
Villa holiday rentals in The Berkshires
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Top-rated villa rentals in The Berkshires
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Popular amenities for The Berkshires villa rentals
Private villa rentals

Ultra Modern Private Oasis with River Views
We absolutely loved our weekend stay here! There was a snaffoo where the heat wasn’t working properly when we arrived and the host was so responsive to get it fixed ASAP and provided a discount without us even asking. It’s a gorgeous property with a lovely view. We will definitely be back!

Mountain Getaway by Legoland and Delaware River
The place was very big and nice. The only thing is that I can tell they were renovating the place and the smell of paint was very strong. Beautiful home and very roomy. However, if you will be staying here, make sure to bring some very warm PJs, not for the bedrooms but the kitchen/dinning and living room areas. The place had lots of window so this is why it was a bit hard to warm up those areas but heaters were available to help warm up the place. Overall it was a beautiful home and the host was very responsive. I just wish that with all these AirBnB's they would allow us to check in earlier since check out is so early. You don't get your money's worth or get to enjoy anything. We are checking if after 4 PM (because that is the normal check in time) then have to leave as soon as you wake up EARLY on a Sunday. So technically you enjoy your stay for a day.

Spacious 1 BR Unit w/ Washer-Dryer and Parking
Space was cozy, laundry amenities were very convenient.
Luxury villa rentals

Awesome Country Retreat - 4BR - Private & Peaceful
the location is great, only 7mins drive to Woodbury Outlets, Ricky is very nice, always respond quickly and helpfully. highly recommend this house

Modern Scandinavian Villa
We had a great time at the airbnb. The house is beautiful, well furnished, and comfortable. The location is great - easy drive from NYC to get out into nature and take a break from the city. Robin was a fantastic host - very communicative and responsive, provided plenty of guidance on what to do in the area. Hope to be able to come again soon.

Exquisite modernism over the Hudson
We had a wonderful Hudson Valley stay at this property. Our grand-daughters loved sleeping together in the bedroom with two double beds; and my wife and I, plus our two daughters and their husbands enjoyed good nights of sleep in the three bedrooms containing a double or queen bed. The kitchen was well equipped; and the huge living room with large dining table was perfect for the children to play, the adults to relax, and all of us to eat. The artwork in the house gave it character, the views of the Hudson River were a treat, and the location was great for visits to Storm King Art Center and Legoland NY. The email which I brought along from AirBnB had the correct street, but the wrong numerical address; however, AirBnB promptly helped us find the correct address and helped us get into the house. Of all the houses which we have rented for family weekends, this was absolute the best one.

Country home with rock climbing gym, pond & creek.
Came for a 9 person family thanksgiving. House was very well laid out for cooking, eating and relaxing. Had a few issues and The hosts and manager were very responsive, especially considering we were there on a holiday weekend. Property is beautiful For walking. Fireplace is lovely and there was plenty of dried wood. Kitchen very well appointed and stocked. If you stay in the winter bring slippers and layers, especially if you are using the basement rooms.

Stonehouse at Stratton
Overall we had great experience at the house. The inner decorations were cozy and comfortable, and the design was awesome! The host was responsive when the new door lock had some issues. 100% recommend staying at this house!

Spacious Waterfront Getaway
I rented this home to accommodate my family of 6 over Christmas. Beautiful home and very comfortable beds, high quality linens and lots of space. I could tell the house was very well set up for summer guests too with plenty of outdoor gathering areas.
Villa rentals with a pool

Dancing Bear Lodge The Charm of Chimney Hill
We had a great stay at Marlene’s guest house. 15 min drive to Mount Snow and 5 min drive to the grocery store. We had plenty of space for two families with bunk beds for the 4 kids on the lower level. The air hockey table and access to the clubhouse swimming pool was a big hit. There were two tvs and board games to keep the group occupied after a long day of skiing. Host was also very responsive to any questions we had. Place was very clean and well stocked. Would highly recommend this place.

Gorgeous Victorian-Style House w/ Hilltop Pool!
Our stay at the house was amazing! Place is very spacious so our guests were very comfortable! Plenty rooms and beds to sleep in. Kitchen is stocked up. There is everything you need ti make meals. We absolutely loved it!! Our group had people whi ski and hike . Everyone had plenty to do!! Definitely recommend that place! If we ever go back to Vermont we’ll stay there for sure!! Thank you so much for having us!

Beautiful farmhouse nature escape 90 min from NYC
Rebecca's place is incredibly comfortable and arranged in a charming, inviting way. It is one of the lovelier homes I've been in. My large family all had enough private space, and were happy to congregate in the two living rooms, big cozy kitchen and ample dining room area. The land/grounds are large and scenic. We used the fire pit for outdoor hangouts and enjoyed our stay very much. There were lots of thoughtful, lovely little details and touches to admire and wonderful linens. In communication, Rebeccas was friendly, professional and responsive. Highly recommended.

Bird Haven Farmhouse: Luxury Villa Living w/ Pool.
My husband and I stayed for a month and we had a fantastic stay. The house was comfortable and clean. The kitchen is very well appointed and easy to work in. The property is so peaceful and serene. We spent most of our time by and in the pool and it was so relaxing. Summer was an amazing host, always responding within just a few minutes.

Serene and Peaceful - Surrounded by Nature
Some exceptional aspects of the home- the beautiful drive from New York to the home, the wonderful physical location, the peaceful and quiet surroundings, the modern architecture, elegant and well-appointed furniture, very comfortable beds and linens, beautiful outdoor spaces, pristine swimming pool, complete chef’s kitchen, excellent internet speed, clean bathrooms with good water pressure, spectacular views and sunsets, and most of all the kindness, warmth, generosity and responsiveness of the hosts.

Best (heated) pool in town Davos
We had a fantastic time, the highlight of our stay was definitely the amazing pool. It was clean, well-maintained, and it also had heating facilities making it perfect for a refreshing swim. The stay was comfortable and beautifully decorated. The kitchen was fully equipped, making it easy for us to cook meals when we wanted to. The bedrooms were cozy, and the bathrooms were spotless. Our host, Israel, was incredibly welcoming and responsive. He provided us with all the information we needed and were quick to address any questions or concerns we had during our stay. Overall, we had a wonderful experience. We would definitely recommend it to anyone looking for a relaxing getaway for a large group of people with a great pool. We hope to visit again soon!

Beautiful 5BR Hudson Valley Villa
We had a fabulous time at this beautiful, spacious, comfortable home in New Paltz. We were nine family members, ages 6-75, who enjoyed four days here after our son’s wedding. It was the perfect place to decompress from a very exciting and magical wedding weekend. The house is spacious and comfortable with a number of areas to relax and enjoy- indoors and out. The pool was a lot of fun, and the house was well provisioned and nicely decorated. It was a rare treat to find a rental house that included basic supplies such as spices, pantry staples like flour and sugar, etc. Ken was an amazing host, very responsive if we had a question and provided a great list of local resources and recommendations that was very helpful. New Paltz is a fun town with a number of good restaurants and more to do in the area than we could manage in four days. Highlights included a day trip to Storm King (fabulous!) and another day to Hyde Park where we visited the Roosevelt homestead and Vanderbilt mansion.
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