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Top Chester hotels

Blue – A Modern Hotel, an Ascend Collection Hotel

Blue – A Modern Hotel, an Ascend Collection Hotel

2.5 out of 5
1080 Riverdale St West Springfield MA
Fully refundable
$115 nightly
The price is $132 total per night from Apr 8 to Apr 9
$132 total
Apr 8 - Apr 9
Total with taxes and fees
This hotel doesn't skimp on freebies - guests receive free WiFi and free self parking. Business travelers can take advantage of the express check-out. There's ...
Highly recommend this was a beautiful hotel. The rooms were beautiful. The staff were so nice and I was so excited when I walked into the room and there was a massage chair.

Reviewed on Mar 9, 2026

Opens in a new windowBlue – A Modern Hotel, an Ascend Collection Hotel
D. Hotel Suites & Spa

D. Hotel Suites & Spa

3 out of 5
1 Country Club Rd Holyoke MA
Fully refundableReserve now, pay when you stay
$121 nightly
The price is $135 total per night from Mar 10 to Mar 11
$135 total
Mar 10 - Mar 11
Total with taxes and fees
A full-service spa, 2 restaurants, and an indoor pool are all featured at this smoke-free hotel. You'll appreciate the gym, bar/lounge, and laundry ...
Excellent spot to get away from the noisy city life

Reviewed on Mar 9, 2026

Opens in a new windowD. Hotel Suites & Spa
Courtyard by Marriott West Springfield

Courtyard by Marriott West Springfield

3 out of 5
885 Riverdale Street West Springfield MA
Fully refundableReserve now, pay when you stay
$127 nightly
The price is $145 total per night from Mar 15 to Mar 16
$145 total
Mar 15 - Mar 16
Total with taxes and fees
This hotel features an indoor pool and a 24-hour gym. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Relax ...
Clean and efficient. Great location to find a meal and get away from the Big E chaos.

Reviewed on Mar 9, 2026

Opens in a new windowCourtyard by Marriott West Springfield
The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham

2.5 out of 5
461 Pittsfield Rd Lenox MA
Fully refundableReserve now, pay when you stay
$93 nightly
The price is $103 total per night from Mar 16 to Mar 17
$103 total
Mar 16 - Mar 17
Total with taxes and fees
This hotel features an indoor pool and a 24-hour gym. Business travelers can take advantage of the free WiFi in public areas. Enjoy the seasonal outdoor pool ...
This area is really starting to build up. There is a small ski area. An Italian restaurant and 110 grill right on that road. About 15 min away Applebees. A lot of pizza and Mexican. Winter not only is there skiing there are a lot of snowmobile trails. Summer there are water falls you can see. Tubing ...

Reviewed on Mar 8, 2026

Opens in a new windowThe Yankee, Trademark Collection by Wyndham
The Ellery

The Ellery

3.5 out of 5
259 Elm Street Northampton MA
Fully refundableReserve now, pay when you stay
$123 nightly
The price is $138 total per night from Mar 22 to Mar 23
$138 total
Mar 22 - Mar 23
Total with taxes and fees
This hotel features free self parking and free WiFi in public areas. Enjoy the free continental breakfast each morning. A garden, a lobby fireplace, and a picnic ...
The Ellery is a super comfortable simple and friendly hotel. It is ideal to visit your students at Smith College.

Reviewed on Mar 9, 2026

Opens in a new windowThe Ellery
Berkshire Mountain Lodge

Berkshire Mountain Lodge

3 out of 5
8 Dan Fox Dr Pittsfield MA
Fully refundableReserve now, pay when you stay
$115 nightly
The price is $128 total per night from Apr 7 to Apr 8
$128 total
Apr 7 - Apr 8
Total with taxes and fees
This lodge features an indoor pool and a hot tub. Traveling on business? Take advantage of the business center and free WiFi in public areas. Free self parking, ...
This was great. I did not really need the kitchen for my stay but for future planning this wil be great! Plenty of room in the living area. Bed was comfortable. Just beautiful

Reviewed on Mar 9, 2026

Opens in a new windowBerkshire Mountain Lodge
Berkshires Untold

Berkshires Untold

3.5 out of 5
194 Pittsfield Rd Lenox MA
Fully refundableReserve now, pay when you stay
$83 nightly
The price is $93 total per night from Mar 23 to Mar 24
$93 total
Mar 23 - Mar 24
Total with taxes and fees
A restaurant and a bar/lounge are featured at this lodge. Guests will appreciate free perks like free self parking and WiFi in public areas. A terrace, a lobby ...
Wonderful place but doors to rooms open on outside halla

Reviewed on Mar 7, 2026

Opens in a new windowBerkshires Untold
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 out of 5
190 Meadow Street South Lee MA
Fully refundable
$131 nightly
The price is $147 total per night from Mar 12 to Mar 13
$147 total
Mar 12 - Mar 13
Total with taxes and fees
This hotel features 2 outdoor pools, 2 indoor pools, and a poolside bar. There's fun for all ages with mini golf and a playground, and families will appreciate ...
Room was awesome and very clean

Reviewed on Mar 8, 2026

Opens in a new windowHoliday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG

3 out of 5
One West Street Pittsfield MA
Fully refundable
$127 nightly
The price is $142 total per night from Mar 31 to Apr 1
$142 total
Mar 31 - Apr 1
Total with taxes and fees
This hotel features a restaurant, an indoor pool, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public ...
Hotel is going through a renovation which makes the place a little rougher than it’s used to be. No parking or limited parking at entrance of hotel. Valet parking personnel were parking cars on entrance round entrance and in the mourning, they were towing those cars from the property. Not a good ...

Reviewed on Mar 8, 2026

Opens in a new windowHoliday Inn & Suites Pittsfield-Berkshires by IHG
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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.

Chester Hotel & Travel Guide\n

You may have noticed there aren't any Travelocity-featured rooms in Chester. Travelers hoping to make memories in Chester should make reservations in one of the 15 hotels within easy driving distance.

The nearest Travelocity-listed room is the Holiday Inn Express & Suites Westfield, Massachusetts, situated 16 miles (25 kilometers) from the urban core of Chester. For an alternative, how about you try the Sunset Inn, located in Massachusetts, which is 14 miles (22 kilometers) from the heart of the city.

14 miles (22 kilometers) from the main part of Chester, you will find the Pilgrim Inn. The Econo Lodge can be found approximately 17 miles (28 kilometers) away. The Super 8 Lee/Berkshires/Outlet Area and also the Quality Inn Westfield - Springfield are some other Travelocity-listed accommodation options worth checking out around Chester.

When you've got the time, adventurous travelers could explore the other cultural and scenic delights of Western Massachusetts. Western Massachusetts is well known for mountains, and common tourist places of interest are history museums. Popular activities in this part of United States of America include skiing.

Looking for things to do? Spend some time exploring Volleyball Hall of Fame and Mount Tom, which you'll find in Holyoke, 18 miles (28 kilometers) east of Chester. The Homewood Suites by Hilton Holyoke-Springfield/North and Howard Johnson Holyoke/Springfield are just some examples of the great short and long-stay options in Holyoke. For another option, stay in Hadley, 20 miles (34 kilometers) east of Chester, where you can choose from the Courtyard by Marriott Hadley Amherst and Old Mill Inn. The Hadley Farm Museum and Porter Phelps Huntington Museum are some of the more frequented attractions to explore when visiting Hadley.

Before you head home, consider spending a few hours enjoying thrills and spills with excited lovers of sports at a local match. Times Union Center is located 45 miles (76 kilometers) to the northwest of Chester. Wise travelers wishing to book a Travelocity-listed hotel nearby can choose from the Hilton Albany or the TownePlace Suites by Marriott Albany Downtown/Medical Center.

Bradley International Airport is a convenient airport, and can be found 30 miles (46 kilometers) outside central Chester. Conveniently located hotel options include Sheraton Hartford Hotel at Bradley Airport and Holiday Inn Express & Suites Bradley Airport.

Frequently asked questions

What are the top kid-friendly hotels in Chester?
From unique amenities to extra space, kid-friendly hotels are equipped with features that can help turn an everyday family vacation into an amazing one. These Chester options make getting away with your youngsters easier: Unpack your bags at Big farmhouse in the foothills of the Berkshires. It comes with a fireplace, pet-friendly facilities and a passion for making families feel welcome. Also check out the deals at Beautiful retreat to the woods to enjoy the winter season.. It comes with a nearby beach, animal viewing activities and plenty of opportunities to hang out as a family.
Where can I find cheap hotels in Chester?
At Travelocity you'll find really nice hotels in Chester at great prices. We source incredible prices with our trusted partners, so you have a tempting selection of cheap hotels to choose from. If you can be flexible on dates and location, consider staying at a hotel near Chester rather than in Chester. We may find you even better rates, too.
How do I find the best Chester hotel deals?
Simple! On Travelocity, look through the fantastic offers we've already found in Chester then use our filters to find a great deal that's perfect for you. Enter your travel dates, select the number of rooms you need, and we'll do the rest. You can get great discounts on flights and car hire, too, when you bundle.
How much does it cost to stay in a hotel in Chester?
The cheapest hotel in Chester is $93. This price was available within the past 7 days, for stays with a check-in date within the next year. Of course, the price you pay depends on your dates of travel, the length of your stay, and the hotel's location. Prices and availability are subject to change. Additional terms apply.
How many hotels are in Chester?
There are 868 hotels in Chester on Travelocity.
What are the best hotels in Chester?
Chester has so many great hotels to choose from at Travelocity — and it's so easy to find the perfect one. Just choose one of our popular pre-selected hotels with great reviews, or you can refine your search to build your ideal stay. Simply filter hotels based on price or star rating, or select properties with a pool, a hot tub, or a range of other amenities and pick the best place to stay in Chester for you!
When is the best time to visit Chester?
If you want the joy of a fun-filled trip in peak season, visit Chester during June, July and August. If you'd prefer the peace of off-season, book a stay during quieter months, such as November, December and January.
When is the cheapest time to stay in Chester?
Based on historic data is usually the cheapest month to visit Chester. However, we have incredible deals all year round, so we're confident you'll find a room in your budget whenever you choose to travel.
Are there any great family-friendly hotels in Chester?
There are multiple hotels in Chester that will please the whole family. Do you need adjoining rooms, babysitting services or a swimming pool? We've got you covered. Use our family filter to narrow your search down and use guest reviews to help you pick the perfect place for your next family trip to Chester. We have plenty of kid-friendly hotels in Chester to choose from on Travelocity!
Why book a hotel in Chester through Travelocity?
Because we have the top hotels in Chester! We want to help you travel more and worry less. That's why we've put the most amazing hotel, car rental, and flight deals in one place. When you search for hotels with us, you know you're getting fantastic prices with no hidden fees and free cancellation on most properties up to 24 hours before your stay. If you become a Travelocity member, you also get exclusive member discounts. Sign up today!
How do I cancel my hotel booking in Chester on Travelocity?
Canceling your booking with Travelocity is easy. Sign into your account and select My Trips. Here, you will see your cancellation options. We offer free cancellation on many properties.

Recent Chester hotel reviews by fellow wanderers

The Ellery

The Ellery

5 out of 5
Posted 1 hour ago
Travelocity Verified Review
"The Ellery is a super comfortable simple and friendly hotel. It is ideal to visit your students at Smith College."
A verified traveler stayed at The Ellery
The Ellery

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