Chester Hotels
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31 Aug - 1 SeptTomorrow
1 Sept - 2 SeptThis weekend
4 Sept - 6 SeptNext weekend
11 Sept - 13 SeptOur top choices for Chester hotels
3. Berkshire Lake Lodge
Berkshire Lake LodgeLee
mike
€141
includes taxes & fees
13 Sept - 14 Sept
4. Quality Inn Lee - Lenox South
Quality Inn Lee - Lenox SouthLee
Christine
€106
includes taxes & fees
21 Sept - 22 Sept
5. The Black Swan Lee - Lenox, an Ascend Collection Hotel
The Black Swan Lee - Lenox, an Ascend Collection HotelLee
Rinat
€123
includes taxes & fees
21 Sept - 22 Sept
6. River Valley Inn
River Valley InnWest Hatfield
Michael
€89
includes taxes & fees
7 Sept - 8 Sept
7. Hampton Inn Westfield
Hampton Inn WestfieldWestfield
Mykola
€116
includes taxes & fees
8 Sept - 9 Sept
8. Howard Johnson by Wyndham Lenox
Howard Johnson by Wyndham LenoxLenox
Sheila
€76
includes taxes & fees
1 Sept - 2 Sept
9. Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHGPittsfield
Steve
€114
includes taxes & fees
8 Sept - 9 Sept
10. Best Western Plus Berkshire Hills Inn & Suites
Best Western Plus Berkshire Hills Inn & SuitesPittsfield
Jermaine
€111
includes taxes & fees
20 Sept - 21 Sept
11. Quality Inn Westfield - Springfield
Quality Inn Westfield - SpringfieldWestfield
Thomas
€102
includes taxes & fees
29 Sept - 30 Sept
12. Berkshire Mountain Lodge
Berkshire Mountain LodgePittsfield
Robert
€97
includes taxes & fees
1 Oct - 2 Oct
13. Econo Lodge Lee - Great Barrington
Econo Lodge Lee - Great BarringtonLee
Anna
€67
includes taxes & fees
7 Sept - 8 Sept
14. The Red Lion Inn
The Red Lion InnStockbridge
Patricia
€195
includes taxes & fees
29 Sept - 30 Sept
15. Hampton Inn & Suites Berkshires-Lenox
Hampton Inn & Suites Berkshires-LenoxLenox
Nancy
€119
includes taxes & fees
13 Sept - 14 Sept
17. Monument Mountain Motel
Monument Mountain MotelGreat Barrington
Charlie
€82
includes taxes & fees
1 Sept - 2 Sept
18. Berkshires Untold
Berkshires UntoldLenox
Christine
€135
includes taxes & fees
28 Sept - 29 Sept
19. Holiday Inn Express Hotel & Suites Great Barrington by IHG
Holiday Inn Express Hotel & Suites Great Barrington by IHGGreat Barrington
BJORN
€111
includes taxes & fees
7 Sept - 8 Sept
20. D. Hotel Suites & Spa
D. Hotel Suites & SpaHolyoke
Kerri
€123
includes taxes & fees
7 Sept - 8 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 waterfalls in Chester!
See all hotels in Chester
Photo by Chris Addams
Top Chester Hotel Reviews
Berkshire Mountain Lodge
10/10 Excellent
"Clean & comfortable stay"
The Black Swan Lee - Lenox, an Ascend Collection Hotel
10/10 Excellent
"We had a fantastic stay at the Black Swan Inn in Lee, MA. Our room was incredibly clean, comfortable, and featured a beautiful view of the lake. Both check-in and check-out were completely hassle-free .A special shoutout goes to Carrie, the breakfast attendant! The breakfast area was exceptionally clean and well-stocked thanks to her hard work. Carrie was not only helpful, pleasant, and polite, but she also worked tirelessly to ensure all food items were fresh and fully available. Her excellent service truly made our mornings. We highly recommend this inn!"
Holiday Inn Club Vacations Oak 'n Spruce Resort
10/10 Excellent
"Great for families"
D. Hotel Suites & Spa
10/10 Excellent
"My room was clean, spacious and comfortable. Breakfast was yummy."
La Quinta Inn & Suites by Wyndham Springfield MA
10/10 Excellent
"👌"
Candlewood Suites West Springfield by IHG
10/10 Excellent
"The staff that helped me check in was super helpful"
Berkshires Untold
10/10 Excellent
"Although an excellent 2-night stay, our comments are intended to make future stays even better. Room temperature: virtually impossible to maintain a comfort level. Basically it was too cold in spite of raising the thermostat temp. At 80 when the heat came on, it was much too hot! Room lighting: too dark; only the bathroom was well lit. Bathroom moisture: in the absence of a ventilation or fan, the bathroom remained damp after a shower and keeping the door open resulted in everything in the bedroom becoming damp. But the positives far outweigh these few items."
Hotel Northampton
10/10 Excellent
"Lovely, central hotel. Highly recommend."
The Red Lion Inn
10/10 Excellent
"Having stayed at the Red Lion over forty times since 1979, when we were pleasantly snowed in and obliged to spend an extra night whilst the roads were plowed, I have watched the inn evolve. The beds were as comfy as always, the pool a delight under the moon, still the delicious Bloody Marys to sip in a rocking chair on the wide, wooden porch, an idyllic perch to chat and watch the town’s visitors to-ing and fro-ing and the small - and not so small-ones riding the lions that frame the entrance. Long carpeted, bumpy hallways framed with an eclectic array of deeds, art, china-stuffed cupboards and dresses still charm and enlighten the journey to one’s room. Contemporary sophistication and New England history blend. Over doors, painted horizontal windows that once served to cool a room, and pre electrified gas switches that controlled the lights allow the guest to transcend time. The food is delicious, as always, the menus having broaden to reflect contemporary tastes. Love the small bar and was pleased to see there was sometimes entertainment in The Lion’s Den. The upstairs gift shop carries an imaginative collection of Red Lion and New England sundries, whilst another shop holds varied treasures, including clothing. Of note, I noticed that that the porch rattan needed repair, the dining area has shrunk to accommodate more seating and the porch table overflowed with empty glasses. Still the rocking steed sits proudly in the back room!"
More cheap stays in Chester
FairBridge Inn Express
16 Cheshire Road Pittsfield MA
€60
1 Sept - 2 Sept
includes taxes & fees
Red Roof Inn PLUS+ West Springfield
1254 Riverdale Street West Springfield MA
€87
10 Sept - 11 Sept
includes taxes & fees
Quality Inn West Springfield
1150 Riverdale St West Springfield MA
€93
14 Sept - 15 Sept
includes taxes & fees
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
1055 South Street Pittsfield MA
€114
8 Sept - 9 Sept
includes taxes & fees
Quality Inn & Suites Northampton - Amherst
117 Conz St Northampton MA
€127
27 Sept - 28 Sept
includes taxes & fees
7.2/10 Good! (1,006 reviews)
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