Photo by Elizabeth Massa Peroulakis
Hotels in Chester
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Where to stay in Chester?
D. Hotel Suites & Spa
D. Hotel Suites & Spa
3.0 star property
Holyoke
9.4 out of 10, Exceptional, (2248)
9.4/10
Exceptional
(2248)
"Jim was fantastic and very engaging. Super friendly!!!
Dave was in training and doing wonderful! But he is a Red Sox fan so slightly imperfect…LOL"
"Jim was fantastic and very engaging. Super friendly!!!
Dave was in training and doing wonderful! But he is a Red Sox fan so slightly imperfect…LOL"
Chris
$134 nightly
The price is $150
$150 total
Nov 18 - Nov 19
Total with taxes and fees
Tru by Hilton Chicopee Springfield
Tru by Hilton Chicopee Springfield
2.5 star property
Chicopee
8.8 out of 10, Excellent, (1003)
8.8/10
Excellent
(1003)
"I stay here once or twice a year. It’s always a nice experience at this price point. The breakfast is better than most (great coffee!) and rooms are comfortable."
"I stay here once or twice a year. It’s always a nice experience at this price point. The breakfast is better than most (great coffee!) and rooms are comfortable."Christina
$87 nightly
The price is $99
$99 total
Dec 1 - Dec 2
Total with taxes and fees
The Black Swan Lee - Lenox, an Ascend Collection Hotel
The Black Swan Lee - Lenox, an Ascend Collection Hotel
3.0 star property
Lee
9.0 out of 10, Wonderful, (1002)
9.0/10
Wonderful
(1002)
"Clean and friendly "
"Clean and friendly "Anthony
$110 nightly
The price is $122
$122 total
Dec 7 - Dec 8
Total with taxes and fees
The Yankee, Trademark Collection by Wyndham
The Yankee, Trademark Collection by Wyndham
2.5 star property
Lenox
9.2 out of 10, Wonderful, (1004)
9.2/10
Wonderful
(1004)
"Staff…great
Room…great
We enjoy it here and stay annually "
"Staff…great
Room…great
We enjoy it here and stay annually "Sharon
$99 nightly
The price is $111
$111 total
Dec 15 - Dec 16
Total with taxes and fees
Pleasant Valley Motel West Stockbridge
Pleasant Valley Motel West Stockbridge
2.0 star property
West Stockbridge
6.8 out of 10, (1001)
6.8/10
(1001)
"No real bells of whistles. It was quiet, clean. The price was fabulous compared to all other properties in a 10-mile radius. The Manager was very pleasant and always smiling. Right off the Mass Turnpike in West Stockbridge just before entering NY.
Again for 1-2 nights I will always return."
"No real bells of whistles. It was quiet, clean. The price was fabulous compared to all other properties in a 10-mile radius. The Manager was very pleasant and always smiling. Right off the Mass Turnpike in West Stockbridge just before entering NY.
Again for 1-2 nights I will always return."Peter
$61 nightly
The price is $67
$67 total
Nov 21 - Nov 22
Total with taxes and fees
Monument Mountain Motel
Monument Mountain Motel
2.5 star property
Great Barrington
9.0 out of 10, Wonderful, (790)
9.0/10
Wonderful
(790)
"Really good place for the budget conscious. Safe, clean and no problems checking in after hours."
"Really good place for the budget conscious. Safe, clean and no problems checking in after hours."Randolph
$67 nightly
The price is $74
$74 total
Nov 18 - Nov 19
Total with taxes and fees
Courtyard by Marriott West Springfield
Courtyard by Marriott West Springfield
3.0 star property
West Springfield
9.2 out of 10, Wonderful, (567)
9.2/10
Wonderful
(567)
"Clean rooms, friendly staff and great breakfast!
"
"Clean rooms, friendly staff and great breakfast!
"William
$118 nightly
The price is $135
$135 total
Nov 23 - Nov 24
Total with taxes and fees
Sunset Inn
Sunset Inn
2.0 star property
Lee
7.6 out of 10, Good, (410)
7.6/10
Good
(410)
"owners was nice, room was clean"
"owners was nice, room was clean"tom
$76 nightly
The price is $85
$85 total
Dec 5 - Dec 6
Total with taxes and fees
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
3.5 star property
South Lee
9.0 out of 10, Wonderful, (783)
9.0/10
Wonderful
(783)
"Our room was so clean. The resort was quiet and the hiking trails were beautiful. "
"Our room was so clean. The resort was quiet and the hiking trails were beautiful. "Jennifer
$147 nightly
The price is $164
$164 total
Dec 15 - Dec 16
Total with taxes and fees
Holiday Inn Express Hotel & Suites Great Barrington by IHG
Holiday Inn Express Hotel & Suites Great Barrington by IHG
2.5 star property
Great Barrington
8.8 out of 10, Excellent, (694)
8.8/10
Excellent
(694)
"Staff was very nice and the room was clean and quiet. "
"Staff was very nice and the room was clean and quiet. "Sharon
$107 nightly
The price is $120
$120 total
Nov 24 - Nov 25
Total with taxes and fees
The Inn at Stockbridge
The Inn at Stockbridge
4.0 star property
Lee
9.8 out of 10, Exceptional, (98)
9.8/10
Exceptional
(98)
"A first class little inn"
"A first class little inn"Philip
$263 nightly
The price is $294
$294 total
Nov 20 - Nov 21
Total with taxes and fees
Howard Johnson by Wyndham Lenox
Howard Johnson by Wyndham Lenox
2.0 star property
Lenox
7.6 out of 10, Good, (824)
7.6/10
Good
(824)
"Room had a musty smell. Carpet not properly vacuumed (found bobby pins on floor). Shower curtain moldy. Bathroom floor dirty. Toilet not set correctly. However, bed was clean and comfortable."
"Room had a musty smell. Carpet not properly vacuumed (found bobby pins on floor). Shower curtain moldy. Bathroom floor dirty. Toilet not set correctly. However, bed was clean and comfortable."Daniel
$79 nightly
The price is $88
$88 total
Nov 18 - Nov 19
Total with taxes and fees
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Holiday Inn & Suites Pittsfield-Berkshires by IHG
3.0 star property
Pittsfield
8.0 out of 10, Very Good, (959)
8.0/10
Very Good
(959)
"Yes, clean and comfortable."
"Yes, clean and comfortable."Evelyn
$88 nightly
The price is $99
$99 total
Nov 21 - Nov 22
Total with taxes and fees
Best Western Plus Berkshire Hills Inn & Suites
Best Western Plus Berkshire Hills Inn & Suites
2.5 star property
Pittsfield
8.6 out of 10, Excellent, (1000)
8.6/10
Excellent
(1000)
"It was close to our entertainment for the night "
"It was close to our entertainment for the night "Pearce
$75 nightly
The price is $84
$84 total
Nov 19 - Nov 20
Total with taxes and fees
Hampton Inn Westfield
Hampton Inn Westfield
2.5 star property
Westfield
8.4 out of 10, Very Good, (810)
8.4/10
Very Good
(810)
"Staff welcoming and helpful"
"Staff welcoming and helpful"June
$111 nightly
The price is $124
$124 total
Dec 10 - Dec 11
Total with taxes and fees
Wagon Wheel Inn
Wagon Wheel Inn
2.0 star property
Lenox
7.0 out of 10, Good, (641)
7.0/10
Good
(641)
"Motel was no frills with economical price. Staff at office was helpful. Bed comforter had various cigarette burn holes in non-smoking room. Heard traffic noise from the room."
"Motel was no frills with economical price. Staff at office was helpful. Bed comforter had various cigarette burn holes in non-smoking room. Heard traffic noise from the room."Heidi
$69 nightly
The price is $77
$77 total
Nov 18 - Nov 19
Total with taxes and fees
Courtyard by Marriott Lenox Berkshires
Courtyard by Marriott Lenox Berkshires
3.0 star property
Lenox
9.2 out of 10, Wonderful, (586)
9.2/10
Wonderful
(586)
"Great accommodating staff . Would stay here again. "
"Great accommodating staff . Would stay here again. "Gloria
$118 nightly
The price is $132
$132 total
Dec 14 - Dec 15
Total with taxes and fees
The Ellery
The Ellery
3.5 star property
Northampton
9.2 out of 10, Wonderful, (891)
9.2/10
Wonderful
(891)
"Nice stay with comfortable king bed and nice breakfast. "
"Nice stay with comfortable king bed and nice breakfast. "kenneth
$148 nightly
The price is $166
$166 total
Nov 23 - Nov 24
Total with taxes and fees
Candlewood Suites West Springfield by IHG
Candlewood Suites West Springfield by IHG
2.5 star property
West Springfield
8.4 out of 10, Very Good, (785)
8.4/10
Very Good
(785)
"We had a great experience here. Very nice staff, very clean room. "
"We had a great experience here. Very nice staff, very clean room. "Sarah
$98 nightly
The price is $112
$112 total
Nov 23 - Nov 24
Total with taxes and fees
Quality Inn
Quality Inn
2.5 star property
Lee
8.4 out of 10, Very Good, (1001)
8.4/10
Very Good
(1001)
"The complimentary breakfast was amazing!"
"The complimentary breakfast was amazing!"Rachel
$93 nightly
The price is $104
$104 total
Nov 30 - Dec 1
Total with taxes and fees
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.
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.
Go beyond your typical stay in Chester
Pet friendly
Family friendly
Cottage
Learn more about Chester
The region around Chester is home to attractions such as Chester Town Hall and Littleville Lake.
Photo by Elizabeth Massa Peroulakis
Open Photo by Elizabeth Massa Peroulakis
Check out reviews of Chester hotels guests love
The Ellery
10/10 Excellent
"Clean, nice room. Comfortable bed. Good breakfast. Nice staff."
Quality Inn West Springfield
10/10 Excellent
"Very courteous staff. Comfortable, clean room. Always interesting people travelling through."
The Yankee, Trademark Collection by Wyndham
10/10 Excellent
"Great stay!"
Berkshire Mountain Lodge
10/10 Excellent
"The suites were large. Nice to have separate bedroom. Kitchen with all the basics. Perfect for a getaway "
Holiday Inn & Suites Pittsfield-Berkshires by IHG
10/10 Excellent
"Very good service "
The Black Swan Lee - Lenox, an Ascend Collection Hotel
10/10 Excellent
"The room was nice, but wish we would have asked for the lake view. The breakfast area was really nice and they had good food. The coffee machine was available 24/7 and it made a pretty good mocha! "
Homewood Suites by Hilton Hadley Amherst
10/10 Excellent
"Really good place to go "
Quality Inn Westfield - Springfield
10/10 Excellent
"Staff was very friendly. Everything was clean and well kept. Small hotel but very cozy and quiet."
Berkshires Untold
10/10 Excellent
"Enjoyed the Clubhouse before retiring in for the evening. Cozy, comfortable, and relaxing atmosphere."
Frequently asked questions
How much does a hotel room cost in Chester?
You can choose a great hotel in Chester from $67 with properties to suit all budgets and needs. If you're looking for an affordable hotel in Chester that meets all of your requirements, just sort hotels by "Price: low to high" after applying your filters when searching on Hotels.com. If you're a member, don't forget to sign in to your account to unlock more savings.
How can I find deals and earn rewards at Chester hotels?
Members can save up to 20% on select hotels in Chester. Plus, Silver, Gold and Platinum members earn extra rewards on VIP Access bookings, making each stay even more rewarding.
Can I book Chester hotels with free cancellation?
In order to book a refundable Chester hotel, simply filter hotels by "Property cancellation options" and select "Fully refundable property". The majority of hotels offer free cancellation, so you can receive a refund if you need to cancel. Some hotels do require cancelling more than 24 hours before check-in, so double-check your booking beforehand.
Are all taxes and fees included in the Chester hotel prices shown on Hotels.com?
Hotels.com provides upfront pricing so you can relax knowing you won't be met with surprise additional fees or taxes when you're ready to confirm your booking. From the time you start your search on Hotels.com, the price you see is what you pay. This makes it much easier to compare properties and secure our best deal for your next getaway.
Can I book a refundable accommodation in Chester?
If you're looking for the flexibility to change your travel plans to Chester, most hotels offer refundable* bookable rates. You can see these accommodations by searching our site and using the "fully refundable" filter to narrow the results down.
What will the weather in Chester be like during my vacation?
July and August are typically the warmest months in Chester when the average temp is 66°F. January and February are the coldest months when the average temperature is 28°F. July and August are the months with the most rain.
Why should I book my Chester hotel through Hotels.com?
There are lots of reasons to book your Chester trip with us: our free cancellations on selected hotels gives you flexibility, and with One Key™, our rewards program, you will be able to earn and use OneKeyCash™* on all eligible bookings such as hotels, car rentals, flights, vacation rentals and more on Hotels.com, Expedia and Vrbo.