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.
By the Sea Guests Bed & Breakfast & Suites
The Langham, Boston
The Inn at Hastings Park, Relais & Chateaux - Boston
Hilton Boston Park Plaza
Raffles Boston

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.

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Chatham Hotel Deals

Chatham Bars Inn

Chatham Bars Inn

5 out of 5
297 Shore Rd Chatham MA
The price is CA $566 per night from May 17 to May 18
CA $566
CA $647 total
May 17 - May 18
includes taxes & fees
9.2/10 Wonderful! (821 reviews)
Absolutely wonderful stay. My room was in the main inn, and it was peaceful and beautiful. I can’t wait to go back!

Reviewed on Apr 23, 2026

Chatham Bars Inn
Chatham Wayside Inn

Chatham Wayside Inn

4 out of 5
512 Main St Chatham MA
The price is CA $317 per night from May 27 to May 28
CA $317
CA $421 total
May 27 - May 28
includes taxes & fees
9.4/10 Exceptional! (664 reviews)
Centrally located. You can go anywhere on the Cape in 30 minutes.

Reviewed on Apr 25, 2026

Chatham Wayside Inn
Captain's House Inn

Captain's House Inn

4 out of 5
369 Old Harbor Road Chatham MA
9.8/10 Exceptional! (217 reviews)
Amazing. Staff was great, breakfast was delicious. Only down side for me was the soft bed. But I like a firm bed.

Reviewed on Apr 19, 2026

Captain's House 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.

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