Book Hotels in Chester, MA

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Top Chester hotels

D. Hotel Suites & Spa

D. Hotel Suites & Spa

3 out of 5
1 Country Club Rd, Holyoke, MA
Fully refundable
$134 nightly
The price is $150 total per night from Nov 3 to Nov 4
$150 total
Nov 3 - Nov 4
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 ...
It was a good stay

Reviewed on Oct 25, 2025

Opens in a new windowD. Hotel Suites & Spa
Berkshire Mountain Lodge

Berkshire Mountain Lodge

3 out of 5
8 Dan Fox Dr, Pittsfield, MA
Fully refundableReserve now, pay when you stay
$113 nightly
The price is $126 total per night from Nov 2 to Nov 3
$126 total
Nov 2 - Nov 3
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, ...
Excellent all the way around

Reviewed on Oct 28, 2025

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
$94 nightly
The price is $105 total per night from Nov 2 to Nov 3
$105 total
Nov 2 - Nov 3
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 ...
Doesn’t look like much from the outside but it’s got a cute bar area, very cozy, and the dinner they serve is very good.

Reviewed on Oct 30, 2025

Opens in a new windowBerkshires Untold
The Ellery

The Ellery

3.5 out of 5
259 Elm Street, Northampton, MA
Fully refundableReserve now, pay when you stay
$101 nightly
The price is $113 total per night from Nov 17 to Nov 18
$113 total
Nov 17 - Nov 18
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 ...
Great housekeeping.

Reviewed on Oct 27, 2025

Opens in a new windowThe Ellery
The Black Swan Lee - Lenox, an Ascend Collection Hotel

The Black Swan Lee - Lenox, an Ascend Collection Hotel

3 out of 5
435 Laurel St, Lee, MA
Fully refundable
$106 nightly
The price is $119 total per night from Nov 6 to Nov 7
$119 total
Nov 6 - Nov 7
Total with taxes and fees
A restaurant and a 24-hour gym are featured at this hotel. There's no skimping on freebies - guests receive free continental breakfast, free WiFi, and free self ...
Awesome Stay
View of the lake was lovely! Breakfast was fine—yogurt, eggs, pancakes and cereal. Coffee was plentiful!

Reviewed on Oct 26, 2025

Opens in a new windowThe Black Swan Lee - Lenox, an Ascend Collection Hotel
La Quinta Inn & Suites by Wyndham Springfield MA

La Quinta Inn & Suites by Wyndham Springfield MA

3 out of 5
100 Congress Street, Springfield, MA
Fully refundableReserve now, pay when you stay
$115 nightly
The price is $130 total per night from Nov 9 to Nov 10
$130 total
Nov 9 - Nov 10
Total with taxes and fees
This hotel features an indoor pool and a gym. Families will appreciate the arcade/game room and onsite laundry facilities. There's no skimping on freebies - ...
I had trouble getting an adequate room temperature. The connection door to the next room was extremely poorly soundproofed. I could hear what they were saying. I would have liked some fresh cut up fruit at breakfast.

Reviewed on Oct 26, 2025

Opens in a new windowLa Quinta Inn & Suites by Wyndham Springfield MA
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
$103 nightly
The price is $115 total per night from Nov 3 to Nov 4
$115 total
Nov 3 - Nov 4
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 ...
Everything is clean

Reviewed on Oct 27, 2025

Opens in a new windowHoliday Inn & Suites Pittsfield-Berkshires by IHG
Quality Inn West Springfield

Quality Inn West Springfield

2.5 out of 5
1150 Riverdale St, West Springfield, MA
Fully refundableReserve now, pay when you stay
$84 nightly
The price is $96 total per night from Nov 16 to Nov 17
$96 total
Nov 16 - Nov 17
Total with taxes and fees
A restaurant and a gym are featured at this hotel. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Enjoy ...
Breakfast was a little cold and had clearly sat prior to the opening of breakfast

Reviewed on Oct 26, 2025

Opens in a new windowQuality Inn West Springfield
Red Roof Inn PLUS+ West Springfield

Red Roof Inn PLUS+ West Springfield

2.5 out of 5
1254 Riverdale Street, West Springfield, MA
Fully refundableReserve now, pay when you stay
$85 nightly
The price is $97 total per night from Dec 1 to Dec 2
$97 total
Dec 1 - Dec 2
Total with taxes and fees
This hotel doesn't skimp on freebies - guests receive free WiFi and free self parking. Staff at the 24-hour front desk can provide around-the-clock ...
Parking good, air conditioning good When I made the reservation didn’t know it was 2 stories walk up. I walk with a cane so that was a bit hard for me to carry my stuff up

Reviewed on Oct 21, 2025

Opens in a new windowRed Roof Inn PLUS+ West Springfield
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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 $96. 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 844 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.

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