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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
$127 nightly
The price is $142 total per night from Jul 6 to Jul 7
$142 total
Jul 6 - Jul 7
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. ...
"It’s easy to miss driving by. Building, parking area and pool are separated from the highway by a tree landscaped berm. The sign is small, tan-ish orange and partially hidden by trees on the berm. Made finding the entrance difficult. Once there, our stay was very enjoyable."

Reviewed on Jun 27, 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
$132 nightly
The price is $147 total per night from Jun 30 to Jul 1
$147 total
Jun 30 - Jul 1
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 ...
"great hotel, would definitely stay again..."

Reviewed on Jun 27, 2026

Opens in a new windowD. Hotel Suites & Spa
The Ellery

The Ellery

3.5 out of 5
259 Elm Street Northampton MA
Fully refundableReserve now, pay when you stay
$111 nightly
The price is $124 total per night from Jul 21 to Jul 22
$124 total
Jul 21 - Jul 22
Total with taxes and fees
This hotel doesn't skimp on freebies - guests receive free continental breakfast, free WiFi, and free self parking. Business travelers can take advantage of ...
"If Expedia got me check in instructions like they were supposed to this trip would have been flawless. Office hours are short but when I called it was answered immediately and I was able to check in without any problems. This was an amazing stay especially when horse showing at 3 county fair ..."

Reviewed on Jun 28, 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
$162 nightly
The price is $181 total per night from Jul 26 to Jul 27
$181 total
Jul 26 - Jul 27
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, ...
"The room in lobby were great. The big front porch was actually a nice thing to have, because the fire pit was closed (and the guy worked the front desk at night said he didn’t have a key to start it.) The bar was closed. The boutique was closed and there really wasn’t anywhere else you could go. ..."

Reviewed on Jun 26, 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
$159 nightly
The price is $178 total per night from Jun 29 to Jun 30
$178 total
Jun 29 - Jun 30
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 ...
"I usually stay here and yes staff are nice and rooms are decent but I’ve seen a decline in amenities. Maybe the expense of things - bathrobe in room, water and snacks were what I was used to seeing .in the room."

Reviewed on Jun 25, 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
$184 nightly
The price is $205 total per night from Jul 1 to Jul 2
$205 total
Jul 1 - Jul 2
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 ...
"Staff"

Reviewed on Jun 27, 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
$116 nightly
The price is $132 total per night from Jul 5 to Jul 6
$132 total
Jul 5 - Jul 6
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 - ...
"Our stay at the hotel was very comfortable. We were in a newly renovated suite overlooking downtown. The hotel staff was very friendly and the breakfast was good. I will stay here again. DSloan"

Reviewed on Jun 26, 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 Jul 19 to Jul 20
$151 total
Jul 19 - Jul 20
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 ...
"Room very clean! Excellent breakfast selections. Staff were very friendly!"

Reviewed on Jun 26, 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
$82 nightly
The price is $94 total per night from Jul 19 to Jul 20
$94 total
Jul 19 - Jul 20
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 ...
"The breakfast was very good and the place for the price was ok, I stayed for two nights on the third floor; the place is currently being renovated. The room was clean, but the hallway -despite being a non-smoking area- smelled like cigarettes on the first day, but smelled much, much better by the ..."

Reviewed on Jun 27, 2026

Opens in a new windowQuality Inn 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 $94. 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 870 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 less than an hour ago
Travelocity Verified Review
"If Expedia got me check in instructions like they were supposed to this trip would have been flawless. Office hours are short but when I called it was answered immediately and I was able to check in without any problems. This was an amazing stay especially when horse showing at 3 county fair grounds."
A verified traveler stayed at The Ellery
The Ellery

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