Photo by Photo courtesy of Berkshire Visitors Bureau

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Check availability on The Berkshires Adventure Hotels

Tonight
Dec 29 - Dec 30
Tomorrow
Dec 30 - Dec 31
This weekend
Jan 2 - Jan 4
Next weekend
Jan 9 - Jan 11

Our top choices for The Berkshires adventure hotels

Exterior
Element Lenox Berkshires

Element Lenox Berkshires

Element Lenox Berkshires
3.0 star property
Lenox
9.6 out of 10, Exceptional, (14)
"Rooms were very clean and spacious."
United States
Morgan
The price is ￥21,137
￥23,610 total
includes taxes & fees
Jan 5 - Jan 6, 2026
Element Lenox Berkshires
Exterior
Courtyard by Marriott Lenox Berkshires

Courtyard by Marriott Lenox Berkshires

Courtyard by Marriott Lenox Berkshires
3.0 star property
Lenox
9.2 out of 10, Wonderful, (594)
"Roomy, clean, the view is fantastic with the foliage, exactly like the photos. "
United States
Mingming
The price is ￥21,763
￥24,310 total
includes taxes & fees
Jan 6 - Jan 7, 2026
Courtyard by Marriott Lenox Berkshires
Exterior
1st Floor Mountain View Suite Ski On/Off At Jiminy- Fully Redone Decor

1st Floor Mountain View Suite Ski On/Off At Jiminy- Fully Redone Decor

1st Floor Mountain View Suite Ski On/Off At Jiminy- Fully Redone Decor
Hancock
8.8 out of 10, Excellent, (8)
"Everything was wonderful…"
United States
Alyne K.
The price is ￥24,738
￥47,395 total
includes taxes & fees
Jan 4 - Jan 5, 2026
1st Floor Mountain View Suite Ski On/Off At Jiminy- Fully Redone Decor
Game room
Family Ski Getaway in the Berkshires

Family Ski Getaway in the Berkshires

Family Ski Getaway in the Berkshires
Great Barrington
9.4 out of 10, Exceptional, (6)
"The host was exceptional and so kind. The location was in close proximity to 3 quaint New England small towns whose downtowns had many restaurants and local shops to enjoy-Great Barrington (GB Eats for breakfast), Stockbridge (best shopping) and Lenox (exceptional dinner at Frankie’s Italian). The house looked updated on the outside but inside looked like early 1900s with a hint of Victorian influence. My only caution is for anyone with mobility issues as all 3 bedrooms and the only (very small)...
United States
Kathy C.
The price is ￥31,584
￥46,429 total
includes taxes & fees
Jan 8 - Jan 9, 2026
Family Ski Getaway in the Berkshires
Microwave, oven, stovetop, dishwasher
Cozy. Clean. Free bagel shop. 3 Fireplaces.

Cozy. Clean. Free bagel shop. 3 Fireplaces.

Cozy. Clean. Free bagel shop. 3 Fireplaces.
Great Barrington
10.0 out of 10, Exceptional, (1)
"The host was very responsive and friendly. The house was well equipped and very comfortable. We did get breakfast at the Great Barrington Bagel Company and had a great breakfast. Highly recommend!"
United States
Mary R.
The price is ￥53,030
￥91,639 total
includes taxes & fees
Jan 7 - Jan 8, 2026
Cozy. Clean. Free bagel shop. 3 Fireplaces.
Lobby
Pilgrim Inn

Pilgrim Inn

Pilgrim Inn
2.5 star property
Lee
5.8 out of 10, (332)
"Was horrible. Unsafe and scarey"
United States
Sharon
The price is ￥12,493
￥13,955 total
includes taxes & fees
Jan 3 - Jan 4, 2026
Pilgrim Inn
Interior
Hideaway Inn Mt. Snow

Hideaway Inn Mt. Snow

Hideaway Inn Mt. Snow
2.0 star property
West Dover
10.0 out of 10, Exceptional, (9)
"Clean rooms/ close to mountain/ nice experience"
United States
Morgan
The price is ￥20,553
￥22,609 total
includes taxes & fees
Jan 6 - Jan 7, 2026
Hideaway Inn Mt. Snow
Front of property
Simsbury 1820 House

Simsbury 1820 House

Simsbury 1820 House
4.0 star property
Simsbury Center
9.2 out of 10, Wonderful, (1004)
"Friendly, welcoming, and helpful staff. The room was beautiful and clean. The bar and restaurant were cozy; drinks and food delicious. "
United States
Christina
The price is ￥24,799
￥31,209 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Simsbury 1820 House
Garden
Big Bears Lodge

Big Bears Lodge

Big Bears Lodge
3.0 star property
West Dover
9.0 out of 10, Wonderful, (185)
"The owners were wonderful: kind, interesting to talk to, and very hospitable."
United States
Margaret
The price is ￥27,802
￥30,581 total
includes taxes & fees
Jan 11 - Jan 12, 2026
Big Bears Lodge
Property grounds
The Creation Station is a cozy place so make yourself at home.

The Creation Station is a cozy place so make yourself at home.

The Creation Station is a cozy place so make yourself at home.
Easthampton Ma.
10.0 out of 10, Exceptional, (72)
"The place is wonderful. Our 2nd visit and will be back. Has everything you need and then some. For us its centrally located so more family came for day trips. "
United States
Connie P.
The price is ￥28,075
￥42,858 total
includes taxes & fees
Jan 12 - Jan 13, 2026
The Creation Station is a cozy place so make yourself at home.
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top The Berkshires Hotel Reviews

Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG

10/10 Excellent
"Did not have breakfast. Wish it was free but the hotel staff was amazing and the valet was great too! "
Rakhee 2-night trip
Posted 1 day ago
Holiday Inn & Suites Pittsfield-Berkshires by IHG

Frequently asked questions

How much do hotels for couples in The Berkshires cost?
You'll pay between ￥13,955 and ￥91,639 per night for hotels for couples in The Berkshires. Whatever your budget, you'll find the perfect stay on Expedia. These prices were available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.
How many hotels for couples are there in The Berkshires?
Choose from 68 hotels for couples in The Berkshires. Whether you're looking to take a break without the kids or just want to make some precious new memories with your honey, Expedia makes it a cinch to find the perfect place.
What are the best cheap hotels for couples in The Berkshires?
Enjoy savings on your romantic The Berkshires break by reserving hotels for couples from just ￥13,955 per night. Getting ready to explore the top attractions of Lenox? Get comfortable at The Yankee, Trademark Collection by Wyndham, a budget-friendly option with pool sun loungers and mountain views. If you're headed to Williamstown, Fairfield Inn & Suites by Marriott Williamstown is a superb choice. Make use of amenities like a swimming pool and mountain views, and enjoy some quality one-on-one time. There are plenty of free and fabulous attractions wherever you go in The Berkshires. If your adventures take you to Lenox, explore Canoe Meadows Wildlife Sanctuary. You can also sightsee without spending a dime in Williamstown. Mount Greylock is one of the best free things to do here. This price was available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.
Are there any 5-star hotels for couples in The Berkshires?
In The Berkshires, 5-star hotels for couples are difficult to come by. However, there are some 4-star options available. If your destination is Lenox, one fantastic option is Garden Gables Inn. It comes with amenities like dining romance packages and designer toiletries. Alternatively, spend some quality together time at Hampton Terrace Inn, also in Lenox. Conveniences here include a tennis court and concierge services.
Why book your hotel for couples in The Berkshires with Expedia?
We think that a trip with your sweetheart should be hassle-free, so if you're chasing a hotel for couples in The Berkshires at a great price, Expedia has got you covered. Stick to the budget and choose a comfortable motel, or splurge and book a luxury hotel break to surprise your favorite person.
How can I find cheap hotels for couples in The Berkshires?
With Expedia's user-friendly filter tool, booking cheap hotels for couples in The Berkshires is a piece of cake. To find accommodations that'll make your pocket and partner smile, narrow your search results by amenities, star rating and budget.
What is there to do in The Berkshires near my hotel for couples?
Whatever your interests, there are almost endless things to keep you entertained in The Berkshires. If you're off to Williamstown, swing by Sterling and Francine Clark Art Institute, Williams College Museum of Art and Hopkins Observatory. Taking off to Pittsfield? Bousquet Ski Area, Barrington Stage Company and Berkshire Museum are among the top attractions in this city.

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