The Berkshires Hotel Guide - Adventure Sport Hotels in The Berkshires, Massachusetts

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Check availability on The Berkshires Adventure Sport Hotels

Tonight
29 Apr - 30 Apr
Tomorrow
30 Apr - 1 May
This weekend
1 May - 3 May
Next weekend
8 May - 10 May

Our top choices for The Berkshires adventure hotels

Suite, Multiple Beds, Non Smoking, Fireplace (with Sofabed)

Best Western Plus Berkshire Hills Inn & Suites

Best Western Plus Berkshire Hills Inn & Suites
2.5 star property
Pittsfield
8.6 out of 10, Excellent, (1,001 reviews)
"Room was clean. Breakfast was fresh and the area was pristine. All staff was pleasant. "
United States
Melinda
The price is €101
includes taxes & fees
6 May - 7 May
Best Western Plus Berkshire Hills Inn & Suites
Property amenity

Courtyard by Marriott Lenox Berkshires

Courtyard by Marriott Lenox Berkshires
3.0 star property
Lenox
9.2 out of 10, Wonderful, (620 reviews)
"Beautiful outdoor space. "
United States
Jairo
The price is €166
includes taxes & fees
11 May - 12 May
Courtyard by Marriott Lenox Berkshires
Indoor pool, a heated pool

1st FL Mtn View Woodland Suite on Jiminy Sleeps 4 Ski On/Off, Fully Redone Count

1st FL Mtn View Woodland Suite on Jiminy Sleeps 4 Ski On/Off, Fully Redone Count
Hancock
9.4 out of 10, Exceptional, (6 reviews)
"Convenience to slopes and restaurants really great….,had a nice stay"
United States
Thomas S.
The price is €202
includes taxes & fees
30 Apr - 1 May
1st FL Mtn View Woodland Suite on Jiminy Sleeps 4 Ski On/Off, Fully Redone Count
Outdoor dining

Downtown | Waterfront | Walk to Shops

Downtown | Waterfront | Walk to Shops
Williamstown
10.0 out of 10, Exceptional, (7 reviews)
"Perfect setup for anyone visiting Williamstown."
United States
Michael P.
The price is €248
includes taxes & fees
17 May - 18 May
Downtown | Waterfront | Walk to Shops
Interior

Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!

Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!
Sherwood Forest
10.0 out of 10, Exceptional, (5 reviews)
"We loved it! Lots of local hiking trails and a wonderful relaxing place."
United States
Sharon K.
The price is €322
includes taxes & fees
11 May - 12 May
Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!
A heated pool

Comfortable Berkshires retreat on mtn resort, SISO

Comfortable Berkshires retreat on mtn resort, SISO
Hancock
8.8 out of 10, Excellent, (8 reviews)
"Kind and responsive host."
United States
Javier
The price is €456
includes taxes & fees
30 Apr - 1 May
Comfortable Berkshires retreat on mtn resort, SISO
Exterior

North Getaway Cottage

North Getaway Cottage
Williamstown
9.2 out of 10, Wonderful, (24 reviews)
"We stayed here on a beautiful fall weekend so that my son could tour William's college. It was perfect!"
United States
Carole S.
The price is €378
includes taxes & fees
11 May - 12 May
North Getaway Cottage
Interior

Cozy Riverside Berkshires Retreat

Cozy Riverside Berkshires Retreat
Great Barrington
9.2 out of 10, Wonderful, (14 reviews)
"Close to a great bakery and near to a farm market and shopping mall. "
United States
Cristine C.
The price is €269
includes taxes & fees
30 Apr - 1 May
Cozy Riverside Berkshires Retreat
A heated pool

Mountain View Suite at Jiminy Peak - Ski On Off - Near Elevator, Pool, and Lobby

Mountain View Suite at Jiminy Peak - Ski On Off - Near Elevator, Pool, and Lobby
Hancock
9.6 out of 10, Exceptional, (5 reviews)
"My family loved our stay here at Jiminy! You can’t beat the ski in and ski out feature, in addition to dining and several amenities all within the resort. Howard was an attentive and communicative host, ensuring we had everything our needed to have the best stay possible. We will definitely be returning!"
United States
katie s.
The price is €202
includes taxes & fees
30 Apr - 1 May
Mountain View Suite at Jiminy Peak - Ski On Off - Near Elevator, Pool, and Lobby
Outdoor dining

3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!

3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!
Pittsfield
7.8 out of 10, Good, (7 reviews)
"The space was well situated to our plans, food,lake and hiking and very clean but smelled sooo strongly of dogs that we limited our time inside."
United States
Liz V.
The price is €424
includes taxes & fees
1 May - 2 May
3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!
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

The Red Lion Inn

The Red Lion Inn

10/10 Excellent
"The best!"
Mark 2-night trip
Posted 11 hours ago
The Red Lion Inn

Frequently asked questions

How much do hotels for couples in The Berkshires cost?
You'll pay between €101 and €456 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 €101 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 favourite 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 accommodation 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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