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.
Hotel Brookmere & Arbor Spa

Hotel Brookmere & Arbor Spa

4 out of 5
Price was $519, price is now $482 per person
$482
per person
Apr 3 - Apr 5
found 1 day ago
Roundtrip flight included
Atlanta (ATL) 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.
Saratoga Casino Hotel

Saratoga Casino Hotel

4 out of 5
Price was $570, price is now $492 per person
$492
per person
Apr 3 - Apr 5
found 1 day ago
Roundtrip flight included
Atlanta (ATL) 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.
Lodges At Cresthaven

Lodges At Cresthaven

4 out of 5
Price was $792, price is now $709 per person
$709
per person
Apr 3 - Apr 5
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Albany (ALB)
A 24-hour gym, free self parking, and laundry facilities are featured at this lodge. WiFi in public areas is free. A business center, a terrace, and a picnic area are also on offer.
La Quinta Inn & Suites by Wyndham Lake George

La Quinta Inn & Suites by Wyndham Lake George

3 out of 5
Price was $535, price is now $501 per person
$501
per person
Apr 3 - Apr 5
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Albany (ALB)
This hotel features an indoor pool and a gym. There's fun for all ages with a waterslide and a playground, and families will appreciate the onsite laundry facilities. Enjoy the hot tub and free perks like continental breakfast and free self parking.
Bluebird Spa City Motor Lodge

Bluebird Spa City Motor Lodge

3 out of 5
Downtown Saratoga Springs
Price was $533, price is now $500 per person
$500
per person
Apr 3 - Apr 5
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Albany (ALB)
This hotel features free WiFi in public areas, concierge services, and self parking. Express check-out and luggage storage are also provided.

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
$128 nightly
The price is $143 total per night
$143 total
Mar 31 - Apr 1
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
Berkshire Mountain Lodge

Berkshire Mountain Lodge

3 out of 5
8 Dan Fox Dr Pittsfield MA
Free Cancellation
Reserve now, pay when you stay
$121 nightly
The price is $136 total per night
$136 total
Mar 31 - Apr 1
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

The Williams Inn

4 out of 5
101 Spring Street Williamstown MA
Free Cancellation
Reserve now, pay when you stay
$187 nightly
The price is $209 total per night
$209 total
Mar 3 - Mar 4
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
The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham

2.5 out of 5
461 Pittsfield Rd Lenox MA
Free Cancellation
Reserve now, pay when you stay
$93 nightly
The price is $103 total per night
$103 total
Mar 9 - Mar 10
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
Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG

3 out of 5
One West Street Pittsfield MA
Free Cancellation
$122 nightly
The price is $136 total per night
$136 total
Mar 7 - Mar 8
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
Berkshires Untold

Berkshires Untold

3.5 out of 5
194 Pittsfield Rd Lenox MA
Free Cancellation
Reserve now, pay when you stay
$107 nightly
The price is $120 total per night
$120 total
Mar 3 - Mar 4
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
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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.

St Mary's of the Assumption Church

Frequently asked questions

How much are vacation packages to Cheshire?
With vacation packages on offer for just $482, 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

An autumn view of Cheshire Lake in the Berkshire Mountains of Western Massachusetts.
An autumn view of Cheshire Lake in the Berkshire Mountains of Western Massachusetts.
An autumn view of Cheshire Lake in the Berkshire Mountains of Western Massachusetts.
An autumn view of Cheshire Lake in the Berkshire Mountains of Western Massachusetts.
The road less traveled sometimes is absolutely beautiful. In a month this will be a great spot for Autumn. I will repost the exact same foliage shot and see if I am correct. Excited to do it actually..