Chatham Holidays

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Chatham Holiday

Our pick of the best Chatham Hotel Deals

Chatham Bars Inn
Chatham Bars Inn
5 out of 5
297 Shore Rd, Chatham, MA
The price is NZ$770 per night from 1 May to 2 May
NZ$770
includes taxes & fees
1 May - 2 May
9/10 Wonderful! (752 reviews)
"Amazing place for a quick getaway or a long stay. The campus was gorgeous and the staff was delightful."

Reviewed on 30 Mar. 2025

Chatham Bars Inn
Chatham Wayside Inn
Chatham Wayside Inn
4 out of 5
512 Main St, Chatham, MA
The price is NZ$456 per night from 17 Apr to 18 Apr
NZ$456
includes taxes & fees
17 Apr - 18 Apr
9.2/10 Wonderful! (479 reviews)
Wayside Never Disappoints
"Freshly baked chocolate chunk cookies were lovely. Gentleman who checked us in late st night was our favorite desk clerk. Location was excellent in quaint downtown Chatham. Continental breakfsst had a nice selection of fresh pastries, fruit and yogurt. Boiled eggs were rubbery and In edible bed was ..."

Reviewed on 10 Apr. 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 Oct. 2024

Greyfinch Chatham Inn
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 holiday package cost?
Offering excellent value package deals on Expedia, you’ll be pleasantly surprised at how much a holiday 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 holiday packages. Choosing to travel in quieter periods means you’ll typically find better prices on accommodation and flights.
How many days is enough for Chatham?
We’d recommend booking a Chatham holiday for a minimum of 3 days. This gives you time to tick off top attractions including Chatham Drama Guild and Monomoy National Wildlife Refuge, and also explore neighbourhoods like South Chatham and South Harwich. You could even squeeze in one or two day trips beyond Chatham.
Is it worth booking a holiday package to Chatham?
Chatham has everything you need for a wonderful escape. Begin your Chatham holiday on a high note by checking out top attractions like Ridgevale Beach.
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 holiday as a package?
An Expedia holiday 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 holiday 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 customised Chatham holiday package.

Discover the most popular places to visit in Chatham

What to do in Chatham

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