Photo by Photo courtesy of Berkshire Visitors Bureau

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

Start date: Check-in selected.
To Date
End date: Check-out

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check availability on The Berkshires Adventure Sport Hotels

Tonight
26 Nov - 27 Nov
Tomorrow
27 Nov - 28 Nov
This weekend
28 Nov - 30 Nov
Next weekend
5 Dec - 7 Dec

Top The Berkshires Adventure Sport Hotels

Property amenity
Courtyard by Marriott Lenox Berkshires

Courtyard by Marriott Lenox Berkshires

3.0 star property
Lenox
9.2 out of 10, Wonderful, (587)
"Roomy, clean, the view is fantastic with the foliage, exactly like the photos. "
United States
Mingming
The price is €118
includes taxes & fees
24 Dec - 25 Dec
Courtyard by Marriott Lenox Berkshires
Exterior
Element Lenox Berkshires

Element Lenox Berkshires

3.0 star property
Lenox
9.8 out of 10, Exceptional, (11)
"New hotel very nice"
United States
joel
The price is €127
includes taxes & fees
11 Dec - 12 Dec
Element Lenox Berkshires
Outdoor dining
Downtown | Waterfront | Walk to Shops

Downtown | Waterfront | Walk to Shops

Williamstown
10.0 out of 10, Exceptional, (7)
"Perfect setup for anyone visiting Williamstown."
United States
Michael P.
The price is €245
includes taxes & fees
8 Dec - 9 Dec
Downtown | Waterfront | Walk to Shops
Exterior
North Getaway Cottage

North Getaway Cottage

Williamstown
9.2 out of 10, Wonderful, (24)
"The cottage was the perfect accommodations for our overnight stay in town for a funeral. Thank you Claudia. "
United States
Mary Alice H.
The price is €400
includes taxes & fees
1 Dec - 2 Dec
North Getaway Cottage
Games room
Pet Friendly Riverfront Home in Great Barrington

Pet Friendly Riverfront Home in Great Barrington

Great Barrington
9.4 out of 10, Exceptional, (6)
The price is €264
includes taxes & fees
30 Nov - 1 Dec
Pet Friendly Riverfront Home in Great Barrington
Fridge, microwave, oven, stovetop
Luxe Berkshires Ski Retreat w/ Fireplace, King Bed, Chef's Kitchen, Washer/Dryer

Luxe Berkshires Ski Retreat w/ Fireplace, King Bed, Chef's Kitchen, Washer/Dryer

Great Barrington
The price is €329
includes taxes & fees
30 Nov - 1 Dec
Luxe Berkshires Ski Retreat w/ Fireplace, King Bed, Chef's Kitchen, Washer/Dryer
Lobby
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 €95
includes taxes & fees
28 Nov - 29 Nov
Pilgrim Inn
Front of property
Simsbury 1820 House

Simsbury 1820 House

4.0 star property
Simsbury Center
9.2 out of 10, Wonderful, (1006)
"Very nice room, pleasant and helpful staff"
United States
Concetta
The price is €173
includes taxes & fees
30 Nov - 1 Dec
Simsbury 1820 House
Interior detail
Valley Craft Ales

Valley Craft Ales

2.0 star property
Wilmington
8.4 out of 10, Very good, (181)
"Fun place to stay!!"
United States
Brian
Valley Craft Ales
Seasonal outdoor pool
Farm Road Estate

Farm Road Estate

3.0 star property
West Dover
10.0 out of 10, Exceptional, (76)
"Beautiful, peaceful friendly convenience"
United States
Tammy
Farm Road Estate
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.
View all properties

Top The Berkshires Hotel Reviews

Hotel On North

Hotel On North

10/10 Excellent
"Wonderful stay, as usual. I have business in the Pittsfield area, 3 or 4 times a year and wouldn’t think of staying anywhere else. Quiet, comfortable….staff is always helpful and friendly….restaurant in the building is just another plus."
Michael 1-night trip
Posted 5 days ago
Hotel On North

Explore a world of travel with Expedia

Frequently asked questions

How much do hotels for couples in The Berkshires cost?
You'll pay between €95 and €400 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 €95 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.