Vacation rentals with a pool in The Berkshires

We had a lovely time with our family! We were with 2 young children and my elderly father who cannot walk well (uses a walker). The house was perfectly designed to accommodate my father and had great living areas for us to spend time together. A very cozy, warm and welcoming home (with lots of amenities!). Yael is a very friendly, responsive host. We’d gladly come back for another winter or perhaps a summer stay! Thank you Yael!

I absolutely enjoyed my weekend here. The home is beautiful. Everything you could possibly need was provided In the home. Everything was clean, and neat. House is filled with light. The pool and hot tub were enjoyable. The host were amazing and had great communication, assisted us when needed right away. I would highly recommend staying here, and they are pet friendly which is always a plus for me. The yard is fenced in. Which made it easy to let the dog out, and great for the dog to explore. A++++ Will probably be back sometime In the future.

Really a great time and they were very accommodating and communicative. The view is incredible and very close to great restaurants. We used the hot tub every night. Haha

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!

My husband and I had a wonderfully relaxing time at the Little Owl Teahouse. It’s a cozy and well-outfitted cabin with a super comfy bed and a great leather reading chair. Drank lots of the delicious mountain well water. Made breakfast in kitchen — love the pans and electric cooktop. Short drive to Woodstock for dinner. And oh the beauty of the surroundings - scenic views everywhere. Our two little doggies were happy to romp in the fenced in yard. Little too chilly when we were there but pool looks so appealing. Lisa is a proactive and super responsive host.

Great environment, quiet area, close to attractions and private. Clean and spacey house with enough things to do. Mostly every necessity is provided and more. Clear instructions posted around the house with friendly owners. I would definitely recommend from couples to families this house is perfect and has everything u need for a good getaway. Furniture is extremely comfy and the house is well insulated.

We selected this amazing property as the location for our mini-wedding and we could not have been happier. The house is brilliant in every way. The floor plan, the furnishings, the decor, and the grounds are all thoughtful and stunningly beautiful. The property manager was always responsive and kind. This is truly a top property and you will not be disappointed. We cannot wait to visit again.

Kelsey is flexible and responsive. You can tell she thought about how to curate a great stay by all of the amenities and presentation of the house. It’s cozy! Kelsey does have house rules but they’re not overbearing and if anything it was nice to have clear expectations communicated from the beginning.

Beautiful gem, fantastic hosts. Wouldn’t change a thing. Thank you!

Our family enjoyed our stay at Rafael's condo. The space was very clean and comfy, and exactly matched the description and photos posted here. The fireplace was a great draw, too. If you're planning on skiing at Mt. Snow, the Moover shuttle bus stop is located right outside of this building, which made for a very convenient and quick way to get to Mt. Snow for my family of 4. We would certainly stay here again in the future.

The Villa was exactly as described! Easy communication with owner. A perfect getaway weekend, every amenity we could want or need! Look forward to visiting again in the near future!

We had a great time and the property was immaculate! The hosts came by with extra towels quickly upon request and it was a holiday. Recommended!

This is a wonderful property that is close to everything we like to do! Krista is a wonderful host and I’m always excited if her place is available.

We booked the place for a family stay near Woodstock. It was easy to get in. There’s automated messages for every step of the stay with instructions which was very nice and helpful. We had a great stay in a worm and clean space. Would definitely go back.

The place was cozy and comfortable, with great amenities like a parking garage, pool, and sauna. The WiFi was excellent, and the unit was clean and well-equipped for a relaxing stay. There wasn’t much to do since it was the off-season, but it’s a great spot if you’re looking for a quiet retreat. Would recommend for a peaceful getaway.

such a good price for being about 4 minutes away from mohegan sun and around 20 minutes away from foxwoods. texted me with very clear instructions and didn’t have a problem the whole time, would happily stay here again :).