Chester hotels from RM282
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12 Sept - 13 SeptTomorrow
13 Sept - 14 SeptNext weekend
18 Sept - 20 SeptIn two weeks
25 Sept - 27 SeptOur top choices for Chester hotels
1. Quality Inn Lee - Lenox South
Quality Inn Lee - Lenox SouthLee
Christine
RM436
RM487 total
includes taxes & fees
27 Sept - 28 Sept
2. Becket Motel
Becket MotelBecket
Paul
RM427
RM614 total
includes taxes & fees
14 Sept - 15 Sept
3. D. Hotel Suites & Spa
D. Hotel Suites & SpaHolyoke
Karen
RM494
RM579 total
includes taxes & fees
23 Sept - 24 Sept
4. Berkshire Lake Lodge
Berkshire Lake LodgeLee
mike
RM618
RM691 total
includes taxes & fees
20 Sept - 21 Sept
5. Hampton Inn Westfield
Hampton Inn WestfieldWestfield
Mykola
RM473
RM528 total
includes taxes & fees
7 Oct - 8 Oct
6. Best Western Plus Berkshire Hills Inn & Suites
Best Western Plus Berkshire Hills Inn & SuitesPittsfield
Joe
RM447
RM499 total
includes taxes & fees
16 Sept - 17 Sept
7. The Yankee Inn
The Yankee InnLenox
Karen
RM472
RM527 total
includes taxes & fees
22 Sept - 23 Sept
8. Holiday Inn Express Hotel & Suites Great Barrington by IHG
Holiday Inn Express Hotel & Suites Great Barrington by IHGGreat Barrington
BJORN
RM545
RM608 total
includes taxes & fees
20 Sept - 21 Sept
9. The Black Swan Lee - Lenox, an Ascend Collection Hotel
The Black Swan Lee - Lenox, an Ascend Collection HotelLee
Susan
RM508
RM567 total
includes taxes & fees
22 Sept - 23 Sept
10. Quality Inn Westfield - Springfield
Quality Inn Westfield - SpringfieldWestfield
Thomas
RM398
RM444 total
includes taxes & fees
11 Oct - 12 Oct
11. Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
Fairfield Inn & Suites by Marriott Great Barrington Lenox/BerkshiresGreat Barrington
Bruce
RM757
RM845 total
includes taxes & fees
17 Sept - 18 Sept
12. Econo Lodge Lee - Great Barrington
Econo Lodge Lee - Great BarringtonLee
Anna
RM282
RM315 total
includes taxes & fees
22 Sept - 23 Sept
13. Hampton Inn West Springfield
Hampton Inn West SpringfieldWest Springfield
Francisco
RM497
RM569 total
includes taxes & fees
27 Sept - 28 Sept
14. Homewood Suites by Hilton Holyoke-Springfield/North
Homewood Suites by Hilton Holyoke-Springfield/NorthHolyoke
Andrew
RM597
RM667 total
includes taxes & fees
4 Oct - 5 Oct
15. Howard Johnson by Wyndham Lenox
Howard Johnson by Wyndham LenoxLenox
COLLEEN
RM321
RM359 total
includes taxes & fees
14 Sept - 15 Sept
16. Hotel Northampton
Hotel NorthamptonNorthampton
steven
RM504
RM563 total
includes taxes & fees
13 Sept - 14 Sept
17. The Cornell Inn, Lenox & The Berkshires
The Cornell Inn, Lenox & The BerkshiresLenox
Sarah
RM669
RM767 total
includes taxes & fees
14 Sept - 15 Sept
18. Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHGPittsfield
Steve
RM515
RM575 total
includes taxes & fees
13 Sept - 14 Sept
19. The Ellery
The ElleryNorthampton
Scott
RM545
RM609 total
includes taxes & fees
16 Sept - 17 Sept
20. Courtyard by Marriott Lenox Berkshires
Courtyard by Marriott Lenox BerkshiresLenox
Tracy
RM797
RM890 total
includes taxes & fees
22 Sept - 23 Sept
Stay near popular Chester attractions
Chester Town Hall
You can get tickets for a performance at Chester Town Hall on your trip to Chester. Wander the lakeside and forests in this relaxing area.
Learn more about Chester
Experience the hiking, camping and theatre in Chester!
See all hotels in Chester
Photo by Chris Addams
Top Chester Hotel Reviews
Berkshires Untold
10/10 Excellent
"excellent hotelโฆ Excellent staffโฆ Great price. Highly recommended."
The Yankee Inn
10/10 Excellent
"Nasically a large motel with both an outdoor and indoor pool. A bit tired, but reasonably close to Lenox and to Tabglewood."
Hampton Inn West Springfield
10/10 Excellent
"I always love staying here when I visit Springfield! The front desk staff are consistently friendly, welcoming, and helpful, which really makes a difference. The rooms are a little dated, but theyโre spacious, clean, and have everything I need for a comfortable stay. The breakfast also has a great variety of options, and parking is always easy to find. I also love that they have snacks available at the front deskโperfect when you need a little something after a long day. Overall, this is definitely one of my go-to places to stay when Iโm in the area!"
La Quinta Inn & Suites by Wyndham Springfield MA
8/10 Good
"amazing, hust breakfast wasnt as good"
D. Hotel Suites & Spa
10/10 Excellent
"All around great hotel."
The Whitlock
10/10 Excellent
"My husband and I enjoyed our two-night stay at The Whitlock. This historical inn was well located in town and very walkable. The bed was comfortable, bathroom updated, quiet and when we did encounter staff, Logan and Mary Ann, they were incredibly pleasant and helpful. Thank you for your hospitality."
Quality Inn West Springfield
8/10 Good
"Not bad. Pool was nice."
Berkshire Mountain Lodge
8/10 Good
"Loved having a full Kitchen, lots of space"
Hotel Northampton
8/10 Good
"Very clean and big room with very comfortable beds and views of Northampton. The staff were extremely pleasant and welcoming."
More cheap stays in Chester
FairBridge Inn Express
16 Cheshire Road Pittsfield MA
RM252
RM282 total
13 Sept - 14 Sept
includes taxes & fees
5.4/10 (904 reviews)
Blue A Modern Hotel, an Ascend Collection Hotel
1080 Riverdale St West Springfield MA
RM412
RM471 total
11 Oct - 12 Oct
includes taxes & fees
Quality Inn West Springfield
1150 Riverdale St West Springfield MA
RM421
RM482 total
1 Oct - 2 Oct
includes taxes & fees
7.2/10 Good! (1,003 reviews)
The Yankee Inn
461 Pittsfield Rd Lenox MA
RM472
RM527 total
22 Sept - 23 Sept
includes taxes & fees
9.2/10 Wonderful! (1,002 reviews)
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
1055 South Street Pittsfield MA
RM515
RM575 total
13 Sept - 14 Sept
includes taxes & fees
Quality Inn & Suites Northampton - Amherst
117 Conz St Northampton MA
RM516
RM576 total
4 Oct - 5 Oct
includes taxes & fees
