Search Deals onChesterwood Vacation Packages
Chesterwood Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.

Travelodge by Wyndham Lake George NY
Price was $541, price is now $466 per person
$466
per person
Oct 7 - Oct 14
found 1 day ago
Roundtrip flight included
Orlando (MCO) to Albany (ALB)
Book a stay at this business-friendly motel in Lake George. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the property condition in our reviews. Popular attractions Six Flags Great Escape and Goony Golf are located nearby.

The Equinox Golf Resort & Spa
Price was $1,472, price is now $1,144 per person
$1,144
per person
Oct 12 - Oct 16
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Albany (ALB)
Stay at this 4.5-star luxury hotel in Manchester. Enjoy free parking, an outdoor pool, and a full-service spa. Our guests praise the property condition in our reviews. Popular attractions Golf Club at Equinox and American Museum of Fly Fishing are located nearby.

The Motel Montreal
Price was $822, price is now $706 per person
$706
per person
Oct 7 - Oct 14
found 1 day ago
Roundtrip flight included
Orlando (MCO) 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 Six Flags Great Escape and Lakeside Trail are located nearby.

Super 8 by Wyndham Lake George/Warrensburg Area
Price was $578, price is now $504 per person
$504
per person
Oct 7 - Oct 14
found 1 day ago
Roundtrip flight included
Orlando (MCO) to Albany (ALB)
Book a stay at this business-friendly motel in Lake George. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Warren County Nature Trails and Hickory Ski Center are located nearby.

Mohican Resort Motel
Price was $773, price is now $688 per person
$688
per person
Oct 7 - Oct 14
found 17 hours ago
Roundtrip flight included
Orlando (MCO) to Albany (ALB)
Book a stay at this family-friendly motel in Lake George. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Six Flags Great Escape and Lumberjack Pass Mini Golf are located nearby.

The Springwater B&B
Price was $974, price is now $903 per person
$903
per person
Oct 30 - Nov 4
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Albany (ALB)
Stay at this 4-star B&B in Saratoga Springs. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Saratoga Race Course and Saratoga Performing Arts Center are located nearby.

Saratoga Casino Hotel
Price was $966, price is now $896 per person
$896
per person
Oct 30 - Nov 4
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Albany (ALB)
Stay at this 4-star hotel in Saratoga Springs. Enjoy free WiFi, free parking, and a casino. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Saratoga Race Course and Saratoga Performing Arts Center are located nearby.

Surfside On The Lake
Price was $818, price is now $758 per person
$758
per person
Oct 7 - Oct 14
found 12 hours ago
Roundtrip flight included
Orlando (MCO) to Albany (ALB)
Book a stay at this beach hotel in Lake George. Enjoy free parking, 2 restaurants, and a private beach. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Six Flags Great Escape and Black Mountain Loop are located nearby.

The Inn at Saratoga
Price was $890, price is now $827 per person
$827
per person
Oct 30 - Nov 4
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Albany (ALB)
Stay at this 3-star hotel in Saratoga Springs. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Saratoga Race Course and Saratoga Performing Arts Center are located nearby.

Hotel Brookmere & Arbor Spa
Price was $778, price is now $609 per person
$609
per person
Nov 1 - Nov 5
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Albany (ALB)
Stay at this 4-star spa hotel in Saratoga Springs. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Saratoga Race Course and Saratoga Performing Arts Center are located nearby.

Hilton Garden Inn Albany Airport
Price was $724, price is now $614 per person
$614
per person
Nov 1 - Nov 5
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) 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.

La Quinta Inn & Suites by Wyndham Latham Albany Airport
Price was $624, price is now $542 per person
$542
per person
Nov 1 - Nov 5
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) 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.
3-4 Night Vacations in Chesterwood
Price found within the past 48 hours. Click for updated prices.



5-7 Night Vacations in Chesterwood
Price found within the past 48 hours. Click for updated prices.



Chesterwood Last Minute Hotel Deals

The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
26 Glendale Road, RR 183, Stockbridge, MA
Stay at this 4.5-star luxury B&B in Stockbridge. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Tanglewood Music Center and Chesterwood ...

The Red Lion Inn
30 Main Street, Stockbridge, MA
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 ...

Tanglewood Suites
MA-102, Stockbridge, MA
Stay at this B&B in Stockbridge. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Tanglewood Music Center and Naumkeag Museum are located ...

1 Mi to Dtwn: Cottage w/ Large Yard in Stockbridge
Glendale
Stay at this 3-star cottage in Glendale. Enjoy free parking, in-room fireplaces, and air conditioning. Popular attractions Tanglewood Music Center and Mission ...

Woodland Zen by Avantstay Modern Design + Patio
58 Glendale Rd, Housatonic, MA
Stay at this 3-star cottage in Housatonic. Enjoy free parking, patios, and in-room washers/dryers. Popular attractions Art et Industrie and Chesterwood are located ...

Stockbridge Retreat w/ Pool & Hot Tub!
Glendale
Stay at this 3-star cottage in Glendale. Enjoy free parking, a garden, and patios. Popular attractions Tanglewood Music Center and Mission House are located ...

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
190 Meadow Street, South Lee, MA
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 ...

Pleasant Valley Motel West Stockbridge
42 Stockbridge Rd, West Stockbridge, MA
Stay at this motel in West Stockbridge. Enjoy free WiFi, free parking, and daily housekeeping. Our guests praise the clean rooms in our reviews. Popular attractions ...
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.
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