Waterboro Vacation Packages

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  • Better together

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

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

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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.
Club Quarters Hotel Faneuil Hall, Boston

Club Quarters Hotel Faneuil Hall, Boston

4 out of 5
Downtown Boston
Price was CA $1,644, price is now CA $1,138 per person
CA $1,138
per person
Jan 12 - Jan 19
found 1 day ago
Roundtrip flight included
Ottawa (YOW) to Boston (BOS)
9/10 Wonderful! (3,501 reviews)

Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Price was CA $4,415, price is now CA $2,164 per person
CA $2,164
per person
Jan 12 - Jan 19
found 1 day ago
Roundtrip flight included
Ottawa (YOW) 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

Eurostars The Boxer

Eurostars The Boxer

4 out of 5
West End
Price was CA $1,975, price is now CA $1,259 per person
CA $1,259
per person
Jan 12 - Jan 19
found 1 day ago
Roundtrip flight included
Ottawa (YOW) to Boston (BOS)
8.8/10 Excellent! (1,636 reviews)

Raffles Boston

Raffles Boston

5 out of 5
Back Bay
Price was CA $2,338, price is now CA $1,593 per person
CA $1,593
per person
Dec 10 - Dec 13
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Boston (BOS)
9.6/10 Exceptional! (343 reviews)
Amazing hotel Great rooms and helpful, professional staff. Couldn’t fault it.

Reviewed on Nov 8, 2026

The Verb Hotel

The Verb Hotel

3.5 out of 5
Fenway–Kenmore
Price was CA $1,632, price is now CA $1,150 per person
CA $1,150
per person
Jan 12 - Jan 19
found 2 hours ago
Roundtrip flight included
Ottawa (YOW) to Boston (BOS)
9.6/10 Exceptional! (2,164 reviews)

Ready to book your vacation to Waterboro?

 

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Waterboro Hotel Deals

Casco Bay Hotel Portland Airport - Maine Mall, an Ascend Collection Hotel

Casco Bay Hotel Portland Airport - Maine Mall, an Ascend Collection Hotel

3.5 out of 5
80 John Roberts Rd. South Portland ME
Fully refundable
The price is CA $107 per night from Nov 29 to Nov 30
CA $107
CA $117 total
Nov 29 - Nov 30
includes taxes & fees
8.4/10 Very good! (2,970 reviews)
"Exterior side door to lobby remained unlocked., weatherstripping on door peeling off"

Reviewed on Nov 9, 2026

Casco Bay Hotel Portland Airport - Maine Mall, an Ascend Collection Hotel
Ogunquit - The Milestone

Ogunquit - The Milestone

2 out of 5
687 Main Street Ogunquit ME
8.8/10 Excellent! (1,629 reviews)
"This motel was clean, quiet and reasonably priced to fit our needs. I have stayed here before and would stay again."

Reviewed on Nov 7, 2026

Get rates
Ogunquit - The Milestone
Spark by Hilton Portland Airport Maine Mall

Spark by Hilton Portland 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 $95 per night from Nov 29 to Nov 30
CA $95
CA $103 total
Nov 29 - Nov 30
includes taxes & fees
Spark by Hilton Portland Airport Maine Mall
See all 2,988 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.
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Frequently asked questions

How much does a Waterboro vacation package cost?
You can snap up a vacation package to this destination from CA $1,138 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.