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Compare and book 4 Star hotels in Chester, Massachusetts

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Check availability on Chester 4 Star Hotels

This weekend
6 Nov - 8 Nov
Next weekend
13 Nov - 15 Nov

Our top choices for Chester 4-star hotels

A building with a registration sign above the entrance, a white porch railing, and flower baskets on the railing.

1. The Central Downtown Inn & Suites

The Central Downtown Inn & Suites
4.0 star property
Pittsfield
8.4 out of 10, Very good, (434 reviews)
"Consistently, a clean, quiet, convenient location and comfortable stay."
United States
Debra
The price is £82
includes taxes & fees
9 Nov - 10 Nov
The Central Downtown Inn & Suites
An indoor dining area with a central table and chairs, surrounded by a decorative archway and greenery.

2. Seven Hills Inn

Seven Hills Inn
4.0 star property
Lenox
7.8 out of 10, Good, (467 reviews)
"Great location, nice breakfast and clean rooms"
United States
Christopher
Seven Hills Inn
A spacious living room with a fireplace, a dining area with a table and chairs, and large windows offering a view of the outdoors.

3. Devonfield Inn B&B

Devonfield Inn B&B
4.0 star property
Lee
10.0 out of 10, Exceptional, (141 reviews)
"Wonderful location and hosts are amazing. Breakfast was great. Clean."
United States
Sebastien
The price is £306
includes taxes & fees
13 Nov - 14 Nov
Devonfield Inn B&B
A white house with a balcony, green shutters, and a front door with a decorative glass panel. There are two large flower pots on the steps.

4. Hampton Terrace Inn

Hampton Terrace Inn
4.0 star property
Lenox
9.0 out of 10, Wonderful, (45 reviews)
"Comfortable bed. Quiet location. Excellent breakfast. Friendly host."
United States
Kathleen
The price is £191
includes taxes & fees
12 Nov - 13 Nov
Hampton Terrace Inn
A two-story house with a brick entrance and a white facade.

5. The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood

The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
4.5 star property
Stockbridge
9.4 out of 10, Exceptional, (120 reviews)
"The property is conveniently located for access to Stockbridge, Lenox, and Tanglewood."
United States
Philippe
The price is £343
includes taxes & fees
2 Dec - 3 Dec
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
A dining area with round tables set for two, a fireplace, and a mural on the wall.

6. The Old Inn On The Green

The Old Inn On The Green
4.0 star property
Great Barrington
9.2 out of 10, Wonderful, (96 reviews)
"Lovely property.unique historic buildings and rooms with updated amenities! Quiet and peaceful beautiful dinner!"
United States
mary ellen
The price is £260
includes taxes & fees
9 Nov - 10 Nov
The Old Inn On The Green
A two-story white house with a front porch, a central entrance, and a small tower-like structure on the roof.

7. 33 Main

33 Main
4.0 star property
Lenox
10.0 out of 10, Exceptional, (77 reviews)
"Beautiful place. Wonderful owner and staff. Our stay there was a total delight."
United States
James
33 Main
A wooden deck with wicker furniture and a view of a lake.

8. Lakehouse Inn

Lakehouse Inn
4.0 star property
Lee
9.6 out of 10, Exceptional, (303 reviews)
"Staff wonderful, homemade breakfasts, outstanding experience!"
United States
Kathleen
Lakehouse Inn
Front of property

9. The Inn at Stockbridge

The Inn at Stockbridge
4.0 star property
Stockbridge
9.6 out of 10, Exceptional, (108 reviews)
"Wonderful place… clean, cosy room, comfy bed, friendly staff, great breakfast. Delightful location near Norman Rockwell museum."
United States
Kimberly
The price is £233
includes taxes & fees
9 Nov - 10 Nov
The Inn at Stockbridge
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Frequently asked questions

How much does it cost to stay in a 4-star hotel in Chester?
Expedia can help you easily find the ideal 4-star hotel for your getaway in Chester. Use our filter tool to tailor your search by things like budget, conveniences and star rating and get access to unbeatable deals in a few clicks.

  • Search for the lowest price from £82

What's the difference between 5-star and 4-star hotels in Chester?
If you decide to book a stay at a 4-star hotel in Chester, you'll typically find loads of conveniences to ensure you're comfortable, such as a restaurant, gym and pool. You can enjoy top-quality service and upscale accommodation. Opt for a 5-star hotel and you'll have access to a few more perks — think on-site spas, concierge assistance and nightly turndown services. You're likely to get additional amenities and first-class services at a 5-star stay, though both are awesome options for luxury guests.
Does Chester have any 4-star all-inclusive resorts?
Finding holiday bliss in Chester is as easy as typing in your travel details and selecting our "All inclusive" filter. Stay and play where just about everything is already taken care of like your accommodation, meals and activities, or go for a standard 4-star resort in or around this much-loved destination.

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