Chatham Vacations

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Find the Best Chatham Vacation Packages

Chatham Hotel Deals

Chatham Bars Inn
Chatham Bars Inn
5 out of 5
297 Shore Rd, Chatham, MA
The price is SAR 1,419 per night from May 1 to May 2
SAR 1,419
SAR 1,705 total
includes taxes & fees
1 May - 2 May
9/10 Wonderful! (751 reviews)
"Amazing place for a quick getaway or a long stay. The campus was gorgeous and the staff was delightful."

Reviewed on 30 March 2025

Chatham Bars Inn
Chatham Wayside Inn
Chatham Wayside Inn
4 out of 5
512 Main St, Chatham, MA
The price is SAR 747 per night from Apr 6 to Apr 7
SAR 747
SAR 1,005 total
includes taxes & fees
6 Apr - 7 Apr
9.2/10 Wonderful! (477 reviews)
"Everything was great! Smart TVs would be nice."

Reviewed on 30 March 2025

Chatham Wayside Inn
Greyfinch Chatham Inn
Greyfinch Chatham Inn
3 out of 5
946 Main Street (Rte 28), Chatham, MA
8.6/10 Excellent! (213 reviews)
Loved it
"I really enjoyed my three night stay here while I attended a painting workshop at the Creative Arts Centre. The rooms have been totally renovated and it was a very well done reno. Very clean and in a convenient location. Love the big walk in shower with the rain shower head. There is a Keurig coffee ..."

Reviewed on 12 October 2024

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Greyfinch Chatham Inn
See all 4,821 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.

Frequently asked questions

How much does a Chatham vacation package cost?
Offering excellent value package deals on Expedia, you’ll be pleasantly surprised at how much a vacation to Chatham costs! Our packages mean less travel planning for you and greater savings.
What are the cheapest months to go to Chatham?
January, February and March are great times to search for cheap Chatham vacation packages. Choosing to travel in quieter periods means you’ll typically find better prices on accommodations and flights.
How to find the best Chatham package deals?
Start your search for a Chatham package deal by entering your destination and preferred trip dates under our “Packages” tab. Then add a few filters, like “Popular locations” and “Amenities,” to fine-tune the results to your exact needs. You can also sort by “Package discount” and browse offers that come with big savings. If you don’t find the ideal Chatham package deal straight away, just play around with your dates and search again. Remember 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 great savings when compared to booking flights and stays individually. Better still, you can tailor your Chatham trip to fit your exact needs. Choose your preferred flight time, select the hotel type and add a car rental. Browse our bundle deals and find out how much you can save.
When to book a vacation package to Chatham?
If you’re planning a spur-of-the-moment Chatham adventure, check out our last-minute deals that can be booked up to one week before you take off. Prefer not to wait until the last minute? You can score incredible deals on your hotels and flights by booking well in advance.
How to plan a trip to Chatham?

  1. Pick the perfect time to travel: Your schedule, preferred season and the type of weather you enjoy can all impact your decision on when to travel to Chatham.
  2. Work out your budget: Ensure you have enough money to cover everything from meals and transportation to activities and airfares. Your hotel will probably be the largest expense during your trip to Chatham.
  3. Determine how many days away: Start by compiling a list of the sights and activities you want to get to in Chatham. Then, estimate how long you’ll need for each, along with any travel time.
  4. Bundle your bookings: With your travel dates in place, you can combine your hotels, flights, car rental and more into a customized Chatham vacation package.

Discover the most popular places to visit in Chatham

Chatham Lighthouse

Chatham Lighthouse

4.5/5(31 reviews)

Learn about the local history of Chatham when you spend time at Chatham Lighthouse. Wander the beautiful beaches and seaside in this trendy area.

Chatham Lighthouse
Enjoy the view, watch the fishing boats come in and unload their catch, and pick up fresh fish or seafood to take home for dinner at the market.

Chatham Fish Pier

4.5/5(8 reviews)

Explore the waterfront in Chatham with a trip to Chatham Fish Pier. Wander the beautiful beaches and seaside in the area.

Chatham Fish Pier
This windmill, The Godfrey Windmill, in Chase Park has none of its sheets mounted to the vanes. The expression "three sheets to the wind" originated because a windmill with only three sheets deployed will not

Chatham Windmill

Chatham Windmill is just one of the places to see in Chatham, so why not enjoy the other things to explore during your travels? Stroll along the beautiful beaches in this trendy area, or check out its seafood restaurants.

Chatham Windmill