Waterboro Vacations from $608

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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.
Brewster Green Resort

Brewster Green Resort

3.5 out of 5
Price was $813, price is now $608 per person
$608
per person
Jan 22 - Jan 25
found 6 hours ago
Roundtrip flight included
Los Angeles (LAX) to Boston (BOS)
9.4/10 Exceptional! (152 reviews)

The Newbury Boston

The Newbury Boston

5 out of 5
Back Bay
Price was $2,573, price is now $1,494 per person
$1,494
per person
Dec 8 - Dec 13
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to Boston (BOS)
9.4/10 Exceptional! (744 reviews)
Beautiful hotel and the staff was wonderful. They gave us a corner room with a great view of the city. The room was spacious with a comfortable seating area.

Reviewed on Nov 7, 2026

Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Price was $1,651, price is now $979 per person
$979
per person
Dec 11 - Dec 14
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Boston (BOS)
9.8/10 Exceptional! (1,004 reviews)

The Langham, Boston

The Langham, Boston

5 out of 5
Downtown Boston
Price was $1,308, price is now $974 per person
$974
per person
Jan 11 - Jan 14
found 19 hours ago
Roundtrip flight included
Dallas (DAL) to Boston (BOS)
9.8/10 Exceptional! (1,003 reviews)
Coffee machine in our room did not work and unfortunately our room located near the stair exit was not the most quiet. Other than that, was a very nice hotel with lovely staff.

Reviewed on Nov 7, 2026

The Onset Beach Compound-Cape Cod Beach Resort & Oceanic Habitat

The Onset Beach Compound-Cape Cod Beach Resort & Oceanic Habitat

3 out of 5
Price was $2,175, price is now $1,629 per person
$1,629
per person
Dec 23 - Dec 26
found 1 day ago
Roundtrip flight included
San Juan (SJU) to Boston (BOS)
10/10 Exceptional! (11 reviews)
We had a great experience staying in the crab house. The cottage was well maintained and had everything we needed to enjoy our stay. The staff was friendly, helpful, and genuinely care. Ken was fantastic, you can really tell he cares about ensuring guests have a great experience. 10/10 experience, would recommend this spot to anyone looking for a great stay on the cape.

Reviewed on Jul 27, 2026

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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
$76 nightly
The price is $82 total per night from Nov 29 to Nov 30
$82 total
Nov 29 - Nov 30
Total with taxes and fees
8.4/10 Very Good! (2,964 reviews)
"Very clean rooms great price and best of all coffee in the lobby"

Reviewed on Nov 7, 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

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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
$67 nightly
The price is $73 total per night from Nov 29 to Nov 30
$73 total
Nov 29 - Nov 30
Total with taxes and fees
Spark by Hilton Portland Airport Maine Mall
See all 2,972 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 $608 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.