Cheshire Vacation Packages 2026 from $442

Cheshire flight + hotel vacation packages

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

The Dewey

$442

per person

Mar 16 - Mar 19

found 1 day ago

Roundtrip flight included

Orlando (MCO) to Albany (ALB)

This guesthouse doesn't skimp on freebies - guests receive free WiFi and free self parking. A terrace, a garden, and a lobby fireplace are also on offer.

Prospect Berkshires

$523

per person

Mar 16 - Mar 19

found 1 day ago

Roundtrip flight included

Orlando (MCO) to Albany (ALB)

This hotel features a restaurant, an outdoor pool, and a bar/lounge. Enjoy the sauna and perks like free self parking and free WiFi. A coffee shop, a grocery/convenience store, and a picnic area are also on offer.

The Landing Hotel at Rivers Casino & Resort

Nothside

$617

per person

Mar 6 - Mar 10

just found

Roundtrip non-stop flight included

Austin (AUS) to Albany (ALB)

A casino, 5 restaurants, and a 24-hour gym are all featured at this smoke-free hotel. Traveling on business? Take advantage of the free WiFi in public areas, conference center, and conference space. Free self parking is free for guests, and you can enjoy a meal in one of the 2 coffee shops/cafes.

Gedney Farm

$466

per person

Mar 16 - Mar 19

found 1 day ago

Roundtrip flight included

Orlando (MCO) to Albany (ALB)

A restaurant and a bar/lounge are featured at this hotel. There's no skimping on freebies - guests receive free continental breakfast, free WiFi, and free self parking. A terrace, a garden, and a communal living room are also on offer.

The Cornell Inn, Lenox & The Berkshires

$503

per person

Mar 16 - Mar 19

found 1 day ago

Roundtrip flight included

Orlando (MCO) to Albany (ALB)

A restaurant and a bar/lounge are featured at this bed & breakfast. There's no skimping on freebies - guests receive free full breakfast, free WiFi, and free self parking. A coffee shop, a terrace, and a garden are also on offer.

Top Cheshire hotels deals

Vacation Village in the Berkshires

276 Brodie Mountain Rd Williamstown MA

Free Cancellation

Reserve now, pay when you stay

$126 nightly

$141 total

Jan 12 - Jan 13

Total with taxes and fees

This condo features an outdoor pool and an indoor pool. Bring the family and enjoy the children's pool, playground, and arcade/game room. Enjoy the gym and perks like free self parking and free WiFi.

Pool

Parking included

Hotel Downstreet, an Ascend Collection Hotel

40 Main St North Adams MA

Free Cancellation

$125 nightly

$140 total

Feb 2 - Feb 3

Total with taxes and fees

This hotel features an indoor pool and a 24-hour gym. Traveling on business? Take advantage of the 2 conference rooms, free WiFi in public areas, and express check-out. Enjoy the hot tub and perks like free self parking.

Pool

Hot Tub

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.

Pool

Pet friendly

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

Berkshire Mountain Lodge

8 Dan Fox Dr Pittsfield MA

Free Cancellation

Reserve now, pay when you stay

$108 nightly

$120 total

Feb 9 - Feb 10

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

The Williams Inn

101 Spring Street Williamstown MA

Free Cancellation

Reserve now, pay when you stay

$186 nightly

$208 total

Jan 12 - Jan 13

Total with taxes and fees

This hotel features a restaurant, a gym, and a bar/lounge. Traveling on business? Take advantage of the free WiFi in public areas, conference center, and conference space. Free self parking, a coffee shop, and a terrace are also offered.

Pet friendly

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

St Mary's of the Assumption Church

St Mary's of the Assumption Church is just one of the places to see in Cheshire, so why not enjoy the other things to explore during your travels? Discover the area's mountain views, or seek out its ski slopes.

Frequently asked questions

How much are vacation packages to Cheshire?

With vacation packages on offer for just $442, it's not necessary to drain your bank balance to visit Cheshire. Travelocity can help. Bundle up flights, hotels and experiences into a package and score fantastic discounts. The more you book, the bigger the savings.

How long should my Cheshire vacation be?

Around 3 nights is the average time frame travelers vacation in Cheshire. But the ideal trip length all comes down to how many magical memories you want to create. Why not stay a little longer and uncover some hidden treasures?

Where can I get the best vacation package deals for Cheshire?

You'll discover an amazing range of Cheshire package deals on Travelocity. With 400 airlines and 1,000,000 properties worldwide, putting together the perfect vacation will be a piece of cake.

Why should I book my Cheshire vacation package with Travelocity?

With our Price Match Guarantee, we'll match any cheaper price you find. Add on our 24/7 customer support and first-rate service and your perfect vacation is well within reach.

Can I save money on my Cheshire car rental if I book it with a hotel or flight?

With a Cheshire vacation package, you can bundle your car, hotel and flight bookings and save loads. If you'd love to uncover the best of this wonderful region, why not check out Fenway Park? This well-known sight is 110 mi from Cheshire. With your own wheels, you'll be there before you know it.

Which airport is best for Cheshire?

Cheshire has a couple of major airports you can fly to — Bradley Intl. Airport (BDL) (50 mi away from the city center) and Albany Intl. Airport (ALB) (35 mi away from central Cheshire).

What is there to do in Cheshire?

St Mary's of the Assumption Church is one of the memorable sights that make Cheshire such a great place to visit. But give yourself enough time to explore the city's lesser-known attractions too. This is often where the best memories are created.

Where should I stay when visiting Cheshire?

Many people opt to check in to the Harbour House Inn. It's a great base for your Cheshire vacation.