Deals on vacations and trips to Chester

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Top Chester hotels deals

D. Hotel Suites & Spa

D. Hotel Suites & Spa

3 out of 5
1 Country Club Rd Holyoke MA
Free Cancellation
Reserve now, pay when you stay
$121 nightly
The price is $135 total per night
$135 total
Jan 18 - Jan 19
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 facilities.
Pool
Hot Tub
Berkshire Mountain Lodge

Berkshire Mountain Lodge

3 out of 5
8 Dan Fox Dr Pittsfield MA
Free Cancellation
Reserve now, pay when you stay
$121 nightly
The price is $136 total per night
$136 total
Feb 16 - Feb 17
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, laundry facilities, and barbecue grills are also on offer.
Pool
Hot Tub
Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG

3 out of 5
One West Street Pittsfield MA
Free Cancellation
$98 nightly
The price is $109 total per night
$109 total
Jan 23 - Jan 24
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 areas. Enjoy the gym and perks like free self parking.
Pool
Pet friendly
Berkshires Untold

Berkshires Untold

3.5 out of 5
194 Pittsfield Rd Lenox MA
Free Cancellation
Reserve now, pay when you stay
$90 nightly
The price is $101 total per night
$101 total
Jan 20 - Jan 21
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 fireplace, and express check-in are also on offer.
Pet friendly
Parking included
The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham

2.5 out of 5
461 Pittsfield Rd Lenox MA
Free Cancellation
Reserve now, pay when you stay
$93 nightly
The price is $103 total per night
$103 total
Jan 25 - Jan 26
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 and free perks like buffet breakfast and free self parking.
Pool
Hot Tub
Courtyard by Marriott West Springfield

Courtyard by Marriott West Springfield

3 out of 5
885 Riverdale Street West Springfield MA
Free Cancellation
Reserve now, pay when you stay
$118 nightly
The price is $135 total per night
$135 total
Jan 29 - Jan 30
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 with a drink at the bar/lounge and enjoy perks like free self parking.
Pool
Parking included
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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.

Popular places to visit

Chester Town Hall

You can get tickets for a performance at Chester Town Hall during your trip to Chester. Wander the lakeside and forest in this relaxing area.

Chester Town Hall

Frequently asked questions

How much are vacation packages to Chester?
With offers starting from as little as , hotel and flight packages are an excellent way to make your budget stretch further. Get ready Chester — here you come!
Where can I get the best vacation package deals for Chester?
You'll discover a terrific range of Chester package deals on Travelocity. With as many as 400 airlines and 1,000,000 worldwide properties, piecing together your ideal vacation will be a piece of cake.
Why should I book my Chester vacation bundle via Travelocity?
Travel should be about making cherished memories and leaving all your stresses behind — which is why we have a friendly team of customer service experts available round-the-clock should you need them. On top of that, our Price Match Guarantee ensures you'll always get the best deal available on our terrific range of getaway packages. So what are you waiting for? There's no time like the present to lock in the vacation you've always dreamed of.
Can I save money on my Chester car rental if I book it with a hotel or flight?
Bundling your hotel, car and flight into a Chester vacation package is a great way to score the best deal. Plus, having your own car rental gives you absolute freedom to make your way to all those famous sights you'd like to check out. Located 120 mi from Chester, Times Square is one attraction that should be on your agenda. Fasten your seat belt and make a day trip of it.
Which airport is best for Chester?
Bradley Intl. Airport (BDL) (30 mi away from the city center), Albany Intl. Airport (ALB) (55 mi away from central Chester) and Hartford, CT (HFD-Hartford - Brainard) (40 mi away from central Chester) are the top options for Chester.
Where should I stay when visiting Chester?
The Cozy Berkshires Vacation Rental Near Hiking! is the first choice of many visitors. Book as soon as possible before it's too late.

Photos of local treasures

Browse Chester vacation photos for more inspiration

Photo by Elizabeth Massa Peroulakis
Photo by Elizabeth Massa Peroulakis
Photo by Elizabeth Massa Peroulakis
Photo by Elizabeth Massa Peroulakis
Photo by Chris Addams
Photo by Chris Addams
Photo by Chris Addams
Photo by Chris Addams