Chatham Vacation Packages

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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.
Boston Lodge and Suites

Boston Lodge and Suites

Dorchester
CA $665
per person
Sep 7 - Sep 9
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Boston (BOS)
8.4/10 Very good! (190 reviews)
Parking was not easy. It was advertised as free parming and the explanation made it seem simple enough but finding free street parking in the area is not easy and you co stantly have to move your vehicles.

Reviewed on May 19, 2026

Iris Hotel Boston

Iris Hotel Boston

Coolidge Corner
CA $1,585
per person
Oct 17 - Oct 24
found 12 hours ago
Roundtrip non-stop flight included
Vancouver (YVR) to Boston (BOS)
9.4/10 Exceptional! (612 reviews)
Staff was amazing to deal with. Room was beautiful. Comfortable bed. Great location. I would recommend.

Reviewed on Aug 6, 2026

Boston Harbor Hotel

Boston Harbor Hotel

North End
CA $2,176
per person
Sep 30 - Oct 4
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9.8/10 Exceptional! (1,006 reviews)
This hotel is a dream to stay in. We love it and hope to stay again soon.

Reviewed on Aug 6, 2026

Pier 7 Condominiums

Pier 7 Condominiums

Bass River
CA $854
per person
Sep 6 - Sep 12
found 1 day ago
Roundtrip flight included
Montreal (YUL) to Boston (BOS)
8.6/10 Excellent! (13 reviews)
I loved this place so much! The place was extremely clean and I felt very comfortable during my stay. The air conditioning ran super cold, the kitchen provided most things needed to make a quick meal, and the pool was very comfortable. They also have games and ping pong available.

Reviewed on Aug 6, 2026

By the Sea Guests Bed & Breakfast & Suites

By the Sea Guests Bed & Breakfast & Suites

CA $700
per person
Oct 26 - Oct 29
found 16 hours ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9.4/10 Exceptional! (203 reviews)
Gorgeous location, room and common areas with lots of historic charm mixed with thoughtful touches throughout. Lovely to have the well-kept private beach all set up and ready to enjoy. Room was bright and cheerful and breakfast was delicious as well. If you’re looking for peaceful and quiet, this is a great choice.

Reviewed on Aug 7, 2026

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 $1,019
CA $1,166 total
Sep 3 - Sep 4
includes taxes & fees
9.2/10 Wonderful! (855 reviews)
"For the high cost of"

Reviewed on Aug 5, 2026

Chatham Bars Inn
Queen Anne Inn

Queen Anne Inn

70 Queen Anne Rd Chatham MA
CA $377
CA $432 total
Sep 3 - Sep 4
includes taxes & fees
Queen Anne Inn
Chatham Wayside Inn

Chatham Wayside Inn

512 Main St Chatham MA
CA $555
CA $697 total
Aug 31 - Sep 1
includes taxes & fees
9.2/10 Wonderful! (715 reviews)
"We had to wait for an hour to get into our room. No one was at the desk. We called the number, rang the bell, looked throughout the property, etc. We were about to sleep in our car and finally someone showed up. No apology. We only slept a few hours."

Reviewed on Aug 4, 2026

Chatham Wayside Inn
See all 5,056 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)
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.
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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.
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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.
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A beach at sunset with the sun low on the horizon, casting long shadows on the sand.
Photo by Janice Schlegel

Monomoy National Wildlife Refuge

9.8/10 (14 reviews)
Explore the great outdoors at Monomoy National Wildlife Refuge, a lovely green space in Chatham. Amble around this trendy area's beautiful beaches and enjoy its seafood restaurants.
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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.
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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.
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Caleb Nickerson House

6.0/10 (1 review)
You can spend an afternoon exploring the galleries in Caleb Nickerson House during your trip to Chatham. Amble around this family-friendly area's beautiful beaches and enjoy its seafood restaurants.
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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.
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Frequently asked questions

How much does a Chatham vacation package cost?
You can grab a vacation package to this destination from CA $665 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.