Chatham Holidays

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Chatham Beach Holiday

There's nothing that can beat a Chatham holiday. Whether you're indulging in fancy cocktails at a local hot spot or flipping through a book by the shore, your trip to Chatham is the perfect time to live out your beachy dreams. Many travellers will tell you to stay near Ridgevale Beach, located just 3 kilometres from the town centre. However, you'll also find a fantastic range of Chatham holiday packages close to Hardings Beach and Cockle Cove Beach, two other well-loved nearby options.

Top hotels in Chatham

Chatham Bars Inn

Chatham Bars Inn

5 out of 5
297 Shore Rd Chatham MA
The price is S$1,530 per night from 21 Jul to 22 Jul
S$1,530
21 Jul - 22 Jul
includes taxes & fees
9.2/10 Wonderful! (843 reviews)
"Nice location with short walk into Chatham. Restaurants were good with great views. Overall we had a very nice stay."

Reviewed on 5 Jul, 2026

Chatham Bars Inn
Chatham Wayside Inn

Chatham Wayside Inn

4 out of 5
512 Main St Chatham MA
The price is S$495 per night from 7 Jul to 8 Jul
S$495
7 Jul - 8 Jul
includes taxes & fees
9.2/10 Wonderful! (702 reviews)
"Our stay at the Chatham Wayside Inn was a very pleasant 5-night stay. The staff was friendly and the king room we had was very clean and well appointed. They have a continental breakfast, which does include scrambled eggs and a nice variety of breads and muffins. The fresh fruit was also amazing! ..."

Reviewed on 3 Jul, 2026

Chatham Wayside 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 S$418 per night from 20 Jul to 21 Jul
S$418
20 Jul - 21 Jul
includes taxes & fees
8.8/10 Excellent! (247 reviews)
"My wife and I stayed in the Balcony Queen. The check in/out process was very simple. The room was quaint and we were pretty comfortable. I liked the balcony space to relax and use as an extra space if I didn't want to stay inside. The bathroom could use with some modern touches but it had plenty ..."

Reviewed on 4 Jul, 2026

Queen Anne Inn
See all 5,036 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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What to do in Chatham

Private Vacation Photoshoot with Photographer in Cape Cod

Private Vacation Photoshoot with Photographer in Cape Cod

S$409
per adult
Private Vacation Photoshoot with Photographer in Cape Cod
See all activities in Chatham

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.

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. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.