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

La Quinta Inn & Suites by Wyndham Latham Albany Airport
per person
Aug 29 - Sep 2
found 1 day ago
Roundtrip 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.

The Equinox Golf Resort & Spa
per person
Aug 22 - Aug 27
found 15 hours 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.

Modern Farm Home 2hr NYC BOS Peaceful Wifi
Save 100% on your flight
per person
Aug 27 - Sep 3
found 1 day ago
Roundtrip non-stop flight included
Tampa (TPA) 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.

Tiny House 2 5 hrs NYC and Boston Waterfront Wifi
Save 100% on your flight
per person
Aug 27 - Sep 3
found 1 day ago
Roundtrip non-stop flight included
Tampa (TPA) 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.

Park Manor Hotel
per person
Aug 29 - Sep 2
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Albany (ALB)
Stay at this 4-star hotel in Clifton Park. Enjoy free parking, 24-hour room service, and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Regal Clifton Park and The Edge Halfmoon are located nearby.

DoubleTree by Hilton Schenectady Downtown
per person
Aug 29 - Sep 2
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Albany (ALB)
Stay at this 4-star eco-certified hotel in Schenectady. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the property condition in our reviews. Popular attractions Rivers Casino & Resort and Museum of Innovation and Science are located nearby.

The Landing Hotel at Rivers Casino & Resort
per person
Aug 29 - Sep 2
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Albany (ALB)
Stay at this 4-star business-friendly hotel in Schenectady. Enjoy free WiFi, free parking, and 5 restaurants. Our guests praise the helpful staff and the property condition in our reviews. Popular attractions Rivers Casino & Resort and Scene One Movieland are located nearby.

Community Court Motel
per person
Aug 27 - Sep 3
found 1 day ago
Roundtrip non-stop flight included
Tampa (TPA) to Albany (ALB)
Stay at this hotel in Saratoga Springs. Enjoy free parking, daily housekeeping, and a picnic area. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Saratoga Race Course and Saratoga Racetrack are located nearby.

Hotel Trilogy Albany Airport, Tapestry Collection by Hilton
per person
Aug 27 - Sep 3
found 1 day ago
Roundtrip non-stop flight included
Tampa (TPA) to Albany (ALB)
Stay at this 3.5-star business-friendly hotel in Latham. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. Popular attractions Colonie Center Mall and Crossgates Mall are located nearby.

Hilton Garden Inn Albany Airport
per person
Aug 29 - Sep 2
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Albany (ALB)
Stay at this 3-star business-friendly hotel in Latham. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Colonie Center Mall and Crossgates Mall are located nearby.

Hyatt Place Albany/Downtown
per person
Aug 29 - Sep 2
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Albany (ALB)
Stay at this 3-star business-friendly hotel in Albany. Enjoy free breakfast, free WiFi, and a 24-hour fitness center. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions MVP Arena and The Egg are located nearby.

Hampton Inn Schenectady Downtown
per person
Aug 29 - Sep 2
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Albany (ALB)
Stay at this hotel in Schenectady. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular attractions Rivers Casino & Resort and Proctors 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 ...

Tranquil 3 BR Stockbridge House w/ Private Deck!
South Lee
Stay at this 3-star cottage in South Lee. Enjoy free parking, in-room fireplaces, and air conditioning. Popular attractions Tanglewood Music Center and Berkshire ...

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 ...
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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Hotels Near Points of Interest in Chesterwood
- Hotels near Tanglewood Music Center
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