
Vacation home rentals in The Berkshires
Find and book unique vacation home rentals on Airbnb
Top-rated vacation home rentals in The Berkshires
Guests agree: these vacation home rentals are highly rated for location, cleanliness, and more.
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for The Berkshires vacation home rentals
Family-friendly vacation home rentals

3 block to Warren ST with a Yard and parking ga
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.

Bright and Airy 2 blocks from Warren ST eb
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.

Chalet on the Hill
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.

2 blocks to Warren ST w/ a yard and parking
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!

2BRT 3 blocks to Warren ST
A really great place with clear instructions and wonderful flexibility from the host. Has everything you could need and is very cozy too.

2 blocks to Warren ST with an office and a yard cb
Booked the place for a guest visiting. They loved the place. Was clean and spacious. Would rent again.
Vacation home rentals with a patio

Modern Coastal Home with Pool
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 .

La Maison Hudson: Charming 1BR In Prime Location
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.

Lake View w/ Pickleball Court
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

Cozy Glens Falls home near Lake George & Saratoga
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

Charming Vacation House w/ Pool & HotTub
Beautiful place. Comfortable beds. Quiet neighborhood. Michele was communicative. Really enjoyed my memorial day weekend.

Cozy Catskills retreat w/views & fireplace
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.

Riverfront, cozy farmhouse near Rhinebeck
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!

UNIQUE and GORGEOUS historic loft style rental
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

Mountain escape in Hunter/Tannersville
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.

Modern HOT TUB House 3mins to Belleayre
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.

Malkita Aria | Mountainview Retreat
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.

Once in a Lifetime Hudson River Views
Wonderful home and beautiful surroundings. Jean was very responsive.

Perfect Serene Waterfront All Season Retreat!
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!

Explore the Berkshires from this charming home.
Lovely place, exactly what my family needed

Beautiful 4bedroom home overlooking Saratoga lake.
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.

The Barn Loft- Spacious stream-side Catskill home
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
- Rentals with beach access The Berkshires
- Lakehouse rentals The Berkshires
- Rentals with an EV charger The Berkshires
- Cabin rentals The Berkshires
- Pet-friendly rentals The Berkshires
- Farmstay rentals The Berkshires
- Rentals with outdoor seating The Berkshires
- Cottage rentals The Berkshires
- Family-friendly rentals The Berkshires
- Private suite rentals The Berkshires
- Rentals with pools The Berkshires
- Apartment rentals The Berkshires
- Hotel rentals The Berkshires
- Rentals with a patio The Berkshires
- Rentals with an accessible height toilet The Berkshires
- Bed and breakfasts The Berkshires
- Rentals with lake access The Berkshires
- Kid-friendly rentals The Berkshires
- Smoking-friendly rentals The Berkshires
- Aparthotel rentals The Berkshires
- Rentals with breakfast The Berkshires
- Waterfront rentals The Berkshires
- Rentals with a home theater The Berkshires
- Boutique hotel rentals The Berkshires
- Villa rentals The Berkshires
- Rentals with a fire pit The Berkshires
- Guesthouse rentals The Berkshires
- Ski-in/ski-out rentals The Berkshires
- Rentals with a fireplace The Berkshires
- House rentals The Berkshires
- Fitness-friendly rentals The Berkshires
- Chalet rentals The Berkshires
- Condo rentals The Berkshires
- Rentals with a washer and dryer The Berkshires
- Rentals with a sauna The Berkshires
- Rentals with a kayak The Berkshires
- Beachfront rentals The Berkshires
- Luxury rentals The Berkshires
- Rentals with a hot tub The Berkshires
- Townhouse rentals The Berkshires
- Vacation home rentals United States
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom