Search Castles in Chester from CA $78

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Check prices for these dates

Next weekend
Nov 13 - Nov 15
In two weeks
Nov 20 - Nov 22
In one month
Dec 4 - Dec 6
In two months
Jan 1 - Jan 3
No exact matches found, but these alternatives could be just right

Recommended hotels in Chester

A lodge with a large lawn, outdoor seating, and a dock.

1. Berkshire Lake Lodge

Berkshire Lake Lodge
Lee
9.8 out of 10, Exceptional, (27 reviews)
"excellent lakeside view"
United States
mike
The price is CA $153
CA $171 total
includes taxes & fees
Nov 8 - Nov 9
Berkshire Lake Lodge
An outdoor patio with a table and chairs, surrounded by wooden deck and greenery.

2. Becket Motel

Becket Motel
2.5 star property
Becket
6.6 out of 10, (64 reviews)
"Comfortable stay "
United States
Paul
The price is CA $154
CA $219 total
includes taxes & fees
Nov 9 - Nov 10
Becket Motel
A Super 8 motel with a two-story building, a parking lot, and a picnic table.

3. Quality Inn Lee - Lenox South

Quality Inn Lee - Lenox South
2.5 star property
Lee
8.6 out of 10, Excellent, (1,001 reviews)
"Perfect for a travel stop-over."
United States
James
The price is CA $119
CA $133 total
includes taxes & fees
Dec 2 - Dec 3
Quality Inn Lee - Lenox South
A lodge with a large building and a dock by a lake, surrounded by forest.

4. 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
The price is CA $150
CA $168 total
includes taxes & fees
Dec 3 - Dec 4
The Black Swan Lee - Lenox, an Ascend Collection Hotel
A Holiday Inn Express & Suites building with a clear entrance, a covered parking area, and a stone facade.

5. 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
The price is CA $116
CA $130 total
includes taxes & fees
Dec 7 - Dec 8
Holiday Inn Express Hotel & Suites Great Barrington by IHG
A motel with a central entrance, a flag, and a parking area with several cars.

6. 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
The price is CA $79
CA $88 total
includes taxes & fees
Dec 1 - Dec 2
Econo Lodge Lee - Great Barrington
A hotel with a covered entrance, a registration desk, and a parking area.

7. 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
The price is CA $156
CA $174 total
includes taxes & fees
Dec 2 - Dec 3
The Yankee Inn
A green kayak in front of a wooden cabin with a porch, surrounded by trees.

8. Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!

Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!
Sherwood Forest
10.0 out of 10, Exceptional, (10 reviews)
"My wife and I had a lovely time staying here. Great location, only a couple of miles away from Jacobs Pillow. The lakes are clean and great for paddle boarding. Check in and out was a breeze, Nicole was a pleasure to work with. Thanks for a nice get away."
United States
Brian C.
The price is CA $204
CA $504 total
includes taxes & fees
Nov 9 - Nov 10
Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!
A multi-story hotel with a classic facade, large windows, and a prominent entrance.

9. 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
The price is CA $163
CA $182 total
includes taxes & fees
Nov 29 - Nov 30
Hotel On North
A brick building with a sign reading "The Ellery."

10. The Ellery

The Ellery
3.5 star property
Northampton
9.4 out of 10, Exceptional, (1,008 reviews)
"great and quaint stay"
United States
Adalie
The price is CA $142
CA $158 total
includes taxes & fees
Dec 7 - Dec 8
The Ellery
A large, multi-story hotel with a symmetrical facade, multiple balconies, and a well-lit entrance.

11. 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
The price is CA $176
CA $197 total
includes taxes & fees
Nov 15 - Nov 16
Courtyard by Marriott Lenox Berkshires
A hotel lobby with a reception desk, seating area, and a dining section.

12. 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
The price is CA $156
CA $174 total
includes taxes & fees
Dec 7 - Dec 8
Hampton Inn Westfield
A motel with a two-story structure, multiple rooms with red doors, and a central staircase.

13. 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
The price is CA $111
CA $124 total
includes taxes & fees
Nov 8 - Nov 9
Travelodge by Wyndham Great Barrington Berkshires
A multi-story building with a symmetrical facade, multiple balconies, and a central tower.

14. 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
The price is CA $155
CA $200 total
includes taxes & fees
Nov 8 - Nov 9
Holiday Inn Club Vacations Oak n' Spruce Resort in the Berkshires
A modern hotel with a large entrance, multiple floors, and a well-lit facade.

15. 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
The price is CA $144
CA $161 total
includes taxes & fees
Dec 6 - Dec 7
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
Exterior

16. Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (1,257 reviews)
"Comfortable stay, well stocked kitchen and room."
United States
Charline
The price is CA $108
CA $151 total
includes taxes & fees
Dec 6 - Dec 7
Berkshire Mountain Lodge
A rustic cabin with a gravel path leading to a bench in a forested area.

17. Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing

Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing
Sherwood Forest
9.6 out of 10, Exceptional, (20 reviews)
"Great place and welcoming stay!"
United States
Frank M.
The price is CA $225
CA $528 total
includes taxes & fees
Nov 9 - Nov 10
Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing
A Quality Inn by Choice Hotels with a simple, modern design, featuring a prominent sign and a parking lot.

18. 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
The price is CA $131
CA $146 total
includes taxes & fees
Nov 29 - Nov 30
Quality Inn Westfield - Springfield
A hotel entrance with a covered driveway, a sign for Hampton Inn & Suites by Hilton, and a brick building with multiple windows.

19. 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
The price is CA $154
CA $172 total
includes taxes & fees
Nov 12 - Nov 13
Hampton Inn & Suites Berkshires-Lenox
A swimming pool with a fenced area, lounge chairs, and a warning sign.

20. Sunset Inn

Sunset Inn
2.0 star property
Lee
7.6 out of 10, Good, (447 reviews)
"Super friendly staff, the room was very clean, even if dated. Very quiet and great for a one night stay while visiting Tanglewood."
United States
Lauren
The price is CA $108
CA $120 total
includes taxes & fees
Nov 8 - Nov 9
Sunset 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.
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Learn more about Chester

Experience the hiking, camping, and theater in Chester!

See all hotels in Chester
A bridge over a calm river with trees and buildings in the background.

Top reviews in Chester

A lodge with a large building and a dock by a lake, surrounded by forest.
The Black Swan Lee - Lenox, an Ascend Collection Hotel

The Black Swan Lee - Lenox, an Ascend Collection Hotel

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

10/10 Excellent

Clean rooms and lovely view
Canada
Laraib
Reviewed May 21, 2026
The Black Swan Lee - Lenox, an Ascend Collection Hotel

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