South Chatham Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to CA $4,200 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place

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.

Top South Chatham Vacation Deals

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

The Newbury Boston

5 out of 5
Back Bay
Price was CA $1,841, price is now CA $1,320 per person
CA $1,320
per person
Jan 29 - Feb 1
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Boston (BOS)
9.4/10 Exceptional! (744 reviews)

Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Price was CA $2,776, price is now CA $1,478 per person
CA $1,478
per person
Dec 13 - Dec 17
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Boston (BOS)
9.8/10 Exceptional! (1,004 reviews)
All the staff was very helpful and responsive I would recommend this hotel to everyone planning to stay in Boston.

Reviewed on Nov 9, 2026

Four Seasons Hotel Boston

Four Seasons Hotel Boston

5 out of 5
Bay Village
Price was CA $2,360, price is now CA $1,524 per person
CA $1,524
per person
Jan 29 - Feb 1
found 11 hours ago
Roundtrip flight included
Toronto (YYZ) to Boston (BOS)
9.4/10 Exceptional! (491 reviews)
The best location and the beat service! The best swimming pool

Reviewed on Nov 9, 2026

Raffles Boston

Raffles Boston

5 out of 5
Back Bay
Price was CA $2,311, price is now CA $1,580 per person
CA $1,580
per person
Jan 29 - Feb 1
found 11 hours ago
Roundtrip flight included
Toronto (YYZ) to Boston (BOS)
9.6/10 Exceptional! (343 reviews)
Great place to stay!!

Reviewed on Nov 9, 2026

The Langham, Boston

The Langham, Boston

5 out of 5
Downtown Boston
Price was CA $1,983, price is now CA $1,406 per person
CA $1,406
per person
Dec 13 - Dec 17
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Boston (BOS)
9.8/10 Exceptional! (1,003 reviews)

Ready to book your vacation to South Chatham?

 

Choose your dates

South Chatham Hotel Deals

Chatham Tides

Chatham Tides

2.5 out of 5
394 Pleasant St South Chatham MA
The price is CA $202 per night from Nov 11 to Nov 12
CA $202
CA $232 total
Nov 11 - Nov 12
includes taxes & fees
Chatham Tides
Chatham Bars Inn

Chatham Bars Inn

5 out of 5
297 Shore Rd Chatham MA
The price is CA $498 per night from Nov 11 to Nov 12
CA $498
CA $570 total
Nov 11 - Nov 12
includes taxes & fees
9.2/10 Wonderful! (876 reviews)
"Amazing place to stay. Can't wait to go back."

Reviewed on Oct 30, 2026

Chatham Bars Inn
Fairfield Inn & Suites by Marriott Cape Cod Hyannis

Fairfield Inn & Suites by Marriott Cape Cod Hyannis

3 out of 5
867 Iyannough Road Hyannis MA
Fully refundableReserve now, pay when you stay
The price is CA $179 per night from Nov 16 to Nov 17
CA $179
CA $205 total
Nov 16 - Nov 17
includes taxes & fees
8.8/10 Excellent! (762 reviews)
"We stayed two nights and our stay was excellent. The hotel is very clean and bright, our room was very pleasant and a nice size. We had plenty of room for all our stuff and the bed was quite comfortable. The bathroom was roomy and the shower was excellent! Breakfast was pretty much the regular hotel ..."

Reviewed on Nov 9, 2026

Fairfield Inn & Suites by Marriott Cape Cod Hyannis
See all 4,783 properties in South 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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

Stay near popular South Chatham attractions

Forest Beach

9.6/10 (13 reviews)
Why not spend a lazy afternoon at Forest Beach during your trip to South Chatham? While you're in the area, stroll along the beaches.
See properties

Frequently asked questions

How much does a South Chatham vacation package cost?
Offering excellent value package deals from CA $1,320 on Expedia, you'll be thrilled with how little a vacation to South Chatham costs! Expedia's packages mean less travel planning for you and greater savings.
What are the cheapest months to go to South Chatham?
If you're hoping to score a cheap South Chatham vacation package, consider planning a trip in December, January and February. You'll typically find better rates on hotels and airfares during these quieter months — perfect for a budget-friendly break.
How many days is enough for South Chatham?
Allow around 3 days for your South Chatham vacation if you want to immerse yourself in everything that makes this place special. Explore key areas, including Northwest Harwich and South Harwich. Then head to the major sights like Chatham Lighthouse Beach and Cape Cod Theatre Company – Home of the Harwich Jr. Theatre. With a well-planned itinerary, you can keep busy with room for some rest time too. Want to go beyond South Chatham? Consider fitting in an excursion or two.
How to find the best South Chatham package deals?
Bagging a cheap South Chatham package deal is a cinch with Expedia. Once you've entered your preferred dates and destination under our "Packages" tab, set your budget range, apply a couple of filters and see what's available. You can tailor your search by "Property class," "Number of bedrooms," "Traveller experience" and more. Order the results by "Price: low to high" to discover the most affordable South Chatham package deals. Want a simple trick to get the biggest savings? Have some flexibility with your departure dates and consider travelling on a weekday, when prices are typically lower.
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. Check the "Package" heading, then select your destination and travel dates to view the best hotel and flight prices. Bundle everything into a neat package and you can save hundreds of dollars. Consider adding a car rental and you may land a better deal.
When to book a vacation package to South Chatham?
Land fantastic discounts by booking your flights in advance with Expedia. If being spontaneous is more your thing, snap up one of our last-minute deals for a spur-of-the-moment South Chatham trip.
How to plan a trip to South Chatham?

  1. Choose the ideal time to travel: Your schedule, preferred season and the type of weather you like can all impact your decision on when to go to South Chatham.
  2. Budget wisely: On top of the price of your stay, you'll need to factor in other expenses. These include flights, food and transportation. Also, put aside a little extra for unexpected expenses that could arise during your trip to South Chatham.
  3. Work out your trip length: Consider how long you want to spend discovering South Chatham. Plan your itinerary so you can get to all the activities and attractions you're interested in at a comfortable pace.
  4. Bundle your hotel and flights: Awesome destination, check. Length of stay, check. All that's left now is to find a South Chatham vacation package that brings all your bookings together.

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