Chatham Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to CA $4,200 when you book a flight and hotel together*
  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
  • Rest easy

    Plan, book, and manage your trip all in one place

Your Chatham Vacation

Spend less time travel planning and more time having thrilling adventures with a Chatham vacation package. The neighborhood of Harwich Center, which is great for golfing and festivals, makes a great base for your city escape. If your trip to Chatham includes some sightseeing, take in renowned attractions like Chatham Lighthouse Beach, Bank Street Beach and Chatham Lighthouse. Check out Expedia's extensive range of travel options and begin planning your ultimate vacation to Chatham now.

Top Chatham Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Nantucket Inn

Nantucket Inn

CA $1,594
per person
Sep 28 - Oct 2
found 3 hours ago
Roundtrip flight included
Toronto (YYZ) to Boston (BOS)
9.2/10 Wonderful! (759 reviews)
Iris Hotel Boston

Iris Hotel Boston

Coolidge Corner
CA $1,633
per person
Oct 26 - Nov 2
found 22 hours ago
Roundtrip non-stop flight included
Vancouver (YVR) to Boston (BOS)
9.4/10 Exceptional! (624 reviews)
all good

Reviewed on Aug 14, 2026

The Langham, Boston

The Langham, Boston

Downtown Boston
CA $1,805
per person
Oct 8 - Oct 11
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9.6/10 Exceptional! (1,002 reviews)
I’ve stayed at the Langham before and have never been disappointed! The staff is incredible, housekeeping is superb and the property itself is just beautiful!

Reviewed on Aug 13, 2026

Four Seasons Hotel Boston

Four Seasons Hotel Boston

Bay Village
CA $5,610
per person
Oct 18 - Oct 25
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9.4/10 Exceptional! (475 reviews)
Overrated

Reviewed on Aug 10, 2026

The Whitney Hotel

The Whitney Hotel

Beacon Hill
CA $1,898
per person
Oct 8 - Oct 11
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9.6/10 Exceptional! (600 reviews)

Things to do in and around Chatham

Chatham, Massachusetts, is perfect for a beach and outdoor vacation, offering scenic views and activities for the whole family. Enjoy golf at local courses, unwind at playgrounds, and partake in tennis programs. Whether you're planning a family holiday or a golf getaway, Chatham's charming beaches and inviting atmosphere make it an ideal destination for relaxation and recreation.

Shopping

In Chatham, visit the Chatham Fish Pier for local seafood vibes and unique finds. For a short drive, check out Rail Trail Bike Shop, just 11.3km away. If you're up for a drive, head to Atlantic Spice Company, located 40.2km from Chatham, for specialty items.

Recreation

Experience the cultural charm at Chatham Drama Guild, where live performances create unforgettable memories. Enjoy the energetic atmosphere at Veterans Field, perfect for sports enthusiasts. For a serene outdoor escape, tee off at Captain's Cove Golf Course, just 6.4km away, surrounded by picturesque landscapes.

Adventure

Experience thrilling fun at Orleans Bowling Center, an arcadeAdventureZone located 11.3km from Chatham, perfect for family excitement. For adrenaline, head to Bud's Go Karts, also 11.3km away, where you can race against friends. Explore the outdoors at Harwich Herring Run, situated 12.9km from Chatham, and enjoy the natural beauty.

Nightlife

Chatham's nightlife offers a charming coastal vibe. Enjoy fresh seafood and local wines at The Impudent Oyster. For a laid-back evening, visit Chatham Squire for lively music and a friendly atmosphere. Don't miss the stunning sunset views at the beach before heading out for the night.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

Find the best attractions near Chatham

Chatham, Massachusetts, is a fantastic destination for beach lovers and outdoor enthusiasts alike. Explore its stunning beaches, picturesque golf courses, and charming neighbourhoods. Enjoy a mix of culture and nature on Chatham Island, and don’t hesitate to ask locals any questions you have about the area. With its beautiful scenery and array of activities, Chatham promises a memorable vacation experience.

  • Skaket Beach: Located 12.9km from Chatham, Skaket Beach offers beautiful sandy shores and stunning sunsets. It's an ideal spot for families looking to enjoy beach vibes, swimming, and beachcombing along the calm waters of Cape Cod Bay.
  • Hardings Lighthouse: Just 3.2km from Chatham, this historic lighthouse is rich in maritime culture. Visitors can marvel at its architecture and enjoy picturesque views of the coastline, making it a perfect spot for history enthusiasts and photographers alike.
  • Cape Cod Museum of Natural History: Situated 14.5km from Chatham, this museum provides a family-friendly experience with engaging exhibits about local ecosystems and wildlife. It's an excellent opportunity to learn and appreciate the natural history of Cape Cod.

Best time to go to Chatham

The best time to visit Chatham is dependent on what kind of holiday you are seeking. August is its hottest month on average. At this time, visitor numbers are moderately high and weather is mostly sunny with light rain. February is its coolest month on average. At this time, visitor numbers are average and weather is mostly cloudy with light rain.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January35.6°F (2.0°C)Light RainMostly CloudyAverageSlightly Low
February35.4°F (1.9°C)Light RainMostly CloudyAverageSlightly Low
March38.5°F (3.6°C)Light RainMostly CloudyAverageSlightly Low
April45.3°F (7.4°C)Light RainMostly SunnyAverageAverage
May53.1°F (11.7°C)Light RainMostly SunnyAverageAverage
June61.7°F (16.5°C)Light RainMostly SunnyModerately HighSlightly High
July69.6°F (20.9°C)Light RainMostly SunnyModerately HighSlightly High
August70.3°F (21.3°C)Light RainMostly SunnyModerately HighSlightly High
September65.7°F (18.7°C)Light RainMostly SunnyAverageAverage
October57.9°F (14.4°C)Light RainMostly SunnyModerately LowAverage
November48.6°F (9.2°C)Light RainMostly SunnyModerately LowAverage
December41.5°F (5.3°C)Light RainMostly CloudyModerately LowAverage

Tips to save on your trip to Chatham

  • Combine your flights, hotels and car rentals on Expedia—bundling can result in significant savings.
  • Consider traveling to Chatham during the low season (January to March) for more affordable options.
  • Use the Price per traveler filter on Expedia to find a package deal that suits your budget.
  • Check the VIP Access properties filter to discover outstanding hotels with added member perks at select properties.

Chatham Beach Vacation

There's nothing that can beat a Chatham vacation. 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 travelers will tell you to stay near Ridgevale Beach, located just 3 kilometres from the town center. However, you'll also find a fantastic range of Chatham vacation packages close to Hardings Beach and Cockle Cove Beach, two other well-loved nearby options.

Ready to book your vacation to Chatham?

Choose your dates

Chatham Hotel Deals

Chatham Bars Inn

Chatham Bars Inn

297 Shore Rd Chatham MA
CA $806
CA $922 total
Sep 14 - Sep 15
includes taxes & fees
Chatham Bars Inn
Chatham Wayside Inn

Chatham Wayside Inn

512 Main St Chatham MA
CA $552
CA $692 total
Sep 1 - Sep 2
includes taxes & fees
9.2/10 Wonderful! (718 reviews)
"Spacious room, lovely pool, clean, great location (heart of downtown)"

Reviewed on Aug 12, 2026

Chatham Wayside Inn
Queen Anne Inn

Queen Anne Inn

70 Queen Anne Rd Chatham MA
8.6/10 Excellent! (268 reviews)
"Amenities? What amenities? There was a pool nice, balcony nice, ice none broken machine, room above constant stomping in room above early morning and evening. Didn't clean room second day until late afternoon, came back to 4 people in the room. Refridgerator in room very noisy sounded like a machine ..."

Reviewed on Aug 10, 2026

Get rates
Queen Anne Inn
See all 5,033 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 lighthouse with a glass enclosure and metal railing, set against a partly cloudy sky.

Chatham Lighthouse

9.4/10 (173 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.
See properties
A windmill, a boat, and a beach.

Chatham Windmill

9.2/10 (38 reviews)
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 seaside in this trendy area, or check out its seafood restaurants.
See properties
A calm sea with several boats anchored near the shore.

Chatham Fish Pier

9.4/10 (107 reviews)
After visiting Chatham Fish Pier, make a plan to see the other sights and activities in Chatham. Wander the beautiful beaches and seaside in the area.
See properties

Chatham Drama Guild

8.4/10 (6 reviews)
You can enjoy a show at Chatham Drama Guild during your trip to Chatham. Wander the area's beautiful beaches or simply enjoy one of its seafood restaurants.
See properties

Chatham Seaside Links

9.2/10 (20 reviews)
Enjoy a round of golf in Chatham at Chatham Seaside Links. Wander the area's beautiful beaches or simply enjoy one of its seafood restaurants.
See properties

Mayo House

8.0/10 (3 reviews)
Learn about the local history of Chatham when you take a trip to Mayo House. Wander the area's beautiful beaches or simply enjoy one of its seafood restaurants.
See properties

Atwood House Museum

6.0/10 (1 review)
You can spend an afternoon studying the exhibits at Atwood House Museum during your travels in Chatham. Stroll along the beautiful beaches in this trendy area, or check out its seafood restaurants.
See properties

Chatham Railroad Museum

8.8/10 (3 reviews)
You can spend an afternoon browsing the exhibits at Chatham Railroad Museum during your travels in Chatham. Stroll along the area's beautiful beaches, or simply savor its seafood restaurants.
See properties

Frequently asked questions

How much does a Chatham vacation package cost?
You can grab a vacation package to this destination from CA $1,594 on Expedia. But how much your vacation to Chatham costs will depend on factors like the season, length of stay and hotel choice.
What are the cheapest months to go to Chatham?
You're likely to find lower rates and greater availability in January, February and March. Explore our cheap Chatham vacation packages and you could land some great off-season discounts.
How many days is enough for Chatham?
We'd recommend booking a Chatham vacation for at least 3 days. This gives you time to check off key attractions including Bank Street Beach and Ridgevale Beach, as well as explore neighbourhoods like South Chatham and South Harwich. You could even make time for a day trip (or two) beyond Chatham.
Is it worth booking a vacation package to Chatham?
Chatham offers everything you need for a wonderful trip. Get your Chatham vacation off to a flying start by visiting top attractions like Ridgevale Beach.
How to find the best Chatham package deals?
Use Expedia's filters to find some tempting Chatham package deals. When you start your search, simply set your maximum budget and then order the results by "Price: low to high." If you're looking to save, plan your adventure for midweek, or look for Chatham package deals in the low season. Play around with your travel dates and you may land even better discounts. As a rule of thumb, it's usually best to lock in your vacation package well in advance.
Is it cheaper to book a Chatham vacation as a package?
An Expedia vacation package could land you considerable savings when compared to booking flights and stays individually. Better still, you can personalize your Chatham trip to fit your exact style. Pick your preferred flight time, select the hotel type and add a car rental. Check out our great deals to see how much you can save.
When to book a vacation package to Chatham?
Enjoy amazing discounts by reserving your flights in advance with Expedia. If being spontaneous is more your style, snap up one of our last-minute deals for a spur-of-the-moment Chatham trip.
How to plan a trip to Chatham?
  1. Choose your dates: The things you want to do in Chatham and your favourite season can help you decide when to go.
  2. Plan your budget wisely: On top of the price of your accommodations, you should consider other expenses too. These include flights, transportation and food. Also, put aside a little extra for unexpected costs that could crop up during your trip to Chatham.
  3. Set the duration of your trip: Start by compiling a list of the activities and attractions you want to experience in Chatham. Then, estimate how long you'll need at each, including any travel time.
  4. Combine your airfare and accommodations: Once you've nailed down your dates and duration, lock in the perfect Chatham vacation package for you.

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.