Villa holiday rentals in The Berkshires

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Popular amenities for villa rentals in The Berkshires

Private villa rentals

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.
Villa in Port Jervis
4.65 out of 5 average rating, 65 reviews

Mountain Getaway by Legoland and Delaware River

AnelRating, 5 stars4 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.
Villa in New Paltz
4.93 out of 5 average rating, 27 reviews

Country home with rock climbing gym, pond & creek.

KarinRating, 5 stars3 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 favourite
Villa in East Meredith
4.9 out of 5 average rating, 29 reviews

Private oasis in the Catskills, The Stewart Manor

DoloresRating, 5 stars5 months ago
We loved this house! It was extremely clean, with sheets and towels that looked brand new. The kitchen was fully equipped with everything we needed. Entering the house was super easy. It was so peaceful, with a beautiful view to enjoy. We’d definitely stay here again!
Villa in Pound Ridge
5 out of 5 average rating, 4 reviews

Pool and tenis court, 5 bedroom beautiful home

HowardRating, 5 stars12 months ago
Outstanding stay. Property is very well located, equipped, landscaped, maintained, and furnished.
Guest favourite
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!
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.
Guest favourite
Villa in Norwich
4.93 out of 5 average rating, 30 reviews

Quiet Villa by Mohegan Sun w/ Pool & Hot Tub

AleroRating, 5 stars4 weeks ago
This place was perfect for my trip to the CT Barber Expo!! 3 minutes away from Mohegan sun which was perfect !! Super beautiful community peaceful clean and quiet. Truly found high class top tier spot for this trip . I’m beyond happy with my choice and would definitely pick this place again next year !!

Luxury villa rentals

Superhost
Villa in New Windsor
5 out of 5 average rating, 3 reviews

The Carriage House on Hudson

GeorgeRating, 5 stars3 weeks ago
This home, and its amazing history, far exceed the image we got from the description. It’s absolutely incredible, and it was very clean, better than many expensive hotels I’ve stayed in. For a group (we were there for West Point Graduation with family & friends), it’s just totally ideal! Everyone in our group loved it. And Richard was extremely helpful and gracious. I wish I had found this house a few years earlier! Highly recommend for a hotel type stay, or for an event space, retreat, etc.
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!
Top guest favourite
Villa in New Paltz
5 out of 5 average rating, 12 reviews

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

JessicaRating, 5 stars3 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 favourite
Villa in Waterford
5 out of 5 average rating, 17 reviews

Spacious Waterfront Getaway

KimRating, 5 stars1 day ago
Beautiful home with plenty of room for everyone to spread out and have privacy as well as spend lots of time in the common areas together cooking, playing games and enjoying the spectacular view. The home is well appointed with everything you need. Hope to stay here again! Thank you so much.
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
Villa in Bloomingburg
4.81 out of 5 average rating, 67 reviews

Spacious 6BR Villa | Serene Scenic Mountain Escape

Maria NormaRating, 5 stars1 week ago
The house was very comfortable for 13 of us. It is in a very small town with nothing to do but it is close enough to drive where you need to. It has beautiful views and very peaceful surroundings.
Guest favourite
Villa in Liberty
5 out of 5 average rating, 9 reviews

Catskills Pond Getaway

ShubhangiRating, 5 stars3 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 Norwich
4.89 out of 5 average rating, 62 reviews

Lovely Norwich Villa, On Golf Course w/ Amenities!

JessicaRating, 5 stars4 months ago
We had a wonderful stay!! The lock was stuck upon check-in but the host called us (it was the middle of the night) and walked us through getting it open. She was so friendly and helpful! The place itself was perfect. Great kitchen, sleeping areas, clean and wonderfully decorated. Even with the lock issue, this was a 5 star stay and we have absolutely no complaints. We had 3 people and we felt like we had plenty of room. It’s also right down the street from the Mohegan Sun!!! So perfect place to stay if you want to visit the resort. You can’t get a better location. Also very quiet area.
Guest favourite
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 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.
Superhost
Villa in Lake George
4.74 out of 5 average rating, 34 reviews

Sun Castle Resort - Luxury Lakefront Villa

NicoleRating, 5 stars5 days ago
Amazing stay! Exactly as described in the listing. It was the perfect location for us, short drive to both Lake George and Bolton Landing. We were traveling with our 10 month old and there was plenty of space for him to play. The view of the lake was 10/10!
Top guest favourite
Villa in Longmeadow
5 out of 5 average rating, 54 reviews

Comfort and Luxury - 180 year Old Gothic Estate

TomRating, 5 stars4 weeks ago
We’ve stayed in many places over the years (domestic & international)…this may be the best place we’ve stayed in. Paul was fantastic - super friendly, extremely responsive and very helpful. I can’t recommend this property enough - the house itself is beautiful and spacious…plenty of (comfortable) seating throughout the house…bedrooms are big with king size beds…just an awesome experience all around. We were there for a college graduation - this property was absolutely ideal for big family get-aways/celebrations.
Guest favourite
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 favourite
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.
Top guest favourite
Villa in Norwich
5 out of 5 average rating, 20 reviews

Newly renovated, cozy 2 bedroom villa!

JustinRating, 5 stars1 month ago
Cute and cozy space for the 4 of us! The house was great to accommodate our family and this weekend’s events. Jana was a wonderful host, very responsive and proactive to a local power grid outage and made sure we were taken care of throughout the afternoon until power was restored. Very flexible in letting us check in an hour early as we arrived earlier than scheduled. Overall great experience and perfect host!

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