Waterboro Vacations from $786

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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.
Ogunquit River Inn & Suites

Ogunquit River Inn & Suites

3 out of 5
Price was $1,088, price is now $786 per person
$786
per person
May 18 - May 23
found 1 day ago
Roundtrip flight included
Houston (IAH) to Portland (PWM)
9/10 Wonderful! (1,000 reviews)
The room was very clean!

Reviewed on Oct 31, 2025

Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Save 100% on your flight
Price was $2,335, price is now $1,422 per person
$1,422
per person
Apr 29 - May 2
found 1 day ago
Roundtrip non-stop flight included
Burbank (BUR) to Boston (BOS)
9.8/10 Exceptional! (1,001 reviews)
Everything was great, however the pool itself was not heated, it was cold and no one really stayed in it for that reason. Thankfully there was a hot tub.

Reviewed on Mar 23, 2026

Beachside Village Resort

Beachside Village Resort

3 out of 5
Save 100% on your flight
Price was $2,060, price is now $1,363 per person
$1,363
per person
May 22 - May 26
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Boston (BOS)
9.4/10 Exceptional! (101 reviews)
Very clean and quiet place to relax. Very friendly and professional! We will come back!

Reviewed on Nov 10, 2025

Portland Harbor Hotel

Portland Harbor Hotel

4 out of 5
Downtown Portland
Price was $1,641, price is now $1,187 per person
$1,187
per person
Jun 14 - Jun 19
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Portland (PWM)
9.2/10 Wonderful! (1,776 reviews)
Very nice room, hotel was clean, staff kind and attentive. The location of thos hotel is great.

Reviewed on Mar 24, 2026

The Westin Waltham-Boston

The Westin Waltham-Boston

4 out of 5
Save 100% on your flight
Price was $2,065, price is now $1,507 per person
$1,507
per person
Jun 13 - Jun 19
found 13 hours ago
Roundtrip flight included
Dallas (DFW) to Boston (BOS)
8.8/10 Excellent! (1,095 reviews)
Awesome breakfast views!

Reviewed on Mar 13, 2026

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Waterboro Hotel Deals

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
$81 nightly
The price is $88 total per night from Apr 2 to Apr 3
$88 total
Apr 2 - Apr 3
Total with taxes and fees
8/10 Very Good! (1,372 reviews)
It was a smooth check in, friendly staff

Reviewed on Mar 25, 2026

DoubleTree by Hilton Hotel Portland
Tru by Hilton Portland Airport Area

Tru by Hilton Portland Airport Area

3 out of 5
369 Maine Mall Road South Portland ME
Fully refundableReserve now, pay when you stay
$81 nightly
The price is $88 total per night from Apr 19 to Apr 20
$88 total
Apr 19 - Apr 20
Total with taxes and fees
8.8/10 Excellent! (1,761 reviews)
The property was clean the staff friendly. There's no microwave in the room and the gym is really small.

Reviewed on Mar 23, 2026

Tru by Hilton Portland Airport Area
Long Creek Hotel by IHG

Long Creek Hotel by IHG

2.5 out of 5
171 Philbrook Ave South Portland ME
Fully refundable
$78 nightly
The price is $85 total per night from Mar 30 to Mar 31
$85 total
Mar 30 - Mar 31
Total with taxes and fees
7.4/10 Good! (1,001 reviews)
Won’t return sludge in our bathroom. We had to use our towels over again because there was none! And house keeping had not come yet. We are talking 8 in the morning at this point!!

Reviewed on Mar 24, 2026

Long Creek Hotel by IHG
See all 3,008 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 $786 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.