Find 4 Star Hotels in Chester, MA from $99

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Check availability on Chester 4 Star Hotels

Tonight
Apr 28 - Apr 29
Tomorrow
Apr 29 - Apr 30
This weekend
May 1 - May 3
Next weekend
May 8 - May 10

Our top choices for Chester 4-star hotels

Exterior

The Central Downtown Inn & Suites

The Central Downtown Inn & Suites
4.0 star property
Pittsfield
8.6 out of 10, Excellent, (361 reviews)
"The place is wonderful, clean, quiet, convenient to everything and can be recommended to a family and small group. The staff is accomodating."
Canada
Agnes
$89 nightly
The price is $99
Apr 29 - Apr 30
Total with taxes and fees
The Central Downtown Inn & Suites
Porch

Lakehouse Inn

Lakehouse Inn
4.0 star property
Lee
9.6 out of 10, Exceptional, (299 reviews)
"Staff wonderful, homemade breakfasts, outstanding experience!"
United States
Kathleen
Lakehouse Inn
Front of property - evening/night

Devonfield Inn B&B

Devonfield Inn B&B
4.0 star property
Lee
10.0 out of 10, Exceptional, (137 reviews)
"The inn has an excellent location and amenities."
United States
Christopher
$259 nightly
The price is $289
Apr 29 - Apr 30
Total with taxes and fees
Devonfield Inn B&B
Breakfast, lunch, dinner served; American cuisine

The Old Inn On The Green

The Old Inn On The Green
4.0 star property
Great Barrington
9.2 out of 10, Wonderful, (91 reviews)
"Beautiful Inn and outstanding chef"
United States
Catherine
$336 nightly
The price is $368
Apr 29 - Apr 30
Total with taxes and fees
The Old Inn On The Green
Front of property

The Inn at Stockbridge

The Inn at Stockbridge
4.0 star property
Lee
9.8 out of 10, Exceptional, (99 reviews)
"Well-run and elegant property. "
United States
Steven
$276 nightly
The price is $308
May 4 - May 5
Total with taxes and fees
The Inn at Stockbridge
Luxury Room, 1 King Bed, Bathtub | Premium bedding, individually decorated, iron/ironing board, free WiFi

33 Main

33 Main
4.0 star property
Lenox
10.0 out of 10, Exceptional, (74 reviews)
"Beautiful place. Wonderful owner and staff. Our stay there was a total delight."
United States
James
$536 nightly
The price is $599
Apr 29 - Apr 30
Total with taxes and fees
33 Main
Front of property

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
Suite, Private Bathroom (RedBird Suite) | View from room

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
9.2 out of 10, Wonderful, (111 reviews)
"Great breakfast, friendly helpful staff, pretty yard, good location "
United States
Deborah
$335 nightly
The price is $374
May 12 - May 13
Total with taxes and fees
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
Exterior detail

Hampton Terrace Inn

Hampton Terrace Inn
4.0 star property
Lenox
9.0 out of 10, Wonderful, (44 reviews)
"Comfortable bed. Quiet location. Excellent breakfast. Friendly host."
United States
Kathleen
$230 nightly
The price is $257
Apr 29 - Apr 30
Total with taxes and fees
Hampton Terrace Inn
Classic Queen - Room 8 | Premium bedding, down comforters, pillowtop beds, individually decorated

Garden Gables

Garden Gables
4.0 star property
Lenox
$242 nightly
The price is $270
Apr 29 - Apr 30
Total with taxes and fees
Garden Gables
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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 $99

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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