Hotel holiday rentals in The Berkshires

Find and book unique hotel rentals on Airbnb

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Popular amenities for hotel rentals in The Berkshires

Family-friendly hotel rentals

Superhost
Hotel room in Saugerties
5 out of 5 average rating, 3 reviews

Cozy Room with private bathroom in Victorian home

KellyRating, 5 stars7 months ago
What a charming home. Cozy room, loved the electric fireplace..spacious private bathroom, super clean and great water pressure (I love a good shower)! Justine and David were super friendly, communicative, and thoughtful. We hope to stay again next October!
Superhost
Hotel room in Saugerties
4.92 out of 5 average rating, 65 reviews

Village Inn - Tribeca suite - Saugerties NY

TimRating, 5 stars3 months ago
We had a great stay! The host was super communicative and made sure we had all the information we needed to find the parking lot, check in, etc. They even gave us a heads-up when the weather started to turn, so that we could plan accordingly. The room was comfortable and very spacious, and the location was super convenient. Even with a winter storm hitting, we were able to walk to coffee shops, great restaurants, and multiple bookstores. Would definitely recommend!
Hotel room in Cornwall
4.94 out of 5 average rating, 17 reviews

Cornwall Lodge - Queen Room (pet friendly)

BelindaRating, 5 stars13 months ago
Lovely place, very clean. Will be back.
Hotel room in Fort Montgomery
4.77 out of 5 average rating, 120 reviews

Bear Mountain Bridge Motel (Rooms 1, 2, 4, 5)

AidanRating, 5 stars1 month ago
I came to Bear Mountain for a weekend of hiking. This was perfectly placed to be able to access the nearby shops and restaurants (I recommend the Barnstormers BBQ!) as well as most importantly an easy distance to hike to get to the trail heads. The owners were friendly and helpful, full of advice for the area as well as sharing stories about themselves and other hikers. I couldn't have asked for more - and if I'm ever back in the area or I get my wish to hike the Appalachian Trial, I'll be sure to stay here again. Thanks very much!
Hotel room in Whitingham
4.93 out of 5 average rating, 169 reviews

The Engel House Room 3: Mt Snow/Wilmington VT Area

HeRating, 5 stars17 months ago
Really nice place for stay and thanks for the hospitality, Liz is super friendly and responsive :)
Guest favourite
Hotel room in Cold Spring
4.84 out of 5 average rating, 98 reviews

Room 1 Cold Spring Hotel (Main St.)

RobRating, 5 stars1 week ago
Jimmy is a respectful, kind & gracious Host. He was there to greet us, was very attentive, had great recommendations for places to go in town and was so accommodating. The room & bathroom were very clean, it is a quiet location and incredibly convenient. Everything is within walking distance in the center of town. He also had a very kind and courteous support staff when we checked out in the morning, simply a wonderful and peaceful stay.
Top guest favourite
Hotel room in Woodstock
4.94 out of 5 average rating, 17 reviews

Room 6 - Second Floor - Twin Gables of Woodstock

PaulaRating, 5 stars2 weeks ago
We had the best time!! Leanne was so very friendly and absolutely she is as cool as TWIN GABLES which is saying a lot! We had a gracious welcome and tour and then chatted about the sister hotels and their locations. Our bathroom was SPARKLING and modern and efficient. The artwork through the property was colorful, fun and interesting and a great intro to Woodstock. I just cant believe I was able to secure the room via Airb&b what a total surprise and JACKPOT!!….GOOD karma abides at Twin Gables in Woodstock, NY. I hope to be back and also visit the other hotels all in unique town.
Guest favourite
Hotel room in Hancock
4.87 out of 5 average rating, 15 reviews

Wyndham Bentley Brook ** 2BR Deluxe

KateRating, 5 stars3 months ago
This was a great place to stay as a family for a ski trip! Easy ski on/ski off access to the mountain with ski lockers was a huge plus. Easy enough to walk to a few restaurants. The kids love the movie theater, pool and game room. Very clean and friendly/helpful staff at front desk.

Hotel rentals with a pool

Hotel room in Dover
4.62 out of 5 average rating, 52 reviews

Cozy Queen at Mountaineer Inn

JamesRating, 5 stars2 months ago
Great place to stay for a ski trip to Mt Snow. Cool decor and easy to get to lifts and local restaurants.
Hotel room in Enfield
4.88 out of 5 average rating, 50 reviews

New, modern hotel in Enfield, CT RM3 2 Queens

Dong,HRating, 5 stars9 months ago
Ended up getting the room right next to ours. It had a connecting room which I can rent separately and worked out great.
Superhost
Hotel room in Dover
5 out of 5 average rating, 7 reviews

Luxury King Suite w/balcony in Historic Inn, rm 1

SamirRating, 5 stars29 months ago
Location to Mt Snow was perfect. Amenities were great. Will be back for sure. Very good and welcoming staff that made you feel at ease and comfortable as you’re home.
Hotel room in Shelton
4.75 out of 5 average rating, 76 reviews

Comfort retreat: Guest Room allure

LeilaRating, 5 stars2 weeks ago
A very nice hotel, room was very clean. the host was very helpful with my questions and I appreciate that they allowed me to check-in an hour early. will definitely book again.
Guest favourite
Hotel room in Wilmington
5 out of 5 average rating, 8 reviews

Brook Bound Inn-Main Lodge-King Room 201-2nd Floor

VictoriaRating, 5 stars4 months ago
This place was everything we could have asked for. Incredible place! Will definitely book again! Easy to access and right nearby town. Driveway was cleared of snow. Very clean room, comfortable bedding. Felt safe staying here.
Private room in Elka Park
4.78 out of 5 average rating, 163 reviews

Lodge Rooms in Historic Elka Park

VeronicaRating, 5 stars2 weeks ago
Theresa's accommodations was really cozy and felt like being in home. Everything was cleaned and we loved the location. Highly recommended!
Superhost
Hotel room in Lee

Great place|2 BD|Kitchen| Pool 

ChelsieRating, 5 stars7 months ago
Wow! We had a wonderful experience at this airbnb. My mom and I planned a trip to Stockbridge and we are so grateful that we were able to stay here. We each got the luxury and privacy of our own bedroom and our own bathroom. The accommodations were comfortable, spacious, clean, functional and well designed. The kitchen was very well stocked, enabling us to eat in most nights. We took advantage of the conveniently located laundry facilities. Instructions on how to access the airbnb were very clear and trouble free. We felt it was reasonably priced. It was a superb stay! We would love to come back.
Guest favourite
Hotel room in Lake Luzerne
5 out of 5 average rating, 7 reviews

Sunrise Kitchen Studio (Amazing Lake View)

AnthonyRating, 5 stars8 months ago
as far as price and access to the beach it already was great. Then they even provided kayaks, canoes , fire pits and fast response time service. The view at sunrise and at night make give this place 6 outta 5 stars

Hotel rentals with a patio

Hotel room in Shaftsbury
4.67 out of 5 average rating, 3 reviews

Dog friendly Queen Room

HarryRating, 5 stars22 months ago
We stayed very briefly but everything was clear and easy, the place was lovely and very clean. Would stay again.
Guest favourite
Hotel room in Shelburne Falls
5 out of 5 average rating, 7 reviews

Shelburne Springs

JoRating, 5 stars11 months ago
We really loved our stay at Shelburne Springs! The suite was immaculate & so very beautiful. Each finish, fabric & fixture felt hand picked by an artisan. Janelle, who makes your breakfast, is worth her weight in gold. The entire experience was absolute perfection.
Top guest favourite
Private room in Jamaica
5 out of 5 average rating, 56 reviews

Corsica 2 room Suite at the Jamaicahaus

AndrewRating, 5 stars2 weeks ago
This was our second visit and we were reminded why we loved the Jamaica Haus the first time! We love the quiet atmosphere, the beautiful antiques, and the feeling of staying in a friend’s home. We’ll definitely be staying here again!
Guest favourite
Hotel room in Greenwood Lake
4.93 out of 5 average rating, 14 reviews

Unique lakeside lodging steps from the lake

MattRating, 5 stars4 weeks ago
Great stay at The Breezy. The convenience of the restaurant deck was nice, and the location is beautiful!
Superhost
Private room in Rhinebeck

The Harlow House: Lotus Suite

MichaelRating, 5 stars7 months ago
A little pricey for what we got in a single room out of town in the woods with no kitchen or breakfast. we come quite often to run back and stay in many places with two bedrooms, a kitchen, etc., for less. The area around the house has no Wi-Fi so could be difficult getting there sometimes.
Superhost
Private room in New Haven
4.88 out of 5 average rating, 33 reviews

Peaceful Private Room - The “Dutch Room”

JoelRating, 5 stars2 weeks ago
I was visiting for my daughter’s graduation at Yale, so unfortunately did not take time to use the fully equipped and clean kitchen, or sample some of Sascha’s cooking. The home is situated next to one of the 2+ mile trails around Maltby Lakes, where I enjoyed morning walks in the forest and along the lakes. The home concentrates on supporting native plants. I would like to return in the fall for more homemade chocolate and sample some of Sascha’s vegetarian cooking, which includes cuisines from South America and Asia. The stay was enjoyable with clean comfortable rooms and friendly atmosphere.
Hotel room in Winhall
4.8 out of 5 average rating, 10 reviews

Bromley View Inn Suite #5

JessicaRating, 5 stars4 months ago
This was our first stay at Bromley Inn and it did not disappoint. Check-in was easy, the room was meticulously clean and service was stellar! The location was perfect for access to Bromley, Mt Snow, Magic and Okemo. Lots of great restaurants close by too! Our pups were welcome and we are grateful for this accomodation- they travel with us everywhere:) thankyou for a wonderful stay- we will definitely come back!
Guest favourite
Hotel room in Albany
5 out of 5 average rating, 7 reviews

Hudson 1 at The Argus Hotel

FreddieRating, 5 stars11 months ago
Great place to stay while in Albany. Clean and comfortable. Great complimentary breakfast. Will be back if I visit area.

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