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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.
The Ponds at Foxhollow

The Ponds at Foxhollow

3 out of 5
Save 100% on your flight
Price was $936, price is now $648 per person
$648
per person
Oct 22 - Oct 26
found 1 day ago
Roundtrip flight included
New York (NYC) 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.
Quiet property. Convenient location.

Reviewed on Aug 2, 2026

The Cornell Inn, Lenox & The Berkshires

The Cornell Inn, Lenox & The Berkshires

3.5 out of 5
Price was $1,328, price is now $899 per person
$899
per person
Oct 22 - Oct 26
found 24 hours ago
Roundtrip flight included
New York (NYC) 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 Wiltwyck

The Wiltwyck

3.5 out of 5
Price was $1,295, price is now $999 per person
$999
per person
Sep 30 - Oct 6
found 1 day ago
Roundtrip flight included
New York (NYC) 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.

Prospect Berkshires

Prospect Berkshires

3 out of 5
Price was $2,140, price is now $1,692 per person
$1,692
per person
Sep 30 - Oct 6
found 1 day ago
Roundtrip flight included
New York (NYC) to Albany (ALB)
Stay at this hotel in Great Barrington. Enjoy free WiFi, free parking, and a sauna. Popular attractions Catamount Aerial Adventure Park and Catamount Ski Area are located nearby.
It was beautiful but quite expensive. There was no housekeeping included so trash was not picked up and the breakfasts were grossly overpriced!

Reviewed on Aug 19, 2026

The Nightingale by Avantstay Historic Catskills Retreat Lake Views + Near Hudson Sleeps 18

The Nightingale by Avantstay Historic Catskills Retreat Lake Views + Near Hudson Sleeps 18

3 out of 5
Price was $4,189, price is now $3,424 per person
$3,424
per person
Sep 30 - Oct 6
found 1 day ago
Roundtrip flight included
New York (NYC) to Albany (ALB)
Stay at this cottage in Earlton. Enjoy free parking, patios, and in-room washers/dryers. Popular attractions Thunderhart Golf Course and Cairo Lockwood State Forest are located nearby.

Hotel Kinsley

Hotel Kinsley

3.5 out of 5
Price was $1,013, price is now $828 per person
$828
per person
Sep 27 - Oct 1
found 1 day ago
Roundtrip flight included
New York (NYC) to Albany (ALB)
Book a stay at this business-friendly hotel in Kingston. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Birch Body Care and Volunteer Fireman's Hall and Museum of Kingston are located nearby.
bathroom needs to be more thoroughly cleaned

Reviewed on Aug 21, 2026

Farmhouse at Leeds by Avantstay Catskills Farmhouse + Barn Suite + Firepit Mins to Hudson + Kaaterskill Falls

Farmhouse at Leeds by Avantstay Catskills Farmhouse + Barn Suite + Firepit Mins to Hudson + Kaaterskill Falls

3 out of 5
Price was $2,379, price is now $1,947 per person
$1,947
per person
Sep 30 - Oct 6
found 1 day ago
Roundtrip flight included
New York (NYC) to Albany (ALB)
Stay at this cottage in Leeds. Enjoy free parking, patios, and in-room fireplaces. Popular attractions Catskill Golf Club and Thomas Cole National Historic Site 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
Price was $3,558, price is now $2,926 per person
$2,926
per person
Sep 30 - Oct 6
found 1 day ago
Roundtrip flight included
New York (NYC) 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.

Cheshire Vacation Packages 3-4 Night Stays

Price found within the past 48 hours. Click for updated prices.
Hampton Inn & Suites Albany-Downtown

Hampton Inn & Suites Albany-Downtown

2.5 out of 5
Downtown Albany
Price was $634, price is now $523 per person
$523
per person
Oct 22 - Oct 26
found 1 day ago
Roundtrip flight included
New York (NYC) to Albany (ALB)
The Cornell Inn, Lenox & The Berkshires

The Cornell Inn, Lenox & The Berkshires

3.5 out of 5
Price was $1,328, price is now $899 per person
$899
per person
Oct 22 - Oct 26
found 24 hours ago
Roundtrip flight included
New York (NYC) to Albany (ALB)
The Ponds at Foxhollow

The Ponds at Foxhollow

3 out of 5
Save 100% on your flight
Price was $936, price is now $648 per person
$648
per person
Oct 22 - Oct 26
found 1 day ago
Roundtrip flight included
New York (NYC) to Albany (ALB)
Hotel Kinsley

Hotel Kinsley

3.5 out of 5
Stockade District
Price was $1,013, price is now $828 per person
$828
per person
Sep 27 - Oct 1
found 1 day ago
Roundtrip flight included
New York (NYC) 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 $1,295, price is now $999 per person
$999
per person
Sep 30 - Oct 6
found 1 day ago
Roundtrip flight included
New York (NYC) to Albany (ALB)
Hotel Kinsley

Hotel Kinsley

3.5 out of 5
Stockade District
Price was $1,615, price is now $1,208 per person
$1,208
per person
Sep 30 - Oct 6
found 1 day ago
Roundtrip flight included
New York (NYC) to Albany (ALB)
Prospect Berkshires

Prospect Berkshires

3 out of 5
Price was $2,140, price is now $1,692 per person
$1,692
per person
Sep 30 - Oct 6
found 1 day ago
Roundtrip flight included
New York (NYC) to Albany (ALB)
The Nightingale by Avantstay Historic Catskills Retreat Lake Views + Near Hudson Sleeps 18

The Nightingale by Avantstay Historic Catskills Retreat Lake Views + Near Hudson Sleeps 18

3 out of 5
Price was $4,189, price is now $3,424 per person
$3,424
per person
Sep 30 - Oct 6
found 1 day ago
Roundtrip flight included
New York (NYC) 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, Sep 17 - Sun, Sep 27
FLL
Fort Lauderdale - Hollywood Intl.
ALB
Albany Intl.
$144 Roundtrip, found 3 hours ago
$144
Roundtrip
found 3 hours ago
Select Allegiant Air flight, departing Thu, Sep 17 from Fort Lauderdale - Hollywood Intl. to Albany Intl., returning Sun, Sep 27, priced at $144 found 3 hours ago
Breeze Airways
Fri, Sep 25 - Sat, Oct 3
TPA
Tampa Intl.
ALB
Albany Intl.
$280 Roundtrip, found 3 hours ago
$280
Roundtrip
found 3 hours ago
Select Breeze Airways flight, departing Fri, Sep 25 from Tampa Intl. to Albany Intl., returning Sat, Oct 3, priced at $280 found 3 hours ago
Bargain Flight
Mon, Sep 21 - Sun, Sep 27
ATL
Hartsfield-Jackson Atlanta Intl.
ALB
Albany Intl.
$291 Roundtrip, found 20 hours ago
$291
Roundtrip
found 20 hours ago
Select Bargain Flight flight, departing Mon, Sep 21 from Hartsfield-Jackson Atlanta Intl. to Albany Intl., returning Sun, Sep 27, priced at $291 found 20 hours ago
Bargain Flight
Thu, Dec 3 - Thu, Dec 10
PHX
Sky Harbor Intl.
ALB
Albany Intl.
$291 Roundtrip, found 2 hours ago
$291
Roundtrip
found 2 hours ago
Select Bargain Flight flight, departing Thu, Dec 3 from Sky Harbor Intl. to Albany Intl., returning Thu, Dec 10, priced at $291 found 2 hours ago