How much does a Chatham vacation package cost?

Offering excellent value package deals from $271 on Expedia, you'll be pleasantly surprised at how much a vacation to Chatham costs! Our packages mean less travel planning for you and greater savings.

What are the cheapest months to go to Chatham?

October, November and December are the best times to look for cheap Chatham vacation packages. Choosing to travel in quieter months means you'll typically find lower prices on flights and accommodations.

How many days is enough for Chatham?

Chatham vacations can be short or long, but to get a real feel for this destination, we reckon 3 days is a good ballpark. This will mean you can fit in top sights like Chatham Fish Pier and Chatham Lighthouse and seek out some hidden gems. Don't forget to explore cool neighborhoods such as Harwich Center and South Harwich either. If you're smart with your time, you may even be able to take a day trip or two from Chatham too.

Is it worth booking a vacation package to Chatham?

It's easy to see why a Chatham vacation is on the must-do list of many travelers. Major attractions like Chatham Fish Pier are just the start of things to keep you busy here.

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 vacation as a package?

An Expedia vacation 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 vacation 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?

Pick your dates: The things you'd like to do in Chatham and your favorite season will help you decide when to go. Plan your budget wisely: As well as the price of your stay, you'll need to factor in other expenses. These include transportation, food and flights. Also, set aside a little extra for unexpected costs that may come up during your trip to Chatham. Explore Chatham using Expedia's trip planning tool : Gain insights into the top attractions and best properties for your trip to Chatham. You can also save your must-visit places, collaborate with your group and manage your plans in one place. Set the duration of your trip: Start by making a list of all the attractions and activities you'd like to get to in Chatham. Then, estimate how long you'll need at each, along with any travel time. Bundle your bookings: With your travel dates in order, you can combine your hotels, car rental, flights and more into a customized Chatham vacation package. Book activities and experiences in advance: Whether it's entrance to a big attraction or a day trip, you won't have to worry about missing out on the best Chatham has to offer. Find all the exciting things to do in Chatham with our dedicated travel guide.

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

Your Chatham break should be a relaxing escape from your busy life, not a reason for money-related stress. So to give you extra flexibility, we've teamed up with online lender Affirm to bring you our Book Now, Pay Later vacations. Pick one of our vacation packages with payment plans and split up the total cost over 3, 6 or 12 months. Plus, there are no hidden costs or late payment fees to worry about.

Chatham Vacation Packages 2026 from $271

Name: Chatham Wayside Inn
Price range: $179 total
Rating: 9.2

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.

D. Hotel Suites & Spa

Save 100% on your flight

$271

per person

Feb 26 - Mar 1

found 1 day ago

Roundtrip flight included

Miami (MIA) to Boston (BOS)

9.4/10 Exceptional! (2,242 reviews)

Nice room with separate living room. We enjoyed the gym, pool and hot tub. We stayed on second floor and there is only one elevator, so you have to wait sometime. I wish there is stairs to walk down.

Reviewed on Jan 6, 2026

The Inn at Hastings Park, Relais & Chateaux - Boston

Save 100% on your flight

$885

per person

Mar 13 - Mar 18

found 1 day ago

Roundtrip flight included

Dallas (DFW) to Boston (BOS)

9.6/10 Exceptional! (247 reviews)

Beautiful property! Room was excellent. Great amenities and free continental breakfast brought to our room.

Reviewed on Oct 21, 2025

The Charles Hotel

West Cambridge

Save 100% on your flight

$562

per person

Mar 13 - Mar 16

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Boston (BOS)

9.4/10 Exceptional! (1,003 reviews)

Such a warm and cozy place with great amenities!

Reviewed on Dec 31, 2025

Boston Harbor Hotel

North End

Save 100% on your flight

$688

per person

Apr 2 - Apr 4

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Boston (BOS)

9.8/10 Exceptional! (1,005 reviews)

Great place Closet room floor slippery

Reviewed on Jan 10, 2026

Global Luxury Suites Downtown Boston

Chinatown

Save 100% on your flight

$724

per person

Mar 14 - Mar 17

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Boston (BOS)

8/10 Very Good! (621 reviews)

The area around the property was excellent. It felt very safe and quiet, with plenty of shopping and dining options nearby. Everything was walkable, which made the stay very convenient. Parking was easy, and transportation access was great. Overall, a great location and an enjoyable stay.

Reviewed on Jan 1, 2026

Don't see what you're looking for?

See all available trips from Columbus to Chatham

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Chatham Hotel Deals

Chatham Bars Inn

297 Shore Rd Chatham MA

$364 nightly

$417 total

Jan 14 - Jan 15

Total with taxes and fees

9/10 Wonderful! (802 reviews)

Room was very clean but a little dated also there is very little space to put your clothes away…no dressers

Reviewed on Jan 3, 2026

Chatham Wayside Inn

512 Main St Chatham MA

Fully refundableReserve now, pay when you stay

$156 nightly

$179 total

Jan 11 - Jan 12

Total with taxes and fees

9.2/10 Wonderful! (614 reviews)

I’ve always been curious about the Wayside Inn because my mom worked there a gazillion years ago when she was in high school. It’s so cozy and clean and staff was very friendly. They also upgraded us which was super nice! The only thing was outlets in the room were kind of oddly positioned— but we ...

Reviewed on Jan 4, 2026

Surfside Inn Chatham

25 Holway St Chatham MA

8/10 Very Good! (159 reviews)

This is a beautiful property very centrally located. I highly recommend the surfside inn.

Reviewed on Oct 15, 2025

Get rates

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.

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.

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

Language

English

Currency

U.S dollars

Closest Airport

Nantucket Memorial Airport (ACK)

Population

1,400

Max Temp Winter

40ºF

Max Temp Summer

70ºF