Pet-friendly vacation rentals in West Stockbridge

Find and book unique pet-friendly homes on Airbnb

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Popular amenities for West Stockbridge pet-friendly home rentals

Pet-friendly house rentals

Top guest favorite
Home in Valatie
5 out of 5 average rating, 115 reviews

Escape to Lakefront Leisure—Amazing views!

BryanRating, 5 stars2 weeks ago
We had the BEST TIME at this fantastic Lakeside house in Valatie!  The house itself has 3 good bedrooms – 2 large bedrooms upstairs with a nice bathroom and tub.  The downstairs has the other cute bedroom, another full bathroom,  a good sized kitchen open to a great and large living and dining area. The VIEW from the main room is stunning and was our ‘TV’ for the week.  The lake is just gorgeous!  It has a little dock with kayaks and plenty of nice seating and lounge chairs.  It’s great to have a full grass lawn !  The pups loved the house and the yard and the lake!  The house was super clean and roomy but cozy in it’s feel.  So many great little towns nearby – it was just the perfect house to get away from the city!  The community was chill, even tho it was Memorial Day weekend.  Thanks to Michael who was super responsive (not that we needed anything!) but if we had a question. Etc.  Thank you Michael ! We hope to be back for another visit !!!  
Guest favorite
Home in Lenox
4.88 out of 5 average rating, 161 reviews

Spacious 4-Bedroom Colonial Gem in Downtown Lenox

NancyRating, 5 stars1 month ago
Our group of 5 were very happy with our stay in Lenox. Location was perfect in that it was close to everything we had planned in the area. Everything went very smoothly in booking the rental and all the communication involved. The place was very nice.
Guest favorite
Home in Germantown
4.97 out of 5 average rating, 336 reviews

Fantasy Cottage/Mountain Views/Trails/Fire pit

DenzeylRating, 5 stars1 week ago
Martina’s cottage was fantastic. Everything was as advertised. Fantastic lighting, large space and, unbelievable views.
Guest favorite
Home in Woodstock
4.94 out of 5 average rating, 338 reviews

Woodstock Historic Artist Estate - The Pond House

CodyRating, 5 stars1 month ago
No notes, incredible escape even in the pouring rain. The ambience, even down to the little things like walking through the door to classical music, was truly top notch.
Superhost
Home in New Marlborough
4.88 out of 5 average rating, 134 reviews

Lake House in the Berkshire (Access Dock & Canoe

ShwuRating, 5 stars3 months ago
We enjoyed our stay at the house. Mitchell was very responsive and communication was easy. The house is near butternut and GB. Hopefully we will come back in the summer to enjoy the outdoors.
Guest favorite
Home in Copake
4.96 out of 5 average rating, 194 reviews

Lakefront +pets +skiing +bbq +firepit +games

MelanieRating, 5 stars1 month ago
We had a wonderfully relaxing stay at Frank’s beautiful home! The house was spotless, well-equipped, and had everything we could have needed for a comfortable visit. We especially enjoyed the easy access to the lake and the close proximity to great hiking trails. It was the perfect spot to unwind and connect with nature. We would love to come back again soon!
Top guest favorite
Home in Great Barrington
4.99 out of 5 average rating, 95 reviews

Private Home in The Berkshires (New Hot Tub!)

DanielleRating, 5 stars2 weeks ago
Great stay! This is our second time staying at Bradley’s place and it was exactly the same as last time, in a good way. Place was clean, great neighborhood, very quiet!
Top guest favorite
Home in Saugerties
4.98 out of 5 average rating, 153 reviews

The Stone House

AdeleRating, 5 stars1 week ago
We enjoyed our stay at Kevin's place. As many others have said, the surroundings are even more beautiful in person. There is another rental unit right across the yard, which we didn't realize, but ultimately we found it nice knowing there were other people around. The kitchen and bathroom(s) were notably gorgeous and comfortable - though we didn't cook, I've never seen a better stocked kitchen in terms of cooking tools at an Airbnb. A spacious and peaceful retreat.

Pet-friendly home rentals with a pool

Guest favorite
Condo in Windham
4.89 out of 5 average rating, 193 reviews

Cozy Hideaway Windham, Hunter ,Pool,Pickleball.

SuzanneRating, 5 stars1 week ago
Beautiful gem, fantastic hosts. Wouldn’t change a thing. Thank you!
Guest favorite
Tiny home in Ghent
4.97 out of 5 average rating, 156 reviews

Country Getaway Tiny House in woods w/Pool/Sauna

FrankRating, 5 stars7 months ago
Robert was an excellent host. Proactively reached out with help to find the home, and a whole host of recommendations. Great space, very private, and had everything you could need.
Guest favorite
Cottage in Kingston
4.92 out of 5 average rating, 376 reviews

Kapitan’s Cottage: Private Retreat with Salt Pool

LydiaRating, 5 stars2 weeks ago
The house and property were absolutely lovely, clean, and peaceful. We had everything we needed. When there was a big rain storm and the internet had some issues, the hosts responded immediately and reset the modem and offered to call Spectrum. Issue was fixed right away. The pool was perfect temp and so restorative. Would 12/10 recommend staying here.
Guest favorite
Home in Rhinebeck
4.89 out of 5 average rating, 143 reviews

4Br Mountain Brook House on 130 acres w/ trails

DanielaRating, 5 stars2 weeks ago
Rick's House (Hemlock House) was a wonderful getaway! We unfortunately didnt hit the best weather but the house was perfect for a cool and rainy long weekend both indoors and out. The open first floor with huge kitchen was great for hanging out and cooking with alot of cozy nooks to read and relax. There was a lot of various outdoor spaces and decks to lounge on as well and the hot tub was perfect for the cooler cloudy weather. The bedrooms were all comfy and each room having its own bathroom was another plus. We all loved the sounds of the creek and being able to walk around the trails in the back. The House is in a fantastic location - only 10 minutes from Rhinebeck which has everything you need and is great for walking around, shopping and dining. Rick was informative and provided a great guidebook with clear instructions and local resources and recommendations. Thanks for a lovely stay!
Guest favorite
Cottage in Averill Park
4.94 out of 5 average rating, 140 reviews

Cozy cottage with pool, walking distance to lake

KristenRating, 5 stars5 days ago
We really enjoyed our stay, it was perfect distance from family and friends. Would highly recommend this place.
Guest favorite
Guesthouse in Stanfordville
4.93 out of 5 average rating, 181 reviews

Eco Cottage in the Woods

KymRating, 5 stars1 week ago
The Eco Cottage was a perfect, tiny gem tucked away in the middle of the beautiful green woods. It was so private, peaceful, and serene. It truly felt like my own little retreat and since I was there to go on a retreat, this was the perfect place to lay my head at night. I loved walking the trails and wow, the pool, which looked so inviting (even if it was a bit too chilly to use this time!). Everything was clean, and the instructions were clear and easy to follow. Hosts checked in regularly but gave me my privacy. I really enjoyed my stay SO MUCH and will absolutely be booking here again the next time I’m in the area. Highly recommend!
Top guest favorite
Cabin in Red Hook
4.96 out of 5 average rating, 352 reviews

Modern Upstate Cabin, near Rhinebeck NY

EllieRating, 5 stars2 weeks ago
We recently stayed at Tina's and had a great time. The location is secluded, incredibly peaceful and quiet — all you can hear are the birds in the morning. The home itself is clean and looks just like the photos. We also loved that we could bring our dog along with us. We live in the city so our pup doesn't get to touch much grass, and he had a blast running through the fenced-in yard. Although we originally booked because the house has a pool and we were hoping for good weather, it rained almost the entire time we were there... Nonetheless, it felt like the coziest home for a rainy weekend, and we really enjoyed our stay. We loved sitting inside by the fire to watch a movie, cooking in the kitchen and building a fire outside when the rain stopped. The location was also great for driving into Rhinebeck, Red Hook, Hudson and surrounding breweries and wineries.
Superhost
Cottage in Hudson
4.81 out of 5 average rating, 106 reviews

Saltwater Pool & Cottage@ Hudsons ClearCreekFarm

NatalieRating, 5 stars1 month ago
Had a beautiful stay and would 100% return and tell friends about it. Cute and cozy stay, lovely little town and beautiful views.

Private, pet-friendly home rentals

Guest favorite
Barn in East Chatham
4.98 out of 5 average rating, 83 reviews

Luxury Barn Retreat — All-Season Escape Awaits!

JoshuaRating, 5 stars1 month ago
A lovely break from the city - which is exactly what we wanted. Our dog loved it too. The barn is spacious and well appointed and the grounds are perfectly maintained.
Top guest favorite
Home in Canaan
4.96 out of 5 average rating, 54 reviews

Private Retreat: Hot Tub! Movie Room! Pool Table!

MusserRating, 5 stars1 week ago
This was a bit of a last minute decision to come to the Berkshires and I was grateful that Tiffany could accommodate some quick changes. The house is just as described--lots of space, nice setting, pool table was fun (and cool in the basement), and I appreciated that our two dogs could be included. Even though the house is in NY, it is not far from the hiking trails and museums. We would like to come back--a lot more to see and do in this area.
Guest favorite
Cottage in Austerlitz
4.93 out of 5 average rating, 88 reviews

Harvey Mountain Lodge by State Forest

LauraRating, 5 stars6 days ago
Lisa’s place was wonderful, and I highly recommend it. She was very responsive to questions, and I appreciated the helpful notes around the house. The space was thoughtfully made dog-friendly, with couch covers that kept things worry-free. The garden was beautiful, and the property offered great outdoor spaces—a back deck, a front grill with seating, and a creekside trail (not fully cleared, but enjoyable). My dog and I loved it. We stayed on the top floor and loved the airy living room with high ceilings and skylights. Lisa’s nature-inspired decor on the desk and fireplace mantle added charm. The bedroom was spacious, and the extra-large bed was incredibly comfortable. The house having three bathrooms was a nice bonus.
Top guest favorite
Loft in Great Barrington
5 out of 5 average rating, 14 reviews

The Nest 5 min walk to downtown Great Barrington

ShanaRating, 5 stars2 weeks ago
We really enjoyed our stay and wish we would have had more time. Appreciated how updated, clean, and free of clutter the place felt. It is a very quiet and peaceful street, but still walkable to the main street, and there is so much to do in the area within an easy drive. We would definitely look to stay here again on a future visit.
Top guest favorite
Cabin in Saugerties
5 out of 5 average rating, 35 reviews

Luxury A-Frame Cabin w/ Hot Tub

ChrisRating, 5 stars5 days ago
Fil & Ellie’s place was the perfect stay for our getaway. Their home is amazing. We were very impressed by the amenities, the cleanliness and attention to detail. This place has everything you’ll need for a great stay. The hosts were also very helpful in answering our questions and assisting us with check-in. I would highly recommend staying here if you have the chance.
Top guest favorite
Home in Great Barrington
5 out of 5 average rating, 49 reviews

The Yellow Victorian With Chefs Kitchen

BenRating, 5 stars1 month ago
We loved the Yellow Victorian! Danielle was a great host--clear, honest, responsive. The space is gorgeous, with so many large rooms, each with its own flavor. The beds were comfy, the living room cozy. And the best part were the kitchen and garden. It felt really spacious for the family to cook together, dink coffee, sit outside and chill. The kitchen was well stocked with pots and pans and all the glass and servingware you will need--loved how eclectic the choices were, made the stay fun! We are definitely coming back next time we are in south county :-)
Top guest favorite
Cabin in East Nassau
5 out of 5 average rating, 46 reviews

Luxury Cabin | Breathtaking Views & Outdoor Fun

ChristineRating, 5 starstoday
The space is luxurious and stunning even more beautiful than the photos, so thoughtfully designed and really helped us feel at home at once. Matt and Sarah were so helpful whenever we had any questions. We had such a relaxing stay and feel so grateful to have been able to enjoy the space!
Superhost
Farm stay in New Lebanon
4.86 out of 5 average rating, 29 reviews

1800s Carriage house in Berkshires / Hudson Valley

KarenRating, 5 stars4 weeks ago
A lovely spot with a well maintained, extremely clean, spacious apartment. It was very well appointed, especially the kitchen and bathroom. Anything you needed was there. Great bed and comfortable furniture. Close to a few good restaurants and a wonderful farmers market. I would return in a minute.

Quick stats about vacation rentals that are pet-friendly in West Stockbridge

  • Total rentals

    30 properties

  • Nightly prices starting at

    R2,693 ZAR before taxes and fees

  • Total number of reviews

    810 reviews

  • Family-friendly rentals

    20 properties are a good fit for families

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wifi availability

    30 properties include access to wifi

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