Chalet holiday rentals in Jamaica

We stayed here with another couple and their dog two years back and had a wonderful time. I am so grateful that we came back this year with our dog, Chili, and she had the absolute best time! Old Manchester rd is really quiet and is great for off leash walks. Chili loved frequently seeing the other neighbors and their dogs (who were all friendly) on her walks. We’re also runners and so the road is great for running (mostly flat, minimal traffic, frequently plowed, amazing views of Bromley). Jennifer and Dan are both very friendly too. Jennifer did a good job of reaching out to us often making sure we had what we needed. Dan often came by to plow the driveway which was really nice too. Our last day was during a snow storm and they were flexible with checkout which was really helpful. This place really has everything you need and the location is excellent (close to Stratton, Manchester which has a dog park, and downtown Peru which has an outdoor ice skating rink

We had an issue with our previous rental and needed to find a place to stay that is pet friendly and available. Rad and Carol responded quickly to our reservation request. The house was made available to us early in the day and hot tub prepped last minute for us to enjoy! The Chalet is beautiful and spacious, the location is private and relaxing. The wood stove kept us warm and cozy while we enjoyed watching light snow fall. We would definitely stay there again and bring our family with us!

Couldn't say enough great things about both the hosts and the property. Just lovely home - very spacious, and clean and cosy. The area is gorgeous, with a lot to do. Mt. Snow and Hermitage skiing are very close, and Wilmington and the area are charming. Host was very gracious and kind..thank you!

Great place to stay for okemo mountain!! Very close to local restaurants and the mountain

Another wonderful stay at The Chalet! The property and home are beautiful, very quiet and peaceful. We look forward to coming back every year. Plenty of space for a big family, and our dogs enjoy playing outside.

The chalet is secluded, quiet and peaceful. We appreciated its location in the woodland, right near a stream. It was comfortable for our family and we would return again in the future.

Stop scrolling, you found your next vacation. Bob is a fantastic host with a stunning home. We have stayed with Bob many times and he continues to invest in the property and ensures your stay is nothing short of fantastic. Cannot recommend the ski chalet enough.

Our stay was fantastic. The house was conveniently located relative to Stratton mountain, very comfortable, and the host was fantastic

Beautiful spot with a cozy yet spacious house. Instructions were very clear on how to get in and the different features of the house. Perfect for a relaxing get-away with friends!

Lovely stay in a cozy, comfortable house only 15 minutes from Mount Snow. We enjoyed post ski-day nights by the fire, with plenty of comfortable seating and board games galore. The yard was great for our dogs and features like the koi pond and hot tub were easy to enjoy in a peaceful and private environment. We’ll be back!

Linda was awesome! She was super responsive and helpful. We ran into several snags with our trip due to weather but we kept in constant communication and it all worked out. The house is cute and has a certain charm to it. The hot tub wasn't working but that was communicated to us a day before so we were aware. The bathrooms are a bit small, particularly the showers. Overall we had a great trip. Very close to Mt Snow. Quiet and scenic location. Fireplace was nice to have. We replenished with kindling and dry wood just so we could keep a nice warm fire going. Lovely host & lovely home.

Tommy's place was perfect for our weekend family getaway and even more beautiful than we expected! The rental process, communication with Tommy and the property itself significantly exceeded our expectations. The online guidebook Tommy provided answered every question we could have had. There was plenty of room for our group (11 adults) and so much for us to do without leaving the property! We all ate together at the large dining table, had a few pool tournaments and played board games and poker in the gorgeous game room! The kitchen was stocked with everything we could have needed (and even some things we didn't know we should have!). Every single bed was incredibly comfortable, there was ample space for everyone to relax, and we thoroughly enjoyed the fire pit, fire table and huge yard. Our family is already looking at dates for next year's trip. Tommy was the best host I've ever worked with on an Air BnB rental, and we look forward to staying at one of his properties again!

We had the most amazing weekend getaway with a group of 12 close friends! The house was cozy, beautifully decorated, and felt like the perfect home away from home. Despite it being a rainy Memorial Day weekend, we had the best time just enjoying the space together. The backyard was stunning, a great place for walking out in the morning with your cup of coffee. The kitchen was a total highlight: spacious, well-stocked with everything we needed, and perfect for cooking and feasting with a group. This stay gave us such great memories, and we’re so grateful to the hosts for creating such a warm and welcoming space. Would absolutely recommend and hope to return someday!

This was an enjoyable stay. Slept 6 comfortably. We also had such a great time in the game room playing pool, watching tv, and utilizing the arcade games. Totally recommend!

My family and I had a great week at Gabriella's place in Mt. Holly. It is a 5 min drive from Jackson Gore Base at Okemo, which made for very easy skiing (and parking!). Gabriella was responsive and friendly when we checked in. We happened to be there during a snowstorm and the drive was plowed by midmorning the next day. It was also very cold, and despite the somewhat quirky heating, we were able to stay warm while at the house. My husband and daughter enjoyed the foosball in the basement (not heated, but does have plug in heater). Hot tub was great. Only thing guests might want to note is that there are limited pots and cooking supplies so it was challenging to make meals. Also, the dishes provided are melamine/not microwave safe so we bought paper plates for when we wanted to reheat food. The home is, however, well stocked with glasses, coffee cups, baking dishes, and pans. Beds were comfy. Heated mats on front steps were very helpful. All in all, a great stay and would rent again!

Great place to stay if you are looking to travel with a mid-sized group. There was always something to do at the house and it was reachable from downtown Manchester and the Stratton Village.