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
4.92 out of 5 average rating, 65 reviews

Village Inn - Tribeca suite - Saugerties NY

TimRating, 5 stars1 month 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 Fort Montgomery
4.76 out of 5 average rating, 117 reviews

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

MichałRating, 5 stars1 month ago
It was a really amazing time in an unique place. Al is a great person that gives a lot information both on local history and guiding on visiting the area. He's s very helpful with anything that is needed during stay. We'll be back!
Superhost
Hotel room in Lake George
4.83 out of 5 average rating, 36 reviews

Romeo's Haven (Rm 4 - Romeo & Giulietta's Inn/B&B)

ShaneRating, 5 stars19 months ago
Kimberly was an amazing host and super friendly. The breakfast provided was great and she and her family were super nice. She offered helpful information for things to do nearby in Lake George as well. 11/10 would love to come back sometime. The air bnb was beautiful and the privacy we had while staying was refreshing. The room we got to stay in was astoundingly well decorated with impeccable taste just like the pictures. It was very comfortable and quiet at the air bnb. Worth another trip in the future for sure. Thank you so 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 stars15 months ago
Really nice place for stay and thanks for the hospitality, Liz is super friendly and responsive :)
Superhost
Hotel room in Cummington
4.82 out of 5 average rating, 85 reviews

Singing Bridge Harmony Room

EileenRating, 5 stars2 months ago
Wonderful place perfect for our weekend get away with our “ fur baby” felt very welcoming
Hotel room in Watertown
4.84 out of 5 average rating, 31 reviews

The Depot Square Inn - Room 525

JenniferRating, 5 stars6 months ago
My husband and I were in the area just for the night to pick up a family member for a road trip. The location in the Depot Square connected to me, as my mom used to take me to the Farm Shoppe when I was little. I wish I had the time to eat there but we left very early. The location was convenient, different for sure - but well done. Easy, spacious, comfortable & clean. Very reasonably priced. Would absolutely stay again when visiting back home.
Guest favourite
Hotel room in Woodstock
4.91 out of 5 average rating, 34 reviews

Room 9 - Third Floor - Twin Gables of Woodstock

AudreyRating, 5 stars19 months ago
loving twin gables as ever; leeann the innkeeper is the BEST and always makes me feel welcome and fully received :) (my 2nd stay this summer) thank you for the HEART you put into your caretaking of this place, it's seen and valued. <3
Hotel room in Hancock
5 out of 5 average rating, 4 reviews

Wyndham Bentley Brook * Studio

LaurelaRating, 5 stars50 months ago
We had such a great time at Rob&Julia's place. Very good communication, great location, the place was sparkling clean! I will definitely come back again with my family! One of my best experiences

Hotel rentals with a pool

Top guest favourite
Private room in Stone Ridge
4.97 out of 5 average rating, 79 reviews

VlyHouse - Room 5

YimengRating, 5 stars3 months ago
Second time here, really wish to stay here longer. Such a cozy place I love it a lot! The bed is way too comfortable just can’t get up. We came back to see The host Mrs Doris and her husband Jon. Jon was also surprised to see us and we are happy to see him still as happy as before! Definitely a nice place to stay for getaway!
Superhost
Hotel room in Lee
5 out of 5 average rating, 3 reviews

Beautiful place|2 BD|Kitchen| Pool

ChristianRating, 5 stars5 months ago
This rental was the perfect fit for what I was looking for. I came out to the Berkshires with some family to take advantage of the outdoors and local communities. I've been coming out to the Berkshires for years, so I was familiar with the area, and couldn't have asked for a more convenient location with the rental being close enough to lots of great towns and main roads or highways. There was lots to do at the resort, and everything was open much later than I would have expected. The rental space itself was vary spacious and having separate bedrooms and a full kitchen and balcony were great aspects that totally added to the whole experience. I felt it was a great value for what's available in the area. We didn't have any issues with any part of our stay, so I was very pleased and would highly recommend it to anyone interested in taking advantage of everything the Berkshires has to offer.
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 stars27 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.
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 stars2 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.
Superhost
Hotel room in Londonderry
4.7 out of 5 average rating, 30 reviews

Economy Room at The Upper Pass Lodge

Gian CarloRating, 5 stars2 months ago
Incredible place, very welcoming and friendly.
Guest favourite
Resort in Cromwell
4.91 out of 5 average rating, 11 reviews

Cozy Creative Colonial

DruRating, 5 stars6 days ago
I stayed at Jennifer's place for business and loved it. I loved the hardwood floors and antique furniture. Jennifer was wonderfully hospitable and I had a relaxing evening before a long day of work -- Just what I needed.
Superhost
Hotel room in Lee
4.67 out of 5 average rating, 3 reviews

Great Place|2 BD|Kitchen| Pool 

JoRating, 5 stars1 month ago
This stay was perfect in all ways. It was a nice setting and a great place for families to stay with big apartments and great amenities. The host and staff were helpful and responsive. The kitchen had all we needed for meal prep.
Hotel room in Hancock
4.63 out of 5 average rating, 16 reviews

Skion/Skioff Jiminy Peak Resort

SydneyRating, 5 stars1 month ago
Great place to stay! The room was right on the resort and walking distance from everything! Perfect place for our short weekend getaway!

Hotel rentals with a patio

Superhost
Hotel room in Manchester
4.8 out of 5 average rating, 5 reviews

4 Prickly Pear, double room

BrianRating, 5 stars2 months ago
Great location with easy check in and check out. Whether you are passing through for a night or staying for the week this is a great option. The snack room was great with light fare and snacks available to all guests 24/7
Guest favourite
Hotel room in Shelburne Falls
5 out of 5 average rating, 7 reviews

Shelburne Springs

JoRating, 5 stars9 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, 52 reviews

Corsica 2 room Suite at the Jamaicahaus

MorganRating, 5 stars1 month ago
We had a great stay! Mercedes was a lovely host. The inn is so cozy and had everything we needed. We loved being able to spread out in the communal space. The little market across the street is super convenient too! Would definitely stay here again.
Superhost
Private room in New Haven
4.87 out of 5 average rating, 31 reviews

Peaceful Private Room - The “Dutch Room”

JiRating, 5 stars7 months ago
Sascha is an absolutely wonderful host -- always ready to offer help, and to make sure you feel at home. Her place is impeccably clean, and has both the privacy and the community that you might need, especially in a long stay. Highly recommend.
Guest favourite
Hotel room in Kingston
4.97 out of 5 average rating, 75 reviews

Grace and Favor - welcoming one bedroom suite

ThomasRating, 5 stars1 month ago
We had a lovely stay. Very cozy and welcoming with a sense of history on the picturesque property. The outdoor tree lights were stunning as we pulled in after dark. Check in was easy and we felt right at home immediately. There were lots of little extras that made us feel special: book lights in the bedside tables, coffee/tea, yogurt and milk in the fridge, cookies/biscuits and fruits, lots of throw pillows and blankets. It was a really nice setup for working or lounging. The bathroom is beautiful! Huge shower with an artisanal bar of soap. The bed was very comfortable and the heat was easy to adjust. Everything was scrupulously clean and well-labeled. The wall and ceiling candelabras cast a warm light and were all dim-able. Lovely touches all around! We would come back again!
Superhost
Hotel room in Greenwood Lake
4.71 out of 5 average rating, 7 reviews

Unique lakeside lodging steps from Greenwood Lake

DanielRating, 5 stars22 months ago
I can honestly say it was way better than expected. Host reached out to me before I even realized I might miss the check in window and took care of me and my family. Thank you so much.
Superhost
Hotel room in Lake Luzerne
5 out of 5 average rating, 3 reviews

Lake George B&B - Breakfast - Fire Pit - Wine Bar

CharlesRating, 5 stars6 months ago
Stayed here 33 years ago on our last minute change on our honeymoon, loved the place then and now 33 years later love it even more. The staff was very accommodating and friendly the breakfast is to die for nice menu and daily specials make it even more special. Loved the outdoor fire pit and sitting at night on the porch oh! And they have a wine bar with cheese platter accompanied by live music. Definitely be back in the near future. Maria & Charles B

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