Search Deals onChesterwood Vacation Packages
Chesterwood Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.
Super 8 by Wyndham Kingston
per person
Oct 4 - Oct 8
found 13 hours ago
Roundtrip flight included
Tampa (TPA) to Albany (ALB)
Book a stay at this business-friendly motel 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 Dietz Stadium and Birch Body Care are located nearby.
Prospect Berkshires
Save 100% on your flight
per person
Oct 4 - Oct 8
found 13 hours ago
Roundtrip flight included
Tampa (TPA) 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.
Pocketbook Hotel and Bath
Save 100% on your flight
per person
Oct 4 - Oct 8
found 13 hours ago
Roundtrip flight included
Tampa (TPA) to Albany (ALB)
Book a stay at this spa hotel in Hudson. Enjoy free WiFi, a full-service spa, and a 24-hour front desk. Popular attractions Hudson Area Library and Stoddard Corner are located nearby.
Club Wyndham Bentley Brook
Save 100% on your flight
per person
Oct 4 - Oct 8
found 13 hours ago
Roundtrip flight included
Tampa (TPA) 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.
The Old Catskill Game Farm Inn
Save 100% on your flight
per person
Oct 4 - Oct 8
found 9 hours ago
Roundtrip flight included
Tampa (TPA) to Albany (ALB)
Stay at this 3.5-star historic guesthouse in Catskill. Enjoy free WiFi, free parking, and private hot tubs. Popular attractions Kaaterskill Falls and North-South Lake Campground & Day Use Area are located nearby.
The Wiltwyck
Save 100% on your flight
per person
Oct 4 - Oct 8
found 13 hours ago
Roundtrip flight included
Tampa (TPA) to Albany (ALB)
Stay at this 3.5-star 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.
Secluded w/ Deck Views, Hot Tub, & Ping Pong Hudson in the Berks by Avantstay
Save 100% on your flight
per person
Oct 4 - Oct 8
found 13 hours ago
Roundtrip flight included
Tampa (TPA) to Albany (ALB)
Stay at this 3-star cottage in East Chatham. Enjoy free parking, balconies, and in-room washers/dryers. Popular attractions Queechy Lake and Shaker Museum and Library are located nearby.
The Springs Motel
Save 100% on your flight
per person
Oct 4 - Oct 8
found 13 hours ago
Roundtrip flight included
Tampa (TPA) to Albany (ALB)
Stay at this motel in New Ashford. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular attractions Jiminy Peak Mountain Resort and Brodie Mountain are located nearby.
Relax in Style at Historic Modern on Main With Modern Amenities & Wooded Views
Save 100% on your flight
per person
Oct 4 - Oct 8
found 9 hours ago
Roundtrip flight included
Tampa (TPA) to Albany (ALB)
Stay at this 3-star cottage in Stone Ridge. Enjoy free parking, patios, and air conditioning. Popular attractions Mohonk Lake and Tongore Park Beach are located nearby.
Hampton Inn Schenectady Downtown
per person
Oct 9 - Oct 13
found 18 hours ago
Roundtrip flight included
Charlotte (CLT) 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 ...
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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Hotels Near Points of Interest in Chesterwood
- Hotels near Tanglewood Music Center
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