Deals on vacations and trips to Cheshire
Save when you book Cheshire package deals
Cheshire flight + hotel vacation packages
Price found within the past 48 hours. Click for updated prices.
Hampton Inn Albany-Wolf Road (Airport)
Price was $791, price is now $641 per person
$641
per person
May 22 - May 25
found 2 days ago
Roundtrip non-stop flight included
Austin (AUS) to Albany (ALB)
This hotel doesn't skimp on freebies - guests receive free on-the-go breakfast, free self parking, and a free airport shuttle. Traveling for business? Take advantage of the free WiFi in public areas, express check-out, and conference space. A computer station, dry cleaning, and luggage storage are also on offer.
The Landing Hotel at Rivers Casino & Resort
Nothside
Price was $1,190, price is now $755 per person
$755
per person
Jul 2 - Jul 6
found 1 day ago
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.
Holiday Inn Express Hotel & Suites West Coxsackie by IHG
Price was $1,055, price is now $874 per person
$874
per person
May 22 - May 25
found 1 day ago
Roundtrip non-stop flight included
Austin (AUS) to Albany (ALB)
This hotel doesn't skimp on freebies - guests receive free buffet breakfast, free WiFi, and free self parking. Traveling on business? Take advantage of the 24-hour business center and free internet in public areas. Enjoy the 24-hour gym and conveniences like a 24-hour front desk and laundry facilities.
Park Manor Hotel
Price was $967, price is now $817 per person
$817
per person
Jul 2 - Jul 6
found 1 day ago
Roundtrip non-stop flight included
Austin (AUS) to Albany (ALB)
This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Guests will appreciate free perks like free self parking and WiFi in public areas. A 24-hour business center, a coffee shop, and a snack bar/deli are also on offer.
Hotel Brookmere & Arbor Spa
Price was $805, price is now $682 per person
$682
per person
May 22 - May 25
found 1 day ago
Roundtrip non-stop flight included
Austin (AUS) to Albany (ALB)
A full-service spa, a 24-hour gym, and a restaurant are all featured at this smoke-free hotel. Traveling on business? Take advantage of the 4 conference rooms, along with free WiFi in public areas. Enjoy the seasonal outdoor pool and perks like free self parking.
Top Cheshire hotels deals
Vacation Village in the Berkshires
276 Brodie Mountain Rd Williamstown MA
Free Cancellation
Reserve now, pay when you stay
$110 nightly
The price is $123 total per night
$123 total
Apr 19 - Apr 20
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
$131 nightly
The price is $146 total per night
$146 total
May 13 - May 14
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
Berkshire Mountain Lodge
8 Dan Fox Dr Pittsfield MA
Free Cancellation
Reserve now, pay when you stay
$108 nightly
The price is $120 total per night
$120 total
May 17 - May 18
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
Berkshires Untold
194 Pittsfield Rd Lenox MA
Free Cancellation
Reserve now, pay when you stay
$87 nightly
The price is $97 total per night
$97 total
Apr 21 - Apr 22
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
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
190 Meadow Street South Lee MA
Free Cancellation
$130 nightly
The price is $145 total per night
$145 total
Apr 21 - Apr 22
Total with taxes and fees
This hotel features 2 outdoor pools, 2 indoor pools, and a poolside bar. There's fun for all ages with mini golf and a playground, and families will appreciate the picnic area. Enjoy the seasonal outdoor pool and conveniences like a coffee shop and barbecue grills.
Pool
Air conditioning
The Williams Inn
101 Spring Street Williamstown MA
Free Cancellation
Reserve now, pay when you stay
$254 nightly
The price is $284 total per night
$284 total
Apr 21 - Apr 22
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
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
Photos of local treasures
Browse Cheshire vacation photos for more inspiration
