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4 Star Hotels in Chester, Massachusetts

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Check availability on Chester 4 Star Hotels

Tonight
11 Aug - 12 Aug
Tomorrow
12 Aug - 13 Aug
This weekend
14 Aug - 16 Aug
Next weekend
21 Aug - 23 Aug

Our top choices for Chester 4-star hotels

Exterior
Exterior
50-inch flat-screen TV with cable channels, TV, streaming services
Deluxe Double Suite- NO PETS ALLOWED

1. The Central Downtown Inn & Suites

The Central Downtown Inn & Suites
Pittsfield
United States
Rena
€88
includes taxes & fees
3 Sept - 4 Sept
The Central Downtown Inn & Suites
Front of property
Exterior
The Fox Den in the Mainhouse
Lobby

2. The Inn at Stockbridge

The Inn at Stockbridge
Stockbridge
United Kingdom
Michele
€401
includes taxes & fees
8 Sept - 9 Sept
The Inn at Stockbridge
Suite, Private Bathroom (RedBird Suite) | View from room
Lobby sitting area
Suite, Private Bathroom (Parlour Suite)
Seasonal outdoor pool, open 9:00 AM to 6:00 PM, pool loungers

3. 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
Stockbridge
United States
Philippe
€346
includes taxes & fees
24 Aug - 25 Aug
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
Front of property
Bicycling
Dining
Staircase

4. Seven Hills Inn

Seven Hills Inn
Lenox
United States
Christopher
Seven Hills Inn
Luxury Room, 1 King Bed, Bathtub
Exterior
Restaurant
Premium bedding, iron/ironing board, free WiFi, individually decorated

5. 33 Main

33 Main
Lenox
United States
Tatyana
€640
includes taxes & fees
31 Aug - 1 Sept
33 Main
Breakfast, lunch, dinner and brunch served
Thayer House, Room 201, 1 King bed, Jetted tub
Front of property
Interior

6. The Old Inn On The Green

The Old Inn On The Green
Great Barrington
United States
Catherine
€333
includes taxes & fees
1 Sept - 2 Sept
The Old Inn On The Green
Exterior detail
Dining
Lobby sitting area
Fireplace

7. Hampton Terrace Inn

Hampton Terrace Inn
Lenox
United States
Kathleen
€212
includes taxes & fees
10 Sept - 11 Sept
Hampton Terrace Inn
Porch
Grand Suite, 1 Bedroom, Private Bathroom, Lake View | Living area
Porch
Front of property

8. Lakehouse Inn

Lakehouse Inn
Lee
United States
Angela
Lakehouse Inn
Front of property – evening/night
Room #10 Queen's Cottage | View from room
Room #4 - Roosevelt Suite, 1 King Bed, Fireplace, not pet friendly
Room #10 Queen's Cottage | Living room

9. Devonfield Inn B&B

Devonfield Inn B&B
Lee
United States
Christopher
€376
includes taxes & fees
3 Sept - 4 Sept
Devonfield Inn B&B
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A stone bridge over a flowing river with rocks and autumn foliage.
Photo by Chris Addams

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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 €88
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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