Lodging Image

Search Cottages in Chester

  • 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 prices for these dates

In two weeks
17 Jul - 19 Jul
In two months
28 Aug - 30 Aug
In three months
25 Sep - 27 Sep
In four months
23 Oct - 25 Oct
No exact matches found, but these alternatives could be just right

Recommended hotels in Chester

Exterior

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, (1,003 reviews)
"clean room, friendly staff, great breakfast"
United States
charles
The price is AED 497
AED 555 total
includes taxes & fees
5 Jul - 6 Jul
Best Western Plus Berkshire Hills Inn & Suites
View from room

The Yankee Inn

The Yankee Inn
2.5 star property
Lenox
9.2 out of 10, Wonderful, (1,017 reviews)
"Great location for sightseeing in the Berkshires. Clean and comfortable room, friendly staff."
Canada
Mark
The price is AED 467
AED 522 total
includes taxes & fees
6 Jul - 7 Jul
The Yankee Inn
Exterior

River Valley Inn

River Valley Inn
2.0 star property
West Hatfield
8.6 out of 10, Excellent, (176 reviews)
"It's a really nice place to stay!"
United States
Vidita
The price is AED 383
AED 427 total
includes taxes & fees
5 Jul - 6 Jul
River Valley Inn
Desk, iron/ironing board, free WiFi, bed sheets

FairBridge Inn Express

FairBridge Inn Express
2.5 star property
Pittsfield
5.4 out of 10, (837 reviews)
"Plenty of parking. Staff was friendly"
United States
William
The price is AED 214
AED 239 total
includes taxes & fees
16 Jul - 17 Jul
FairBridge Inn Express
Exterior

Baldwin Inn & Suites, SureStay Collection by Best Western

Baldwin Inn & Suites, SureStay Collection by Best Western
2.5 star property
West Springfield
7.6 out of 10, Good, (217 reviews)
"Front desk staff was very friendly and informative. Great location for the local colleges."
United States
Chris
The price is AED 379
AED 434 total
includes taxes & fees
5 Jul - 6 Jul
Baldwin Inn & Suites, SureStay Collection by Best Western
Front of property

The Ellery

The Ellery
3.5 star property
Northampton
9.2 out of 10, Wonderful, (1,008 reviews)
"Very nice, clean, love the parking. Great hotel"
United States
Thomas Howard
The price is AED 511
AED 571 total
includes taxes & fees
22 Jul - 23 Jul
The Ellery
Front of property

D. Hotel Suites & Spa

D. Hotel Suites & Spa
3.0 star property
Holyoke
9.2 out of 10, Wonderful, (2,154 reviews)
"Breakfast was excellent."
United States
Candyce
The price is AED 416
AED 486 total
includes taxes & fees
28 Jul - 29 Jul
D. Hotel Suites & Spa
Porch

Naomi's Inn Bed & Breakfast

Naomi's Inn Bed & Breakfast
3.5 star property
Liberty Heights
9.0 out of 10, Wonderful, (443 reviews)
"He room was very clean, the staff was engaging and the breakfast was delicious. "
United States
John
The price is AED 433
AED 492 total
includes taxes & fees
5 Jul - 6 Jul
Naomi's Inn Bed & Breakfast
Exterior

Hampton Inn West Springfield

Hampton Inn West Springfield
2.5 star property
West Springfield
8.2 out of 10, Very Good, (1,000 reviews)
"Our room was very clean, staff was very friendly. We would stay here again."
United States
Sherry
The price is AED 389
AED 445 total
includes taxes & fees
5 Jul - 6 Jul
Hampton Inn West Springfield
BBQ/picnic area

Berkshire Lake Lodge

Berkshire Lake Lodge
Lee
10.0 out of 10, Exceptional, (3 reviews)
"Everything was perfect!!"
United States
Grzegorz
The price is AED 673
AED 752 total
includes taxes & fees
30 Jul - 31 Jul
Berkshire Lake Lodge
Property grounds

Berkshire Inn

Berkshire Inn
2.0 star property
Pittsfield
7.8 out of 10, Good, (870 reviews)
"I really enjoyed my stay at the Berkshire Inn, it was safe, clean, and in a convenient part of Pittsfield. Parking was a breeze and I was comfortable in my room. I would definitely book again!"
United States
Hannah
The price is AED 286
AED 319 total
includes taxes & fees
7 Jul - 8 Jul
Berkshire Inn
Meeting facility

The Red Lion Inn

The Red Lion Inn
3.5 star property
Stockbridge
8.8 out of 10, Excellent, (1,005 reviews)
"Clean room and breakfast"
United States
Raphael
The price is AED 576
AED 807 total
includes taxes & fees
9 Jul - 10 Jul
The Red Lion Inn
Exterior

Quality Inn Westfield - Springfield

Quality Inn Westfield - Springfield
2.5 star property
Westfield
7.2 out of 10, Good, (955 reviews)
"The coffee was fantastic. Rooms were quiet"
United States
Richard
The price is AED 372
AED 415 total
includes taxes & fees
26 Jul - 27 Jul
Quality Inn Westfield - Springfield
Front of property

The Little Lion

The Little Lion
3.0 star property
Great Barrington
8.6 out of 10, Excellent, (572 reviews)
"Such a peaceful and easy stay!"
United States
Mia
The price is AED 411
AED 460 total
includes taxes & fees
5 Jul - 6 Jul
The Little Lion
Exterior

Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox
2.0 star property
Lenox
7.6 out of 10, Good, (876 reviews)
"Hotel was ok. Great for the price. But the bed was terrible. Old and soft. "
United States
robert
The price is AED 364
AED 406 total
includes taxes & fees
5 Jul - 6 Jul
Howard Johnson by Wyndham Lenox
Room, 1 King Bed, Accessible (Roll-In Shower) | Premium bedding, desk, laptop workspace, blackout drapes

Hampton Inn Westfield

Hampton Inn Westfield
2.5 star property
Westfield
8.4 out of 10, Very Good, (876 reviews)
"very friendly, room was nice and breakfast was great"
United States
Lawrence
The price is AED 479
AED 535 total
includes taxes & fees
8 Jul - 9 Jul
Hampton Inn Westfield
Exterior

Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
2.5 star property
Pittsfield
9.4 out of 10, Exceptional, (118 reviews)
"Most comfortable hotel bed I've ever slept in"
United States
Matthew
The price is AED 628
AED 702 total
includes taxes & fees
6 Jul - 7 Jul
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
Property entrance

Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (1,005 reviews)
"The staff was very helpful. It was very clean and the bed was comfortable. We would stay there again."
United States
Andrew
The price is AED 491
AED 630 total
includes taxes & fees
2 Aug - 3 Aug
Berkshire Mountain Lodge
Exterior

Quality Inn Lee - Lenox South

Quality Inn Lee - Lenox South
2.5 star property
Lee
8.4 out of 10, Very Good, (1,005 reviews)
"It was a clean, friendly hotel."
United States
Cheri
The price is AED 520
AED 581 total
includes taxes & fees
6 Jul - 7 Jul
Quality Inn Lee - Lenox South
Exterior

East Rock Inn

East Rock Inn
2.0 star property
Great Barrington
9.4 out of 10, Exceptional, (49 reviews)
"The East Rock Inn is great. It's comfortable, clean and close to downtown Great Barrington. This was my second time staying here."
United States
Laura
The price is AED 532
AED 594 total
includes taxes & fees
16 Jul - 17 Jul
East Rock Inn
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
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Chester Hotel Reviews

The Black Swan Lee - Lenox, an Ascend Collection Hotel

The Black Swan Lee - Lenox, an Ascend Collection Hotel

10/10 Excellent
"A lovely stay at the Black Swan hotel in Lee for my birthday. Room was nice and comfortable, sweet balcony area to watch the sunset over the lake. Close to many attractions, ie, Norman Rockwell museum, outlets, pretty town, Botanical gardens and more. Would definitely go back again. Thank you"
rose 2-night trip
Posted 3 hours ago
The Black Swan Lee - Lenox, an Ascend Collection Hotel

Frequently asked questions

Why book your cottage in Chester with Expedia?
We think a getaway should be a piece of cake, so if you're after cottages in Chester at an affordable rate, Expedia has got you covered. Keep the budget under control and pick an economical option far away from the downtown buzz, or book an upmarket cottage to pamper your loved ones.
How can I find cheap cottages in Chester?
With Expedia's filter tool, comparing cheap cottages in Chester couldn't be easier. To view accommodations that are very pocket friendly, narrow down your search by amenities, star rating and budget.

Explore a world of travel with Expedia