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Best Resorts in Chester

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Check prices for these dates

Next weekend
Oct 16 - Oct 18
In two weeks
Oct 23 - Oct 25
In one month
Nov 6 - Nov 8
In two months
Dec 4 - Dec 6
No exact matches found, but these alternatives could be just right

Recommended hotels in Chester

A reception area with a fireplace, seating, and a doormat with the logo "Quality".

1. Quality Inn Lee - Lenox South

Quality Inn Lee - Lenox South
2.5 star property
Lee
8.6 out of 10, Excellent, (1,004 reviews)
"Very nice stay"
United States
Christine
$93 nightly
The price is $103
Nov 1 - Nov 2
Total with taxes and fees
Quality Inn Lee - Lenox South
A building with a flat roof, multiple windows, and a satellite dish.

2. 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
Oct 7 - Oct 8
Total with taxes and fees
Becket Motel
A lakeside setting with Adirondack chairs and a covered seating area, surrounded by trees and hills in the background.

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, (1,003 reviews)
"Beautiful setting, clean facilities. Thoroughly enjoyed my stay."
United States
Bob
$116 nightly
The price is $129
Nov 1 - Nov 2
Total with taxes and fees
The Black Swan Lee - Lenox, an Ascend Collection Hotel
A calm lake at dusk with a wooden dock and two chairs facing the water.

4. Berkshire Lake Lodge

Berkshire Lake Lodge
Lee
9.6 out of 10, Exceptional, (23 reviews)
"excellent lakeside view"
United States
mike
$117 nightly
The price is $130
Nov 5 - Nov 6
Total with taxes and fees
Berkshire Lake Lodge
A modern bathroom with a freestanding bathtub, a fireplace, and two framed posters on the wall.

5. The Yankee Inn

The Yankee Inn
2.5 star property
Lenox
9.2 out of 10, Wonderful, (1,007 reviews)
"The room was spacious, clean and comfortable. I will definitely stay there again."
United States
William
$106 nightly
The price is $118
Nov 1 - Nov 2
Total with taxes and fees
The Yankee Inn
A modern hotel lobby with seating areas, tables, and a reception desk.

6. Holiday Inn Express Hotel & Suites Great Barrington by IHG

Holiday Inn Express Hotel & Suites Great Barrington by IHG
2.5 star property
Great Barrington
9.0 out of 10, Wonderful, (832 reviews)
"The location is very convenient. We have been going and staying at this hotel for the past 6 years every time we come to the Berkshire area."
United States
Maria Dulce
$95 nightly
The price is $106
Nov 1 - Nov 2
Total with taxes and fees
Holiday Inn Express Hotel & Suites Great Barrington by IHG
A modern outdoor patio with seating, a fire pit, and a building with large windows and stone pillars.

7. Courtyard by Marriott Lenox Berkshires

Courtyard by Marriott Lenox Berkshires
3.0 star property
Lenox
9.2 out of 10, Wonderful, (662 reviews)
"Nice hotel."
United States
Tracy
$126 nightly
The price is $140
Nov 1 - Nov 2
Total with taxes and fees
Courtyard by Marriott Lenox Berkshires
A hotel room with a bed, a desk, and two wall-mounted lamps.

8. Econo Lodge Lee - Great Barrington

Econo Lodge Lee - Great Barrington
2.0 star property
Lee
6.4 out of 10, (702 reviews)
"Have stayed here several times and it is a basic, decent place. It is in a great location, relatively clean and comfortable. Would return again."
United States
Anna
$65 nightly
The price is $73
Oct 26 - Oct 27
Total with taxes and fees
Econo Lodge Lee - Great Barrington
A hotel room with a large bed, bedside lamps, a desk with a computer, a microwave, and framed pictures on the wall.

9. Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox
2.0 star property
Lenox
7.6 out of 10, Good, (920 reviews)
"Clean, big rooms!"
United States
Mark
$79 nightly
The price is $88
Oct 7 - Oct 8
Total with taxes and fees
Howard Johnson by Wyndham Lenox
A living room with a red patterned carpet, a red sofa, a round coffee table, and a dining area with a wooden table and chairs.

10. Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (1,174 reviews)
"Our visit was very nice. Facilities were beautiful!"
United States
marilyn
$115 nightly
The price is $128
Nov 4 - Nov 5
Total with taxes and fees
Berkshire Mountain Lodge
A building with a porch and multiple windows, surrounded by purple flowers.

11. 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, (1,000 reviews)
"The facilities and property made for a wonderful family visit to the Bershires."
United States
Jared
$129 nightly
The price is $144
Oct 8 - Oct 9
Total with taxes and fees
Holiday Inn Club Vacations Oak n' Spruce Resort in the Berkshires
A cozy attic bedroom with a sloped ceiling, wooden beams, a large window with a view of trees, a bed, a desk, and a kitchenette.

12. 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, (9 reviews)
"We loved it! Lots of local hiking trails and a wonderful relaxing place."
United States
Sharon K.
$335 nightly
The price is $374
Oct 7 - Oct 8
Total with taxes and fees
Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!
A large, multi-story building with a swimming pool, surrounded by dense greenery and trees.

13. The Red Lion Inn

The Red Lion Inn
3.5 star property
Stockbridge
8.8 out of 10, Excellent, (1,004 reviews)
"Great staff, clean room and quiet."
United States
Stephan
$191 nightly
The price is $214
Nov 4 - Nov 5
Total with taxes and fees
The Red Lion Inn
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, (923 reviews)
"It was a good family hotel."
United States
Shaleen
$119 nightly
The price is $133
Nov 1 - Nov 2
Total with taxes and fees
Hampton Inn Westfield
A hotel room with two beds, a bedside table with a lamp, and a window with a view of greenery.

15. Monument Mountain Motel

Monument Mountain Motel
2.5 star property
Great Barrington
9.0 out of 10, Wonderful, (919 reviews)
"Super clean and cozy and safe"
United States
Andrea
$67 nightly
The price is $74
Nov 1 - Nov 2
Total with taxes and fees
Monument Mountain Motel
An indoor swimming pool with clear water, tiled floors, and a blue wall.

16. 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, (227 reviews)
"Most helpful staff, very clean and best breakfast around"
United States
Sheldon
$103 nightly
The price is $115
Nov 4 - Nov 5
Total with taxes and fees
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
A modern dining area with a high ceiling, large windows, and a mix of wooden and upholstered furniture.

17. Quality Inn Westfield - Springfield

Quality Inn Westfield - Springfield
2.5 star property
Westfield
7.2 out of 10, Good, (1,001 reviews)
"Breakfast was decent waffle station eggs sausage and the usual continental fare. Everything was clean the room was a little dark and dismal but everything was new so was fine"
United States
Jennifer
$94 nightly
The price is $104
Nov 1 - Nov 2
Total with taxes and fees
Quality Inn Westfield - Springfield
A brick building with a green door, white porch chairs, and a pathway lined with pink flowers.

18. The Ellery

The Ellery
3.5 star property
Northampton
9.2 out of 10, Wonderful, (1,003 reviews)
"This is a great stop. Nice beds, clean, and excellent breakfast."
United States
Travis
$127 nightly
The price is $141
Oct 27 - Oct 28
Total with taxes and fees
The Ellery
A hot tub with a string of lights above it, set against a dark night sky.

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

Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing
Sherwood Forest
9.8 out of 10, Exceptional, (18 reviews)
"Great place and welcoming stay!"
United States
Frank M.
$340 nightly
The price is $380
Oct 13 - Oct 14
Total with taxes and fees
Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing
A building entrance with a large planter with purple flowers and a small tree.

20. Hotel On North

Hotel On North
3.5 star property
Pittsfield
9.6 out of 10, Exceptional, (937 reviews)
"Great place!"
United States
Lawrence
$127 nightly
The price is $141
Nov 1 - Nov 2
Total with taxes and fees
Hotel On North
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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Top Chester Hotel Reviews

Hotel On North

Hotel On North

10/10 Excellent
"Beautiful boutique hotel. We will be back!"
Rebecca 1-night trip
Posted 4 hours ago
Hotel On North

Find out more about Chester

Chester Resorts information

Number of reviews
12,273
Accommodation
4 Resorts
Lowest Price
$73
Highest Price
$380

Frequently asked questions

What is Chester like for a resort vacation?
You deserve to get away, and a resort is the ideal place to find all the amenities and services you need for a relaxing stay in Chester. One of the comfortable resorts in the area might be just what you're looking for, whether you're hoping for great restaurants on site, a state-of-the-art fitness center, or activities for the kids.
What's the best resort for my stay in Chester?
Our top-rated resorts around Chester: Welcome to Holiday Inn Club Vacations Oak 'n Spruce Resort, South Lee, MA - 15 mi (24.1 km) from Chester. Has a fitness center. Welcome to Holiday Inn Club Vacations Oak 'n Spruce Resort, South Lee, MA - 15 mi (24.1 km) from Chester. Enjoy the fitness center. July 12-19 2026: Resort with 2 bedrooms and AC in the delightful Berkshires - 15.2 mi (24.4 km) from Chester. Amenities include a fitness center.
What can I do in Chester?
Experience the local theater scene at Chester Town Hall, or bring the kids to Ashintully Gardens for some family fun. In the area, other attractions include Glendale Falls and Pyramid Lake.
What's the weather like in Chester?
The hottest months are usually July and August with an average temp of 66°F, while the coldest months are January and February with an average of 28°F. The snowiest months in Chester are January, February, November, and March, with each month seeing an average of 6 inches of snowfall.
What's the best way to get to and around Chester?
Fly into Westfield, MA (BAF-Barnes Municipal), which is located 15.4 mi (24.7 km) from the heart of the city. You can also search for flights into Pittsfield, MA (PSF-Pittsfield Municipal), which is 18.9 mi (30.4 km) away. If you'd like to venture out around the area, you may want to rent a car for your trip.

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