South Chatham Vacations from $482
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Your South Chatham Vacation
Let our vacation packages to South Chatham inspire your next great adventure. You'll find a whole lot to love about this exciting city, starting with the neighborhood of Harwich Center, which is great for golfing and festivals. Ocean Edge Golf Club, Sea Street Beach and Nickerson State Park are just a few of the many sights you'll want to check out during your trip to South Chatham. A few clicks is all it takes to put together your ideal South Chatham vacation on Expedia.
The Latest South Chatham Vacation Packages
- Boston Lodge and Suites
Jan 6 - Jan 11Boston Lodge and Suites + Flight
Dorchester5 nights4.0 star property8.4/10 - Very good (194 reviews)"The accommodation was great and spacious enough for a large group. There were five of us, and it was perfect for our needs. The apartment was clean, and everything we needed was provided, including towels, soap, dishwasher detergent, and more. We turned on the oven to make dinner, but we were unable to turn it off because the buttons weren’t working. We called for assistance and received a response very quickly, which made us feel supported and taken care of. Overall, we had a great stay! The..."Reviewed October 17, 2026Roundtrip • Los Angeles (LAX) - Boston (BOS)LAX - BOS • Nonstop BOS - LAX • 1 stop$1,473$482found 23 hours agoper traveler - Boston Harbor Hotel
Jan 15 - Jan 18Boston Harbor Hotel + Flight
North End3 nights5.0 star property9.8/10 - Exceptional (1,008 reviews)"!"Reviewed November 10, 2026Roundtrip • Los Angeles (LAX) - Boston (BOS)LAX - BOS • Nonstop BOS - LAX • Nonstop$1,483$900found 1 day agoper traveler - Four Seasons Hotel Boston
Dec 13 - Dec 19Four Seasons Hotel Boston + Flight
Bay Village6 nights5.0 star property9.4/10 - Exceptional (497 reviews)"The best location and the beat service! The best swimming pool"Reviewed November 9, 2026Roundtrip • Miami (MIA) - Boston (BOS)MIA - BOS • Nonstop BOS - MIA • 1 stop - The Onset Beach Compound-Cape Cod Beach Resort & Oceanic Habitat
Jan 27 - Jan 31The Onset Beach Compound-Cape Cod Beach Resort & Oceanic Habitat + Flight
East Wareham4 nights3.0 star property10/10 - Exceptional (11 reviews)"We had a great experience staying in the crab house. The cottage was well maintained and had everything we needed to enjoy our stay. The staff was friendly, helpful, and genuinely care. Ken was fantastic, you can really tell he cares about ensuring guests have a great experience. 10/10 experience, would recommend this spot to anyone looking for a great stay on the cape."Reviewed July 27, 2026Roundtrip • Chicago (ORD) - Boston (BOS)ORD - BOS • Nonstop BOS - ORD • Nonstop$1,431$1,014found 5 hours agoper traveler - The Langham, Boston
Jan 15 - Jan 18The Langham, Boston + Flight
Downtown Boston3 nights5.0 star property9.6/10 - Exceptional (1,005 reviews)Roundtrip • Los Angeles (LAX) - Boston (BOS)LAX - BOS • Nonstop BOS - LAX • Nonstop$1,068$763found 1 day agoper traveler
Where to stay near South Chatham
Chatham
Discover Chatham, a welcoming destination perfectly suited for couples and families seeking a blend of beach bliss and outdoor adventure. Nestled about 3 miles by car from South Chatham, this charming town boasts stunning scenery and attractions like the historic Chatham Lighthouse and the beautiful Chatham Lighthouse Beach. With a variety of activities such as golf and playgrounds, Chatham invites travelers to enjoy its vibrant coastal atmosphere. Choosing Chatham for your stay ensures a delightful and memorable vacation experience.
Brewster
Experience the charm of Brewster, an ideal retreat for families and outdoor enthusiasts eager to enjoy beautiful beaches and stunning scenery. Just a short drive from South Chatham, Brewster offers access to popular spots like Skaket Beach, perfect for sun-soaked days, and the Ocean Edge Golf Club for those looking to tee off. With its seasonal visitor peaks from June to August, Brewster promises a vibrant atmosphere. Choosing Brewster for your stay ensures a delightful blend of relaxation and adventure.
Dennis Port
If you are a family-focused traveler, look no further than Dennis Port, which features beautiful beaches and outdoor activities perfect for creating lasting memories. With nearby attractions like West Dennis Beach and Harwich Port, you can enjoy sun-soaked days and scenic views. Just about a 6-mile drive from South Chatham, Dennis Port makes accessing family-friendly venues like playgrounds and golf courses a breeze. Choosing Dennis Port for your stay ensures a delightful vacation experience.
Harwich
Immerse yourself in Harwich, where outdoor enthusiasts and families can easily access beautiful beaches and scenic views. This charming city is perfect for those looking to enjoy activities like golf at Ocean Edge Golf Club and relaxing days at Mayflower Beach. With its peak visitor season from July to September, Harwich offers a vibrant atmosphere during the summer months. Located about 5 miles by car from South Chatham, it’s a smart choice for your next vacation.
Harwich Port
Looking for the perfect spot? Harwich Port is designed to delight couples and families seeking a beach getaway, with its beautiful local beaches and scenic outdoor activities. Visitors can enjoy the popular West Dennis Beach for sun-soaked relaxation, explore the picturesque Cape, or challenge themselves at the Ocean Edge Golf Club. Located about 3 miles by car from South Chatham, Harwich Port offers a seamless travel experience, making it a smart choice for your vacation stay.
South Chatham Hotel Deals
Wequassett Resort and Golf Club
Wequassett Resort and Golf Club
An English Garden Bed & Breakfast
An English Garden Bed & Breakfast"Lovely spot, welcoming hosts, views of water from our room and deck and short walk to the beach. Great location to access Cape Cod rail trails, we enjoyed many gorgeous fall bike rides. J&M Cameron"
"Staff was very nice and accommodating. Very clean rooms and parking was very easy."
Frequently Asked Questions
How much does a South Chatham vacation package cost?
You can grab a vacation package to this popular destination from $482 on Expedia. But how much your vacation to South Chatham costs will depend on factors like your hotel choice, season and length of stay.
What are the cheapest months to go to South Chatham?
You're likely to find lower prices and greater availability in September, October and December. Check out our cheap South Chatham vacation packages and you could score some excellent off-season deals.
How many days is enough for South Chatham?
With a well-planned itinerary, you can easily hit the top South Chatham attractions in a few days. But if you want to discover lesser-known spots or take day trips, think about booking your South Chatham vacation for longer.
How to find the best South Chatham package deals?
Use Expedia's filter tool to help you find some of the best South Chatham package deals. When you begin your search, just set your maximum budget and then sort the results by "Price: low to high." If you want to save, plan your break for midweek, or browse for South Chatham package deals in the off-season. Play around with your travel dates and you may score even better discounts. As a rule of thumb, it's usually best to book your vacation package as soon as possible.
Is it cheaper to book a South Chatham vacation as a package?
You can enjoy significant savings on your South Chatham escape by booking a tailored vacation package. Click on the "Package" heading, then enter your travel dates and destination to view the best hotel and flight prices. Bundle everything into a great-value package and you can save hundreds of dollars. Consider adding a rental car and you may land a better deal.
When to book a vacation package to South Chatham?
If you've got your South Chatham vacation dates finalized, book as soon as you can to snap up some incredible deals. With Expedia, you can generally reserve some flights up to one year in advance. Prefer spontaneous adventures? Our last-minute deals are perfect for impromptu escapes.
Does Expedia offer Book Now, Pay Later South Chatham vacation packages?
Set off on your dream getaway to South Chatham with help from our Book Now, Pay Later vacations. There's no need to scrimp and save or wait until your next payday — we've joined forces with online lender Affirm to offer you financial flexibility. Our vacation packages with payment plans allow you to split the cost across 3, 6 or 12 months. With no hidden or late payment fees, it's easy to stay on budget and snap up travel deals while they last.