Pet-friendly vacation rentals in Monterey

The house was perfect for our stay, our daughter had reunion at Hotchkiss. We were able to visit and catch up with her friends and families and others from Hotchkiss, great location great gathering spot in the kitchen at the table !

We had a wonderful time at Michelle’s place. The house is spacious and full of charm, nestled in lush greenery that made the stay even more relaxing. Michelle was incredibly friendly and responsive, and we felt right at home.

Great stay! Thank you so much.

Martina’s cottage was fantastic. Everything was as advertised. Fantastic lighting, large space and, unbelievable views.

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!

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.

This house was great for a winter weekend getaway! Great Barrington, Lenox, and Stockbridge are all adorable towns to visit and are a 15 - 30m drive away. The house itself was cozy and had all the amenities we needed. Shay was very responsive. Something to know about the area is that ride shares and cabs are hard to come by, so having a car that fit everyone we were traveling with was crucial for our group to get around town.

We enjoyed the perfect escape from the city in this magical barn with gorgeous antiques and pristine views. Definitely will be back for future celebrations!

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.

Very nice place, beautiful big deck, awesome creativity to the lighting around the property. A walking path, fire pit, hot tub, big deck to relax on, and a fully equipped stage. It is a step above camping but not quite glamping. A lot of fun, and Apple is a sweet bonus hostess.

Highly recommend Patrick and Monica’s location. You feel right at home when you walk! The pool and patio views are breathtaking. The beds are very comfortable. Patrick was super responsive to my messages regarding restaurants.

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.

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 home, on a beautiful property. The natural pool is really special, and we loved staying here. Hope to be back.

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!

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.

Taryn's place is perfect for the quirky individual who is looking for eye catching and unique decor that you would not expect in a rural setting. The books, games, music selections were perfect for us and of course the "bad art" with the hilarious descriptions made for such a fun interactive experience. My only critique, which really is not the hosts fault is that my dog was able to slip through some spots of the backyard, so if you have an adventurous small doggo who cannot help but explore the beautiful surroundings on their own, please make sure they are supervised in the back yard area. My dog is about 16lbs, so if you have a medium or larger dog you might be okay with the fencing. Thank you Taryn and Bryan for the experience, I would definitely stay again.

Rachel’s carriage house is a charming and beautifully maintained property—just as described and shown in the photos. Even though the weather wasn’t ideal during our stay, we thoroughly enjoyed cozying up and relaxing in the warm, inviting space. One of our favorite features was the natural light streaming through the tall paned windows in the kitchen and dining area, overlooking the garden—a perfect setting for our morning coffee. The carriage house was thoughtfully stocked with everything we needed for a comfortable and restful getaway. It’s clear that Rachel has put a lot of care into creating a welcoming experience for her guests. We truly enjoyed our time in the Berkshires and would happily return!

We absolutely loved our stay at this cozy, charming cabin! It’s the perfect place to unplug and unwind. Nestled in a peaceful, quiet setting, the cabin feels like a true retreat from everyday life. We especially enjoyed the screened-in porch for morning coffee and evening chats. The nearby waterfalls (a 30–40 minute walk or 10-minute drive) were a wonderful way to enjoy the area’s natural beauty. The two-person soaking tub was a highlight—so relaxing after a hike! The cabin is thoughtfully equipped with a small but functional kitchen, which made it easy to prepare simple meals. We also appreciated the high-quality linens and comfortable bed—such a nice touch that made our stay feel special. While it’s ideal for unplugging, there is Wi-Fi if you need it. There are also some cute towns nearby, full of antique shops and local charm. It was the perfect blend of nature, comfort, and low-key exploration. We’re already dreaming of our next visit!

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.

What a wonderful treat it was to stay at Andrew and Suzanne’s! The space is incredibly comfortable and feels very homey. The place gives the feeling as if you’re staying with family but with all the pampered touches of a hotel. Great location to base yourself from if you want to jet set around the Berkshires!

Loved the quick weekend getaway from the city! Wanted somewhere we could stretch out into.. which Ayren’s house fully is.. loved playing the many board games provided and watching movies in the late evenings.. plus a few walks down to the lake and drive to town which is less than 15 min away.. A very communicative host with clear instructions and well laid out amenities and basic kitchen condiments.. Thanks again for a great weekend !

This was a great weekend getaway for two of us. The apartment is pristine and private. It was a great base camp for outings in the Berkshires. Stockbridge is just one mile away up the road and has tons of cute shops and restaurants.

Timothy’s place is so relaxing. His place was perfect for our group of 8. Plenty of space for all. Timothy was very responsive when we reached out with a question. The location was perfect. It was very peaceful sitting out on the porch listening to the birds. This place is in walking distance to the Appalachian Trail. We will definitely be booking again.