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Cheshire Vacation Packages

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Cheshire Flight + Hotel Packages

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

Gedney Farm

3.5 out of 5
Price was $1,110, price is now $787 per person
$787
per person
Jul 2 - Jul 6
found 1 hour ago
Roundtrip non-stop flight included
Minneapolis (MSP) to Albany (ALB)
Stay at this hotel in Great Barrington. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Questing and New Marlborough Town Library are located nearby.
The Cornell Inn, Lenox & The Berkshires

The Cornell Inn, Lenox & The Berkshires

3.5 out of 5
Save 100% on your flight
Price was $3,448, price is now $2,164 per person
$2,164
per person
Jul 2 - Jul 6
found 1 hour ago
Roundtrip non-stop flight included
Minneapolis (MSP) to Albany (ALB)
Stay at this B&B in Lenox. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the comfy rooms in our reviews. Popular attractions Tanglewood Music Center and National Shrine of the Divine Mercy are located nearby.
The Perch Hotel

The Perch Hotel

2 out of 5
Price was $1,145, price is now $799 per person
$799
per person
May 21 - May 24
found 1 day ago
Roundtrip non-stop flight included
Minneapolis (MSP) to Albany (ALB)
Stay at this hotel in Cornwallville. Enjoy free WiFi, free parking, and a garden. Popular attractions Elm Ridge Wild Forest and Zoom Flume are located nearby.
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

3.5 out of 5
Price was $1,287, price is now $916 per person
$916
per person
Jul 2 - Jul 6
found 1 hour ago
Roundtrip non-stop flight included
Minneapolis (MSP) to Albany (ALB)
Book a stay at this family-friendly hotel in South Lee. Enjoy 2 outdoor pools, a business center, and a snack bar/deli. Our guests praise the helpful staff in our reviews. Popular attractions National Shrine of the Divine Mercy and Tanglewood Music Center are located nearby.
Chester by Avantstay Amazing Views, Secluded Home, A True City Escape!

Chester by Avantstay Amazing Views, Secluded Home, A True City Escape!

3 out of 5
Save 100% on your flight
Price was $4,721, price is now $3,425 per person
$3,425
per person
Jul 2 - Jul 6
found 1 hour ago
Roundtrip non-stop flight included
Minneapolis (MSP) to Albany (ALB)
Stay at this cottage in Austerlitz. Enjoy balconies, in-room washers/dryers, and in-room fireplaces. Popular attraction Art et Industrie is located nearby.
Whitney by Avantstay Private Berkshires Estate

Whitney by Avantstay Private Berkshires Estate

3 out of 5
Save 100% on your flight
Price was $2,438, price is now $1,854 per person
$1,854
per person
Jul 2 - Jul 6
found 1 hour ago
Roundtrip non-stop flight included
Minneapolis (MSP) to Albany (ALB)
Stay at this cottage in Sheffield. Enjoy in-room washers/dryers and an in-room coffeemaker. Popular attractions Thom Reed UFO Monument Park and Three Mile Pond Wildlife Management Area are located nearby.
The Red Lion Inn

The Red Lion Inn

3.5 out of 5
Save 100% on your flight
Price was $1,733, price is now $1,326 per person
$1,326
per person
Jul 2 - Jul 6
found 1 hour ago
Roundtrip non-stop flight included
Minneapolis (MSP) to Albany (ALB)
Book a stay at this historic hotel in Stockbridge. Enjoy free WiFi, 3 restaurants, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. Popular attractions National Shrine of the Divine Mercy and Tanglewood Music Center are located nearby.
The Wiltwyck

The Wiltwyck

3.5 out of 5
Price was $1,126, price is now $889 per person
$889
per person
May 22 - May 25
found 1 day ago
Roundtrip non-stop flight included
Minneapolis (MSP) to Albany (ALB)
Stay at this guesthouse in Kingston. Enjoy free WiFi, free parking, and Netflix. Popular attractions Senate House State Historic Site and Volunteer Fireman's Hall and Museum of Kingston are located nearby.

Cheshire Vacation Packages 3-4 Night Stays

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

Gedney Farm

3.5 out of 5
Price was $1,110, price is now $787 per person
$787
per person
Jul 2 - Jul 6
found 1 hour ago
Roundtrip non-stop flight included
Minneapolis (MSP) to Albany (ALB)
The Cornell Inn, Lenox & The Berkshires

The Cornell Inn, Lenox & The Berkshires

3.5 out of 5
Save 100% on your flight
Price was $3,448, price is now $2,164 per person
$2,164
per person
Jul 2 - Jul 6
found 1 hour ago
Roundtrip non-stop flight included
Minneapolis (MSP) to Albany (ALB)
The Perch Hotel

The Perch Hotel

2 out of 5
Price was $1,145, price is now $799 per person
$799
per person
May 21 - May 24
found 1 day ago
Roundtrip non-stop flight included
Minneapolis (MSP) to Albany (ALB)
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

3.5 out of 5
Price was $1,287, price is now $916 per person
$916
per person
Jul 2 - Jul 6
found 1 hour ago
Roundtrip non-stop flight included
Minneapolis (MSP) to Albany (ALB)

Cheshire Vacation Packages 5-7 Night Stays

Price found within the past 48 hours. Click for updated prices.
Quality Inn Schenectady - Albany

Quality Inn Schenectady - Albany

2.5 out of 5
Rotterdam
Price was $780, price is now $665 per person
$665
per person
May 18 - May 25
found 11 hours ago
Roundtrip non-stop flight included
Fort Lauderdale (FLL) to Albany (ALB)
Hampton Inn Albany-Wolf Road (Airport)

Hampton Inn Albany-Wolf Road (Airport)

2.5 out of 5
Price was $1,084, price is now $913 per person
$913
per person
Jun 21 - Jun 27
found 11 hours ago
Roundtrip non-stop flight included
Fort Lauderdale (FLL) to Albany (ALB)
Home2 Suites by Hilton Albany Wolf Rd

Home2 Suites by Hilton Albany Wolf Rd

3 out of 5
Price was $964, price is now $817 per person
$817
per person
Jun 21 - Jun 27
found 11 hours ago
Roundtrip non-stop flight included
Fort Lauderdale (FLL) to Albany (ALB)
Quality Inn Lee - Lenox South

Quality Inn Lee - Lenox South

2.5 out of 5
Price was $866, price is now $738 per person
$738
per person
May 18 - May 25
found 19 hours ago
Roundtrip non-stop flight included
Fort Lauderdale (FLL) to Albany (ALB)

Top Flight Deals

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

American Airlines
Tue, May 19 - Sat, May 30
FLL
Fort Lauderdale - Hollywood Intl.
ALB
Albany Intl.
$187 Roundtrip, found 8 hours ago
$187
Roundtrip
found 8 hours ago
Select American Airlines flight, departing Tue, May 19 from Fort Lauderdale - Hollywood Intl. to Albany Intl., returning Sat, May 30, priced at $187 found 8 hours ago
Bargain Flight
Wed, May 27 - Sat, May 30
CLT
Charlotte-Douglas Intl.
ALB
Albany Intl.
$266 Roundtrip, found 5 days ago
$266
Roundtrip
found 5 days ago
Select Bargain Flight flight, departing Wed, May 27 from Charlotte-Douglas Intl. to Albany Intl., returning Sat, May 30, priced at $266 found 5 days ago
Bargain Flight
Tue, Aug 4 - Wed, Aug 12
DFW
Dallas-Fort Worth Intl.
ALB
Albany Intl.
$291 Roundtrip, found 1 day ago
$291
Roundtrip
found 1 day ago
Select Bargain Flight flight, departing Tue, Aug 4 from Dallas-Fort Worth Intl. to Albany Intl., returning Wed, Aug 12, priced at $291 found 1 day ago
United
Thu, May 21 - Sun, May 24
ATL
Hartsfield-Jackson Atlanta Intl.
ALB
Albany Intl.
$291 Roundtrip, found 8 hours ago
$291
Roundtrip
found 8 hours ago
Select United flight, departing Thu, May 21 from Hartsfield-Jackson Atlanta Intl. to Albany Intl., returning Sun, May 24, priced at $291 found 8 hours ago