Search Deals onChesterwood Vacation Packages
Chesterwood Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.
Valley Craft Ales
Price was $452, price is now $371 per person
$371
per person
Nov 26 - Nov 30
found 15 hours ago
Roundtrip flight included
Orlando (MCO) to Albany (ALB)
Stay at this lodge in Wilmington. Enjoy free WiFi, free parking, and a fireplace in the lobby. Popular attractions South Main Street and Jim McGrath Gallery and Studio are located nearby.
Brook Bound Inn
Save 100% on your flight
Price was $868, price is now $604 per person
$604
per person
Nov 26 - Nov 30
found 15 hours ago
Roundtrip flight included
Orlando (MCO) 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 Equinox Golf Resort & Spa
Price was $770, price is now $569 per person
$569
per person
Nov 20 - Nov 24
found 1 day ago
Roundtrip non-stop flight included
Austin (AUS) 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 White House Inn
Price was $663, price is now $496 per person
$496
per person
Nov 26 - Nov 30
found 15 hours ago
Roundtrip flight included
Orlando (MCO) to Albany (ALB)
Stay at this 3.5-star hotel in Wilmington. Enjoy free WiFi, free parking, and a garden. Our guests praise the helpful staff and the property condition in our reviews. Popular attractions South Main Street and Pettee Memorial Library are located nearby.
Kimpton Taconic Hotel by IHG
Price was $718, price is now $587 per person
$587
per person
Nov 20 - Nov 24
found 1 day ago
Roundtrip non-stop flight included
Austin (AUS) to Albany (ALB)
Stay at this 4-star golf hotel in Manchester. Enjoy an outdoor pool, breakfast (surcharge), and room service. Our guests praise the helpful staff and the property condition in our reviews. Popular attractions Golf Club at Equinox and American Museum of Fly Fishing are located nearby.
Hotel Vervana, Trademark Collection by Wyndham
Price was $567, price is now $474 per person
$474
per person
Nov 26 - Nov 30
found 15 hours ago
Roundtrip flight included
Orlando (MCO) to Albany (ALB)
Book a stay at this ski hotel in Bennington. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Hemmings Motor News Car Lover's Convenience Store & Vehicle Display and Bennington Museum are located nearby.
Club Wyndham Bentley Brook
Price was $744, price is now $625 per person
$625
per person
Nov 20 - Nov 24
found 1 day ago
Roundtrip non-stop flight included
Austin (AUS) to Albany (ALB)
Stay at this 3-star ski hotel in Hancock. Enjoy free WiFi, free parking, and a 24-hour fitness center. Our guests praise the helpful staff and the property condition in our reviews. Popular attractions Jiminy Peak Mountain Resort and Mountain Coaster are located nearby.
Aspen At Manchester
Price was $612, price is now $522 per person
$522
per person
Nov 20 - Nov 24
found 1 day ago
Roundtrip non-stop flight included
Austin (AUS) to Albany (ALB)
Stay at this hotel in Manchester Center. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Dana L. Thompson Memorial Park and Lye Brook Falls are located nearby.
TownePlace Suites Latham Albany Airport
Price was $627, price is now $539 per person
$539
per person
Nov 8 - Nov 12
found 11 hours ago
Roundtrip non-stop 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 helpful staff and the clean rooms in our reviews. Popular attractions Colonie Center Mall and Crossgates Mall are located nearby.
Vacation Village in the Berkshires
Price was $563, price is now $489 per person
$489
per person
Nov 20 - Nov 24
found 1 day ago
Roundtrip non-stop flight included
Austin (AUS) to Albany (ALB)
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 in our reviews. Popular attractions Jiminy Peak Mountain Resort and Mountain Coaster are located nearby.
South Shire
Price was $701, price is now $617 per person
$617
per person
Nov 20 - Nov 24
found 1 day ago
Roundtrip non-stop flight included
Austin (AUS) to Albany (ALB)
Stay at this 4-star inn in Bennington. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. Popular attractions Bennington Arts Guild Gallery and Fiddlehead at Four Corners 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 ...
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 ...
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 ...
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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