Villa vacation rentals in The Berkshires

Find and book unique villas on Airbnb

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Popular amenities for The Berkshires villa rentals

Private villa rentals

An airy great room features a striking red accent wall, complemented by wooden beams and large windows allowing natural light to fill the space. A stylish black sofa is positioned near a fireplace, with a collection of plants and bookshelves adding to the decor.
Villa in Newburgh
4.71 out of 5 average rating, 17 reviews

Exquisite modernism over the Hudson

RobertRating, 5 stars20 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.
A modern villa is set against a serene backdrop, featuring large windows that reflect the landscape. A small bridge leads over a private fishing pond, while trees line the property, inviting a peaceful atmosphere. Bright red doors stand out against the neutral exterior.
Villa in Port Jervis
4.65 out of 5 average rating, 65 reviews

Mountain Getaway by Legoland and Delaware River

AnelRating, 5 stars3 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.
An inviting living area features a stone fireplace accompanied by a large flat-screen TV. Colorful artwork and decorative accents include modern furniture and plush seating. Large windows allow natural light to fill the space, while a dining area is visible in the background.
Villa in Bridgeport
4.79 out of 5 average rating, 14 reviews

Indulge in Prime Luxury 3BR 3-7 Guest

RebeccaRating, 5 stars1 month ago
Such a great stay at this lakeside spot in Bridgeport! The place was very modern and beautifully designed. Everything felt fresh and up to date. The lake view was amazing, and we enjoyed hanging out outside by the water. It was perfect for our large family and worked out well for our long stay while our house was being fixed. It felt nice and private, but still so close to everything we needed. Daymane was a great host—friendly and easy to stay in touch with the whole time. Would def stay here again!
A charming red house with a covered porch features large windows and a welcoming front entrance. Green shrubs and flowers line the pathway, which leads to the entrance. An American flag hangs proudly by the door, complemented by well-kept grass on the front lawn.
Villa in Dolgeville
4.56 out of 5 average rating, 27 reviews

Cheerful 3 Bedroom Villa with a fireplace

BenjaminRating, 5 stars5 months ago
Little pricy, but worth it. Nice place.
Villa in Monroe
4.72 out of 5 average rating, 79 reviews

Awesome Country Retreat - 4BR - Private & Peaceful

LuciRating, 5 stars1 month ago
It was a great place for 8 of us to stay and enjoy an upstate weekend. An easy drive from NYC and easy access to many attractions. Kitchen is well equipped and fully functional. Ricky was very responsive. Overall I would stay here again.
Superhost
The house features a light blue exterior with a welcoming front porch that has several steps leading to the entrance. Large windows allow natural light to fill the home. Surrounding greenery adds to the tranquil setting of the property.
Villa in Rosendale
4.77 out of 5 average rating, 13 reviews

Whole Modern House on Trestle Trail

CalebRating, 5 stars2 weeks ago
We had a great stay! The house is right next to the Empire State Trail, which was great for walking our dogs! We will definitely be back!
A spacious living area is shown, featuring a grand piano positioned beside large windows that offer views of the surrounding nature. A cozy armchair and a plush sofa provide comfortable seating, while a patterned area rug adds warmth to the wood flooring.
Villa in Tannersville
4.61 out of 5 average rating, 18 reviews

Hunter Mountain Ski House. MT-top Retreat HotTub

JamesRating, 5 stars11 months ago
My friends and I had the most incredible time at this Airbnb! From the moment we arrived, we were blown away by the stunning views and the warm welcome from our host Joe. The property itself was immaculate — beautifully decorated, clean, and equipped with everything we needed for a comfortable stay. The location was perfect too! Just a short walk from hikes, and local cafes, we were able to enjoy lazy mornings by the and evenings exploring the charming neighborhood. Our host went above and beyond to make sure we had everything we needed, offering great recommendations for activities and dining spots nearby. We truly felt like we were staying with friends rather than in a rental property. Overall, our experience exceeded all expectations. We can't wait to return to this Airbnb for another relaxing getaway. Highly recommended for anyone looking to unwind and enjoy a slice of paradise!
Superhost
A large white boat navigates the calm waters of Lake George, reflecting its silhouette on the surface. Lush green hills frame the background, contrasting with the clear blue sky overhead.
Villa in Lake George
4.75 out of 5 average rating, 52 reviews

Stumble Abode - 3

GigiRating, 5 stars7 months ago
We visited Stumble Abode over a long weekend. The beautiful cottage was clean and cozy. It was perfect for two adults and two small children. Parking was easy and close by. It had all the amenities we needed and more. We hope to visit again soon, and definitely recommend others to stay there!

Luxury villa rentals

The country-side home features a charming exterior with a blue metal roof and inviting front porch. Lush greenery surrounds the property, enhancing the tranquil outdoor setting. A stone pathway leads to the entrance, framed by manicured hedges and flower beds.
Villa in New Paltz
4.93 out of 5 average rating, 27 reviews

Country home with rock climbing gym, pond & creek.

KarinRating, 5 stars2 weeks ago
We had a lovely stay- large family in town for a college graduation. The kitchen was great for cooking, large dining tables both inside and on the large screened porch. We particularly enjoyed the fireplace, which was stocked with plenty of wood and the pool table. We had one issue and the owners were very responsive. Make sure you bring slippers because shoes aren’t allowed in the house and the basement floor is chilly. Definitely recommend the house.
Guest favorite
An aerial view showcases the property surrounded by lush greenery and trees. A private two-acre pond is visible, reflecting the landscape. The home is positioned nearby, set against the backdrop of rolling hills, highlighting the tranquility of the natural environment.
Villa in East Meredith
4.89 out of 5 average rating, 28 reviews

Private oasis in the Catskills, The Stewart Manor

MarcosRating, 5 stars7 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 favorite
A spacious entertainment area is featured, showcasing a wet bar and a pool table, with comfortable seating arranged around the space. Large windows allow natural light to fill the room, while a television is mounted on the wall. A dining table is visible in the corner.
Villa in Winhall
4.91 out of 5 average rating, 23 reviews

Stonehouse at Stratton

DebbieRating, 5 stars4 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!
Guest favorite
A spacious bedroom features a king size bed against a wall with large windows offering pleasant views. Two green chairs are positioned around a small table, creating a cozy seating area. Light wood accents on the ceiling enhance the room's airy feel.
Villa in New Paltz
5 out of 5 average rating, 12 reviews

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

JessicaRating, 5 stars2 weeks ago
Everything was absolutely amazing. We felt at home the entire stay and had everything we needed. Carl was really easy to work with. I mistakenly booked the trip a day shorter than needed. At the last minute I realized my mistake and Carl was quick to respond that adding an extra day was no problem. The system had a problem though allowing me to book an overnight stay on the same day I “checked out,” but Carl worked back and forth with me and with AirBnb help until I was finally able to book that extra night. Carl remained professional, calm, and polite, even though I know that was probably stressful and a pain to deal with. The problem was 100% on me, but he helped to fix it with such grace. I really appreciate the professionalism. I highly recommend both Carl and this specific rental. Thank you!
Top guest favorite
A wooden table is set for outdoor dining, surrounded by woven chairs. Two lanterns are placed in the center, with a large umbrella providing shade. Views of the tranquil water and lush greenery are visible in the background, creating a serene setting.
Villa in Waterford
5 out of 5 average rating, 15 reviews

Spacious Waterfront Getaway

JenRating, 5 stars2 weeks ago
Our stay at this stunning lake house was nothing short of amazing. The moment we arrived, we were welcomed by a breathtaking panoramic view of the lake that instantly set the tone for a peaceful and relaxing getaway. The house is incredibly spacious, with a well-designed open layout and large windows that flood the space with natural light. Every room felt bright, airy, and inviting. Cleanliness was top-notch—the entire place was spotless and clearly very well cared for. We loved how quiet and serene the surroundings were; it felt like our own private retreat away from the noise and rush of everyday life. Mornings spent sipping coffee on the deck and kayaking over the water by the backyard lake were highlights of our trip. Whether you're looking to unwind, connect with nature, or simply enjoy some peace and quiet in a beautiful setting, this lake house is the perfect place. We’re already dreaming of our next visit and would recommend it without hesitation.
An aerial view reveals a bright dining area with large glass doors allowing natural light to fill the space. A wooden table is surrounded by modern white chairs, while a cozy chair and textured rug add warmth to the minimalist decor.
Villa in Wallkill
5 out of 5 average rating, 3 reviews

Modern Scandinavian Villa

MiguelRating, 5 stars5 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, 8 reviews

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

RobertRating, 5 stars11 months ago
Great setting, lots of beautiful areas to explore, and very private. Paula was a great host, and also gave great local recommendations.
Superhost
A charming two-story villa is set amidst lush greenery, showcasing light blue siding and large windows. A circular driveway leads to a spacious garage, while outdoor seating is arranged with four chairs near a small table, inviting gatherings in the serene surroundings.
Villa in Bloomingburg
4.8 out of 5 average rating, 64 reviews

Spacious 6BR Villa | Serene Scenic Mountain Escape

RomonaRating, 5 stars1 week ago
Cindy was kind and responsive. The house has plenty of room and the beds were very comfortable.

Villa rentals with a pool

The Victorian home is framed by lush greenery and features a wraparound porch with black shutters. The white exterior is complemented by a decorative top turret. A stone wall borders the entrance, leading to a welcoming approach.
Villa in Rupert
4.33 out of 5 average rating, 60 reviews

Gorgeous Victorian-Style House w/ Hilltop Pool!

SilenaRating, 5 stars1 month ago
Beautiful old home full of an eclectic art collection. It served my group's needs well. Never did find the lockbox for the keys. Had to get them from the on-site groundskeeper, which was a difficult task given we had a significant language barrier. The outside of the house could use some maintenance, so if that is important to you, this may not be the place for you. My one complaint is that they expect you replace the paper towels and toilet paper you use. I would expect those to be included at any price, but especially for the price you pay for this location. Overall, it was a great stay for two nights and we had fun exploring the house.
Guest favorite
A tranquil winter scene depicts a classic farmhouse and a red barn surrounded by a blanket of fresh snow. A path is visible in the snow, leading toward the inviting buildings, and tall trees are present in the background, adding to the serene atmosphere.
Villa in Wingdale
4.87 out of 5 average rating, 15 reviews

Beautiful farmhouse nature escape 90 min from NYC

LeviRating, 5 stars10 months ago
The accommodations were perfect for our needs. A peaceful setting.
Guest favorite
An aerial view of the property reveals a spacious lawn surrounded by manicured gardens and trees. The charming farmhouse is visible along with a patio area, swimming pool, and additional buildings, set against a backdrop of vibrant greenery under a clear blue sky.
Villa in Putnam Valley
5 out of 5 average rating, 18 reviews

Bird Haven Farmhouse: Luxury Villa Living w/ Pool.

DebRating, 5 stars9 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 Woodridge
4.57 out of 5 average rating, 14 reviews

Best (heated) pool in town Davos

AnanyaRating, 5 stars11 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 favorite
The exterior of a spacious home is displayed, surrounded by lush green lawn and trees. A private pool and gazebo can be seen in the backyard, framed by cloudy skies, creating a peaceful outdoor setting.
Villa in New Paltz
4.91 out of 5 average rating, 23 reviews

Beautiful 5BR Hudson Valley Villa

CindyRating, 5 stars9 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.
Guest favorite
Villa in Wilmington
4.95 out of 5 average rating, 22 reviews

Dancing Bear Lodge The Charm of Chimney Hill

EmilyRating, 5 stars3 months ago
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.
An outdoor heated pool surrounded by a brick patio is framed by a wooden fence and lush greenery. Two lounge chairs are positioned nearby under a large umbrella, providing a relaxing space for sunbathing. The serene setting invites enjoyment of the fresh air.
Villa in Hopewell Junction
4.84 out of 5 average rating, 37 reviews

Hudson Valley Haven in Hopewell

KathyRating, 5 stars4 months ago
Our second time at Hopewell Junction did not disappoint. We love this home because Anuja really understands what a guest needs and would like - so many extra touches, like beautiful linens, nice soaps and shampoos, wood for fire, lots of cookware and serving pieces, and beautiful art. Beds are comfy and towels are top notch. It snowed while we were there, beautiful, and the drive was promptly plowed. Our friends speak Danish, and they kept using the word hygge for the house. (Cosy and welcoming) We agree and will definitely be back. Thank you Anuja for another lovely stay!
Guest favorite
An indoor heated pool house features a tranquil pool surrounded by large windows allowing natural light. Two turquoise lounge chairs are positioned for relaxation, and wooden walls create a cozy atmosphere. The ceiling is finished with wood planks and includes a ceiling fan for comfort.
Villa in Lanesville
4.89 out of 5 average rating, 94 reviews

Log cabin with INDOOR POOL foot of hunter mountain

MarionRating, 5 stars3 months ago
Alexander’s place is as described and look like the pictures. We stayed for one week end with friends to enjoy one day skiing and it was great! We had some trouble making the sauna and pool work at the beginning but Alexander sent someone to help quickly which was much appreciated 3’ drive from the slopes of Hunter and enough space to comfortably fit 12 people Would definitely recommend for a week end between friends or a big family reunion Thank you!

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