Pet-friendly holiday rentals in Monterey

If there were more stars this place would warrant them. Incredibly clean and thoughtfully stocked. The appliances were great, the cupboards were full of dishes, pots and pans. Bed linens were pristine. Very spacious and quiet. We were very happy here.

Great stay! Thank you so much.

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

Beautiful area and beautiful house – well-designed, spotless, and equipped with everything we needed. It looked even better in person than in the photos. The open family area was amazing and spacious. We also had a lot of fun exploring the farm and surrounding property. Definitely one of the loveliest Airbnbs we've stayed at. Highly recommend!

Niki and Adam’s place was wonderful! Space for everyone, well equipped, comfortable and clean. Communication responses were quick and clear. All 3 generations of my family thoroughly enjoyed their home and its surroundings. Highly recommend!

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 stayed here for the weekend of our son’s graduation nearby, and it was the perfect place to land. The house is beautiful and full of charm, with original artwork, comfy chairs, and inviting spaces to gather and relax. You can really feel the care and attention the hosts put into making it special. Thanks to a stretch of spring rain in the area, the landscape around the stone house was vividly green, lush, quiet, and full of life. One of our favorite moments was sitting on the bed and being surprised by a hummingbird visiting our window. Such a lovely and memorable stay!

we had a lovely time at Seth’s cottage by the river. Everything was very well appointed and comfortable. I think the beds were the best I’ve had an Airbnb. There was easy access to new Paltz and kingston. I have no hesitation in recommending Seth’s place.

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.

Patrick and Monica were incredibly welcoming, making us feel right at home. They were communicative, helpful, and especially great with our dogs. We loved the property and left feeling fully rested. We would love to come back!

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.

We truly enjoyed our stay at Wilderkill Barn. Maria Cristina and William were exceptional hosts—warm, attentive, and genuinely committed to making our visit special. They went above and beyond to make us feel welcome. The home was a haven, with a hot tub, sauna, pool, fire pit, pool table, and immersive sound and movie systems—all of which made our stay delightful despite the cold, dreary May weather. We can't thank them enough. ***That said, we feel it's necessary to address a serious issue with Airbnb itself that arose while booking this property, unrelated to the property itself. An unexpected tax was added after booking, and Airbnb has yet to provide a clear explanation. After years of loyalty, we were disappointed by their evasive and unhelpful customer support. This experience has made us reconsider using the platform in the future. We urge potential users to scrutinize all fees carefully and be aware that Airbnb’s support may be difficult to navigate if problems arise.***

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

Home is very beautiful. Jim and Susan were very responsive when needed we felt right at home everything was right at our fingertips when needed. We came for a weekend girls getaway and this home helped us achieve that peace we needed. Very spacious we will be back again.

My family and I took a weekend trip here with our two dogs, and had a very cozy stay! The cottage was cute, clean, and felt homey. Rachel was a responsive host and set up a time to chat beforehand, which I really appreciated. I would definitely book another stay here!

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!

What more could you want? This quaint cabin situated in the woods offers privacy, unique architecture, comfort, and peace. It’s equipped with everything you could possibly need, and the hosts were truly some of the most responsive and kind people I have ever interacted with. They truly went above and beyond for us. We stayed with a toddler and two dogs, and they all loved the property and the cabin. We will most definitely be back!

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.

What a beautiful place to stay! Jaryn made it easy to check in, gave clear instructions, and offered any help we needed. As other reviewers noted, if you know you have limited access to cooking, you'll be fine. We maximized the fridge and microwave and used the coffeemaker each morning. The barn conversion is incredible - my husband is an architect and was very impressed. Our favorite was the screened-in porch, and we spent lots of time sipping coffee, writing, and enjoying meals out there (I brought my blanket!). Monterey is an incredible place to stay. Beautiful everywhere you go, but close to so much.

We really enjoyed our long weekend at Jake’s rental. I love the aesthetic of the space. It was very comfortable for myself, my husband and our mini Aussie dog. It is a quick drive to Great Barrington. We loved Mooncloud which features interesting cocktails and charcuterie. Down the street from the house is access to the Appalachian Trail. It was an easy drive to Pittsfield for my brother’s birthday. Would love to come again!

We had such a fab time in the Berkshires while staying at Suzy + Marc’s cabin! It felt like I was in countryside novel. A great location as it’s tucked into the woods but a quick drive to Great Barrington and for food and things to do. They were also very accommodating and communicative! Hope to come back in the fall!