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Cheshire Vacation Packages

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An autumn view of Cheshire Lake in the Berkshire Mountains of Western Massachusetts.

Cheshire
Massachusetts
United States of America
North America
Hotwire.com

Cheshire Flight + Hotel Packages

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

The Motel Montreal

2 out of 5

Price was $618, price is now $511 per person

$511

per person

Jul 26 - Jul 30

found 3 hours ago

Roundtrip flight included

New York (NYC) to Albany (ALB)

Stay at this motel in Lake George. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff in our reviews. Popular attractions Lake George Steamboat Company and Million Dollar Beach are located nearby.

Paradise Resort and Cabins

2.5 out of 5

Save 100% on your flight

Price was $2,053, price is now $1,650 per person

$1,650

per person

Sep 14 - Sep 17

found 12 hours ago

Roundtrip flight included

New York (NYC) to Albany (ALB)

Stay at this motel in Gansevoort. Enjoy free WiFi, free parking, and room service. Popular attractions Ulysses S. Grant Cottage and Moreau Lake State Park are located nearby.

Lodges At Cresthaven

4 out of 5

Price was $1,028, price is now $837 per person

$837

per person

Sep 14 - Sep 17

found 12 hours ago

Roundtrip flight included

New York (NYC) to Albany (ALB)

Book a stay at this beach lodge in Lake George. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff in our reviews. Popular attractions Lake George Steamboat Company and Million Dollar Beach are located nearby.

Lake Haven Motel

2.5 out of 5

Price was $893, price is now $745 per person

$745

per person

Jul 26 - Jul 30

found 3 hours ago

Roundtrip flight included

New York (NYC) to Albany (ALB)

Stay at this motel in Lake George. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Six Flags Great Escape and Lake George Steamboat Company are located nearby.

Sundowner on Lake George

2.5 out of 5

Price was $1,269, price is now $1,062 per person

$1,062

per person

Jul 26 - Jul 30

found 3 hours ago

Roundtrip flight included

New York (NYC) to Albany (ALB)

Book a stay at this beach motel in Lake George. Enjoy free parking, an outdoor pool, and a private beach. Popular attractions Lake George Steamboat Company and Fort William Henry Museum are located nearby.

The Equinox Golf Resort & Spa

4.5 out of 5

Save 100% on your flight

Price was $1,287, price is now $1,083 per person

$1,083

per person

Aug 11 - Aug 18

found 7 hours ago

Roundtrip non-stop flight included

Fort Lauderdale (FLL) to Albany (ALB)

Book a stay at this luxury hotel in Manchester. Enjoy free parking, an outdoor pool, and a full-service spa. Popular attractions Golf Club at Equinox and American Museum of Fly Fishing are located nearby.

Bluebird Spa City Motor Lodge

3 out of 5

Price was $690, price is now $584 per person

$584

per person

Sep 14 - Sep 17

found 12 hours ago

Roundtrip flight included

New York (NYC) to Albany (ALB)

Stay at this hotel in Saratoga Springs. Enjoy free WiFi, parking (surcharge), and daily housekeeping. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Saratoga Racetrack and Saratoga Casino and Raceway are located nearby.

Hampton Inn Albany-Wolf Road (Airport)

2.5 out of 5

Price was $662, price is now $562 per person

$562

per person

Sep 14 - Sep 17

found 12 hours ago

Roundtrip flight included

New York (NYC) to Albany (ALB)

Book a stay at this business-friendly hotel in Albany. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Colonie Center Mall and Crossgates Mall are located nearby.