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 Ponds at Foxhollow by Capital Vacations

The Ponds at Foxhollow by Capital Vacations

3 out of 5
per person
Apr. 25 - Apr. 28
found 2 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Albany (ALB)
8.6/10 Excellent! (120 reviews)
Very comfortable property in a lovely setting

Reviewed on Dec. 18, 2024

Gedney Farm

Gedney Farm

3.5 out of 5
per person
Apr. 25 - Apr. 28
found 2 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Albany (ALB)
9.2/10 Wonderful! (118 reviews)
A perfect little getaway!

Reviewed on Nov. 27, 2024

Little Cat Lodge

Little Cat Lodge

2 out of 5
per person
Apr. 25 - Apr. 28
found 2 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Albany (ALB)
9.2/10 Wonderful! (32 reviews)
Delightful stay at the Little Car Lodge - Kimberley was attentive to every little details to make our stay fantastic! We received a call to indicates s’mores packages were available, our table was dressed for 4, including dining set and chair for our daughter’s doll… a magical Holiday week 2 steps from the slopes!

Reviewed on Dec. 31, 2024

Wilder House Berkshires

Wilder House Berkshires

2 out of 5
per person
Apr. 25 - Apr. 28
found 2 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Albany (ALB)
10/10 Exceptional! (15 reviews)
Beautiful, charming property. The rooms are clean and comfortable. The owner makes you feel like you’re home! Breakfast was delicious, thank you!

Reviewed on Jan. 26, 2025

Berkshire Mountain Lodge

Berkshire Mountain Lodge

3 out of 5
per person
Apr. 25 - Apr. 28
found 2 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Albany (ALB)
8.8/10 Excellent! (424 reviews)
Nice place kind of dirty though found 2 dead bugs and a spider as soon as we walked in dusty too and a few outlets didn’t work in room too hot tub and pool were nice just needs to be clean hallways/elevator and room not cleaned well people and front Desk people are miserable

Reviewed on Jan. 13, 2025

Ready to book your vacation to Chatham?

 

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Chatham Hotel Deals

Life House Berkshires
Life House Berkshires
3.5 out of 5
194 Pittsfield Rd, Lenox, MA
Fully refundableReserve now, pay when you stay
The price is CA $140 per night from Feb. 2 to Feb. 3
CA $140
CA $156 total
includes taxes & fees
Feb 2 - Feb 3
9/10 Wonderful! (485 reviews)
"Rooms were very clean. Entire place smelled amazing. Very comfortable!"

Reviewed on Jan. 27, 2025

Life House Berkshires
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 $142 per night from Feb. 7 to Feb. 8
CA $142
CA $162 total
includes taxes & fees
Feb 7 - Feb 8
7.8/10 Good! (926 reviews)
"Great place to stay and accesible"

Reviewed on Jan. 21, 2025

Comfort Inn Glenmont - Albany South
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires, an IHG Hotel
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires, an IHG Hotel
3.5 out of 5
190 Meadow Street, South Lee, MA
Fully refundable
The price is CA $171 per night from Mar. 3 to Mar. 4
CA $171
CA $212 total
includes taxes & fees
Mar 3 - Mar 4
8.8/10 Excellent! (591 reviews)
"Plenty of room. Good location to local skiing. Clean."

Reviewed on Jan. 21, 2025

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires, an IHG Hotel
See all 1,519 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.

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 $769 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.