Waterboro Vacation Packages

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

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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.
The Atlas Hotel

The Atlas Hotel

4.5 out of 5
Allston
Price was CA $1,254, price is now CA $761 per person
CA $761
per person
Aug 20 - Aug 23
found 9 hours ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9.4/10 Exceptional! (177 reviews)
Great hotel staff, great location, great room :)

Reviewed on Jul 8, 2026

Ogunquit River Inn & Suites

Ogunquit River Inn & Suites

3 out of 5
Moody
Price was CA $1,358, price is now CA $896 per person
CA $896
per person
Sep 25 - Sep 30
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Portland (PWM)
9/10 Wonderful! (1,008 reviews)
Wonderful view, wonderful staff, good breakfast, quiet but convenient location. Higher recommend

Reviewed on Jul 6, 2026

The Inn at Hastings Park, Relais & Chateaux - Boston

The Inn at Hastings Park, Relais & Chateaux - Boston

4 out of 5
Price was CA $1,956, price is now CA $1,320 per person
CA $1,320
per person
Aug 21 - Aug 25
found 9 hours ago
Roundtrip flight included
Montreal (YUL) to Boston (BOS)
9.6/10 Exceptional! (258 reviews)
Staff was super friendly and accommodating, and we very much enjoyed our stay. Room was good, location is great right on the edge of town and easily accessible.

Reviewed on Jul 8, 2026

The Meadowmere Resort

The Meadowmere Resort

2.5 out of 5
Price was CA $3,183, price is now CA $2,162 per person
CA $2,162
per person
Aug 20 - Aug 25
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Portland (PWM)
8.6/10 Excellent! (1,000 reviews)
Wonderful but be prepared to pay for breakfast. They have coffee and a sweet something but nothing healthy or hot unless you pay for it. Great location.

Reviewed on Jul 8, 2026

Four Seasons Hotel Boston

Four Seasons Hotel Boston

5 out of 5
Bay Village
Price was CA $3,502, price is now CA $2,440 per person
CA $2,440
per person
Sep 8 - Sep 11
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9.4/10 Exceptional! (474 reviews)
perfecto

Reviewed on Jun 8, 2026

Ready to book your vacation to Waterboro?

 

Choose your dates

Waterboro Hotel Deals

Comfort Inn South Portland Airport

Comfort Inn South Portland Airport

2.5 out of 5
90 Maine Mall Rd South Portland ME
Fully refundable
The price is CA $196 per night from Jul 12 to Jul 13
CA $196
CA $214 total
Jul 12 - Jul 13
includes taxes & fees
8.6/10 Excellent! (2,203 reviews)
"Nice breakfast. Great staff."

Reviewed on Jul 9, 2026

Comfort Inn South Portland Airport
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 $214 per night from Jul 12 to Jul 13
CA $214
CA $233 total
Jul 12 - Jul 13
includes taxes & fees
8.4/10 Very good! (2,988 reviews)
"I stay here every week and every week it is spectacular and immaculate and reasonable"

Reviewed on Jul 8, 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
The price is CA $248 per night from Jul 27 to Jul 28
CA $248
CA $270 total
Jul 27 - Jul 28
includes taxes & fees
9/10 Wonderful! (1,383 reviews)
"Great spot for the price!"

Reviewed on Jul 8, 2026

Ogunquit - The Milestone
See all 3,186 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
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Family Vacations
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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 $761 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.

Explore a world of travel with Expedia

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