Waterboro Vacation Packages

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Your Waterboro Vacation

Build a custom vacation package to Waterboro and get ready to experience this exciting city the way you want. Consider spending some time in the neighborhood of South Sanford, which is great for walking and tons more. If taking in sights is on the agenda during your trip to Waterboro, visit top attractions like Little Ossipee Pond, Kennebunk Pond and Swan Pond. No matter your travel plans or budget, organizing your ultimate tailored Waterboro vacation is a walk in the park with Expedia.

Top Waterboro Vacation Deals

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

Sea Mist Resort

3 out of 5
per person
Sep 3 - Sep 7
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Boston (BOS)
8.8/10 Excellent! (127 reviews)
Great resort with suites, very cosy with great amenities, close to excellent beach and shopping.

Reviewed on Aug. 2, 2025

Studio Allston Hotel

Studio Allston Hotel

3.5 out of 5
Brighton
per person
Sep 17 - Sep 22
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to Boston (BOS)
8.6/10 Excellent! (1,033 reviews)
Great stay. Nice location. Parking was very convenient with quite reasonable price. We also enjoyed the pool table and pingpong table in the lobby.

Reviewed on Jul. 29, 2025

Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
per person
Sep 28 - Sep 30
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9.8/10 Exceptional! (1,001 reviews)
Favorite hotel in Boston amazing pool and gym

Reviewed on Aug. 2, 2025

The Langham, Boston

The Langham, Boston

5 out of 5
Downtown Boston
per person
Sep 4 - Sep 7
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Boston (BOS)
9.6/10 Exceptional! (1,016 reviews)
I had an amazing stay over the 4th of July, the bubbly left in my room was a great treat! Nothing but luxuries throughout my stay and i will be returning!!

Reviewed on Jul. 28, 2025

Raffles Boston

Raffles Boston

5 out of 5
Back Bay
per person
Sep 4 - Sep 7
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Boston (BOS)
9.6/10 Exceptional! (132 reviews)
Excellent, elegant, great service in every way possible. Friendly, helpful and responsive staff too.

Reviewed on Jul. 14, 2025

Ready to book your vacation to Waterboro?

 

Choose your dates

Waterboro Hotel Deals

Days Inn by Wyndham Airport/Maine Mall

Days Inn by Wyndham Airport/Maine Mall

2 out of 5
461 Maine Mall Rd, South Portland, ME
Fully refundableReserve now, pay when you stay
The price is CA $151 per night from Aug 24 to Aug 25
CA $151
CA $165 total
Aug 24 - Aug 25
includes taxes & fees
7.8/10 Good! (1,101 reviews)
"Outside wasn't well kept up. The room was average, clean."

Reviewed on Jul. 31, 2025

Days Inn by Wyndham Airport/Maine Mall
Ogunquit - The Milestone

Ogunquit - The Milestone

2 out of 5
687 Main Street, Ogunquit, ME
The price is CA $151 per night from Sep 1 to Sep 2
CA $151
CA $165 total
Sep 1 - Sep 2
includes taxes & fees
8.8/10 Excellent! (1,108 reviews)
"Friendly check in. Room is small but comfortable. Shower curtain doesn’t stay put while showering which is odd. Wallpaper is peeling in the bathroom."

Reviewed on Jul. 31, 2025

Ogunquit - The Milestone
Comfort Inn Airport

Comfort Inn Airport

2.5 out of 5
90 Maine Mall Rd, South Portland, ME
Fully refundableReserve now, pay when you stay
The price is CA $185 per night from Aug 5 to Aug 6
CA $185
CA $202 total
Aug 5 - Aug 6
includes taxes & fees
8.4/10 Very Good! (1,444 reviews)
"Very friend staff"

Reviewed on Aug. 1, 2025

Comfort Inn Airport
See all 3,102 properties in Waterboro
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

Frequently asked questions

How much does a Waterboro vacation package cost?
You can snap up a vacation package to this destination from CA $933 on Expedia. But how much your vacation to Waterboro costs will depend on the length of stay, hotel choice and season.
What are the cheapest months to go to Waterboro?
If you're hoping to score a cheap Waterboro vacation package, consider visiting in January, February and March. You're likely to find lower rates on flights and accommodations during these quieter months — ideal for a budget-friendly getaway.
How many days is enough for Waterboro?
The ideal length for your Waterboro vacation depends on what you'd like to see and do. Typically, a handful of days to a week will give you enough time to check out all the leading sights and explore some hidden gems along the way.
How to find the best Waterboro package deals?
Use Expedia's handy filters to find some fabulous Waterboro package deals. When you start your search, just set your maximum budget and then sort the results by "Price: low to high." If you're looking to save, plan your trip for midweek, or search for Waterboro package deals in the low season. Play around with your travel dates and you may land even bigger 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 Waterboro vacation as a package?
Expedia vacation packages are designed to give you more bang for your buck. Bundle your hotel, flight and car rental into one great-value price and you could save hundreds of dollars. You'll generally land a better deal than booking each component individually. And you'll still enjoy the flexibility to create a customized Waterboro vacation by choosing your preferred type of stay, airline and car class.
When to book a vacation package to Waterboro?
If you've got your Waterboro travel dates locked in, book early to score some incredible deals. With Expedia, you can often reserve some flights up to one year in advance. Prefer spur-of-the-moment adventures? Our last-minute deals are perfect for quick escapes.
How to plan a trip to Waterboro?

  1. Pick the perfect time to travel: Your schedule, preferred season and the type of weather you enjoy can all impact your decision on when to visit Waterboro.
  2. Set your budget: Consider costs such as flights, meals and transportation when calculating how much to put aside for your trip to Waterboro. Then, choose a property that fits your budget, whether that's an affordable option or a more luxurious getaway.
  3. Decide how long to go for: Now that you know more about Waterboro, you can figure out the perfect length of your vacation. Create a rough itinerary and allocate enough time to get through everything on your must-do list.
  4. Bundle your hotel and flights: Epic destination, check. Length of stay, check. All that's left now is to choose a Waterboro 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.