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

The Manchester View
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
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.


Brook Bound Inn
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.


Aspen At Manchester
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
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
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
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
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
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
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.



Chesterwood Last Minute Hotel Deals

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 ...

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 ...

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 ...

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 ...

The Little Lion
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 ...

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.
Discover Other Travel Deals
- Legoland Florida
- Universal Studios Hollywood®
- Legoland California
- Broadway New York
- The Wizarding World of Harry Potter
- Sanibel Captiva Island
- Paseo de España
- Universal Studios Florida
- San Antonio SeaWorld
- Siargao Island
- Australia Zoo
- Busch Gardens Tampa Bay
- SeaWorld® Orlando
- Tolantongo Caves
- Eleuthera and Harbour Island
- Biltmore Estate
- Blue Lagoon
- Swiss Alps
- Silver Dollar City
- Lackland Air Force Base
- Grand Teton National Park
- San Diego Zoo
- Holy Land Experience
- Grand Ole Opry
- Ark Encounter
- Levi's Stadium
- Breckenridge Ski Resort
- Alcatraz Island
- Six Flags Magic Mountain
- Walt Disney World®
- Dollywood
- Kalahari Waterpark Resort
- Giza Pyramid Complex
- Casino at Don Laughlin's Riverside Resort
- Hoover Dam
- Hollywood Beach
- Faisalabad Clock Tower
- Venice Beach Boardwalk
- Blue Lagoon Beach
- Moraine Lake
- Family Hotels in South Lee
- Hotel Wedding Venues in South Lee
- Historic Hotels in South Lee
- Hotels with Free Parking in South Lee
- Romantic Hotels in South Lee
- Adults Only Resorts & Hotels in South Lee
- Hotels with Hot Tubs in South Lee
- Resorts & Hotels with Spas in South Lee
- Pet-friendly Hotels in South Lee
- Luxury Hotels in South Lee
- Upstate New York Hotels
- Lenox Hotels
- Hudson Hotels
- The Berkshires Hotels
- Williamstown Hotels
- Pittsfield Hotels
- Great Barrington Hotels
- Hudson Valley Hotels
- Stockbridge Hotels
- Lee Hotels
- Hancock Hotels
- Appalachian Mountains Hotels
- Otis Hotels
- Western Massachusetts Hotels
- South Lee Hotels
- Housatonic Hotels
Hotels Near Points of Interest in Chesterwood
- Hotels near Tanglewood Music Center
- Hotels near National Shrine of the Divine Mercy
- Hotels near Catamount Ski Area
- Hotels near Ski Butternut
- Hotels near Lee Premium Outlets
- Hotels near Norman Rockwell Museum
- Hotels near Jacob's Pillow
- Hotels near Bousquet Ski Area
- Hotels near The Mount
- Hotels near Taconic State Park
- Hotels near Naumkeag Museum
- Hotels near Hancock Shaker Village
- Hotels near Housatonic River Walk
- Hotels near Berkshire Botanical Garden
- Hotels near Shakespeare and Company
- Hotels near Catamount Aerial Adventure Park
Car Rentals in Chesterwood
- Car rentals in Upstate New York
- Car rentals in Lenox
- Car rentals in Hudson
- Car rentals in The Berkshires
- Car rentals in Williamstown
- Car rentals in Pittsfield
- Car rentals in Great Barrington
- Car rentals in Hudson Valley
- Car rentals in Stockbridge
- Car rentals in Lee
- Car rentals in Hancock
- Car rentals in Appalachian Mountains
- Car rentals in Otis
- Car rentals in Western Massachusetts
- Car rentals in South Lee
- Car rentals in Housatonic