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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.
Brook Bound Inn

Brook Bound Inn

2 out of 5
Price was $852, price is now $579 per person
$579
per person
Oct 7 - Oct 10
found 24 hours ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Albany (ALB)
Book a stay at this golf hotel in Wilmington. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Mount Snow and North Branch Deerfield River are located nearby.
The cabin and grounds are well-maintained. The pool was crystal clear and the slide was a nice addition. Gorgeous views!

Reviewed on Jun 28, 2026

The Cornell Inn, Lenox & The Berkshires

The Cornell Inn, Lenox & The Berkshires

3.5 out of 5
Price was $1,865, price is now $1,331 per person
$1,331
per person
Sep 16 - Sep 21
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) 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 The Bookstore are located nearby.

The Perch Hotel

The Perch Hotel

2 out of 5
Price was $1,691, price is now $1,250 per person
$1,250
per person
Sep 12 - Sep 19
found 1 day ago
Roundtrip non-stop flight included
New York (JFK) 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.
It was a wonderful stay the room was very clean and spacious. The common area downstairs was my favorite part of my whole stay. Wide variety of games to play with other guest that are also staying.

Reviewed on Jul 16, 2026

The Ponds at Foxhollow

The Ponds at Foxhollow

3 out of 5
Price was $1,348, price is now $1,018 per person
$1,018
per person
Sep 16 - Sep 21
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Albany (ALB)
Stay at this aparthotel in Lenox. Enjoy free WiFi, free parking, and a fitness center. Popular attractions Tanglewood Music Center and The Mount are located nearby.

Sundowner on Lake George

Sundowner on Lake George

2.5 out of 5
Price was $1,413, price is now $1,071 per person
$1,071
per person
Sep 4 - Sep 8
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) 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.
Nothing like the pictures. No staffs to receive you, you have to call a phone number. The place is old and outdated.

Reviewed on May 3, 2026

Studio 6 Lake George, NY - Adirondacks

Studio 6 Lake George, NY - Adirondacks

2 out of 5
Price was $871, price is now $671 per person
$671
per person
Sep 4 - Sep 8
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Albany (ALB)
Stay at this hotel in Lake George. Enjoy free parking, an outdoor pool, and a fitness center. Popular attractions Six Flags Great Escape and Outlets at Lake George are located nearby.
Comfy

Reviewed on Jul 30, 2026

Kimpton Taconic Hotel by IHG

Kimpton Taconic Hotel by IHG

4 out of 5
Save 100% on your flight
Price was $1,420, price is now $1,095 per person
$1,095
per person
Oct 7 - Oct 10
found 24 hours ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Albany (ALB)
Book a stay at this golf hotel in Manchester. Enjoy an outdoor pool, breakfast (surcharge), and room service. Our guests praise the helpful staff in our reviews. Popular attractions Golf Club at Equinox and American Museum of Fly Fishing are located nearby.

The Wiltwyck

The Wiltwyck

3.5 out of 5
Price was $1,101, price is now $871 per person
$871
per person
Sep 14 - Sep 21
found 23 hours ago
Roundtrip non-stop flight included
New York (JFK) 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.
Very cozy and clean. Walkable to restaurants

Reviewed on Jul 29, 2026

Cheshire Vacation Packages 3-4 Night Stays

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

Brook Bound Inn

2 out of 5
Price was $852, price is now $579 per person
$579
per person
Oct 7 - Oct 10
found 24 hours ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Albany (ALB)
Sundowner on Lake George

Sundowner on Lake George

2.5 out of 5
Price was $1,413, price is now $1,071 per person
$1,071
per person
Sep 4 - Sep 8
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Albany (ALB)
Studio 6 Lake George, NY - Adirondacks

Studio 6 Lake George, NY - Adirondacks

2 out of 5
Price was $871, price is now $671 per person
$671
per person
Sep 4 - Sep 8
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Albany (ALB)
Kimpton Taconic Hotel by IHG

Kimpton Taconic Hotel by IHG

4 out of 5
Manchester Village Historic District
Save 100% on your flight
Price was $1,420, price is now $1,095 per person
$1,095
per person
Oct 7 - Oct 10
found 24 hours ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Albany (ALB)

Cheshire Vacation Packages 5-7 Night Stays

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

The Wiltwyck

3.5 out of 5
Price was $1,101, price is now $871 per person
$871
per person
Sep 14 - Sep 21
found 23 hours ago
Roundtrip non-stop flight included
New York (JFK) to Albany (ALB)
The Cornell Inn, Lenox & The Berkshires

The Cornell Inn, Lenox & The Berkshires

3.5 out of 5
Price was $1,865, price is now $1,331 per person
$1,331
per person
Sep 16 - Sep 21
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Albany (ALB)
The Perch Hotel

The Perch Hotel

2 out of 5
Price was $1,691, price is now $1,250 per person
$1,250
per person
Sep 12 - Sep 19
found 1 day ago
Roundtrip non-stop flight included
New York (JFK) to Albany (ALB)
The Ponds at Foxhollow

The Ponds at Foxhollow

3 out of 5
Price was $1,348, price is now $1,018 per person
$1,018
per person
Sep 16 - Sep 21
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Albany (ALB)

Top Flight Deals

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

Allegiant Air
Thu, Aug 27 - Sun, Aug 30
FLL
Fort Lauderdale - Hollywood Intl.
ALB
Albany Intl.
$98 Roundtrip, found 4 hours ago
$98
Roundtrip
found 4 hours ago
Select Allegiant Air flight, departing Thu, Aug 27 from Fort Lauderdale - Hollywood Intl. to Albany Intl., returning Sun, Aug 30, priced at $98 found 4 hours ago
Bargain Flight
Wed, Aug 26 - Tue, Sep 8
ATL
Hartsfield-Jackson Atlanta Intl.
ALB
Albany Intl.
$241 Roundtrip, found 4 days ago
$241
Roundtrip
found 4 days ago
Select Bargain Flight flight, departing Wed, Aug 26 from Hartsfield-Jackson Atlanta Intl. to Albany Intl., returning Tue, Sep 8, priced at $241 found 4 days ago
Bargain Flight
Wed, Aug 26 - Sat, Aug 29
DFW
Dallas-Fort Worth Intl.
ALB
Albany Intl.
$285 Roundtrip, found 2 days ago
$285
Roundtrip
found 2 days ago
Select Bargain Flight flight, departing Wed, Aug 26 from Dallas-Fort Worth Intl. to Albany Intl., returning Sat, Aug 29, priced at $285 found 2 days ago
Bargain Flight
Sat, Aug 29 - Sat, Sep 5
LAX
Los Angeles Intl.
ALB
Albany Intl.
$292 Roundtrip, found 1 hour ago
$292
Roundtrip
found 1 hour ago
Select Bargain Flight flight, departing Sat, Aug 29 from Los Angeles Intl. to Albany Intl., returning Sat, Sep 5, priced at $292 found 1 hour ago