Deals on vacations and trips to Chester

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Top Chester hotels deals

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
Free Cancellation
Reserve now, pay when you stay
$119 nightly
The price is $135 total per night
$135 total
Oct 13 - Oct 14
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 - guests receive free buffet breakfast, free WiFi, and free self parking.
Pool
Breakfast included
Red Roof Inn PLUS+ West Springfield

Red Roof Inn PLUS+ West Springfield

2.5 out of 5
1254 Riverdale Street, West Springfield, MA
Free Cancellation
Reserve now, pay when you stay
$98 nightly
The price is $112 total per night
$112 total
Nov 2 - Nov 3
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 assistance.
Pet friendly
Parking 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
$113 nightly
The price is $126 total per night
$126 total
Nov 2 - Nov 3
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
Quality Inn West Springfield

Quality Inn West Springfield

2.5 out of 5
1150 Riverdale St, West Springfield, MA
Free Cancellation
Reserve now, pay when you stay
$84 nightly
The price is $96 total per night
$96 total
Oct 19 - Oct 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 seasonal outdoor pool and free perks like buffet breakfast and free self parking.
Pool
Breakfast included
Riverdale Inn

Riverdale Inn

2 out of 5
1500 Riverdale Street, On Route 5, West Springfield, MA
Free Cancellation
Reserve now, pay when you stay
$81 nightly
The price is $93 total per night
$93 total
Nov 4 - Nov 5
Total with taxes and fees
This motel 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 assistance.
Parking included
Free WiFi
D. Hotel Suites & Spa

D. Hotel Suites & Spa

3 out of 5
1 Country Club Rd, Holyoke, MA
Free Cancellation
$134 nightly
The price is $150 total per night
$150 total
Oct 8 - Oct 9
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
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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