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Chesterwood Vacation Packages

Chesterwood Flight + Hotel Packages

Price found within the past 48 hours. Click for updated prices.
The Manchester View

The Manchester View

2.5 out of 5
per person
May 22 - May 26
found 1 day ago
Roundtrip non-stop flight included
San Juan (SJU) to Albany (ALB)
Stay at this hotel in Manchester Center. Enjoy free breakfast, free WiFi, and free parking. 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.
The Equinox Golf Resort & Spa

The Equinox Golf Resort & Spa

4.5 out of 5
per person
May 22 - May 26
found 1 day ago
Roundtrip non-stop flight included
San Juan (SJU) 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.
Wilburton Inn

Wilburton Inn

3.5 out of 5
per person
May 22 - May 26
found 1 day ago
Roundtrip non-stop flight included
San Juan (SJU) to Albany (ALB)
Stay at this 3.5-star golf hotel in Manchester. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Museum of Creative Process and Hildene are located nearby.
Brook Bound Inn

Brook Bound Inn

2 out of 5
per person
May 22 - May 26
found 1 day ago
Roundtrip non-stop flight included
San Juan (SJU) 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.
Hill Farm Inn

Hill Farm Inn

4 out of 5
per person
May 22 - May 26
found 1 day ago
Roundtrip non-stop flight included
San Juan (SJU) to Albany (ALB)
Stay at this 4-star B&B in Arlington. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Mount Equinox and Norman Rockwell Exhibition are located nearby.
Aspen At Manchester

Aspen At Manchester

2.5 out of 5
per person
May 22 - May 26
found 1 day ago
Roundtrip non-stop flight included
San Juan (SJU) 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.
South Shire

South Shire

4 out of 5
per person
May 22 - May 26
found 1 day ago
Roundtrip non-stop flight included
San Juan (SJU) 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.
Kimpton Taconic Hotel by IHG

Kimpton Taconic Hotel by IHG

4 out of 5
per person
May 22 - May 26
found 1 day ago
Roundtrip non-stop flight included
San Juan (SJU) 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.
The White House Inn

The White House Inn

3.5 out of 5
per person
May 22 - May 26
found 1 day ago
Roundtrip non-stop flight included
San Juan (SJU) 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.
Toll Road Inn

Toll Road Inn

2 out of 5
per person
May 22 - May 26
found 1 day ago
Roundtrip non-stop flight included
San Juan (SJU) 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 Gander Gallery and Battenkill River are located nearby.
The Four Chimneys Inn

The Four Chimneys Inn

4 out of 5
per person
May 22 - May 26
found 1 day ago
Roundtrip non-stop flight included
San Juan (SJU) to Albany (ALB)
Stay at this 4-star golf B&B in Bennington. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular attractions Old First Congregational Church and Bennington Museum are located nearby.
The Inn at Ormsby Hill

The Inn at Ormsby Hill

3.5 out of 5
per person
May 22 - May 26
found 1 day ago
Roundtrip non-stop flight included
San Juan (SJU) to Albany (ALB)
Stay at this 3.5-star ski B&B in Manchester Center. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Hildene and Museum of Creative Process are located nearby.

3-4 Night Vacations in Chesterwood

Price found within the past 48 hours. Click for updated prices.
The Manchester View

The Manchester View

2.5 out of 5
per person
May 22 - May 26
found 1 day ago
Roundtrip non-stop flight included
San Juan (SJU) to Albany (ALB)
The Equinox Golf Resort & Spa

The Equinox Golf Resort & Spa

4.5 out of 5
per person
May 22 - May 26
found 1 day ago
Roundtrip non-stop flight included
San Juan (SJU) to Albany (ALB)
Wilburton Inn

Wilburton Inn

3.5 out of 5
per person
May 22 - May 26
found 1 day ago
Roundtrip non-stop flight included
San Juan (SJU) to Albany (ALB)
Brook Bound Inn

Brook Bound Inn

2 out of 5
per person
May 22 - May 26
found 1 day ago
Roundtrip non-stop flight included
San Juan (SJU) to Albany (ALB)

Chesterwood Last Minute Hotel Deals

The Red Lion Inn
The Red Lion Inn
3.5 out of 5
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 ...
The Red Lion Inn
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
4.5 out of 5
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 Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
Tanglewood Suites
Tanglewood Suites
2.5 out of 5
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 ...
Tanglewood Suites
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
3.5 out of 5
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 ...
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
The Little Lion
The Little Lion
3 out of 5
506 Stockbridge Road, Great Barrington, MA
Stay at this 3-star motel in Great Barrington. Enjoy free WiFi, free parking, and daily housekeeping. Our guests praise the helpful staff in our reviews. Popular ...
The Little Lion
Pleasant Valley Motel West Stockbridge
Pleasant Valley Motel West Stockbridge
2 out of 5
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 ...
Pleasant Valley Motel West Stockbridge
See all 705 properties in Chesterwood
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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