meadow is depicted, dotted with bright yellow wildflowers. In the background, a classic red barn stands amidst rolling hills and gentle mountains, surrounded by clusters of trees and open fields, showcasing the serene landscape of rural Vermont.
Home in Rochester
4.97 out of 5 average rating, 144 reviews

Modern Farmhouse on 25 Acres - Superb Views

BrandonRating, 5 stars1 month ago
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.
Guest favorite
A view from the window highlights the vibrant autumn foliage surrounding a swimmable pond. The landscaped area features rocks and a grassy lawn, with seating arranged for outdoor gathering. Clear skies and colorful trees frame the serene setting.
Home in Londonderry
4.99 out of 5 average rating, 135 reviews

Modern 3-bedroom A-frame in Londonderry w/ Pond

GeorgiaRating, 5 stars1 week ago
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!
Top guest favorite
A charming wooden house is nestled on a grassy knoll, surrounded by wildflowers and tall grass. The sky is partially covered with clouds, creating a serene backdrop. Trees line the horizon, providing a natural setting that enhances the privacy of the property.
Home in Newbury
4.98 out of 5 average rating, 164 reviews

Wright’s Mountain Retreat with Sauna

NatalieRating, 5 stars3 days ago
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.
Guest favorite
A serene outdoor setting features a two-story house surrounded by greenery. A small pond reflects the landscape, while a fire pit is visible nearby. Rustic wooden chairs provide seating, and smoke can be seen rising from the fire, creating a cozy atmosphere in nature.
Home in Goshen
4.83 out of 5 average rating, 290 reviews

Nature Lover's Paradise

KevinRating, 5 stars2 weeks ago
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!!!
Guest favorite
Home in Rochester
4.95 out of 5 average rating, 196 reviews

The McKinley House

GarethRating, 5 stars3 months ago
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

Top guest favorite
A breathtaking view showcases the sun rising above the horizon, casting warm orange and yellow hues across the sky. The silhouette of Camel's Hump is visible in the distance, framed by softly illuminated clouds. The scene evokes a sense of tranquility and natural beauty.
Apartment in Barre
4.94 out of 5 average rating, 163 reviews

Relax in Recreation Paradise!

JenniferRating, 5 stars3 months ago
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!
Guest favorite
Guest suite in Ryegate
4.92 out of 5 average rating, 229 reviews

Secluded Paradise on the Connecticut River, VT

JatinRating, 5 stars3 weeks ago
beautiful property. very private. our dog really enjoyed. the patio had swings with the river view it was gorgeous.
Top guest favorite
The exterior of a cozy ranch house is shown, framed by lush greenery and flowering shrubs. The front porch is accessible via steps, with a teal door welcoming visitors. A pathway leads through the manicured lawn, enhancing the inviting appearance of the property.
Home in Mendon
4.89 out of 5 average rating, 247 reviews

Ranch at Mendon Mt Orchards

RobinRating, 5 stars4 weeks ago
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!
Guest favorite
A warm living area is highlighted by a wood-burning fireplace, providing a cozy focal point. A comfortable sofa and coffee table fill the space, while a large flat-screen TV is mounted above the fireplace. A friendly dog sits on the floor, enhancing the welcoming vibe.
Condo in Killington
4.94 out of 5 average rating, 258 reviews

AC/Dog-Friendly/Spa Onsite/Pool/Wine Bar

ErinRating, 5 stars4 weeks ago
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.
Superhost
An open living space features a bright red sofa with decorative pillows, complemented by a warm wood dining area with stools. The kitchen, equipped with stainless steel appliances, is visible in the background. Soft lighting creates a welcoming ambiance throughout the suite.
Condo in Killington
4.89 out of 5 average rating, 245 reviews

A Sweet Suite! Modern. Pool. 2RM/2BA. Shuttle. 532

IanRating, 5 stars5 months ago
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.
Superhost
A quaint wooden cabin with a rustic exterior features a decorative star made of lights above the door. The porch is furnished with two comfortable chairs and a small table, surrounded by lush greenery and trees.
Cabin in Warren
4.83 out of 5 average rating, 280 reviews

Bunny Hill Cabin -Pets, Shared Hot Tub & Lap Pool

DillonRating, 5 stars1 week ago
Excellent value, private, relaxing, tons of wildlife
Guest favorite
Condo in Killington
4.97 out of 5 average rating, 147 reviews

2 Bedroom Condo & Loft- POOL + Wine Bar/Cafe!

EileenRating, 5 stars3 months ago
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.
Guest favorite
A serene outdoor area is featured, showcasing a private heated pool surrounded by a brick patio. Lush greenery defines the background, and a rustic wooden table with chairs sits nearby, providing a space for relaxation in nature.
Chalet in Winhall
4.88 out of 5 average rating, 106 reviews

Vermont Chalet w/ Indoor Hot Tub 10Min to Stratton

BrandonRating, 5 stars3 months ago
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

Superhost
The exterior of a red cabin is framed by green grass and colorful yellow flowers. The building features multiple windows and a gabled roof, creating a charming and rustic appearance. A clear pathway leads to the welcoming front door.
Guesthouse in Pawlet
4.91 out of 5 average rating, 318 reviews

Picturesque Cabin on the Mettowee

ClareRating, 5 stars2 weeks ago
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
Guest favorite
Home in Stockbridge
4.91 out of 5 average rating, 22 reviews

Private Farmhouse w/ River Access Fly Fishing Hole

ChaunceyRating, 5 stars3 months ago
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!
Guest favorite
Two treehouse structures are nestled among the trees, with one featuring warm lighting. A wooden walkway connects them, leading to a cozy outdoor fire pit area. Surrounding foliage is lush, and the twilight sky enhances the serene atmosphere.
Treehouse in Hancock
4.96 out of 5 average rating, 480 reviews

The SugarMaple Treehouse @ Vermont ReTREEt

MikaelaRating, 5 stars2 weeks ago
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!
Superhost
A dog walks along a grassy path that leads towards a cabin, framed by trees and wildflowers. The cabin features a red roof and large windows, surrounded by lush greenery under a clear blue sky.
Cabin in Stockbridge
4.91 out of 5 average rating, 45 reviews

Stunning Artist Retreat Cabin

KatelynRating, 5 stars2 weeks ago
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.
Guest favorite
The Cluck House is depicted in a serene setting, nestled among lush green grass and colorful flowerbeds. A flowering tree stands nearby, while the main farmhouse is visible in a blue hue, providing a picturesque backdrop to this charming guest space.
Tiny home in Woodstock
4.99 out of 5 average rating, 136 reviews

The Cluck House

JohnRating, 5 stars2 weeks ago
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
Superhost
A cozy house is set against a snowy landscape, featuring a covered front porch with white railings. The exterior showcases neutral tones and is surrounded by trees, providing a secluded atmosphere. Snow covers the ground, enhancing the peaceful winter scene.
Home in Stockbridge
4.78 out of 5 average rating, 86 reviews

Ski, snow mobile, hiking, fun on slopes & trails!

AnnaRating, 5 stars1 month ago
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!
Top guest favorite
The spacious interior of the yurt features a circular design with natural wood and fabric elements. Comfortable seating areas include a queen-sized futon and a wooden sofa. Large windows allow natural light to fill the space, while a wood stove provides warmth.
Guesthouse in Hartland
4.95 out of 5 average rating, 992 reviews

Yurt In The Woods - Private Refuge

HeidiRating, 5 stars2 weeks ago
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.
Guest favorite
A charming A-frame exterior is seen, featuring a dark grey facade and a distinctive metal roof. Two wreaths decorate the front door, which is framed by a small wooden deck. Freshly fallen snow blankets the surrounding shrubs and landscape.
Barn in Fairlee
4.9 out of 5 average rating, 500 reviews

Private Barn On a Hilltop in Fairlee, Vermont

JenRating, 5 stars2 weeks ago
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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