Exclusive Chesterwood Vacation Deals

Chesterwood vacation package deals

Price found within the past 48 hours. Click for updated prices.
Urban Cowboy Lodge

Urban Cowboy Lodge

5 out of 5
Price was CA $896, price is now CA $891 per person
CA $891
per person
Nov 16 - Nov 20
found 17 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Albany (ALB)
Stay at this 5-star luxury lodge in Big Indian. Enjoy free WiFi, free parking, and a sauna. Our guests praise the helpful staff in our reviews. Popular attractions Catskill Mountains and Catskill State Park are located nearby.
Kingston Carriage House

Kingston Carriage House

4 out of 5
Roundout
Price was CA $2,194, price is now CA $1,676 per person
CA $1,676
per person
Nov 6 - Nov 12
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Albany (ALB)
Stay at this 4-star B&B in Kingston. Enjoy free breakfast, free WiFi, and in-room massages. Popular attractions Hudson River Maritime Museum and Trolley Museum of New York are located nearby.
Relax in Style at Historic Modern on Main With Modern Amenities & Wooded Views

Relax in Style at Historic Modern on Main With Modern Amenities & Wooded Views

3 out of 5
Price was CA $1,956, price is now CA $1,566 per person
CA $1,566
per person
Nov 6 - Nov 12
found 1 day ago
Roundtrip flight included
Toronto (YYZ) 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.
The Hideout Catskills Cottage

The Hideout Catskills Cottage

2 out of 5
Price was CA $1,978, price is now CA $1,696 per person
CA $1,696
per person
Nov 6 - Nov 12
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Albany (ALB)
Stay at this vacation home in Kingston. Enjoy free parking and a garden. Popular attractions Rosendale Trestle and Rosendale Public Library are located nearby.
Saratoga Lakeside Retreat

Saratoga Lakeside Retreat

2 out of 5
Price was CA $2,885, price is now CA $2,473 per person
CA $2,473
per person
Nov 17 - Nov 20
found 18 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Albany (ALB)
Book a stay at this beach aparthotel in Saratoga Springs. Enjoy free WiFi, free parking, and a private beach. Popular attractions Saratoga Performing Arts Center and Saratoga Race Course are located nearby.
Hasbrouck House

Hasbrouck House

4 out of 5
Price was CA $3,499, price is now CA $3,092 per person
CA $3,092
per person
Nov 7 - Nov 14
found 1 day ago
Roundtrip flight included
St. John's (YYT) to Albany (ALB)
Stay at this 4-star business-friendly hotel in Stone Ridge. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Mohonk Lake and Tongore Park Beach are located nearby.

Frequently asked questions

How much are vacation packages to Chesterwood?
Grab an express ticket to an impressive deal with Travelocity's CA $891 Chesterwood vacation package. Not only will you save serious money on your hotel stay and flights, you can also add on some fun local experiences or even a rental vehicle.
Where can I get the best vacation package deals for Chesterwood?
There are fantastic Chesterwood package deals to be snapped up with Travelocity. Did you know we partner with as many as 400 airlines and 665,000 properties worldwide? Remember this the next time you're ready to check another destination off the old bucket list.
Why should I purchase my Chesterwood vacation package with Travelocity?
We take the stress out of travel planning. Whether you're seeking an amazing new place to explore or want to ensure you get the best price on offer, we're here to assist. Our 24/7 customer support, quality service and Price Match Guarantee mean you can confidently book with Travelocity.
Can I go on vacation to Chesterwood at this time?
Don't plan your trip to Chesterwood without the facts about travel restrictions and quarantine policies. Travelocity's Covid-19 Travel Advisor can fill in the blanks. It has all the info you need to make your getaway as relaxed as possible.

Top Chesterwood hotel deals

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
The price is CA $427 per night
CA $427
CA $516 total
Oct 14 - Oct 15
includes taxes & fees
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 are located nearby.
Pool
Breakfast included
The Red Lion Inn

The Red Lion Inn

3.5 out of 5
30 Main Street, Stockbridge, MA
Free cancellation
Reserve now, pay when you stay
The price is CA $239 per night
CA $239
CA $329 total
Sep 28 - Sep 29
includes taxes & fees
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 condition in our reviews. Popular attractions Tanglewood Music Center and Schantz Galleries are located nearby.
Pool
Spa
Secluded Family Home in Serene Stockbridge Woods

Secluded Family Home in Serene Stockbridge Woods

Stay at this vacation home in South Lee. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Tanglewood Music Center and Berkshire Botanical Garden are located nearby.
Kitchen
Washer
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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.

Best Lodging Options Near Chesterwood