A river flowing through a forest with autumn-colored trees.

Chester Chalets

  • Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals

  • OneKeyCash

    Earn OneKeyCash on all your eligible bookings

  • Upfront pricing

    We are not like the others - we include taxes and fees

Check prices for these dates

In two weeks
Nov 20 - Nov 22
In two months
Jan 1 - Jan 3
In three months
Jan 29 - Jan 31
In four months
Feb 26 - Feb 28
No exact matches found, but these alternatives could be just right

Recommended hotels in Chester

A Holiday Inn Express & Suites building with a clear entrance, a covered parking area, and a stone facade.

1. 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, (854 reviews)
"Always a pleasurable stay. The rooms are clean, the amenities are appreciated, and the staff very attentive. Great location and as a single traveler I always feel safe staying here."
United States
Cynthia
$83 nightly
The price is $93
Dec 7 - Dec 8
Total with taxes and fees
Holiday Inn Express Hotel & Suites Great Barrington by IHG
A Super 8 motel with a two-story building, a parking lot, and a picnic table.

2. Quality Inn Lee - Lenox South

Quality Inn Lee - Lenox South
2.5 star property
Lee
8.6 out of 10, Excellent, (1,001 reviews)
"Just perfect lodging place for short time travelers"
United States
Bernardo Jr
$85 nightly
The price is $95
Dec 2 - Dec 3
Total with taxes and fees
Quality Inn Lee - Lenox South
A lodge with a large building and a dock by a lake, surrounded by forest.

3. The Black Swan Lee - Lenox, an Ascend Collection Hotel

The Black Swan Lee - Lenox, an Ascend Collection Hotel
3.0 star property
Lee
9.2 out of 10, Wonderful, (1,000 reviews)
"Amazing place, clean, staff is awesome , amazing location , amazing views! Free breakfast, free coffee bar , free gym and the best it’s pet friendly !"
United States
Gustavo
$107 nightly
The price is $120
Dec 3 - Dec 4
Total with taxes and fees
The Black Swan Lee - Lenox, an Ascend Collection Hotel
A grassy area with a lake, trees, and red chairs arranged around a fire pit.

4. Berkshire Lake Lodge

Berkshire Lake Lodge
Lee
9.8 out of 10, Exceptional, (27 reviews)
"excellent lakeside view"
United States
mike
$110 nightly
The price is $123
Nov 13 - Nov 14
Total with taxes and fees
Berkshire Lake Lodge
Two Adirondack chairs facing a river with a forested hill in the background.

5. The Yankee Inn

The Yankee Inn
2.5 star property
Lenox
9.2 out of 10, Wonderful, (1,000 reviews)
"The location was good for our trip."
United States
Basil
$112 nightly
The price is $125
Nov 12 - Nov 13
Total with taxes and fees
The Yankee Inn
A residential lawn with three geese walking.

6. Becket Motel

Becket Motel
2.5 star property
Becket
6.6 out of 10, (64 reviews)
"Comfortable stay "
United States
Paul
$140 nightly
The price is $156
Nov 8 - Nov 9
Total with taxes and fees
Becket Motel
A building entrance with a large planter with purple flowers and a small tree.

7. Hotel On North

Hotel On North
3.5 star property
Pittsfield
9.6 out of 10, Exceptional, (981 reviews)
"Very nice hotel"
United States
Philip
$119 nightly
The price is $133
Nov 29 - Nov 30
Total with taxes and fees
Hotel On North
A wooden deck with a table and chairs, overlooking a road with a mountain in the distance.

8. Econo Lodge Lee - Great Barrington

Econo Lodge Lee - Great Barrington
2.0 star property
Lee
6.4 out of 10, (713 reviews)
"It was super clean and safe"
United States
Fernando
$56 nightly
The price is $63
Dec 1 - Dec 2
Total with taxes and fees
Econo Lodge Lee - Great Barrington
A brick building with a sign reading "The Ellery."

9. The Ellery

The Ellery
3.5 star property
Northampton
9.4 out of 10, Exceptional, (1,009 reviews)
"great and quaint stay"
United States
Adalie
$101 nightly
The price is $113
Dec 7 - Dec 8
Total with taxes and fees
The Ellery
A motel with a two-story structure, multiple rooms with red doors, and a central staircase.

10. Travelodge by Wyndham Great Barrington Berkshires

Travelodge by Wyndham Great Barrington Berkshires
2.0 star property
Great Barrington
7.4 out of 10, Good, (626 reviews)
"Stay was great. Staff very friendly and helpful. 1 guest was screaming at someone at 4am but other than that it was a great stay"
United States
Sherry
$79 nightly
The price is $88
Nov 8 - Nov 9
Total with taxes and fees
Travelodge by Wyndham Great Barrington Berkshires
A modern hotel with a large entrance, multiple floors, and a well-lit facade.

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

Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
2.5 star property
Pittsfield
9.2 out of 10, Wonderful, (257 reviews)
"The room was clean and well kept, breakfast was amazing!"
United States
Ruth
$103 nightly
The price is $115
Dec 6 - Dec 7
Total with taxes and fees
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
A covered outdoor area with stone pillars and a view of a road and green hills.

12. Courtyard by Marriott Lenox Berkshires

Courtyard by Marriott Lenox Berkshires
3.0 star property
Lenox
9.2 out of 10, Wonderful, (687 reviews)
"Great stay!"
United States
Vandhana
$126 nightly
The price is $140
Nov 15 - Nov 16
Total with taxes and fees
Courtyard by Marriott Lenox Berkshires
Exterior

13. Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (1,258 reviews)
"Comfortable stay, well stocked kitchen and room."
United States
Charline
$105 nightly
The price is $117
Dec 8 - Dec 9
Total with taxes and fees
Berkshire Mountain Lodge
A hotel lobby with a reception desk, seating area, and a dining section.

14. Hampton Inn Westfield

Hampton Inn Westfield
2.5 star property
Westfield
8.4 out of 10, Very good, (933 reviews)
"It was a good family hotel."
United States
Shaleen
$111 nightly
The price is $124
Dec 7 - Dec 8
Total with taxes and fees
Hampton Inn Westfield
A hotel entrance with a covered driveway, a sign for Hampton Inn & Suites by Hilton, and a brick building with multiple windows.

15. Hampton Inn & Suites Berkshires-Lenox

Hampton Inn & Suites Berkshires-Lenox
2.5 star property
Lenox
9.0 out of 10, Wonderful, (1,000 reviews)
"Breakfast was great"
United States
Thomas
$110 nightly
The price is $122
Nov 15 - Nov 16
Total with taxes and fees
Hampton Inn & Suites Berkshires-Lenox
A Best Western Plus hotel with a two-story building, a covered front entrance, and a parking lot.

16. Best Western Plus Berkshire Hills Inn & Suites

Best Western Plus Berkshire Hills Inn & Suites
2.5 star property
Pittsfield
8.4 out of 10, Very good, (1,002 reviews)
"Room was spacious and clean"
United States
James
$93 nightly
The price is $104
Dec 1 - Dec 2
Total with taxes and fees
Best Western Plus Berkshire Hills Inn & Suites
A row of motel rooms with red doors, a covered walkway, and a view of mountains in the background.

17. Monument Mountain Motel

Monument Mountain Motel
2.5 star property
Great Barrington
9.0 out of 10, Wonderful, (941 reviews)
"Easy access to everywhere we went. Clean"
United States
Phillip
$67 nightly
The price is $74
Nov 8 - Nov 9
Total with taxes and fees
Monument Mountain Motel
A multi-story building with a symmetrical facade, multiple balconies, and a central tower.

18. Holiday Inn Club Vacations Oak n' Spruce Resort in the Berkshires

Holiday Inn Club Vacations Oak n' Spruce Resort in the Berkshires
3.5 star property
South Lee
9.2 out of 10, Wonderful, (1,002 reviews)
"Nice place to stay"
United States
Michael
$128 nightly
The price is $143
Nov 8 - Nov 9
Total with taxes and fees
Holiday Inn Club Vacations Oak n' Spruce Resort in the Berkshires
A Quality Inn by Choice Hotels with a simple, modern design, featuring a prominent sign and a parking lot.

19. Quality Inn Westfield - Springfield

Quality Inn Westfield - Springfield
2.5 star property
Westfield
7.2 out of 10, Good, (1,000 reviews)
"Wonderful breakfast, older, but well maintained property fantastic staff"
United States
Jaine
$94 nightly
The price is $104
Nov 29 - Nov 30
Total with taxes and fees
Quality Inn Westfield - Springfield
A multi-story hotel with a prominent entrance, a parking lot, and a flagpole.

20. Hilton Garden Inn Lenox Pittsfield

Hilton Garden Inn Lenox Pittsfield
3.0 star property
Pittsfield
9.2 out of 10, Wonderful, (716 reviews)
"Great place to stay. Great staff and convenient location. Nice restaurant as well."
United States
James
$119 nightly
The price is $133
Nov 15 - Nov 16
Total with taxes and fees
Hilton Garden Inn Lenox Pittsfield
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 Ellery

The Ellery

10/10 Excellent
"Great location, very clean, wonderful staff and beautiful property! Love the lounge area with the cozy fireplace!"
Shannon 1-night trip
Posted 4 hours ago
The Ellery

Find out more about Chester

Chester Chalets information

Number of reviews
4,960
Accommodation
3 Chalets
Lowest Price
$63
Highest Price
$156

Explore a world of travel with Expedia