Chatham Vacation Packages 2026 from $620

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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.

The Latest Chatham vacation packages

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

Boston Lodge and Suites

Dorchester

$620

per person

Nov 9 - Nov 12

found 1 day ago

Roundtrip flight included

Dallas (DFW) to Boston (BOS)

8.4/10 Very Good! (190 reviews)

The apt was tidy. Enough to sleep 8. Bathrooms were clean and updated. Parking can be difficult to find. It's about an hour from Salem.

Reviewed on Oct 4, 2026

Raffles Boston

Back Bay

Save 100% on your flight

$1,210

per person

Dec 16 - Dec 20

found 3 hours ago

Roundtrip non-stop flight included

Atlanta (ATL) to Boston (BOS)

9.6/10 Exceptional! (332 reviews)

The Langham, Boston

Downtown Boston

Save 100% on your flight

$770

per person

Dec 29 - Jan 1

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Boston (BOS)

9.8/10 Exceptional! (1,005 reviews)

The staff were incredibly helpful & nice. The hotel was beautiful & great location

Reviewed on Oct 4, 2026

Battery Wharf Hotel, Boston Waterfront

North End

Save 100% on your flight

$658

per person

Nov 12 - Nov 15

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Boston (BOS)

9/10 Wonderful! (2,041 reviews)

Boston Harbor Hotel

North End

Save 100% on your flight

$1,077

per person

Dec 29 - Jan 1

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Boston (BOS)

9.8/10 Exceptional! (1,008 reviews)

Great location. A bit pricey for the size room. Easy to get most places by walking .

Reviewed on Oct 4, 2026

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Stay near popular Chatham attractions

A beach with people walking and standing on the sand, and the ocean in the background.

Chatham Lighthouse Beach

9.2/10 (46 reviews)

Offering a fun seaside escape for the whole family, this beautiful beach is one of the largest in Chatham and features an iconic lighthouse.

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A lighthouse with an American flag, a white building with a red roof, and a cloudy sky.

Chatham Lighthouse

9.4/10 (173 reviews)

This historic 1808 beacon stands sentinel over Cape Cod's treacherous waters, guiding mariners for generations. Join a free summer Wednesday tour to climb the 48-foot tower for panoramic Atlantic views.

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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. Savor fresh seafood from the on-site market while enjoying panoramic harbor views from the observation deck.

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Chatham Windmill

9.2/10 (38 reviews)

This 1797 gristmill showcases Chatham's agricultural heritage with wooden gears and mechanisms. During summer "Corn Grinding Days," you can witness the historic mill transforming grain just as it did centuries ago.

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Ridgevale Beach

9.6/10 (21 reviews)

Why not spend a carefree afternoon at Ridgevale Beach during your travels in Chatham? Stroll along this trendy area's seaside, or simply enjoy its seafood restaurants.

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Cockle Cove Beach

9.0/10 (28 reviews)

If a restful vacation is part of your travel plans, Cockle Cove Beach might be the perfect place to seek out during your trip to Chatham. Stroll along this trendy area's seaside, or simply enjoy its seafood restaurants.

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Chatham Seaside Links

9.2/10 (20 reviews)

This historic nine-hole course challenges golfers with coastal winds and strategic play along the Atlantic. Enjoy the natural undulations and ocean views while navigating the traditional seaside links layout.

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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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Chatham Hotel Deals

Chatham Bars Inn

297 Shore Rd Chatham MA

$391 nightly

$448 total

Nov 3 - Nov 4

Total with taxes and fees

Chatham Wayside Inn

512 Main St Chatham MA

$217 nightly

$248 total

Nov 1 - Nov 2

Total with taxes and fees

Queen Anne Inn

70 Queen Anne Rd Chatham MA

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See all 4,959 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.

Find the Best Chatham Vacation Packages

Things to do in and around Chatham

Chatham, Massachusetts, is perfect for a beach and outdoor vacation, offering stunning scenery and a variety of activities. Enjoy golf at local courses, explore playgrounds, or embark on exciting boat tours and charter fishing trips. Take a scenic day trip along the waterfront or hike the nature trails to fully appreciate the area's natural beauty.

Shopping

For unique gifts, visit the Chatham Fish Pier, where you can find local seafood and crafts. If you're up for a drive, explore Eden Hand Arts and Scargo Stoneware Pottery & Art Gallery, both offering distinctive handmade items, about 11 and 12 miles away, respectively.

Recreation

Experience the serene greens at Chatham Seaside Links, perfect for golf enthusiasts. Enjoy cultural performances at the Chatham Drama Guild, where family and romance intertwine. For sports lovers, Veterans Field offers thrilling games in a vibrant atmosphere, making it a great spot to cheer on local teams.

Adventure

Experience the thrill at Cape Cod Baseball & Bumper Boats, an arcadeAdventureZone 7 miles from Chatham, offering family-friendly fun. Enjoy high-speed karting at Bud's Go Karts, also 7 miles away, or explore the natural beauty at Harwich Herring Run, located 8 miles from Chatham, perfect for outdoor enthusiasts.

Nightlife

Chatham's nightlife offers a charming coastal vibe with cozy bars and restaurants. Enjoy fresh seafood at The Chatham Squire, then unwind at The Bluefishing Bar for craft cocktails. For live music and dancing, head to the Cape Cod Melody Tent, where you'll find local bands and a fun atmosphere.

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

Find the best attractions in and around Chatham

Chatham, Massachusetts, is a charming coastal destination ideal for beach lovers and outdoor enthusiasts. Visitors can explore popular attractions such as Chatham Lighthouse, Chatham Harbor, and the picturesque Chatham beaches. The town also offers a delightful blend of culture and scenic beauty, making it perfect for a relaxing getaway. Whether you're golfing or soaking up the sun by the lakefront, Chatham provides a memorable vacation experience for every traveler.

Harwich Port: Located 5 miles from Chatham, Harwich Port offers a charming small-town atmosphere with a vibrant community feel. Enjoy local shops, delightful eateries, and scenic views of the harbor, making it a perfect spot for a leisurely stroll or a cozy meal.
Chatham Lighthouse Beach: Just 1 mile from Chatham, this stunning beach features soft sands and beautiful Atlantic views. It's an ideal place for sunbathing, swimming, or simply enjoying a peaceful day by the water while soaking up the sun.
Chatham Lighthouse: Situated within Chatham, this historic lighthouse is a symbol of the town's maritime heritage. Explore its rich history and enjoy picturesque views of the surrounding coastline, offering a glimpse into the area's nautical past.

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.

Calendar Month	Temperature	Precipitation	Cloudiness	Occupancy	Pricing
January	35.6°F (2.0°C)	Light Rain	Mostly Cloudy	Average	Slightly Low
February	35.4°F (1.9°C)	Light Rain	Mostly Cloudy	Average	Slightly Low
March	38.5°F (3.6°C)	Light Rain	Mostly Cloudy	Average	Slightly Low
April	45.3°F (7.4°C)	Light Rain	Mostly Sunny	Average	Average
May	53.1°F (11.7°C)	Light Rain	Mostly Sunny	Average	Average
June	61.7°F (16.5°C)	Light Rain	Mostly Sunny	Moderately High	Slightly High
July	69.6°F (20.9°C)	Light Rain	Mostly Sunny	Moderately High	Slightly High
August	70.3°F (21.3°C)	Light Rain	Mostly Sunny	Moderately High	Slightly High
September	65.7°F (18.7°C)	Light Rain	Mostly Sunny	Average	Average
October	57.9°F (14.4°C)	Light Rain	Mostly Sunny	Moderately Low	Average
November	48.6°F (9.2°C)	Light Rain	Mostly Sunny	Moderately Low	Average
December	41.5°F (5.3°C)	Light Rain	Mostly Cloudy	Moderately Low	Average

Tips to save on your trip to Chatham

Take advantage of package deals on Expedia and combine flights, hotels, or car rentals for a convenient and cost-effective trip to Chatham.
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 2 miles (4 km) 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.

Chatham Essential Information

Language	English
Currency	U.S dollars
Closest Airport	Nantucket Memorial Airport (ACK)
Population	1,400
Max Temp Winter	40ºF
Max Temp Summer	70ºF
Top Sights	Nauset Beach, West Dennis Beach and Skaket Beach

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Frequently asked questions

What is the best time to go to Chatham?

The best time to go for a Chatham vacation package is during the summer months, typically June through August. This period offers a warm-summer climate, with average mean temperatures generally staying below 71.6 °F, making it ideal for enjoying the beaches and outdoor activities.As a popular summer resort, Chatham's population can grow significantly during these months, reaching an estimated 30,000, which means facilities and parking can be more crowded. For a quieter experience, consider visiting just outside this peak season.

How can I save money on a Chatham vacation package?

When you bundle, you can save up to 30%*. To save money on a Chatham package, consider traveling during the quieter months or be flexible with your dates to find more options. Bundling your flights and hotel together often unlocks savings compared to booking separately. *Members only. Savings vary.

What's included in a Chatham vacation package?

A Chatham vacation package lets you combine round-trip flights, a hotel stay, and a rental car, offering convenience for your trip to this beach destination. Many hotels in Chatham offer free breakfast, and many also provide airport shuttle service to and from Boston, MA (BOS-Logan Intl.). As a beach destination, packages often include stays at properties with easy access to the coast.Exactly what's included will vary by hotel and package, so it's worth reviewing the details before you confirm your booking.

What's the best vacation package for Chatham?

For families, a Chatham vacation package built around a stay at Pleasant Bay Village Resort is a strong choice. This resort, rated 9.3 out of 10 and located about 2 miles from central Chatham, offers amenities like a playground, game room, and outdoor pool, with travelers often praising its beautiful overall setting and great staff.Couples seeking a luxury experience can consider a package with a stay at the 5-star Chatham Bars Inn. Rated 8.7 out of 10, this property provides a spa, bar/lounge, and outdoor pool, and travelers frequently highlight its top-notch facilities and perfect overall experience.For those looking for value, a Chatham vacation package with a stay at The Chatham Motel offers a comfortable option. Rated 8.9 out of 10 and costing around $300 per night, it's about 1 mile from central Chatham and features kitchenettes and an outdoor pool, with travelers often mentioning the welcoming staff and clean rooms.*Package availability and prices may change depending on dates and demand.

Is Chatham better suited for a beach vacation or a cultural trip?

Chatham is primarily a beach destination, making it an ideal choice for a Chatham vacation focused on coastal relaxation and outdoor activities. Nearly a third of package hotels offer ocean views, and the area is known for its many beaches, such as Chatham Lighthouse Beach, about 1 mile from central Chatham, and the broader Cape Cod Beaches, about 12 miles away.While beaches are a major draw, Chatham also offers a charming historic side. The town boasts a considerable number of 18th-century buildings and the historic Chatham Lighthouse, which was established in 1808. These elements add a touch of cultural exploration for those interested in the area's heritage.

Is Chatham a good choice for a family vacation package?

Chatham is a strong choice for family vacation packages, offering a blend of comfortable accommodations and engaging activities for all ages. Many family-friendly hotels provide amenities such as family rooms, outdoor pools, game rooms, and playgrounds, with some also offering kitchenettes for added convenience.For example, Pleasant Bay Village Resort, rated 9.3 out of 10 by travelers, features a game room, outdoor pool, and playground, making it a great base for families. Beyond the resorts, families can enjoy the sandy shores of Chatham Lighthouse Beach, about 1 mile from central Chatham, or the expansive Nauset Beach, about 6 miles away, both perfect for a day out by the ocean.

What's included in a Chatham beach vacation package?

Chatham beach vacation packages typically combine flights with a hotel stay, offering a convenient way to explore this coastal destination. Hotels like the 5-star Chatham Bars Inn, rated 8.7 out of 10, provide amenities such as an outdoor pool, restaurant, and spa. Another option is Pleasant Bay Village Resort, rated 9.3 out of 10, which features an outdoor pool, hot tub, playground, and restaurant. While the specific inclusions of a Chatham vacation package depend on the chosen hotel and rate, they generally cover your accommodation and flights, with additional services like meals, drinks, or activities varying by property.

What are the top things to do in Chatham?

A Chatham vacation offers a variety of activities, from exploring scenic beaches to enjoying outdoor recreation:Browse and book things to do in Chatham on Expedia.

Do you need to rent a car in Chatham, or is public transport enough?

For a Chatham vacation package, renting a car offers the most flexibility for exploring the area, especially given its character as a beach destination outside a city. While local taxis and ride services are available, and traffic can be heavy on summer weekends, a car allows you to easily reach various beaches and attractions at your own pace.Chatham has its own Chatham Municipal Airport for local service, but for national and international flights, you'll arrive at Logan International Airport (BOS) in Boston. The Old Colony Rail Trail provides a scenic option for cycling through parts of the town, but for broader travel and day trips, a rental car is highly recommended to make the most of your Chatham beach vacation packages.

Are Chatham vacation package hotels conveniently located?

Chatham vacation package hotels are generally well-located, offering convenient access to the town center and nearby beaches. Many properties are either within walking distance or a short drive from the heart of Chatham.For example, Old Harbor Inn is about a 5-minute walk from central Chatham, making it easy to explore the quaint Main Street. Other options like Chatham Seafarer Inn and The Chatham Motel are about 2 miles and 1 mile respectively from the town center, providing a balance of proximity and a slightly more secluded feel. This allows travelers to choose a location that best suits their preferred pace and access to local attractions.

Can I change or cancel my Chatham vacation package if my plans change?

Yes, you can cancel your vacation package via your itinerary page on Expedia or by contacting customer service. Remember that some packages are fully refundable, but the details vary based on each unique booking. A fully refundable package may depend on how far out from the travel dates you're canceling and what airline you are traveling with.

Do One Key members get extra savings when booking Chatham vacation packages?

Yes, members who join our free One Key™ travel rewards program can instantly unlock additional savings and save 10% or more on over 500,000 stays worldwide with Member Prices and over 1 million car rentals.

Does Expedia offer Book Now, Pay Later Chatham vacation packages?

Yes, with Expedia's Book Now, Pay Later option, powered by Affirm, you can spread the cost of your Chatham vacation over 3, 6, or 12 months. With no late payment fees or hidden costs, it's easy to secure your ideal vacation package as soon as you spot it.

How do I find last-minute vacation packages to Chatham?

To find last-minute vacation packages to Chatham, explore the last-minute deals section for the latest package offers, including flights, departing in the coming weeks. Being flexible with your travel dates and hotel preferences can help you secure the best prices.

How does free cancellation work on Chatham vacation packages?

Free cancellation on a Chatham vacation package depends on the specific hotel and rate combination you book. Many bookings allow free cancellation up to a stated deadline (often a few days before travel) where eligible. Read the cancellation terms carefully when reviewing the package, and visit Expedia help center for further details.

Is it cheaper to book a Chatham vacation as a package or separately?

Booking flights and hotels together can unlock lower overall prices. Better still, you can tailor your Chatham getaway to match your exact preference. Pick your preferred flight time, select the hotel type and add a car rental. Explore our bundles to see how much you can save.

Why should I book my Chatham vacation package with Expedia?

Booking your vacation package on Expedia makes it easier to get more out of your trip from the start. With a wide choice of hotels, you can compare prices, reviews and amenities all in one place, then bundle your hotel with flights which could help you save even more. Flexible booking options on selected stays also make it easier to plan with confidence.

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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.

Chatham Vacations from $620

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Plan, book, travel with confidence

Better together

Find the right fit

Rest easy

Your Chatham Vacation

The Latest Chatham vacation packages

Boston Lodge and Suites

Raffles Boston

The Langham, Boston

Battery Wharf Hotel, Boston Waterfront

Boston Harbor Hotel

Stay near popular Chatham attractions

Chatham Lighthouse Beach

Chatham Lighthouse

Chatham Fish Pier

Chatham Windmill

Ridgevale Beach

Cockle Cove Beach

Chatham Seaside Links

Mayo House

Chatham Hotel Deals

Chatham Bars Inn

Chatham Wayside Inn

Queen Anne Inn

Find the Best Chatham Vacation Packages

Things to do in and around Chatham

Find the best attractions in and around Chatham

Best time to go to Chatham

Tips to save on your trip to Chatham

Chatham Beach Vacation

Chatham Essential Information

More vacations you might like

Frequently asked questions

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