Deals on vacations and trips to Chester

Save when you book Chester package deals

Choose two or more items and save on your trip:

Top Chester hotels deals

D. Hotel Suites & Spa

D. Hotel Suites & Spa

3 out of 5
1 Country Club Rd Holyoke MA
Free Cancellation
$150 nightly
The price is $168 total per night
$168 total
Apr 14 - Apr 15
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
$108 nightly
The price is $120 total per night
$120 total
May 12 - May 13
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
Berkshires Untold

Berkshires Untold

3.5 out of 5
194 Pittsfield Rd Lenox MA
Free Cancellation
Reserve now, pay when you stay
$87 nightly
The price is $97 total per night
$97 total
Apr 14 - Apr 15
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
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
Free Cancellation
$131 nightly
The price is $147 total per night
$147 total
Apr 16 - Apr 17
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 the picnic area. Enjoy the seasonal outdoor pool and conveniences like a coffee shop and barbecue grills.
Pool
Air conditioning
Baldwin Inn & Suites, SureStay Collection by Best Western

Baldwin Inn & Suites, SureStay Collection by Best Western

2.5 out of 5
21 Baldwin Street West Springfield MA
Free Cancellation
Reserve now, pay when you stay
$101 nightly
The price is $116 total per night
$116 total
Apr 26 - Apr 27
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 the express check-out. There's luggage storage and multilingual staff can provide around-the-clock assistance.
Breakfast included
Pet friendly
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
Free Cancellation
$111 nightly
The price is $127 total per night
$127 total
May 4 - May 5
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 a 24-hour gym on site, and laundry facilities and free newspapers are also offered.
Parking included
Free WiFi
Don't see what you're looking for?
See all available properties in Chester
View all properties
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

Chester
Chester
Chester
Chester
Chester