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

Quality Inn West Springfield

Quality Inn West Springfield

2.5 out of 5
1150 Riverdale St West Springfield MA
Free Cancellation
$88 nightly
The price is $101 total per night
$101 total
Nov 2 - Nov 3
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 seasonal outdoor pool and free perks like buffet breakfast and free self parking.
Pool
Breakfast included
Berkshire Mountain Lodge

Berkshire Mountain Lodge

3 out of 5
8 Dan Fox Dr Pittsfield MA
Free Cancellation
Reserve now, pay when you stay
$115 nightly
The price is $128 total per night
$128 total
Nov 4 - Nov 5
Total with taxes and fees
This aparthotel 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
D. Hotel Suites & Spa

D. Hotel Suites & Spa

3 out of 5
1 Country Club Rd Holyoke MA
$142 nightly
The price is $158 total per night
$158 total
Oct 21 - Oct 22
Total with taxes and fees
A full-service spa, 2 restaurants, and an indoor pool are all featured at this smoke-free hotel. Enjoy the gym and free buffet breakfast each morning. You'll appreciate the hot tub, bar/lounge, and laundry facilities.
Pool
Hot Tub
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
$101 nightly
The price is $116 total per night
$116 total
Nov 1 - Nov 2
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
Hampton Inn West Springfield

Hampton Inn West Springfield

2.5 out of 5
1011 Riverdale St West Springfield MA
Free Cancellation
Reserve now, pay when you stay
$122 nightly
The price is $140 total per night
$140 total
Nov 1 - Nov 2
Total with taxes and fees
This hotel features a gym and a seasonal outdoor pool. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Guests will appreciate freebies like buffet breakfast and free self parking.
Pool
Breakfast included
Hotel Northampton

Hotel Northampton

3.5 out of 5
36 King Street Northampton MA
$140 nightly
The price is $157 total per night
$157 total
Oct 12 - Oct 13
Total with taxes and fees
This historic hotel's 2 restaurants, 2 bars/lounges, and 24-hour gym are some of the featured amenities. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Free self parking, a coffee shop, and a terrace 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.

Stay near popular Chester attractions

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.
See properties

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

A snow-covered forest with a narrow stream running through it.
A dog walking on a forest path with trees and moss.
A flowing river with rocks and trees in a forested area.
A stone bridge over a flowing river with rocks and autumn foliage.
A stone bridge over a calm river with autumn foliage.