Holiday home rentals in The Berkshires

Find and book unique holiday home rentals on Airbnb

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Popular amenities for holiday home rentals in The Berkshires

Family-friendly holiday home rentals

Superhost
Holiday 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
Holiday 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.
Holiday 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.
Superhost
Holiday home in Ludlow
4.75 out of 5 average rating, 84 reviews

Ludlow Big Family Fun Home

DerekRating, 5 stars3 months ago
Kelly was super responsive. The house was 5 minutes away from Okemo.
Guest favourite
Holiday home in Hudson
4.9 out of 5 average rating, 126 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!
Guest favourite
Holiday home in Maryland
5 out of 5 average rating, 25 reviews

Silver Linings Self-Healing Retreat or vacation

NachoRating, 5 stars4 months ago
I was looking for a place to rest and recover and I found it here. Private, quiet and comfortable, the place is perfect. The main bedroom has the tempur-pedic cloud mattress and all of the beds had good new perfect size pillows. This is something I’ve never seen on 10 years of airbnb around the world. And shows the level of care and detail the host has put on this place. Chrissy was a great host, always responsive and proactive on making the stay comfortable. This is one of the best places I’ve stayed.
Superhost
Holiday 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
Holiday 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.

Holiday home rentals with a patio

Guest favourite
Holiday home in Westbrook
4.89 out of 5 average rating, 35 reviews

Modern Coastal Home with Pool

SaraRating, 5 stars1 month 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 favourite
Holiday home in Hudson
4.97 out of 5 average rating, 36 reviews

La Maison Hudson: Charming 1BR In Prime Location

NicoleRating, 5 stars4 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.
Top guest favourite
Holiday 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 favourite
Holiday 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 favourite
Holiday 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 favourite
Holiday 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
Holiday home in Woodbury
4.83 out of 5 average rating, 24 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.
Top guest favourite
Holiday home in Guilford
4.99 out of 5 average rating, 97 reviews

Spacious Oceanfront Getaway with Spectacular Views

RachelRating, 5 stars2 weeks ago
I had an amazing stay at Linda’s home! The view is absolutely beautiful and the spacious house made for great relaxation. Amenities made it easy to feel right at home along with games to play and enjoy the space even more. Loved that there were 3 bathrooms as well! Perfect for our group of 6 and we will definitely be back!

Holiday home rentals with a washing machine and dryer

Guest favourite
Holiday 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
Holiday 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.
Guest favourite
Holiday 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
Guest favourite
Holiday 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.
Guest favourite
Holiday home in Caroga Lake
4.94 out of 5 average rating, 86 reviews

Lakefront A-Frame in the ADKs with Watersports

MonicaRating, 5 stars4 days ago
We had such a wonderful weekend at Chandra's A-frame cabin. The space was private, quiet and had a gorgeous view of the lake. We enjoyed kayaking and having a fire on the dock at night. It was the perfect spot for a relaxing weekend with our pups!
Superhost
Holiday 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
Holiday 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 favourite
Holiday 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.

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