Villa holiday rentals in The Berkshires

Find and book unique villas on Airbnb

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Popular amenities for villa rentals in The Berkshires

Private villa rentals

Guest favourite
Villa in Norwich
4.89 out of 5 average rating, 208 reviews

Romantic Spa Retreat minutes to Mohegan Sun Casino

GabrielaRating, 5 stars5 months ago
Everything was amazing ! great place to rest after a fun day & night out. Cozy and comfortable. Definitely will be coming back !
Villa in Port Jervis
4.65 out of 5 average rating, 65 reviews

Mountain Getaway by Legoland and Delaware River

AnelRating, 5 stars2 months ago
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.
Guest favourite
Villa in East Meredith
4.89 out of 5 average rating, 28 reviews

Private oasis in the Catskills, The Stewart Manor

MarcosRating, 5 stars6 months ago
This is now the second time my soccer team and I have stayed at Katie’s property. Just like last year it was perfect! We did miss the paddle boat, but we assumed it was put away for the winter. Nonetheless the property, the home, everything was great. We’re excited to book it again next year for our soccer tournament.
Guest favourite
Villa in Hudson
5 out of 5 average rating, 17 reviews

Mountain-View Retreat @ Hudson

Tim And LilyRating, 5 stars1 week ago
Sourove’s place is great. It is a spacious and well apportioned home that is perfect for a family. The view of the mountains from the front window is beautiful and provides a relaxing sunset view. We absolutely recommend this house for anyone looking for a modern, well equipped place to stay in Hudson. Thanks again!
Guest favourite
Villa in Winhall
4.91 out of 5 average rating, 23 reviews

Stonehouse at Stratton

DebbieRating, 5 stars2 months ago
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!
Villa in Bridgeport
4.73 out of 5 average rating, 11 reviews

Indulge in Prime Luxury 3BR 3-7 Guest

AshleyRating, 5 stars2 months ago
My stay was nothing short of Amazing Check-in was smooth with clear instructions and the home was beautiful as pictured,I really appreciated the hospitality the host showed me and would definitely book again! Thank you Prime Reality
Villa in Dolgeville
4.54 out of 5 average rating, 26 reviews

Cheerful 3 Bedroom Villa with a fireplace

DeborahRating, 5 stars4 months ago
Had to vacate our home due to renovations. It was a great home away from home for those few days. Thank you.
Guest favourite
Villa in Norwich
4.93 out of 5 average rating, 27 reviews

Private Penthouse Paradise

DarcieRating, 5 stars2 weeks ago
The hostess was very helpful and very responsive. The condo was as described and lovely for our family reunion. It was very clean, very comfortable and so welcoming. We were just a couple of minutes away from the Mohegan Sun casino. The area is beautiful. Highly recommend!

Luxury villa rentals

Villa in Newburgh
4.71 out of 5 average rating, 17 reviews

Exquisite modernism over the Hudson

RobertRating, 5 stars18 months ago
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.
Guest favourite
Villa in New Paltz
4.92 out of 5 average rating, 26 reviews

Country home with rock climbing gym, pond & creek.

RoryRating, 5 stars4 months ago
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.
Guest favourite
Villa in New Paltz
5 out of 5 average rating, 11 reviews

Country House, Mountain Views, Dine, Bike, & Hike

AriellaRating, 5 stars3 months ago
Absolutely beautiful home! Carl and Rebecca were wonderful hosts - they were super responsive and accommodating. And their home is lovely down to all the little details, from the soft bathrobes to the warm spaces to hang out in. We had a wonderful stay at their home and would love to come back!
Top guest favourite
Villa in Waterford
5 out of 5 average rating, 14 reviews

Spacious Waterfront Getaway

AntoniaRating, 5 stars4 months ago
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 in Monroe
4.71 out of 5 average rating, 76 reviews

Awesome Country Retreat - 4BR - Private & Peaceful

YingRating, 5 stars1 month ago
the location is great, only 7mins drive to Woodbury Outlets, Ricky is very nice, always respond quickly and helpfully. highly recommend this house
Villa in Wallkill
5 out of 5 average rating, 3 reviews

Modern Scandinavian Villa

MiguelRating, 5 stars3 months ago
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.
Superhost
Villa in Neversink
5 out of 5 average rating, 7 reviews

Lux Catskills Villa-3 hiking trails with 4br 4bath

NicolasRating, 5 stars31 months ago
The place is breathtaking. Located in an incredible land with awesome trails is a marvelous house nicely decorated and amazing rooms. We had an incredible time with my family that we will remember forever. Many thanks to Paula. Always there and really helpful with everything.
Guest favourite
Villa in Liberty
5 out of 5 average rating, 9 reviews

Catskills Pond Getaway

ShubhangiRating, 5 stars2 months ago
Yvette's home was absolutely wonderful! The place was spotless, beautifully decorated, and had all the amenities needed for a comfortable stay. The beds were cozy, the kitchen was well-equipped, and every little detail was thoughtfully arranged. Yvette was an exceptional host—super friendly, responsive, and always communicative. She made sure we had everything we needed and provided great local recommendations. I would definitely stay here again and highly recommend it to anyone looking for a relaxing and enjoyable stay.

Villa rentals with a pool

Villa in Rupert
4.32 out of 5 average rating, 59 reviews

Gorgeous Victorian-Style House w/ Hilltop Pool!

PeterRating, 5 stars3 months ago
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!
Guest favourite
Villa in Wingdale
4.86 out of 5 average rating, 14 reviews

Beautiful farmhouse nature escape 90 min from NYC

MaraRating, 5 stars16 months ago
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.
Guest favourite
Villa in Putnam Valley
5 out of 5 average rating, 18 reviews

Bird Haven Farmhouse: Luxury Villa Living w/ Pool.

DebRating, 5 stars7 months ago
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.
Villa in Pound Ridge
5 out of 5 average rating, 4 reviews

Pool and tenis court, 5 bedroom beautiful home

HowardRating, 5 stars11 months ago
Outstanding stay. Property is very well located, equipped, landscaped, maintained, and furnished.
Top guest favourite
Villa in Longmeadow
5 out of 5 average rating, 52 reviews

Comfort and Luxury - 180 year Old Gothic Estate

EdRating, 5 stars5 months ago
Paul’s place had the style of grand old home but it didn’t feel old: everything worked as it should, the kitchen and baths were updated and gorgeous. Amazing. We visited with family over 3 days and it was a fantastic, comfortable place to be together. Paul was gracious and helpful. Furniture and beds were of high quality and comfy. The grand piano in the living room was an extraordinary instrument and very much in tune - it was played for hours. All the guests gushed about the place, several saying it felt like a classic movie set. Can’t say enough about how much we enjoyed it. We very highly recommend
Villa in Garrison
4.95 out of 5 average rating, 98 reviews

Serene and Peaceful - Surrounded by Nature

AkshayRating, 5 stars57 months ago
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.
Villa in Woodridge
4.57 out of 5 average rating, 14 reviews

Best (heated) pool in town Davos

AnanyaRating, 5 stars10 months ago
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!
Guest favourite
Villa in New Paltz
4.91 out of 5 average rating, 23 reviews

Beautiful 5BR Hudson Valley Villa

CindyRating, 5 stars8 months ago
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.

Destinations to explore