Photo by Elizabeth Massa Peroulakis
Find hotels in Chester, MA from 1.801.521 ₫
Change your mind
Book hotels with free cancellation
Be picky
Search almost a million properties worldwide
Go beyond your typical stay in Chester
Family friendly
Check prices for these dates
Top 10 Chester hotels and places to stay

The Constance by the Lenox Collection
The Constance by the Lenox Collection
8.6 out of 10, Excellent, (492)
The price is 4.431.742 ₫
4.950.257 ₫ total
includes taxes & fees
15 Jul - 16 Jul

The Yankee, Trademark Collection by Wyndham
The Yankee, Trademark Collection by Wyndham
9.2 out of 10, Wonderful, (1013)
The price is 3.306.705 ₫
3.693.589 ₫ total
includes taxes & fees
24 Jul - 25 Jul

The Black Swan Lee - Lenox, Ascend Hotel Collection
The Black Swan Lee - Lenox, Ascend Hotel Collection
9.0 out of 10, Wonderful, (1003)
The price is 4.673.511 ₫
5.220.312 ₫ total
includes taxes & fees
15 Jul - 16 Jul

Berkshires Untold
Berkshires Untold
9.2 out of 10, Wonderful, (632)
The price is 10.550.647 ₫
11.785.081 ₫ total
includes taxes & fees
25 Jul - 26 Jul

The Cornell Inn, Lenox & The Berkshires
The Cornell Inn, Lenox & The Berkshires
9.0 out of 10, Wonderful, (1002)
The price is 4.210.860 ₫
5.724.261 ₫ total
includes taxes & fees
21 Jul - 22 Jul

Candlewood Suites West Springfield by IHG
Candlewood Suites West Springfield by IHG
8.4 out of 10, Very good, (731)
The price is 2.172.269 ₫
2.486.162 ₫ total
includes taxes & fees
27 Jul - 28 Jul
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Save an average of 15% on thousands of hotels when you're signed in
Learn more about Chester
Experience the hiking, camping and waterfalls in Chester!

Photo by Elizabeth Massa Peroulakis
Open Photo by Elizabeth Massa Peroulakis
More cheap stays in Chester
More cheap stays in Chester

Red Roof Inn PLUS+ West Springfield
1254 Riverdale Street, West Springfield, MA
The price is 2.326.077 ₫ per night from 20 Jul to 21 Jul
2.326.077 ₫
2.662.194 ₫ total
20 Jul - 21 Jul
includes taxes & fees
6.8/10 (1,000 reviews)
Hotels in Chester with star rating
Hotels in Chester with star rating

4 Star Hotels
10 properties
Accommodation near Chester attractions
Accommodation near Chester attractions
Explore a world of travel with Expedia
Explore a world of travel with Expedia
Accommodation near Chester attractions
- Hotels near Tanglewood Music Center
- Hotels near Big E
- Hotels near Smith College
- Hotels near Mount Holyoke College
- Hotels near Holyoke Mall
- Hotels near Connecticut River
- Hotels near Norman Rockwell Museum
- Hotels near Ski Butternut
- Hotels near Jacob's Pillow
- Hotels near The Mount
- Hotels near Lee Premium Outlets
- Hotels near Bousquet Ski Area
- Hotels near Berkshire Botanical Garden
- Hotels near Ventfort Hall Mansion and Gilded Age Museum
- Hotels near Historic Northampton
- Hotels near Academy of Music Theater
- Hotels near Naumkeag Museum
- Hotels near Otis Reservoir
- Hotels near Olympia Ice Center
Hotels near Chester Airports
Search Chester Hotel Brands
Hotels Near Chester, Massachusetts
- Springfield Hotels
- New England Hotels
- Lenox Hotels
- Pittsfield Hotels
- Northampton Hotels
- Great Barrington Hotels
- Stockbridge Hotels
- Lee Hotels
- West Springfield Hotels
- Holyoke Hotels
- Chicopee Hotels
- Hadley Hotels
- Westfield Hotels
- Agawam Hotels
- Otis Hotels
- Becket Hotels
- Adams Hotels
- Deerfield Hotels
- West Stockbridge Hotels
- South Deerfield Hotels
More ways to book
Expedia's Latest Trends
Hotels
General