Waterboro Vacations from $363

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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.

The Latest Waterboro vacation packages

Price found within the past 48 hours. Click for updated prices.
The Cove At Yarmouth

The Cove At Yarmouth

3 out of 5
Save 100% on your flight
Price was $587, price is now $363 per person
$363
per person
Feb 19 - Feb 23
found 14 hours ago
Roundtrip non-stop flight included
Miami (MIA) to Boston (BOS)
9.2/10 Wonderful! (243 reviews)
The unit on or suite units are on second floor with no elevator. In addition, the bedroom is on another level. For those with physical issues only.insist on first floor I found 1st floor bath dirty. This is a time share rental which suits families with young kids.

Reviewed on Oct 6, 2025

DoubleTree by Hilton Manchester Downtown

DoubleTree by Hilton Manchester Downtown

4 out of 5
Downtown Manchester
Save 100% on your flight
Price was $545, price is now $364 per person
$364
per person
Jan 26 - Jan 31
found 20 hours ago
Roundtrip non-stop flight included
Miami (MIA) to Boston (BOS)
9/10 Wonderful! (1,061 reviews)
Rooms clean, staff nice, good location

Reviewed on Dec 14, 2025

citizenM Boston Back Bay

citizenM Boston Back Bay

4 out of 5
Fenway–Kenmore
Price was $553, price is now $379 per person
$379
per person
Feb 20 - Feb 23
found 1 day ago
Roundtrip non-stop flight included
Miami (MIA) to Boston (BOS)
9.4/10 Exceptional! (2,013 reviews)
Always enjoy staying there

Reviewed on Dec 13, 2025

The Club at New Seabury

The Club at New Seabury

3.5 out of 5
New Seabury
Save 100% on your flight
Price was $683, price is now $482 per person
$482
per person
Feb 19 - Feb 23
found 14 hours ago
Roundtrip non-stop flight included
Miami (MIA) to Boston (BOS)
9/10 Wonderful! (337 reviews)
Stayed in one of the cottages. It was so cute. Had everything you needed. Only stood overnight wished we had more time.

Reviewed on Sep 22, 2025

By the Sea Guests Bed & Breakfast & Suites

By the Sea Guests Bed & Breakfast & Suites

3.5 out of 5
Save 100% on your flight
Price was $786, price is now $561 per person
$561
per person
Feb 19 - Feb 23
found 14 hours ago
Roundtrip non-stop flight included
Miami (MIA) to Boston (BOS)
9.2/10 Wonderful! (185 reviews)
Our room had an wonderful Ocean View. The room was excellent and meals were awesome. Staff were very helpful. We will be going back next year!

Reviewed on Sep 20, 2025

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Waterboro Hotel Deals

Tru by Hilton Portland Airport Area

Tru by Hilton Portland Airport Area

2.5 out of 5
369 Maine Mall Road South Portland ME
Fully refundableReserve now, pay when you stay
$67 nightly
The price is $73 total per night from Jan 11 to Jan 12
$73 total
Jan 11 - Jan 12, 2026
Total with taxes and fees
8.8/10 Excellent! (1,660 reviews)
Everything was much better than I expected. We were very pleased.

Reviewed on Dec 16, 2025

Tru by Hilton Portland Airport Area
DoubleTree by Hilton Hotel Portland

DoubleTree by Hilton Hotel Portland

4 out of 5
363 Maine Mall Rd South Portland ME
Fully refundableReserve now, pay when you stay
$74 nightly
The price is $81 total per night from Dec 24 to Dec 25
$81 total
Dec 24 - Dec 25
Total with taxes and fees
7.8/10 Good! (1,305 reviews)
Clean rooms and friendly staff! About a 10-15 min drive from downtown Portland.

Reviewed on Dec 10, 2025

DoubleTree by Hilton Hotel Portland
Long Creek Hotel by IHG

Long Creek Hotel by IHG

2.5 out of 5
171 Philbrook Ave South Portland ME
Fully refundable
$76 nightly
The price is $82 total per night from Dec 18 to Dec 19
$82 total
Dec 18 - Dec 19
Total with taxes and fees
7.4/10 Good! (1,000 reviews)
Room was clean. Beds are fulls not queens. For cheap price it’s good

Reviewed on Dec 7, 2025

Long Creek Hotel by IHG
See all 2,925 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.

Find the Best Waterboro Vacation Packages

Waterboro Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Portland Intl. Jetport Airport (PWM)
Population
7,500
Top Sights
Bowl A Rama, Mousam Lake and Blueberry Hill

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Frequently asked questions

How much does a Waterboro vacation package cost?
You can pick up a vacation package to this destination from $363 on Expedia. However, how much your vacation to Waterboro costs will depend on factors like the length of stay, season and hotel choice.
What are the cheapest months to go to Waterboro?
You can generally find reduced prices and greater availability in November, December and January. Take a look at our cheap Waterboro vacation packages and you could score some great off-season deals.
How many days is enough for Waterboro?
With a well-organized travel plan, you can easily tick off the main Waterboro attractions in a few days. But if you'd like to discover lesser-known spots or take day trips, consider booking your Waterboro vacation for longer.
How to find the best Waterboro package deals?
Start your search for a Waterboro package deal by entering your travel dates and destination under our "Packages" tab. Then apply a few filters, like "Guest rating" and "Property type," to tailor the results to your exact needs. You can also sort by "Package discount" and discover offers that come with unbeatable savings. If you don't find the ideal Waterboro package deal right away, simply tweak your dates and search again. Keep in mind that deals are only available for a limited time, so book early and get your Waterboro getaway off to a flying start.
Is it cheaper to book a Waterboro vacation as a package?
You can enjoy significant savings on your Waterboro break by booking a personalized vacation package. Click on the "Package" heading, then enter your travel dates and destination to view some great hotel prices and airfares. Bundle everything into a great-value package and you can save hundreds of dollars. Consider adding a rental car and you may score a better deal.
When to book a vacation package to Waterboro?
If you're considering a spontaneous Waterboro getaway, check out our last-minute deals that can be booked up to a week before you go. Prefer not to wait until the last minute? You can find amazing deals on your hotels and flights by booking well in advance.
Does Expedia offer Book Now, Pay Later Waterboro vacation packages?
If you're anything like us, you love traveling but are not a fan of the big price tag that can come with it. That's why we offer Book Now, Pay Later vacations. With the help of online lender Affirm, you can break down the cost of your Waterboro break over 3, 6 or 12 months. There are also no hidden or late payment fees, so you can snap up cheap vacation packages with payment plans as soon as you spot them.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.