Hotel vacation rentals in The Berkshires

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Popular amenities for The Berkshires hotel rentals

Family-friendly hotel rentals

Hotel room in Fort Montgomery

4.76 out of 5 average rating, 116 reviews

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

MiaRating, 5 stars3 months ago
They were very friendly! Check in was quick and easy. Place was exactly as described and seen on photograph. Hopefully can go again!

Hotel room in Whitingham

4.94 out of 5 average rating, 170 reviews

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

HeRating, 5 stars13 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, 84 reviews

Singing Bridge Harmony Room

CarolineRating, 5 stars5 months ago
Our room was just what we needed while in the area. We enjoyed the common spaces including the back deck despite our short stay, and hope to stay here again in future.

Hotel room in Watertown

4.84 out of 5 average rating, 31 reviews

The Depot Square Inn - Room 525

JenniferRating, 5 stars3 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.

Hotel room in South Hadley

5 out of 5 average rating, 11 reviews

Daniel Stebbins Inn: Francis Perkins Room

RebeccaRating, 5 stars9 months ago
This was by far one of the best Air BNB experiences I have had. We only stayed very briefly for a conference but it was absolutely perfect. It was super close to the college, so easy to find, check-in was a breeze, breakfast was delicious and had lots of options, the room was beautiful and the bed was very comfortable. We felt very at home! We were traveling with a trailer and three mini equines so we didn’t have a lot of room for things to get complicated and Ruth made EVERYTHING so easy and comfortable. I am so grateful for her hospitality and if I attend the conference next year, I will definitely be rebooking! I highly recommend staying here. ☺️

Hotel room in Cornwall

5 out of 5 average rating, 6 reviews

Cornwall Inn - Suite w/2 bedrooms (sorry, no pets)

DianaRating, 5 stars17 months ago
Very beautiful place and peaceful surroundings. Breakfast is really good and hosts are very nice and friendly. The rooms were very clean and spacious. We enjoyed our stay

Hotel room in Sharon Springs

5 out of 5 average rating, 16 reviews

Modern luxury suite in the village

DeanRating, 5 stars30 months ago
Charming location and excellent hosts; within 30 minutes to downtown Cooperstown (beautiful farmland and country drives); adjacent restaurant has an outstanding menu and bar; room was very clean and well-appointed; would stay here again without hesitation!
Superhost

Hotel room in Hancock

5 out of 5 average rating, 4 reviews

Wyndham Bentley Brook * Studio

LaurelaRating, 5 stars47 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

Guest favorite

Private room in Stone Ridge

4.97 out of 5 average rating, 79 reviews

VlyHouse - Room 5

YimengRating, 5 stars2 weeks 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!

Hotel room in Monticello

5 out of 5 average rating, 3 reviews

YO1 Longevity & Health Resort, Lakeview King Suite

RockissRating, 5 stars6 months ago
While the resort was outstanding when it comes to the spa treatments everything was very confusing from the treatments itself, to the staff to them not being organized at all. I’m not sure the treatment was performed by a professional certified masseuse. In fact it was a male for both my wife and I. We were never asked to sign a waiver or fill out any kind of paperwork unlike all other spas we’ve been to. I have been with terrible sciatica pain since Sunday July 7, almost a week now. I believe the male therapist worked my back in a way that he shouldn’t have and pinched a nerve. I am unable to walk, get in and out of car and have been seeing a chiropractor since Monday July 8.

Hotel room in Windsor

4.8 out of 5 average rating, 5 reviews

Revitalized Relaxing in Studio Style

Christine LRating, 5 stars2 weeks ago
I really like the set up not your typical hotel setting, very quiet, nice and clean
Superhost

Hotel room in West Springfield

4.86 out of 5 average rating, 7 reviews

Comfortable Queen Suite + free breakfast at MA

TonyaRating, 5 stars3 weeks ago
Everything was great .. the team was great , responsive & always there if I needed anything … the location is perfect … it’s close to restaurants, grocery stores , interstate , etc … I will definitely stay here again …
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 stars24 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.
Superhost

Hotel room in Wilmington

5 out of 5 average rating, 7 reviews

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

JeanneRating, 5 stars5 months ago
Fantastic - beautiful grounds and nice quiet location. Room was immaculate, nicely decorated and had everything one would need. Would definitely stay here again - Jacob is terrific!

Hotel room in Hancock

4.8 out of 5 average rating, 10 reviews

Skion/Skioff Jiminy Peak Resort

BeverleyRating, 5 stars6 days ago
Great location, clean, comfy bed and comfy mattress on pull out sofa. Kitchen had all we needed. David was really quick to respond. It met our needs perfectly.

Hotel rentals with a patio

Superhost

Hotel room in Manchester

4.67 out of 5 average rating, 3 reviews

Oceans 8, minutes to Manchester Vermont

LizRating, 5 stars1 month ago
Great stay! We had a great time and will be back!
Guest favorite

Hotel room in Shelburne Falls

5 out of 5 average rating, 7 reviews

Shelburne Springs

JoRating, 5 stars6 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.
Guest favorite

Private room in Jamaica

5 out of 5 average rating, 47 reviews

Corsica 2 room Suite at the Jamaicahaus

MatthewRating, 5 stars3 weeks ago
Mercedes was FANTASTIC, after a long day on the mountain and being tired.. Instantly greeted myself and my friends and was so helpful and made us right at home.. Would definitely stay here again!

Hotel room in Mount Tremper

4.8 out of 5 average rating, 5 reviews

Farmhouse Inn in the Heart of the Catskills (Rm 8)

HeatherRating, 5 stars2 months ago
We needed help and William was there. So sorry to bother you William, but you saved us—thank you!!!

Private room in New Haven

4.87 out of 5 average rating, 31 reviews

Peaceful Private Room - The “Dutch Room”

JiRating, 5 stars4 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 favorite

Hotel room in Kingston

4.99 out of 5 average rating, 70 reviews

Grace and Favor - welcoming one bedroom suite

JkRating, 5 stars1 month ago
We enjoyed our stay at Robert's place. The room was beautifully decorated and very comfortable. Linens were of high quality. We are looking forward to return.
Superhost

Private room in Chester

4.78 out of 5 average rating, 63 reviews

Honeymoon Suite with Jacuzzi Tub in Historic Inn

AddisonRating, 5 stars3 weeks ago
Such a neat place to stay. The room was unique, and the jacuzzi tub was fantastic. Check in could not have been easier.

Destinations to explore