Chester Vacation Packages 2026 from $936

Chester flight + hotel vacation packages

Price found within the past 48 hours. Click for updated prices.

Woodland Zen by Avantstay Modern Design + Patio

$936

per person

Mar 16 - Mar 19

found 7 hours ago

Roundtrip flight included

Orlando (MCO) to Pittsfield (PSF)

This cottage doesn't skimp on freebies - guests receive free WiFi and free self parking. A terrace and barbecue grills are also provided.

Top Chester hotels deals

D. Hotel Suites & Spa

1 Country Club Rd Holyoke MA

Free Cancellation

Reserve now, pay when you stay

$121 nightly

$135 total

Jan 11 - Jan 12

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

8 Dan Fox Dr Pittsfield MA

Free Cancellation

Reserve now, pay when you stay

$108 nightly

$120 total

Feb 8 - Feb 9

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.

Holiday Inn & Suites Pittsfield-Berkshires by IHG

One West Street Pittsfield MA

Free Cancellation

$98 nightly

$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.

Quality Inn West Springfield

1150 Riverdale St West Springfield MA

Free Cancellation

Reserve now, pay when you stay

$81 nightly

$93 total

Feb 2 - Feb 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.

The Yankee, Trademark Collection by Wyndham

461 Pittsfield Rd Lenox MA

Free Cancellation

Reserve now, pay when you stay

$101 nightly

$113 total

Jan 19 - Jan 20

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

885 Riverdale Street West Springfield MA

Free Cancellation

Reserve now, pay when you stay

$118 nightly

$135 total

Jan 19 - Jan 20

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.

Frequently asked questions

How much are vacation packages to Chester?

With offers starting from as little as $936, 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.