Deals on vacations and trips to Cheshire

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Price found within the past 48 hours. Click for updated prices.
Country Inn & Suites by Radisson, Downtown Albany New York

Country Inn & Suites by Radisson, Downtown Albany New York

2.5 out of 5
Downtown Albany
Price was $751, price is now $677 per person
$677
per person
Oct 22 - Oct 26
found 5 hours ago
Roundtrip non-stop flight included
San Diego (SAN) to Albany (ALB)
This hotel doesn't skimp on freebies - guests receive free full breakfast, free WiFi, and free self parking. Traveling on business? Take advantage of the 24-hour business center, conference center, and conference space. There's a 24-hour gym on site, and a 24-hour front desk and a fireplace in the lobby are also provided.
Saratoga Casino Hotel

Saratoga Casino Hotel

4 out of 5
Price was $1,092, price is now $869 per person
$869
per person
Oct 22 - Oct 26
found 5 hours ago
Roundtrip non-stop flight included
San Diego (SAN) to Albany (ALB)
This smoke-free hotel features a casino, a nightclub, and a restaurant. Enjoy the indoor pool and perks like free self parking and a free area shuttle. You'll appreciate the 24-hour gym, bar/lounge, and snack bar/deli.
Hyatt Place Albany/Downtown

Hyatt Place Albany/Downtown

3 out of 5
Downtown Albany
Price was $895, price is now $814 per person
$814
per person
Oct 22 - Oct 26
found 5 hours ago
Roundtrip non-stop flight included
San Diego (SAN) to Albany (ALB)
This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Enjoy the free buffet breakfast each morning.
Marriott Albany

Marriott Albany

3.5 out of 5
Price was $842, price is now $771 per person
$771
per person
Oct 22 - Oct 26
found 5 hours ago
Roundtrip non-stop flight included
San Diego (SAN) to Albany (ALB)
This hotel features a restaurant, an indoor pool, and a bar/lounge. Traveling on business? Take advantage of the free WiFi in public areas, express check-in, and free airport shuttle. Enjoy the gym and conveniences like a 24-hour front desk and laundry facilities.
Hyatt Place Saratoga Malta

Hyatt Place Saratoga Malta

3 out of 5
Price was $920, price is now $847 per person
$847
per person
Oct 22 - Oct 26
found 5 hours ago
Roundtrip non-stop flight included
San Diego (SAN) to Albany (ALB)
This hotel features an indoor pool, a 24-hour gym, and a restaurant. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Enjoy the hot tub and free perks like buffet breakfast and free self parking.

Top Cheshire hotels deals

Vacation Village in the Berkshires

Vacation Village in the Berkshires

3 out of 5
276 Brodie Mountain Rd Williamstown MA
Free Cancellation
Reserve now, pay when you stay
$122 nightly
The price is $136 total per night
$136 total
Sep 8 - Sep 9
Total with taxes and fees
This aparthotel 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

Hotel Downstreet, an Ascend Collection Hotel

3 out of 5
40 Main St North Adams MA
Free Cancellation
$143 nightly
The price is $160 total per night
$160 total
Sep 27 - Sep 28
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 free perks like continental breakfast and free self parking.
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
$113 nightly
The price is $126 total per night
$126 total
Oct 1 - Oct 2
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
The Yankee Inn

The Yankee Inn

2.5 out of 5
461 Pittsfield Rd Lenox MA
Free Cancellation
Reserve now, pay when you stay
$116 nightly
The price is $130 total per night
$130 total
Sep 22 - Sep 23
Total with taxes and fees
This hotel features an outdoor pool and an indoor pool. Traveling on business? Take advantage of the free WiFi in public areas and free internet in public areas. Enjoy the 24-hour gym and free perks like buffet breakfast and free self parking.
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
$145 nightly
The price is $162 total per night
$162 total
Sep 28 - Sep 29
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
FairBridge Inn Express

FairBridge Inn Express

2.5 out of 5
16 Cheshire Road Pittsfield MA
$57 nightly
The price is $64 total per night
$64 total
Oct 8 - Oct 9
Total with taxes and fees
This motel doesn't skimp on freebies - guests receive free WiFi and free self parking. Business travelers can take advantage of the business center. The front desk is staffed around-the-clock and laundry facilities are on offer.
Parking included
Free WiFi
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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.

Stay near popular Cheshire attractions

St Mary's of the Assumption Church

10.0/10 (1 review)
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.
See properties

Frequently asked questions

How much are vacation packages to Cheshire?
With vacation packages on offer for just $677, 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.

Photos of local treasures

Browse Cheshire vacation photos for more inspiration

A lake surrounded by autumn-colored trees and hills.
A lake with lily pads and reeds, surrounded by autumn-colored trees and hills.
A lake surrounded by autumn-colored trees with a clear sky.
A rural road with a double yellow line, surrounded by green fields and trees, under a partly cloudy sky.
A frozen lake with a group of ducks swimming in the center.