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

Escape to Lakefront Leisure—Amazing views!
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 !!!

Spacious 4-Bedroom Colonial Gem in Downtown Lenox
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.

Fantasy Cottage/Mountain Views/Trails/Fire pit
Martina’s cottage was fantastic. Everything was as advertised. Fantastic lighting, large space and, unbelievable views.
Woodstock Historic Artist Estate - The Pond House
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.

Lake House in the Berkshire (Access Dock & Canoe
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.

Lakefront +pets +skiing +bbq +firepit +games
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!

Private Home in The Berkshires (New Hot Tub!)
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!

The Stone House
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

Cozy Hideaway Windham, Hunter ,Pool,Pickleball.
Beautiful gem, fantastic hosts. Wouldn’t change a thing. Thank you!

Country Getaway Tiny House in woods w/Pool/Sauna
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.

Kapitan’s Cottage: Private Retreat with Salt Pool
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.

4Br Mountain Brook House on 130 acres w/ trails
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!

Cozy cottage with pool, walking distance to lake
We really enjoyed our stay, it was perfect distance from family and friends. Would highly recommend this place.

Eco Cottage in the Woods
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!

Modern Upstate Cabin, near Rhinebeck NY
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.

Saltwater Pool & Cottage@ Hudsons ClearCreekFarm
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

Luxury Barn Retreat — All-Season Escape Awaits!
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.

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

Harvey Mountain Lodge by State Forest
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.

The Nest 5 min walk to downtown Great Barrington
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.

Luxury A-Frame Cabin w/ Hot Tub
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.

The Yellow Victorian With Chefs Kitchen
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 :-)

Luxury Cabin | Breathtaking Views & Outdoor Fun
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!

1800s Carriage house in Berkshires / Hudson Valley
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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- Hunter Mountain
- Six Flags New England
- John Boyd Thacher State Park
- Jiminy Peak Mountain Resort
- Windham Mountain
- Albany Center Gallery
- Bash Bish Falls State Park
- Taconic State Park
- Catamount Mountain Ski Resort
- Zoom Flume
- Kent Falls State Park
- Mount Snow Ski Resort
- Mount Greylock Ski Club
- Berkshire East Mountain Resort
- Hunter Mountain Resort
- Norman Rockwell Museum
- Mohawk Mountain Ski Area
- Bright Nights at Forest Park
- Hartford Golf Club
- Hancock Shaker Village
- Mount Sugarloaf State Reservation
- Bousquet Mountain Ski Area
- Opus 40
- Naumkeag