Deals on vacations and trips to Cheshire

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Cheshire flight + hotel vacation packages

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

Lake Haven Motel

2.5 out of 5
Price was $1,128, price is now $886 per person
$886
per person
Aug 20 - Aug 25
found 8 hours ago
Roundtrip flight included
Denver (DEN) to Albany (ALB)
A seasonal outdoor pool, free self parking, and barbecue grills are featured at this motel. WiFi in public areas is free. A picnic area and luggage storage are also provided.
Lodges At Cresthaven

Lodges At Cresthaven

4 out of 5
Save 100% on your flight
Price was $3,021, price is now $2,177 per person
$2,177
per person
Aug 20 - Aug 25
found 8 hours ago
Roundtrip flight included
Denver (DEN) to Albany (ALB)
A restaurant and a 24-hour gym are featured at this lodge. Enjoy the seasonal outdoor pool and perks like free self parking and free WiFi. A business center, a terrace, and a picnic area are also on offer.
Hilton Garden Inn Saratoga Springs

Hilton Garden Inn Saratoga Springs

3 out of 5
Save 100% on your flight
Price was $1,613, price is now $1,234 per person
$1,234
per person
Aug 20 - Aug 25
found 8 hours ago
Roundtrip flight included
Denver (DEN) to Albany (ALB)
This hotel features a restaurant, a gym, and a bar/lounge. Traveling for business? Take advantage of the free WiFi in public areas, express check-in, and conference space. Free self parking, a garden, and a lobby fireplace are also offered.
Sundowner on Lake George

Sundowner on Lake George

2.5 out of 5
Price was $1,570, price is now $1,213 per person
$1,213
per person
Aug 20 - Aug 25
found 8 hours ago
Roundtrip flight included
Denver (DEN) to Albany (ALB)
A private beach and a hot tub are featured at this smoke-free motel. Enjoy the seasonal outdoor pool and perks like free self parking. A terrace, a picnic area, and laundry facilities are also on offer.
Best Western Plus Franklin Square Inn Troy/Albany

Best Western Plus Franklin Square Inn Troy/Albany

2.5 out of 5
Save 100% on your flight
Price was $1,732, price is now $1,358 per person
$1,358
per person
Aug 20 - Aug 25
found 8 hours ago
Roundtrip flight included
Denver (DEN) to Albany (ALB)
A 24-hour gym, free self parking, and laundry facilities are featured at this hotel. Guests will appreciate free perks like full breakfast and WiFi in public areas. A business center, a terrace, and a garden are also on offer.

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
$143 nightly
The price is $159 total per night
$159 total
Jul 12 - Jul 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
The Yankee Inn

The Yankee Inn

2.5 out of 5
461 Pittsfield Rd Lenox MA
Free Cancellation
Reserve now, pay when you stay
$135 nightly
The price is $151 total per night
$151 total
Jul 12 - Jul 13
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
Berkshire Mountain Lodge

Berkshire Mountain Lodge

3 out of 5
8 Dan Fox Dr Pittsfield MA
Free Cancellation
Reserve now, pay when you stay
$155 nightly
The price is $173 total per night
$173 total
Aug 9 - Aug 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 Red Lion Inn

The Red Lion Inn

3.5 out of 5
30 Main Street Stockbridge MA
Free Cancellation
Reserve now, pay when you stay
$206 nightly
The price is $230 total per night
$230 total
Jul 13 - Jul 14
Total with taxes and fees
This historic hotel includes 3 restaurants, an outdoor pool, and a 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
Spa
Berkshires Untold

Berkshires Untold

3.5 out of 5
194 Pittsfield Rd Lenox MA
Free Cancellation
Reserve now, pay when you stay
$183 nightly
The price is $205 total per night
$205 total
Jul 12 - Jul 13
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 Express & Suites Pittsfield-Lenox-Berkshires by IHG

Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

2.5 out of 5
1055 South Street Pittsfield MA
Free Cancellation
$142 nightly
The price is $159 total per night
$159 total
Jul 16 - Jul 17
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. Enjoy the hot tub and free perks like buffet breakfast and free self parking.
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.

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 $886, 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.