Chatham Vacation Packages

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Your Chatham Vacation

The adventure-packed city of Chatham is calling. Delve into everything from its highlights to its hidden gems with a Chatham vacation package that's customized to you. Any trip to Chatham needs a well-planned itinerary. Fill yours with attractions like Martin Van Buren National Historic Site, Art Omi International Arts Center - Fields Sculpture Park and The Mac-Haydn Theatre. Browse Expedia's wide range of travel options and start organizing your ideal vacation to Chatham today.

Top Chatham Vacation Deals

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

The Manchester View

2.5 out of 5
per person
Feb. 9 - Feb. 15
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Albany (ALB)
9.4/10 Exceptional! (653 reviews)
All the staff members at Manchester View were friendly and helpful. The location was great for skiing at Stratton and close to some wonderful restaurants.

Reviewed on Dec. 24, 2024

The Equinox Golf Resort & Spa

The Equinox Golf Resort & Spa

4.5 out of 5
Save 100% on your flight
per person
Feb. 9 - Feb. 15
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Albany (ALB)
7.4/10 Good! (427 reviews)
A good place but it did not meet my exoectations of a resort.

Reviewed on Nov. 27, 2024

Aspen At Manchester

Aspen At Manchester

2.5 out of 5
per person
Feb. 9 - Feb. 15
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Albany (ALB)
8.6/10 Excellent! (501 reviews)
Clean, comfortable rooms. Friendly and helpful staff. Will stay again

Reviewed on Dec. 23, 2024

South Shire

South Shire

4 out of 5
per person
Mar. 7 - Mar. 11
found 24 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Albany (ALB)
9.2/10 Wonderful! (79 reviews)
It’s a very nice inn and staff were amazing

Reviewed on Dec. 15, 2024

Kimpton Taconic Hotel, an IHG Hotel

Kimpton Taconic Hotel, an IHG Hotel

4 out of 5
per person
Feb. 9 - Feb. 15
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Albany (ALB)
9.4/10 Exceptional! (727 reviews)
Only thing I was not happy with was no bath tub that I would like to warm up in the tub in cold weather place after winter day activities.

Reviewed on Dec. 8, 2024

Ready to book your vacation to Chatham?

 

Choose your dates

Chatham Hotel Deals

Comfort Inn Glenmont - Albany South
Comfort Inn Glenmont - Albany South
2.5 out of 5
37 Route 9W, Glenmont, NY
Fully refundable
The price is CA $138 per night from Jan. 3 to Jan. 4
CA $138
CA $158 total
includes taxes & fees
Jan 3 - Jan 4, 2025
7.8/10 Good! (913 reviews)
Great price and clean
"Nice clean hotel but hot tub was working and restaurant was not open. Great hotel for the price."

Reviewed on Dec. 15, 2024

Comfort Inn Glenmont - Albany South
The Yankee, Trademark Collection by Wyndham
The Yankee, Trademark Collection by Wyndham
2.5 out of 5
461 Pittsfield Rd, Lenox, MA
Fully refundableReserve now, pay when you stay
The price is CA $140 per night from Jan. 5 to Jan. 6
CA $140
CA $156 total
includes taxes & fees
Jan 5 - Jan 6, 2025
9/10 Wonderful! (1,000 reviews)
"Great check in experience."

Reviewed on Dec. 24, 2024

The Yankee, Trademark Collection by Wyndham
The Red Lion Inn
The Red Lion Inn
3.5 out of 5
30 Main Street, Stockbridge, MA
Fully refundableReserve now, pay when you stay
The price is CA $128 per night from Jan. 5 to Jan. 6
CA $128
CA $208 total
includes taxes & fees
Jan 5 - Jan 6, 2025
8.8/10 Excellent! (1,001 reviews)
"Delightful!"

Reviewed on Dec. 26, 2024

The Red Lion Inn
See all 1,502 properties in Chatham
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.

All Inclusive Vacations

All Inclusive Vacations

Beach Vacations

Beach Vacations

Family Vacations

Family Vacations

Frequently asked questions

How much does a Chatham vacation package cost?
You’ll find cheap prices from CA $959 on Expedia for your Chatham getaway. However, factors like your choice of hotel, the season and length of stay will determine how much your vacation to Chatham costs.
What are the cheapest months to go to Chatham?
The off-season is the best time to visit Chatham if you’re trying to save. Another tip for getting cheap Chatham vacation packages? Try to avoid visiting during public holidays and any major events or festivals.
How many days is enough for Chatham?
The ideal duration for your Chatham vacation depends on what you’d like to see and do. Usually, a few days to a week will give you enough time to go to all the top sights and discover some hidden gems along the way.
How to find the best Chatham package deals?
Begin your search for a Chatham package deal by entering your destination and preferred travel dates under our “Packages” tab. Then select some filters, like “Property type” and “Guest rating,” to tailor the results to your exact style. You can also sort by “Package discount” and browse offers that come with big savings. If you don’t find the perfect Chatham package deal straight away, simply tweak your dates and search again. Bear in mind that deals are only available for a limited time, so book early and get your Chatham escape underway.
Is it cheaper to book a Chatham vacation as a package?
An Expedia vacation package could land you considerable savings when compared to booking accommodations and flights separately. Better still, you can tailor your Chatham escape to fit your exact style. Pick your preferred flight time, select the hotel type and add a car rental. Browse our great deals to see how much you can save.
When to book a vacation package to Chatham?
Secure incredible bargains by reserving your flights ahead of time with Expedia. If being spontaneous is more your style, grab one of our last-minute deals for an impromptu Chatham escape.
How to plan a trip to Chatham?

  1. Pick your dates: What you’d like to do in Chatham and your favorite season will help you decide when to get away.
  2. Plan your budget wisely: Besides the price of your hotel, you’ll need to factor in other expenses. These include flights, food and transportation. Also, put aside some extra funds for unexpected costs that may come up during your trip to Chatham.
  3. Decide your trip length: Think about how much time you’d like to spend exploring Chatham. Plan your itinerary so you can get to all the experiences and attractions you’re interested in at a comfortable pace.
  4. Combine your accommodations and airfare: After you’ve settled on your travel dates and duration, lock in the right Chatham vacation package for you.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.