Hotel holiday rentals in The Berkshires

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Popular amenities for hotel rentals in The Berkshires

Family-friendly hotel rentals

Superhost
Hotel room in Goshen
4.71 out of 5 average rating, 28 reviews

Victorian Rose Room; Historic Brook Rd Inn

GabrielRating, 5 stars12 months ago
Great place to crash at an affordable price!
Superhost
Hotel room in Saugerties
4.92 out of 5 average rating, 65 reviews

Village Inn - Tribeca suite - Saugerties NY

TimRating, 5 stars2 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 Fort Montgomery
4.76 out of 5 average rating, 118 reviews

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

KristinRating, 5 stars2 weeks ago
Second time staying here, and would stay again. The rooms are small, but clean and comfortable. Hosts helpful and responsive. We were able to get a last minute early check-in, which was great. The water pressure in the shower was excellent. We like that it is budget friendly (for the area) and clean, and family owned!
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 stars16 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 stars3 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 stars7 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 stars20 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.
Hotel room in Lenox
5 out of 5 average rating, 5 reviews

★ Romantic King Room w/ Double Jacuzzi & Fireplace

AmandaRating, 5 stars25 months ago
Stan made sure we had information on all of the local restaurants, which was super helpful! The hot tub was wonderful, clean, and was perfect for the two of us to enjoy comfortably. Check in was easy and the room was very comfortable. We would happily return!
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 stars28 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
4.71 out of 5 average rating, 31 reviews

Economy Room at The Upper Pass Lodge

Wendy Rating, 5 stars1 week ago
The Upper Pass Lodge is a Very good value very friendly inn keeper ,Clean I would recommend to anyone traveling in VT
Superhost
Hotel room in Lee
4.67 out of 5 average rating, 3 reviews

Great Place|2 BD|Kitchen| Pool 

JoRating, 5 stars2 months 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 rentals with a patio

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

Room 4 - Prickly Pear, double room

BrianRating, 5 stars3 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, 53 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
4.88 out of 5 average rating, 32 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, 76 reviews

Grace and Favor - welcoming one bedroom suite

SiriRating, 5 stars1 month ago
Robert's place was great for our weekend getaway from the city. We were looking for a cosy place to stay when exploring Catskills and the place was just right. The room is spacious and beautifully decorated; all the little details that the host has put into welcoming their guests were lovely. Another big plus were fruits, yoghurt and delicious cakes. Good location to get to Woodstock, not too far to get to the small towns for restaurants.
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
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!

Destinations to explore