Waterboro Vacations from $478

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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 by Westgate Resorts

The Cove at Yarmouth by Westgate Resorts

3 out of 5
Save 100% on your flight
Price was $712, price is now $478 per person
$478
per person
Apr 30 - May 4
just found
Roundtrip non-stop flight included
Atlanta (ATL) to Boston (BOS)
9.2/10 Wonderful! (254 reviews)
Room was not easy to get to and it was 0 degrees out …1st they put me out in a building where the property was a sheet of ice so I asked to be moved to the main building since I was by myself. Fortunately, they moved me, but the room was confusing to get to. :-( The pool was closed for maintenance, and I was planning to swim. :-( The room was great, clean and a comfortable bed, so I would stay again, but I would request staying closer to the lobby next time.

Reviewed on Jan 31, 2026

Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Save 100% on your flight
Price was $3,647, price is now $2,244 per person
$2,244
per person
May 7 - May 12
found 1 day ago
Roundtrip flight included
Atlanta (ATL) 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

Portland Harbor Hotel

Portland Harbor Hotel

4 out of 5
Downtown Portland
Save 100% on your flight
Price was $1,113, price is now $760 per person
$760
per person
May 11 - May 16
found 1 day ago
Roundtrip non-stop flight included
Chicago (CHI) to Portland (PWM)
9.2/10 Wonderful! (1,776 reviews)
A very nice and unique hotel in a great location. Would definitely stay again.

Reviewed on Mar 21, 2026

The Docent's Collection at 121 Middle Street

The Docent's Collection at 121 Middle Street

3.5 out of 5
Downtown Portland
Save 100% on your flight
Price was $1,160, price is now $803 per person
$803
per person
May 11 - May 16
found 1 day ago
Roundtrip non-stop flight included
Chicago (CHI) to Portland (PWM)
9.6/10 Exceptional! (275 reviews)
Property is in an excellent location with so much to see and do (and eat) in walking distance. My room was clean, quiet, and well maintained. Staff interaction was minimal (by design) but the few times I spoke with the concierge on site she was pleasant and accommodating. My only negative comment is regarding the toiletry products. I’m a toilet paper snob and that angel soft just doesn’t cut it. Overall I am beyond satisfied with my stay and would absolutely stay here again.

Reviewed on Mar 22, 2026

The Inn at Hastings Park, Relais & Chateaux - Boston

The Inn at Hastings Park, Relais & Chateaux - Boston

4 out of 5
Save 100% on your flight
Price was $1,549, price is now $1,102 per person
$1,102
per person
Jun 18 - Jun 21
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
9.6/10 Exceptional! (252 reviews)
Excellent experience- clean and very helpful staff

Reviewed on Mar 9, 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 Mar 31 to Apr 1
$88 total
Mar 31 - Apr 1
Total with taxes and fees
8/10 Very Good! (1,370 reviews)
Good overall. I wished they had complimentary breakfast and wished they had a jacuzzi. Also, you have to walk through the bar and restaurant to get to the pool and gym which is a little awkward, but that can't be fixed without a remodel lol. Staff was very helpful and friendly

Reviewed on Mar 23, 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! (1,760 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 29 to Mar 30
$85 total
Mar 29 - Mar 30
Total with taxes and fees
7.4/10 Good! (1,010 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 2,998 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 $478 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.