Kid-friendly holiday rentals in Monterey

My wife and I stayed here 2 night with our dog and had a great time. The cabin was super cozy and had everything we needed during our stay. Special shoutout to the couch, which was extremely comfortable for late night movie watching! If you are looking for a quiet weekend away to do some hiking, I would certainly recommend staying here. The town of Becket is very rural and food options can be somewhat limited but the house has a full kitchen and grill to use if that's more your style. Overall 5 stars would stay here again.

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.

This was our second time staying at the Hupi House and loved it. House is perfect for 2 families with kids, super comfortable, spacious and cosy, well equipped and lots of things to do in the area. This time we went skiing at the Butternut resort just 10 mins away and was a great experience. Lucas a very friendly and responsive host.

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.

Edson’s place was perfect for my family of 4 for a long weekend, could have easily stayed for a week. Weather was rainy and chilly but the house had everything we needed to cook and play and chill. when the sun came out we really enjoyed paddle boarding and walking around the lake. Would definitely come again

Great location with easy access to Great Barrington and other Berkshire destinations. Perfect house for families or larger groups, we had everything we needed with various sleeping arrangements. Nice open kitchen and decks. We would be happy to return.

Marty’s cabin is perfect for a Great Barrington getaway. We stayed in the cabin for a ski weekend, and it simply met all our expectations and then some. The cabin was kept extremely clean and had a ton of extras (board games, coffee, filtered water, etc.) that added a great touch. Location was perfect for a day at butternut mountain. Highly recommend, and will definitely go back next year. Thank you!

Cute place with a great location. It’s right down the street from Berkshires. Host is great too. Good communication throughout the stay.

Cute, cozy, clean, and super close to the bike trail! Perfect stay for a weekend exploring the towns along the trail.

We booked last minute to stay for a night to attend an event nearby. While our stay was brief, it was super clean, comfortable, and just what we needed. Everything smelled fresh, and Kelly’s recommendations were helpful too.

Very nice place would stay again joy was very friendly had no problems with the place at all tyvm again joy

Went for a Berkshire School reunion the two of us, perfect spot. Charming quiet grounds, perfect location for accessing Berkshire School, clean, Keurig, comfortable bed, amenities as stated (and quick confirmations from host), super easy process for check in and check out. Asked many questions and host responded very quickly and was very friendly in her communications.

We thoroughly enjoyed our stay at the Bennett’s Abode! Larry and Lana’s airbnb had just about everything a visitor would need and they even included a detailed binder full of information and ideas pertaining to the area. Larry was so prompt with his responses and always kept us in the loop. He even provided several great hiking ideas that we utilized throughout our stay at his home. We were so grateful for the overall experience and left with incredible memories!

Cindy was great with communications, and gave me all of the instructions I needed to make it a pleasant stay for me, my dog, and the hosts. I stayed Friday and Saturday nights, and enjoyed the craft beer and locally made sourdough pizza in the evenings with a talented musical duo playing on Saturday night. The taproom closes at 8pm, and after closing time the apartment is very quiet and peaceful. The apartment is cozy with attractive furnishings and a comfortable bed, but it is not a place for people with mobility challenges. There are 17 steps up to the apartment, and the shower in a free-standing claw-foot tub doesn't have handrails. I enjoyed my stay, and give it a 5-star review for physically fit singles or a couple!

Spacious and comfortable one bedroom + studio, lots of natural light, serene atmosphere, we had a great stay and would be love to visit again

My wife, dog, and I had a wonderful and peaceful stay at Michael's place. The land is beautiful, the place itself is actually even nicer than the pictures, and there is plenty to do in the area. We will definitely be coming back!

Pacers Pasture is on a quiet road giving it a cute country experience in a great small town. The space has an amazing unfenced yard which was great for the dogs. Easy access inside with key entry, and we loved the door entry being toward the back of house for added privacy. The house has very comfortable linens, tons of parking, and the hottest water ever - which was perfect after a cold day adventuring. Aaron provides toiletries, some nice kitchen basics likes spices and teas/coffee, fast wifi-TV streaming, and a cozy space perfect for relaxing. Bonus points for being tastefully decorated and not overly cluttered. Would stay again!

Yulia's place was the perfect spot for a Memorial Day weekend getaway. Was even great for an infant! It was comfy and cozy! Loved the patisserie downstairs and the town. Highly recommend!

Muna was incredible start to finish with my stay. Helpful, communicative and accommodating. Place was perfectly as described. Genuinely recommend a stay at her place!

Felt right at home, check in was very easy, beautiful place, very friendly enjoyed his place thinking to coming back again my business send me to Connecticut! Thank you!

Such a unique stay! David gave very helpful instructions for arriving and getting to the property, even supplied photos for extra assistance. The property itself is cozy and in a great part of the city. There’s lots to do nearby, super walkable, and David provides great local recommendations. The shared gallery space was so cool to see too. Great experience!

Cozy apartment, walking distance from the water front. Had a great weekend getaway.

My husband and I loved our stay at Jo Anne’s place, it was quite,clean private, easy access to parking and very affordable . Stocked with the necessities.

Very nice spot for one person or a couple. Convenient access to JP base area and amenities. Neat and tidy space, nicely appointed. Great communication from owner.