Chatham Vacations from $487

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to $1,045 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place

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.

The Latest Chatham vacation packages

Price found within the past 48 hours. Click for updated prices.
The Landing Hotel at Rivers Casino & Resort

The Landing Hotel at Rivers Casino & Resort

4 out of 5
Stockade Historic District
Price was $756, price is now $487 per person
$487
per person
Feb 26 - Mar 3
found 1 day ago
Roundtrip non-stop flight included
Chicago (CHI) to Albany (ALB)
9.2/10 Wonderful! (1,005 reviews)
Everything about our stay was perfect! The lady at check-in was super friendly, the room was extremely clean and modern. Definitely recommend The Landing!

Reviewed on Nov 23, 2025

Brook Bound Inn

Brook Bound Inn

2 out of 5
Save 100% on your flight
Price was $1,190, price is now $760 per person
$760
per person
Feb 19 - Feb 24
just found
Roundtrip non-stop flight included
Miami (MIA) to Albany (ALB)
9.6/10 Exceptional! (11 reviews)
Great property. Amazing views!

Reviewed on Dec 2, 2024

The Manchester View

The Manchester View

2.5 out of 5
Save 100% on your flight
Price was $1,403, price is now $1,037 per person
$1,037
per person
Feb 19 - Feb 24
just found
Roundtrip non-stop flight included
Miami (MIA) to Albany (ALB)
9.4/10 Exceptional! (772 reviews)
I would stay in our original accommodation but I found it small so we upgraded to a room with a king bed and fireplace. Glad we did. It was amazing. The views are fantastic on a clear day. Staff are welcoming and friendly.

Reviewed on Dec 5, 2025

The Equinox Golf Resort & Spa

The Equinox Golf Resort & Spa

4.5 out of 5
Save 100% on your flight
Price was $1,718, price is now $1,285 per person
$1,285
per person
Feb 19 - Feb 24
found 1 day ago
Roundtrip non-stop flight included
Miami (MIA) to Albany (ALB)
7.4/10 Good! (567 reviews)
Nicely decorated for Christmas. Helpful and attentive staff, Lack of heat in some of the public areas like near the library was an issue, but they tried by keeping the fireplace going. As a helpful hint- the fireplace area in the library was drafty and cold. You can go a long way toward fixing this by repairing or replacing that door that leads outside. There’s a 1 inch gap there. Also, while this is an issue, close those 2 inside doors. That works.

Reviewed on Dec 7, 2025

Wilburton Inn

Wilburton Inn

3.5 out of 5
Price was $1,257, price is now $950 per person
$950
per person
Feb 19 - Feb 24
just found
Roundtrip non-stop flight included
Miami (MIA) to Albany (ALB)
9/10 Wonderful! (128 reviews)
Great service all around

Reviewed on Mar 5, 2025

Don't see what you're looking for?
See all available trips from Columbus to Chatham
View all trips

Discover the most popular places to visit in Chatham

The Mac-Haydn Theatre

You can enjoy a show at The Mac-Haydn Theatre on your trip to Chatham. Stroll along this trendy area's riverfront, or simply enjoy its coffeehouses.

The Mac-Haydn Theatre

Chatham Hotel Deals

Vacation Village in the Berkshires

Vacation Village in the Berkshires

3 out of 5
276 Brodie Mountain Rd Williamstown MA
$126 nightly
The price is $141 total per night from Dec 14 to Dec 15
$141 total
Dec 14 - Dec 15
Total with taxes and fees
8.6/10 Excellent! (2,166 reviews)
Clean spacious toom

Reviewed on Dec 6, 2025

Vacation Village in the Berkshires
Comfort Inn Glenmont - Albany South

Comfort Inn Glenmont - Albany South

2.5 out of 5
37 Route 9W Glenmont NY
Fully refundable
$79 nightly
The price is $91 total per night from Dec 19 to Dec 20
$91 total
Dec 19 - Dec 20
Total with taxes and fees
7.8/10 Good! (1,001 reviews)
Very clean and modern room with comfortable beds.

Reviewed on Nov 29, 2025

Comfort Inn Glenmont - Albany South
Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG

3 out of 5
One West Street Pittsfield MA
Fully refundable
$93 nightly
The price is $104 total per night from Dec 14 to Dec 15
$104 total
Dec 14 - Dec 15
Total with taxes and fees
8/10 Very Good! (979 reviews)
Clean room, convenient and tasty restaurant

Reviewed on Dec 5, 2025

Holiday Inn & Suites Pittsfield-Berkshires by IHG
See all 1,590 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.

Find the Best Chatham Vacation Packages

Chatham Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Albany Intl. Airport (ALB)
Population
1,700
Max Temp Winter
30ºF
Max Temp Summer
80ºF
Top Sights
The Mac-Haydn Theatre, Shaker Museum and Library and Hudson Chatham Winery

More vacations you might like

All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Kid Friendly Vacations
Kid Friendly Vacations

Frequently asked questions

How much does a Chatham vacation package cost?
You'll find cheap prices from $487 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?
If you'd like to snag a cheap Chatham vacation package, consider traveling in June, September and October. You'll typically find better rates on flights and hotels during these months — ideal for travelers wishing to save money.
How many days is enough for Chatham?
The ideal length for your Chatham vacation depends on what you'd like to see and do. Typically, a few days to a week will give you time to check out all the top attractions 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.
Does Expedia offer Book Now, Pay Later Chatham vacation packages?
If you're anything like us, you love exploring new places but are not a fan of the price tag that can come with it. That's why we've created Book Now, Pay Later vacations. With the help of online lender Affirm, you can spread the total cost of your Chatham trip over 3, 6 or 12 months. There are also no hidden or late payment fees, so you can snap up cheap vacation packages with payment plans as soon as you spot them.

Explore a world of travel with Expedia

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