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.
Quality Inn Lee - Lenox South

Quality Inn Lee - Lenox South

2.5 out of 5
Price was $899, price is now $724 per person
$724
per person
Jul 16 - Jul 19
found 10 hours ago
Roundtrip flight included
Chicago (ORD) to Albany (ALB)
This hotel doesn't skimp on freebies - guests receive free continental breakfast and free WiFi. Business travelers can take advantage of the express check-in. A restaurant, a 24-hour front desk, and express check-out are also provided.
The Cornell Inn, Lenox & The Berkshires

The Cornell Inn, Lenox & The Berkshires

3.5 out of 5
Save 100% on your flight
Price was $2,667, price is now $1,759 per person
$1,759
per person
Jul 16 - Jul 19
found 10 hours ago
Roundtrip flight included
Chicago (ORD) 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.
Urban Cowboy Lodge

Urban Cowboy Lodge

5 out of 5
Save 100% on your flight
Price was $1,351, price is now $1,062 per person
$1,062
per person
Jul 20 - Jul 25
found 1 day ago
Roundtrip flight included
Detroit (DTW) to Albany (ALB)
This lodge features a restaurant, a sauna, and a bar/lounge. Guests will appreciate free perks like free self parking and WiFi in public areas. A snack bar/deli, a lobby fireplace, and a communal living room are also on offer.
The Wiltwyck

The Wiltwyck

3.5 out of 5
Price was $968, price is now $762 per person
$762
per person
Jul 20 - Jul 25
found 1 day ago
Roundtrip flight included
Detroit (DTW) to Albany (ALB)
Free WiFi in public areas is available at this guesthouse. Take advantage of the free self parking.
The Equinox Golf Resort & Spa

The Equinox Golf Resort & Spa

4.5 out of 5
Manchester Village Historic District
Save 100% on your flight
Price was $4,100, price is now $3,368 per person
$3,368
per person
Jul 15 - Jul 22
found 22 hours ago
Roundtrip flight included
Dallas (DFW) to Albany (ALB)
This luxury hotel features a golf course, a full-service spa, and 4 restaurants. Enjoy the 3 outdoor tennis courts and get free self parking. Make the most of the indoor pool and 24-hour gym, and relax with drinks at one of the 2 bars/lounges.

Top Cheshire hotels deals

Hotel Downstreet, an Ascend Collection Hotel

Hotel Downstreet, an Ascend Collection Hotel

3 out of 5
40 Main St North Adams MA
Free Cancellation
$163 nightly
The price is $182 total per night
$182 total
Jun 14 - Jun 15
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
$155 nightly
The price is $173 total per night
$173 total
Jun 14 - Jun 15
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
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
$136 nightly
The price is $152 total per night
$152 total
Jun 14 - Jun 15
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
$105 nightly
The price is $117 total per night
$117 total
Jun 15 - Jun 16
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
$135 nightly
The price is $151 total per night
$151 total
Jun 16 - Jun 17
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
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
$187 nightly
The price is $209 total per night
$209 total
Jun 22 - Jun 23
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
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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

5/5(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.

St Mary's of the Assumption Church

Frequently asked questions

How much are vacation packages to Cheshire?
With vacation packages on offer for just $724, 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.
Cheshire
Cheshire