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

Find 4 Star Hotels in Chester, MA from $111

Check availability on Chester 4 Star Hotels

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

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
$99 nightly
The price is $111
Nov 8 - Nov 9
Total with taxes and fees
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
$369 nightly
The price is $412
Nov 13 - Nov 14
Total with taxes and fees
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
$230 nightly
The price is $257
Nov 11 - Nov 12
Total with taxes and fees
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
$414 nightly
The price is $462
Nov 26 - Nov 27
Total with taxes and fees
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
$319 nightly
The price is $350
Nov 8 - Nov 9
Total with taxes and fees
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
$281 nightly
The price is $313
Nov 8 - Nov 9
Total with taxes and fees
The Inn at Stockbridge
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Chester Four Star Hotel Information

When you need to book a room with luxurious amazing amenities and the best rates, the 4 star hotels in Chester, Massachusetts are incredible options. Known for their extra perks, first-rate service, and fantastic locations, each of the Chester 4 star hotels offers the ultimate experience for globe-trotting travelers. Relax in your expertly designed room. Kick back with around-the-clock room service.

Get a good night’s sleep with the ultra-plush bedding, and freshen up in the morning with designer-inspired body products. It’s all available when you stay at one of the top book a four star hotels in Chester. What’s more, thanks to Expedia you might even score a cheap great deal on a 4 star hotel in Chester, Massachusetts, areas near the hottest attractions, so you can plan a sightseeing adventure and take advantage of unbeatable discounts in one fell swoop.

Whether you’re putting together a serene getaway or want to revel in the most vibrant entertainment district, 4 star Chester hotels offer everything your heart desires.

Frequently asked questions

How much does it cost to stay in a 4-star hotel in Chester?
To book a 4-star hotel in Chester that's within your budget, use Expedia's handy filter tool. Check out the available options during your getaway dates and use our pricing filter to set your limit. You can also list your results by the most wallet-friendly property first.

  • Search for the lowest price from $111

What's the difference between 5-star and 4-star hotels in Chester?
If you decide to spend your vacation at a 4-star hotel in Chester, you'll typically find plenty of amenities to keep you comfortable, such as a restaurant, gym and pool. You can experience high-quality service and deluxe accommodations. Pick a 5-star hotel and you'll get a few more bells and whistles — think on-site spas, around-the-clock concierge and indulgent turndown services. You're likely to get more amenities and exclusive services at a 5-star retreat, though both are fabulous options for luxury travelers.
Does Chester have any 4-star all-inclusive resorts?
Finding your dream resort in Chester is as easy as entering in your destination and dates, and clicking on our "All inclusive" filter. Stay and play where everything is already taken care of like your room, meals and activities, or go for a standard 4-star resort in or around this top destination.

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