Chatham Holidays

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Top hotels in Chatham

Chatham Bars Inn

Chatham Bars Inn

5 out of 5
297 Shore Rd Chatham MA
The price is 27.188.415 ₫ per night from 26 Jul to 27 Jul
27.188.415 ₫
31.117.142 ₫ total
26 Jul - 27 Jul
includes taxes & fees
9.2/10 Wonderful! (845 reviews)
"Beautiful Cape Cod style Inn with every amenity you could want. Restaurants all had great menu selections"

Reviewed on 10 Jul 2026

Chatham Bars Inn
Queen Anne Inn

Queen Anne Inn

4 out of 5
70 Queen Anne Rd Chatham MA
Fully refundableReserve now, pay when you stay
The price is 7.943.746 ₫ per night from 20 Jul to 21 Jul
7.943.746 ₫
9.091.617 ₫ total
20 Jul - 21 Jul
includes taxes & fees
8.8/10 Excellent! (248 reviews)
"Megan was awesome at the front desk. very helpful and made our stay special. hotel needs a little TLc that's it's going to be getting soon."

Reviewed on 7 Jul 2026

Queen Anne Inn
Chatham Wayside Inn

Chatham Wayside Inn

4 out of 5
512 Main St Chatham MA
The price is 13.034.940 ₫ per night from 15 Jul to 16 Jul
13.034.940 ₫
16.060.866 ₫ total
15 Jul - 16 Jul
includes taxes & fees
9.2/10 Wonderful! (707 reviews)
"We thought the place was good not great. We upgraded to a king room with patio and we got the room right above the restaurant facing the whale art so very little privacy. The rooms advertised online seem much more private. Cute stay though and great location. The breakfast is bare minimum with eggs ..."

Reviewed on 11 Jul 2026

Chatham Wayside Inn
See all 5,037 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.

Stay near popular Chatham attractions

A calm sea with several boats anchored near the shore.

Chatham Fish Pier

9.4/10 (107 reviews)
Watch local fishermen unload their daily catch while seals swim nearby at this authentic working waterfront. Savour fresh seafood from the on-site market while enjoying panoramic harbour views from the observation deck.
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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.

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