Photo by Elizabeth Massa Peroulakis

Search Cottages in Chester

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 prices for these dates

In two weeks
5 Dec - 7 Dec
In two months
16 Jan - 18 Jan
In three months
13 Feb - 15 Feb
In four months
13 Mar - 15 Mar

Cottages in Chester

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, (1000)
"I have stayed here many times and it is consistently a comfortable, clean and quiet place."
United States
Jeanine
The price is AED 240
AED 268 total
includes taxes & fees
23 Nov - 24 Nov
Best Western Plus Berkshire Hills Inn & Suites
Exterior
Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG

3.0 star property
Pittsfield
8.0 out of 10, Very Good, (962)
"Staff was very nice and helpful nice place restaurant was awesome great food and drinks"
United States
Frank
The price is AED 324
AED 362 total
includes taxes & fees
21 Nov - 22 Nov
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Front of property
Blue – A Modern Hotel, an Ascend Collection Hotel

Blue – A Modern Hotel, an Ascend Collection Hotel

2.5 star property
West Springfield
9.6 out of 10, Exceptional, (92)
"Great staff super nice beautiful hotel lots of parking "
United States
Yovelys
The price is AED 399
AED 456 total
includes taxes & fees
8 Dec - 9 Dec
Blue – A Modern Hotel, an Ascend Collection Hotel
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, (99)
"Clean room, friendly staff, good mattress. Not fancy or plush, but perfect for a one or two night place to land while attending events at the Big E. "
United States
Kim
The price is AED 372
AED 426 total
includes taxes & fees
25 Nov - 26 Nov
Baldwin Inn & Suites, SureStay Collection by Best Western
Terrace/patio
Tru by Hilton Chicopee Springfield

Tru by Hilton Chicopee Springfield

2.5 star property
Chicopee
8.8 out of 10, Excellent, (1004)
"Nice place and clean i recommend it. "
Mexico
Jessly
The price is AED 320
AED 363 total
includes taxes & fees
1 Dec - 2 Dec
Tru by Hilton Chicopee Springfield
Exterior
The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham

2.5 star property
Lenox
9.2 out of 10, Wonderful, (1004)
"Great stay!"
United States
Ann
The price is AED 282
AED 315 total
includes taxes & fees
2 Dec - 3 Dec
The Yankee, Trademark Collection by Wyndham
Room, 2 Queen Beds, Refrigerator | 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, (811)
"Good staff, clean, convenient"
United States
Harlan
The price is AED 397
AED 443 total
includes taxes & fees
10 Dec - 11 Dec
Hampton Inn Westfield
Exterior
Holiday Inn Express Hotel & Suites Great Barrington by IHG

Holiday Inn Express Hotel & Suites Great Barrington by IHG

2.5 star property
Great Barrington
8.8 out of 10, Excellent, (695)
"Everything was wonderful....super clean rooms, check-in was fast and smooth, staff was on top of everything. We definitely will be back at Holiday Inn. "
United States
Tabitha
The price is AED 393
AED 439 total
includes taxes & fees
25 Nov - 26 Nov
Holiday Inn Express Hotel & Suites Great Barrington by IHG
Exterior
Monument Mountain Motel

Monument Mountain Motel

2.5 star property
Great Barrington
9.0 out of 10, Wonderful, (791)
"Yes it was clean & staff was very polite. "
United States
Barbara L.
Monument Mountain Motel
Exterior
The Black Swan Lee - Lenox, an Ascend Collection Hotel

The Black Swan Lee - Lenox, an Ascend Collection Hotel

3.0 star property
Lee
9.0 out of 10, Wonderful, (1000)
"The staff was so kind and helpful and the rooms were clean and comfortable. This is now my go-to place to stay in the Berkshires!"
United States
Elisabeth
The price is AED 403
AED 450 total
includes taxes & fees
8 Dec - 9 Dec
The Black Swan Lee - Lenox, an Ascend Collection Hotel
Front of property
D. Hotel Suites & Spa

D. Hotel Suites & Spa

3.0 star property
Holyoke
9.4 out of 10, Exceptional, (2251)
"Very clean room, great variety of food at breakfast, friendly and helpful staff."
United States
Liz
The price is AED 404
AED 469 total
includes taxes & fees
23 Nov - 24 Nov
D. Hotel Suites & Spa
Exterior
Hampton Inn Hadley-Amherst Area

Hampton Inn Hadley-Amherst Area

2.5 star property
Hadley
9.0 out of 10, Wonderful, (953)
"Nice hotel, friendly helpful staff"
United States
Tim
The price is AED 438
AED 489 total
includes taxes & fees
11 Dec - 12 Dec
Hampton Inn Hadley-Amherst Area
Exterior
Quality Inn

Quality Inn

2.5 star property
Lee
8.4 out of 10, Very Good, (1001)
"Clean room and good breakfast "
United States
Kelly
The price is AED 340
AED 380 total
includes taxes & fees
7 Dec - 8 Dec
Quality Inn
Exterior
River Valley Inn

River Valley Inn

2.0 star property
West Hatfield
8.6 out of 10, Excellent, (97)
"Clean room, comfortable bed, nice shower! Owners were very nice - we will definitely stay here again!"
United States
Deb
The price is AED 400
AED 447 total
includes taxes & fees
19 Nov - 20 Nov
River Valley Inn
Exterior
Travelodge by Wyndham Great Barrington Berkshires

Travelodge by Wyndham Great Barrington Berkshires

2.0 star property
Great Barrington
7.6 out of 10, Good, (559)
"The staff were very friendly and accommodating "
United States
Tom
The price is AED 275
AED 308 total
includes taxes & fees
20 Nov - 21 Nov
Travelodge by Wyndham Great Barrington Berkshires
Exterior
Element Lenox Berkshires

Element Lenox Berkshires

3.0 star property
Lenox
9.6 out of 10, Exceptional, (10)
"New hotel very nice"
United States
joel
The price is AED 496
AED 554 total
includes taxes & fees
30 Nov - 1 Dec
Element Lenox Berkshires
Exterior
Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox

2.0 star property
Lenox
7.6 out of 10, Good, (824)
"Staff was very friendly and helpful."
United States
Pamela
The price is AED 290
AED 324 total
includes taxes & fees
19 Nov - 20 Nov
Howard Johnson by Wyndham Lenox
Interior
Sunset Inn

Sunset Inn

2.0 star property
Lee
7.6 out of 10, Good, (410)
"Room was clean, bed comfortable, nearby to restaurants, gas stations. Only one complaint and that is that the room/bathroom was small and felted cramped and slightly difficult to move around, other than that drawback it served it’s purpose "
United States
Kimberly
The price is AED 314
AED 351 total
includes taxes & fees
2 Dec - 3 Dec
Sunset Inn
Exterior
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

2.5 star property
Pittsfield
9.4 out of 10, Exceptional, (60)
"Very clean room, courteous staff. "
United States
Jeffrey
The price is AED 387
AED 432 total
includes taxes & fees
14 Dec - 15 Dec
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
Exterior
La Quinta Inn & Suites by Wyndham Springfield MA

La Quinta Inn & Suites by Wyndham Springfield MA

3.0 star property
Metro Center
8.2 out of 10, Very Good, (1295)
"Great staff, very clean property, and good breakfast. "
United States
Jasmine
The price is AED 406
AED 460 total
includes taxes & fees
20 Nov - 21 Nov
La Quinta Inn & Suites by Wyndham Springfield MA
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

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

10/10 Excellent
"Clean, cozy, workers are very attentive. The bar and activity center is a lot of fun. "
Paige 2-night trip
Posted 2 days ago
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

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.