Cheshire Vacations
Build a Flight + Hotel Bundle & Save up to $536 On Your Vacation*
Photo by Ed Gaffny
Cheshire Flight + Hotel packages
Price found within the past 48 hours. Click for updated prices.
La Quinta Inn & Suites by Wyndham Latham Albany Airport
Price was $641, price is now $529 per person
$529
per person
Oct 9 - Oct 13
found 17 hours ago
Roundtrip flight included
Orlando (MCO) to Albany (ALB)
Stay at this 3-star business-friendly hotel in Latham. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the clean rooms in our reviews. Popular attractions Colonie Center Mall and Curtain Call Theater are located nearby.
Hampton Inn Albany-Wolf Road (Airport)
Price was $673, price is now $553 per person
$553
per person
Oct 9 - Oct 13
found 17 hours ago
Roundtrip flight included
Orlando (MCO) 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.
Secluded Lux Mansion Pool Home With Amazing Views
Save 100% on your flight
Price was $5,071, price is now $4,266 per person
$4,266
per person
Oct 7 - Oct 14
found 24 hours ago
Roundtrip non-stop flight included
Seattle (SEA) to Albany (ALB)
Stay at this vacation home in Nassau. Enjoy free parking and a garden. Popular attractions Brookview Station Winery and Berkshire Retreat Center are located nearby.
Hilton Garden Inn Albany Airport
Price was $696, price is now $588 per person
$588
per person
Oct 9 - Oct 13
found 17 hours ago
Roundtrip flight included
Orlando (MCO) to Albany (ALB)
Stay at this 3-star business-friendly hotel in Albany. Enjoy free WiFi, breakfast (surcharge), and a free airport shuttle. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Colonie Center Mall and Crossgates Mall are located nearby.
Tiny House 2 5 hrs NYC and Boston Waterfront Wifi
Price was $1,930, price is now $1,649 per person
$1,649
per person
Oct 7 - Oct 14
found 24 hours ago
Roundtrip non-stop flight included
Seattle (SEA) to Albany (ALB)
Stay at this apartment in Nassau. Enjoy free parking and a garden. Popular attractions Brookview Station Winery and Berkshire Retreat Center are located nearby.
Modern Farm Home 2hr NYC BOS Peaceful Wifi
Save 100% on your flight
Price was $2,255, price is now $1,927 per person
$1,927
per person
Oct 7 - Oct 14
found 24 hours ago
Roundtrip non-stop flight included
Seattle (SEA) to Albany (ALB)
Stay at this vacation home in Nassau. Enjoy free parking and a garden. Popular attractions Brookview Station Winery and Berkshire Retreat Center are located nearby.
Top Hotel Deals
Hotel Downstreet, an Ascend Collection Hotel
40 Main St, North Adams, MA
15.79 km from city center
Stay at this 3-star hotel in North Adams. Enjoy free WiFi, free parking, and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms ...
Vacation Village in the Berkshires
276 Brodie Mountain Rd, Williamstown, MA
10.45 km from city center
Stay at this 3-star family-friendly condo in Williamstown. Enjoy free parking, a fitness center, and a 24-hour front desk. Our guests praise the helpful staff ...
Berkshire Mountain Lodge
8 Dan Fox Dr, Pittsfield, MA
18.58 km from city center
Stay at this 3-star golf lodge in Pittsfield. Enjoy free WiFi, free parking, and a business center. Our guests praise the helpful staff and the clean rooms in ...
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
190 Meadow Street, South Lee, MA
33.29 km from city center
Stay at this 3.5-star family-friendly hotel in South Lee. Enjoy 2 outdoor pools, a business center, and a snack bar/deli. Our guests praise the helpful staff ...
The Red Lion Inn
30 Main Street, Stockbridge, MA
33.43 km from city center
Stay at this 3.5-star historic hotel in Stockbridge. Enjoy free WiFi, 3 restaurants, and breakfast (surcharge). Our guests praise the helpful staff and the property ...
FairBridge Inn Express
16 Cheshire Road, Pittsfield, MA
10.84 km from city center
Book a stay at this business-friendly motel in Pittsfield. Enjoy free WiFi, free parking, and a 24-hour front desk. Popular attractions Crane Museum of Papermaking ...
Berkshires Untold
194 Pittsfield Rd, Lenox, MA
21.55 km from city center
Stay at this 3.5-star lodge in Lenox. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our ...
Howard Johnson by Wyndham Lenox
462 Pittsfield Rd, Routes 7 and 20, Lenox, MA
19.64 km from city center
Stay at this motel in Lenox. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in our reviews. ...
The Williams Inn
101 Spring Street, Williamstown, MA
16.77 km from city center
Stay at this 4-star business-friendly hotel in Williamstown. Enjoy free WiFi, free parking, and a fitness center. Our guests praise the helpful staff in our ...
Jiminy Peak Mountain Resort
37 Corey Rd, Hancock, MA
10.66 km from city center
Stay at this 3-star ski condo in Hancock. Enjoy free parking, 2 restaurants, and 2 hot tubs. Our guests praise the property condition in our reviews. Popular ...
The Yankee, Trademark Collection by Wyndham
461 Pittsfield Rd, Lenox, MA
19.61 km from city center
Book a stay at this business-friendly hotel in Lenox. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the pool in our ...
The Black Swan Lee - Lenox, an Ascend Collection Hotel
435 Laurel St, Lee, MA
27.9 km from city center
Stay at this 3-star hotel in Lee. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the restaurant in our reviews. Popular ...
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
1055 South Street, Pittsfield, MA
19.05 km from city center
Stay at this hotel in Pittsfield. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Tanglewood Music Center and Guido's Marketplace are ...
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.
Top Flight Deals
These prices were available within the past 7 days. Prices quoted are per person, round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.
Fri, Sep 26 - Fri, Oct 3
TPA
Tampa Intl.
ALB
Albany Intl.
$237 Roundtrip, found 4 days ago
$237
Roundtrip
found 4 days ago
Tue, Sep 23 - Fri, Oct 3
TPA
Tampa Intl.
ALB
Albany Intl.
$239 Roundtrip, found 4 days ago
$239
Roundtrip
found 4 days ago
Sat, Sep 27 - Wed, Oct 1
ATL
Hartsfield-Jackson Atlanta Intl.
ALB
Albany Intl.
$299 Roundtrip, found 1 day ago
$299
Roundtrip
found 1 day ago
Fri, Sep 26 - Sun, Oct 5
TPA
Tampa Intl.
ALB
Albany Intl.
$463 Roundtrip, found 4 days ago
$463
Roundtrip
found 4 days ago