
Hotel holiday rentals in The Berkshires
Find and book unique hotel rentals on Airbnb
Top-rated hotel rentals in The Berkshires
Guests agree: these hotel rentals are highly rated for location, cleanliness and more.
Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for hotel rentals in The Berkshires
Family-friendly hotel rentals

Village Inn - Tribeca suite - Saugerties NY
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!

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

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

The Engel House Room 3: Mt Snow/Wilmington VT Area
Really nice place for stay and thanks for the hospitality, Liz is super friendly and responsive :)

Singing Bridge Harmony Room
Wonderful place perfect for our weekend get away with our “ fur baby” felt very welcoming

The Depot Square Inn - Room 525
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.

Room 9 - Third Floor - Twin Gables of Woodstock
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

Wyndham Bentley Brook * Studio
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

VlyHouse - Room 5
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!

Beautiful place|2 BD|Kitchen| Pool
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.

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

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

Economy Room at The Upper Pass Lodge
Incredible place, very welcoming and friendly.

Cozy Creative Colonial
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.

Great Place|2 BD|Kitchen| Pool
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.

Skion/Skioff Jiminy Peak Resort
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

4 Prickly Pear, double room
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

Shelburne Springs
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.

Corsica 2 room Suite at the Jamaicahaus
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.

Peaceful Private Room - The “Dutch Room”
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.

Grace and Favor - welcoming one bedroom suite
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!

Unique lakeside lodging steps from Greenwood Lake
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.

Lake George B&B - Breakfast - Fire Pit - Wine Bar
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
Destinations to explore
- Farm stay rentals The Berkshires
- Holiday home rentals The Berkshires
- Flat rentals The Berkshires
- Rentals with a cinema The Berkshires
- Rentals with a kayak The Berkshires
- Rentals with pools The Berkshires
- Rentals with a hot tub The Berkshires
- Smoking-friendly rentals The Berkshires
- Cabin rentals The Berkshires
- Family-friendly rentals The Berkshires
- Private suite rentals The Berkshires
- Rentals with a washing machine and dryer The Berkshires
- Rentals with a firepit The Berkshires
- Guest house rentals The Berkshires
- Ski-in/ski-out rentals The Berkshires
- House rentals The Berkshires
- Rentals with an accessible-height toilet The Berkshires
- Beachfront rentals The Berkshires
- Luxury rentals The Berkshires
- Fitness-friendly rentals The Berkshires
- Rentals with outdoor seating The Berkshires
- Townhouse rentals The Berkshires
- Cottage rentals The Berkshires
- Rentals with beach access The Berkshires
- Rentals with breakfast The Berkshires
- Waterfront rentals The Berkshires
- Bed and breakfasts The Berkshires
- Rentals with lake access The Berkshires
- Rentals with an EV charger The Berkshires
- Rentals with a sauna The Berkshires
- Lakehouse rentals The Berkshires
- Aparthotel rentals The Berkshires
- Family-friendly rentals The Berkshires
- Rentals with a patio The Berkshires
- Chalet rentals The Berkshires
- Apartment rentals The Berkshires
- Boutique hotel rentals The Berkshires
- Villa rentals The Berkshires
- Pet-friendly rentals The Berkshires
- Rentals with a fireplace The Berkshires
- Hotel rentals United States
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom