Vacation home rentals in The Berkshires

Find and book unique vacation home rentals on Airbnb

0 of 0 items showing
1 of 3 pages

Popular amenities for The Berkshires vacation home rentals

Family-friendly vacation home rentals

Superhost
Vacation home in Hudson
4.81 out of 5 average rating, 107 reviews

3 block to Warren ST with a Yard and parking ga

EmilyRating, 5 stars6 months ago
My friends & I loved being so close to Warren Street! We were able to walk to all the shops and restaurants. It was so nice not having to drive anywhere.
Superhost
Vacation home in Hudson
4.86 out of 5 average rating, 133 reviews

Bright and Airy 2 blocks from Warren ST eb

RandallRating, 5 stars2 weeks ago
This is the second time I’ve stayed in one of Vladimir’s properties and had a great experience. Everything about the location, accessibility, and furnishings is great! Easy walking distance to amazing restaurants and shopping, but tucked into a quiet street. Would stay here again.
Vacation home in Cairo
4.65 out of 5 average rating, 23 reviews

Chalet on the Hill

StephanieRating, 5 stars48 months ago
We had a lovely stay at Chalet on a Hill and Nadine was lovely to work with. House is very private with great views and close drive to Windham where dinner was recommended. The grocery store nearby has everything you need if you want to make the house feel like home for the weekend. We will certainly look to book again.
Guest favorite
Vacation home in Hudson
4.9 out of 5 average rating, 125 reviews

2 blocks to Warren ST w/ a yard and parking

ErinRating, 5 stars2 weeks ago
We had a great time staying at this Airbnb. It was clean, spacious and close to Warren St. Communication was clear and it was easy for us to get into the apartment. We also appreciated being able to check in early. Thank you!
Superhost
Vacation home in Hudson
4.91 out of 5 average rating, 100 reviews

2BRT 3 blocks to Warren ST

SiddhantRating, 5 stars7 months ago
A really great place with clear instructions and wonderful flexibility from the host. Has everything you could need and is very cozy too.
Superhost
Vacation home in Hudson
4.79 out of 5 average rating, 85 reviews

2 blocks to Warren ST with an office and a yard cb

StefanRating, 5 stars7 months ago
Booked the place for a guest visiting. They loved the place. Was clean and spacious. Would rent again.

Vacation home rentals with a patio

Guest favorite
Vacation home in Westbrook
4.89 out of 5 average rating, 35 reviews

Modern Coastal Home with Pool

SaraRating, 5 stars4 weeks ago
What a beautiful place! We needed accommodations for our family as we attended our daughter’s graduation. This place was perfect . Plenty of space and we had everything we needed . We didn’t want to leave .
Guest favorite
Vacation home in Hudson
4.97 out of 5 average rating, 36 reviews

La Maison Hudson: Charming 1BR In Prime Location

NicoleRating, 5 stars3 days ago
Perfect apartment for a weekend away in Hudson! Quiet and clean, walkable to everything in Hudson. Very easy check in/out, Cybele was in touch and very informative with descriptions and instructions.
Guest favorite
Vacation home in Glen Spey
4.94 out of 5 average rating, 17 reviews

Lake View w/ Pickleball Court

ErikaRating, 5 stars3 weeks ago
Apartment was spacious, clean and very comfortable for our family of 4. Property owner was nearby and was friendly and helpful with around town tips. Would have loved if the weather had cooperated more and could have gotten more use of the lake and firepit. Great place to stay when attending a concert at Bethel Woods. Highly recommend
Top guest favorite
Vacation home in Glens Falls
4.98 out of 5 average rating, 61 reviews

Cozy Glens Falls home near Lake George & Saratoga

AlexRating, 5 stars2 weeks ago
I loved the coziness of the home The accommodations The Neigbors Much better than staying at a hotel for sure Little more costly But surly worth it It rained all day, one day there And it was nice being stuck in doors all day We’re in a hotel You would have been Let’s go to a movie or something We got to get out of this small space Just all around the place added a great addition to my awesome trip Thank you I would diffently stay there again
Guest favorite
Vacation home in Highland
5 out of 5 average rating, 32 reviews

Charming Vacation House w/ Pool & HotTub

ConstanceRating, 5 stars3 weeks ago
Beautiful place. Comfortable beds. Quiet neighborhood. Michele was communicative. Really enjoyed my memorial day weekend.
Guest favorite
Vacation home in Napanoch
4.91 out of 5 average rating, 34 reviews

Cozy Catskills retreat w/views & fireplace

KiaraRating, 5 stars2 weeks ago
I stayed at Israel’s place last year and had to stay there again. Truly a gem in the catskills! Everything you see in the photos is exactly if not better than what you would experience staying at the Swallows nest.
Guest favorite
Vacation home in Salt Point
4.93 out of 5 average rating, 71 reviews

Riverfront, cozy farmhouse near Rhinebeck

HarrietRating, 5 stars1 week ago
This house is perfect for a family getaway, and we enjoyed our stay a lot. The garden, patio, and outdoor seating were so relaxing, and the inside was very well kitted out. It is a fun house with nice decor, and feels very homely. We had a great time!
Superhost
Vacation home in Woodbury
4.87 out of 5 average rating, 23 reviews

UNIQUE and GORGEOUS historic loft style rental

EmilyRating, 5 stars1 month ago
What a lovely homebase for a quick trip to see some pals near my old town. Beautifully clean and cozy, slept like a brick, and the space is so charming and cozy while still having everything one could need.

Vacation home rentals with a washer and dryer

Guest favorite
Vacation home in Tannersville
4.95 out of 5 average rating, 21 reviews

Mountain escape in Hunter/Tannersville

DavidRating, 5 stars5 months ago
Great location for a long ski weekend. Very clean, with clear instructions and communication. Charlie was also very gracious and let us check out later than we planned. Definitely plan to stay again.
Superhost
Vacation home in Fleischmanns
4.81 out of 5 average rating, 62 reviews

Modern HOT TUB House 3mins to Belleayre

LizRating, 5 stars2 months ago
This house is the perfect home base for skiing at nearby Belleayre, which is only a few minutes away by car. We have spent several weekends there. It was clean, had lots of comfortable beds, and space for our ski gear. The kitchen is perfect for preparing simple meals after a day on the slopes. The hot tub is a great place to relax sore muscles. The surroundings are lovely. The host was always responsive if we needed anything. Overall it's a great place to relax in the Catskills however you like.
Superhost
Vacation home in Woodbury
4.87 out of 5 average rating, 83 reviews

Malkita Aria | Mountainview Retreat

AlexandraRating, 5 stars1 month ago
Malka’s place was great for a larger group stay. There was a ton of space for our group to hangout. Comfortable beds, very clean bathrooms, and great hangout areas made this place a 10/10. Would highly recommend.
Guest favorite
Vacation home in Wappingers Falls
4.96 out of 5 average rating, 52 reviews

Once in a Lifetime Hudson River Views

CarolineRating, 5 stars3 months ago
Wonderful home and beautiful surroundings. Jean was very responsive.
Superhost
Vacation home in Becket
4.96 out of 5 average rating, 52 reviews

Perfect Serene Waterfront All Season Retreat!

RachelRating, 5 stars3 months ago
Quiet neighborhood. House and property are welcoming and just as described. We had a snowstorm check-in day and Larry was responsive and made sure the snow and ice were cleared prior to our arrival. The kids and the dog enjoyed exploring the property despite the single digit temps and 20 inch base of snow. This property is close to so many awesome winter activities! We made the most of our 4 night/5 day stay and went cross country skiing at Canterbury Farm, snow tubing at Bousquet Mountain, and snowboarding at Otis Ridge. It was great to have a well appointed kitchen for home cooked meals, and a woodstove with plenty of firewood to beat the frigid temps. Overall - awesome!
Superhost
Vacation home in Pittsfield
4.83 out of 5 average rating, 23 reviews

Explore the Berkshires from this charming home.

NickRating, 5 stars3 months ago
Lovely place, exactly what my family needed
Guest favorite
Vacation home in Saratoga Springs
4.89 out of 5 average rating, 27 reviews

Beautiful 4bedroom home overlooking Saratoga lake.

JamesRating, 5 stars6 months ago
We were looking for a place to host thanksgiving dinner for 7 near my in-laws. Sandra's home near Lake Saratoga worked perfectly. Very large, open concept and huge kitchen with long dining table was exactly what we needed. With 4 bedrooms and 3 baths, it meant staying there was easy with space for us all. The on.y challenge for us was the steep driveway as we got hit with snow and rain. I would highly recommend this Airbnb.
Guest favorite
Vacation home in Roxbury
5 out of 5 average rating, 12 reviews

The Barn Loft- Spacious stream-side Catskill home

YuberkisRating, 5 stars5 months ago
My family and I had a great stay. The house was very spacious and cozy, easy to find, and extremely clean. Susan was very helpful and attentive to our needs. We went snow tubing at Plattekill Mountain which was only 15 mins away, which was perfect because we were able to get back quickly to warm up and enjoy the rest of our evening. I would recommend this house to anyone.

Destinations to explore