Photo by Elizabeth Massa Peroulakis

Compare and book 4 Star hotels in Chester, Massachusetts

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Check availability on Chester 4 Star Hotels

Tonight
4 Jul - 5 Jul
Tomorrow
5 Jul - 6 Jul
This weekend
4 Jul - 6 Jul
Next weekend
11 Jul - 13 Jul

Top Chester 4 Star Hotels

The Central Downtown Inn & Suites
Microwave, oven, stovetop, dishwasher

The Central Downtown Inn & Suites

4.0 star property
8.8 out of 10, Excellent, (292)
"Friendly staff, clean and perfect for a trip with the pups! "
The price is 3.113.516 ₫
3.477.719 ₫ total
includes taxes & fees
28 Jul - 29 Jul
The Central Downtown Inn & Suites
Lakehouse Inn
Aerial view

Lakehouse Inn

4.0 star property
9.6 out of 10, Exceptional, (267)
"Really peaceful and serene property due to the lake. The house was clean and the staff were friendly. "
Lakehouse Inn
The Old Inn On The Green
Room 191, 1 Queen Bed, 1 Single Bed, 1 Sofa Bed | Premium bedding, individually decorated, individually furnished

The Old Inn On The Green

4.0 star property
9.2 out of 10, Wonderful, (84)
"Beautiful room and property. Perfect weekend getaway!"
The price is 7.587.560 ₫
9.155.830 ₫ total
includes taxes & fees
6 Jul - 7 Jul
The Old Inn On The Green
Devonfield Inn B&B
Front of property – evening/night

Devonfield Inn B&B

4.0 star property
10.0 out of 10, Exceptional, (127)
"Very enjoyable comfortable stay"
Devonfield Inn B&B
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
Business centre

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

4.5 star property
9.2 out of 10, Wonderful, (105)
"Great breakfast, friendly helpful staff, pretty yard, good location "
The price is 12.022.329 ₫
14.543.533 ₫ total
includes taxes & fees
14 Jul - 15 Jul
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
Seven Hills Inn
Terrace/patio

Seven Hills Inn

4.0 star property
7.8 out of 10, Good, (467)
"Great location, nice breakfast and clean rooms"
Seven Hills Inn
33 Main
Luxury Room, 1 King Bed, Bathtub | Premium bedding, individually decorated, iron/ironing board, free WiFi

33 Main

4.0 star property
10.0 out of 10, Exceptional, (70)
"33 Main is the best of everything. We have stayed at the location twice and loved each experience. The breakfast is delicious, accommodations are beautifully curated, and it’s perfectly located in Lenox. Highly recommend and we will be back! "
The price is 12.812.551 ₫
14.311.621 ₫ total
includes taxes & fees
28 Jul - 29 Jul
33 Main
The Inn at Stockbridge
Exterior

The Inn at Stockbridge

4.0 star property
9.8 out of 10, Exceptional, (98)
"Well-run and elegant property. "
The Inn at Stockbridge
Hampton Terrace Inn
Seasonal outdoor pool

Hampton Terrace Inn

4.0 star property
9.0 out of 10, Wonderful, (42)
"Beautiful historic house in a great location. Responsive owner. Great visit!"
The price is 9.193.931 ₫
10.269.482 ₫ total
includes taxes & fees
7 Jul - 8 Jul
Hampton Terrace Inn
Garden Gables Inn
Front of property – evening/night

Garden Gables Inn

4.0 star property
9.2 out of 10, Wonderful, (57)
"Rosie the Innkeeper was very friendly and welcoming. The breakfast was outstanding and so was our waitress. Can’t wait to go back again. "
Garden Gables Inn
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Photo by Elizabeth Massa Peroulakis
Open Photo by Elizabeth Massa Peroulakis

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 3.113.516 ₫

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.