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Check prices for these dates

Next weekend
7 Feb - 9 Feb
In two weeks
14 Feb - 16 Feb
In one month
28 Feb - 2 Mar
In two months
28 Mar - 30 Mar

Featured Cottages in The Berkshires and around

Life House Berkshires
Lobby

Life House Berkshires

3.5 star property
9.0 out of 10, Wonderful, (486)
"Rooms were very clean. Entire place smelled amazing. Very comfortable! "
The price is €104
includes taxes & fees
3 Feb - 4 Feb
Life House Berkshires
The Williams Inn
Front of property – evening/night

The Williams Inn

4.0 star property
9.6 out of 10, Exceptional, (408)
"Very modern good restaurant convienent"
The price is €221
includes taxes & fees
5 Feb - 6 Feb
The Williams Inn
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires, an IHG Hotel
Property amenity

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires, an IHG Hotel

3.5 star property
9.0 out of 10, Wonderful, (592)
"Plenty of room. Good location to local skiing. Clean."
The price is €141
includes taxes & fees
3 Mar - 4 Mar
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires, an IHG Hotel
Hotel Downstreet, Ascend Hotel Collection
Hypo-allergenic bedding, laptop workspace, blackout curtains

Hotel Downstreet, Ascend Hotel Collection

3.0 star property
8.6 out of 10, Excellent, (1003)
"The hotel was in a very walkable community. I enjoyed the galleries in the lobby and the art museum nearby."
Hotel Downstreet, Ascend Hotel Collection
The Black Swan Lee - Lenox, Ascend Hotel Collection
Lobby

The Black Swan Lee - Lenox, Ascend Hotel Collection

3.0 star property
9.0 out of 10, Wonderful, (1005)
"Close to Dunkin"
The price is €105
includes taxes & fees
2 Feb - 3 Feb
The Black Swan Lee - Lenox, Ascend Hotel Collection
The Red Lion Inn
Outdoor pool, pool loungers

The Red Lion Inn

3.5 star property
8.8 out of 10, Excellent, (1001)
"The property is historic, so the lodgings are dated along with some of the amenities. I only stayed one night and most likely would have stayed somewhere more modern if it was longer."
The price is €203
includes taxes & fees
2 Mar - 3 Mar
The Red Lion Inn
Holiday Inn & Suites Pittsfield-Berkshires, an IHG Hotel
Exterior

Holiday Inn & Suites Pittsfield-Berkshires, an IHG Hotel

3.0 star property
8.0 out of 10, Very good, (729)
"We stay here often because it is close to our daughter’s school in New York. We love staying here and choose this hotel every time. "
The price is €114
includes taxes & fees
7 Feb - 8 Feb
Holiday Inn & Suites Pittsfield-Berkshires, an IHG Hotel
The Yankee, Trademark Collection by Wyndham
Exterior

The Yankee, Trademark Collection by Wyndham

2.5 star property
9.0 out of 10, Wonderful, (1003)
"Surprisingly excellent property. Desk staff was superb and gracious in handling a reservation foul-up (not their fault). Would gladly return!"
The price is €110
includes taxes & fees
2 Mar - 3 Mar
The Yankee, Trademark Collection by Wyndham
Hotel On North
Front of property – evening/night

Hotel On North

3.5 star property
9.6 out of 10, Exceptional, (680)
"Had a great stay - such a gem of a hotel. "
The price is €122
includes taxes & fees
9 Feb - 10 Feb
Hotel On North
Berkshire Mountain Lodge
Fridge, microwave, stovetop, coffee/tea maker

Berkshire Mountain Lodge

3.0 star property
8.8 out of 10, Excellent, (426)
"It is a 3 day family trip. Our stay was excellent. Room is big and tidy. The staff was very nice and accomodating.. the place is close to all.. restaurant, grocery, gas station etc.. "
The price is €136
includes taxes & fees
3 Feb - 4 Feb
Berkshire Mountain Lodge
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
Lobby lounge

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

2.5 star property
9.2 out of 10, Wonderful, (681)
"My kids said this was their favorite hotel ever likely thanks to the cool game room. It’s pretty annoying they don’t accept animals and don’t have any food options in the hotel. The breakfast was nice "
The price is €163
includes taxes & fees
24 Feb - 25 Feb
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
The Little Lion
Exterior

The Little Lion

3.0 star property
8.8 out of 10, Excellent, (464)
"Quirky quiet cute little place!"
The price is €69
includes taxes & fees
23 Feb - 24 Feb
The Little Lion
The Constance, The Whitlock, & The Dewey By The Lenox Collection
Free WiFi, bed sheets

The Constance, The Whitlock, & The Dewey By The Lenox Collection

3.5 star property
8.6 out of 10, Excellent, (424)
"Great location. Easy walk to restaurants "
The price is €112
includes taxes & fees
25 Feb - 26 Feb
The Constance, The Whitlock, & The Dewey By The Lenox Collection
Quality Inn
Standard Room, 2 Queen Beds, Non Smoking

Quality Inn

2.5 star property
8.2 out of 10, Very good, (1005)
"All went well"
The price is €91
includes taxes & fees
13 Feb - 14 Feb
Quality Inn
The Cornell Inn, Lenox
Porch

The Cornell Inn, Lenox

3.0 star property
9.0 out of 10, Wonderful, (1001)
"My room was adorable...completely charming and well appointed. I appreciated the phone call with detailed late check-in instructions and when I arrived the property manager walked me to my room. Breakfast was lovely and the staff very friendly. Town a is an easy walk."
The price is €137
includes taxes & fees
3 Feb - 4 Feb
The Cornell Inn, Lenox
Best Western Plus Berkshire Hills Inn & Suites
Lobby sitting area

Best Western Plus Berkshire Hills Inn & Suites

2.5 star property
8.6 out of 10, Excellent, (1000)
"Great place for an overnight with my friend!"
The price is €104
includes taxes & fees
6 Feb - 7 Feb
Best Western Plus Berkshire Hills Inn & Suites
Fairfield Inn & Suites by Marriott Williamstown
Exterior

Fairfield Inn & Suites by Marriott Williamstown

2.5 star property
8.8 out of 10, Excellent, (319)
"Great front desk staff"
The price is €153
includes taxes & fees
3 Mar - 4 Mar
Fairfield Inn & Suites by Marriott Williamstown
Hampton Inn & Suites Berkshires-Lenox
Exterior

Hampton Inn & Suites Berkshires-Lenox

2.5 star property
9.2 out of 10, Wonderful, (1001)
"Solid"
The price is €122
includes taxes & fees
23 Feb - 24 Feb
Hampton Inn & Suites Berkshires-Lenox
Chambery Inn
Front of property

Chambery Inn

3.0 star property
9.6 out of 10, Exceptional, (363)
"Chamberry Inn was a nice, quiet, relaxing stay. Enjoyed every second of it. The staff were kind and helpful. Would definitely stay again if I was in the area."
The price is €204
includes taxes & fees
13 Feb - 14 Feb
Chambery Inn
Courtyard by Marriott Lenox Berkshires
Property amenity

Courtyard by Marriott Lenox Berkshires

3.0 star property
9.2 out of 10, Wonderful, (547)
"Very helpful staff. Went above and beyond for our needs. Our room was very comfortable with a comfy couch. The bed was incredible! The pool area is very nice!! "
The price is €140
includes taxes & fees
3 Mar - 4 Mar
Courtyard by Marriott Lenox Berkshires
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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Other property types in The Berkshires

Vacation Village in the Berkshires
Indoor pool, outdoor pool, pool umbrellas

Vacation Village in the Berkshires

3.0 star property
8.6 out of 10, Excellent, (1759)
"Great place "
The price is €167
includes taxes & fees
3 Feb - 4 Feb
Vacation Village in the Berkshires
The Ponds at Foxhollow by Capital Vacations
Property grounds

The Ponds at Foxhollow by Capital Vacations

3.0 star property
8.6 out of 10, Excellent, (120)
"Very comfortable property in a lovely setting "
The price is €248
includes taxes & fees
14 Feb - 15 Feb
The Ponds at Foxhollow by Capital Vacations
Jiminy Peak Mountain Resort
Exterior

Jiminy Peak Mountain Resort

3.0 star property
8.2 out of 10, Very good, (924)
"Staff was exceptionally helpful and friendly."
The price is €199
includes taxes & fees
3 Mar - 4 Mar
Jiminy Peak Mountain Resort
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.

Frequently asked questions

How much do cottages in The Berkshires cost?
Prepare to pay between and per night for cottages in The Berkshires. No matter your budget, an excellent stay is only a click or two away 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 cottages are there in The Berkshires?
Browse through cottages in The Berkshires and lock in your favourite. Whether you’re dreaming of a family getaway or a weekend with besties, your ideal stay is just clicks away with Expedia.
Why book your cottage in The Berkshires with Expedia?
Expedia has some excellent cottages in The Berkshires, so start planning for a memorable holiday close to nature. If you’re sticking to a budget, choose how much you’d like to spend and the star rating of your property. Or, try out our filters to search for cottages with a pool or a kitchen. We’ll help you find the perfect place whatever your plans or bank balance.
How can I find cheap cottages in The Berkshires?
With Expedia’s helpful filter tool, scoring cheap cottages in The Berkshires has never been easier. To discover properties that are friendly on the wallet, narrow down your search by budget, star rating and amenities.
What is there to do in The Berkshires near my cottage?
Whether you’re interested in history, food, shopping or sightseeing, The Berkshires is one place where it’s difficult to be bored! The popular city of Williamstown boasts plenty of activities and attractions, including Sterling and Francine Clark Art Institute, Williams College Museum of Art and Hopkins Observatory. If you’re planning an escape to Pittsfield, Bousquet Ski Area, Barrington Stage Company and Berkshire Museum should be on your to-do list.