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Top Chester hotels

The Yankee Inn

The Yankee Inn

2.5 out of 5
461 Pittsfield Rd Lenox MA
Fully refundableReserve now, pay when you stay
$135 nightly
The price is $151 total per night from Jul 12 to Jul 13
$151 total
Jul 12 - Jul 13
Total with taxes and fees
This hotel features an outdoor pool and an indoor pool. Traveling on business? Take advantage of the free WiFi in public areas and free internet in public areas. ...
"Front desk staff was very accommodating. She was kind to let us check in as soon as rooms were cleaned. We traveled from California and were very sleepy and that made our stay more enjoyable."

Reviewed on Jul 10, 2026

Opens in a new windowThe Yankee Inn
D. Hotel Suites & Spa

D. Hotel Suites & Spa

3 out of 5
1 Country Club Rd Holyoke MA
Fully refundable
$142 nightly
The price is $158 total per night from Jul 12 to Jul 13
$158 total
Jul 12 - Jul 13
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 ...
"The room was very clean and the bed was very comfortable. The gym and pool are small, but clean. The breakfast was basic. The warm donuts were a nice treat. This is a very nice hotel for the price. The only reason I am giving this 4 stars is because we couldn’t turn the AC down. To be fair, we didn’t ..."

Reviewed on Jul 10, 2026

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
$155 nightly
The price is $173 total per night from Aug 9 to Aug 10
$173 total
Aug 9 - Aug 10
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, ...
"Very spacious. Kitchen is a plus"

Reviewed on Jul 11, 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
$183 nightly
The price is $205 total per night from Jul 12 to Jul 13
$205 total
Jul 12 - Jul 13
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 ...
"AC didn’t work and told the staff who really did not care"

Reviewed on Jul 10, 2026

Opens in a new windowBerkshires Untold
The Red Lion Inn

The Red Lion Inn

3.5 out of 5
30 Main Street Stockbridge MA
Fully refundableReserve now, pay when you stay
$206 nightly
The price is $230 total per night from Jul 13 to Jul 14
$230 total
Jul 13 - Jul 14
Total with taxes and fees
This historic hotel includes 3 restaurants, an outdoor pool, and a gym. Traveling on business? Take advantage of the 24-hour business center and free WiFi in ...
"Clean room. Arrived late."

Reviewed on Jul 10, 2026

Opens in a new windowThe Red Lion Inn
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
$119 nightly
The price is $135 total per night from Jul 19 to Jul 20
$135 total
Jul 19 - Jul 20
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 - ...
"The room was perfect for my family's stay"

Reviewed on Jul 10, 2026

Opens in a new windowLa Quinta Inn & Suites by Wyndham Springfield MA
Quality Inn & Suites Northampton - Amherst

Quality Inn & Suites Northampton - Amherst

2.5 out of 5
117 Conz St Northampton MA
Fully refundable
$135 nightly
The price is $151 total per night from Aug 2 to Aug 3
$151 total
Aug 2 - Aug 3
Total with taxes and fees
This hotel doesn't skimp on freebies - guests receive free on-the-go breakfast, free WiFi, and free self parking. Business travelers can take advantage of the ...
"The rooms were very large and clean. Location was great and so was the breakfast."

Reviewed on Jul 8, 2026

Opens in a new windowQuality Inn & Suites Northampton - Amherst
Quality Inn West Springfield

Quality Inn West Springfield

2.5 out of 5
1150 Riverdale St West Springfield MA
Fully refundable
$89 nightly
The price is $102 total per night from Aug 5 to Aug 6
$102 total
Aug 5 - Aug 6
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 ...
"Everything was fine except for the bed. The matress has been havely used. I couldn't get good sleep."

Reviewed on Jul 9, 2026

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
$91 nightly
The price is $104 total per night from Jul 13 to Jul 14
$104 total
Jul 13 - Jul 14
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 ...
"Nothing to chsnge"

Reviewed on Jul 9, 2026

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 $102. 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 877 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

Berkshire Mountain Lodge

Berkshire Mountain Lodge

5 out of 5
Posted 9 hours ago
Travelocity Verified Review
"Very spacious. Kitchen is a plus"
A verified traveler stayed at Berkshire Mountain Lodge
Berkshire Mountain Lodge

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