Waldoboro Vacations from $372

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

    • payments icon

    Better together

    Save up to $1,045 when you book a flight and hotel together*
    lob hotels icon

    Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
    lob packages icon

    Rest easy

    Plan, book, and manage your trip all in one place

Your Waldoboro Vacation

When you organize a vacation package to Waldoboro, you can relax and enjoy your break knowing your travel plans have been worked out ahead of time. Discover the wonders of this vibrant city while based in a neighborhood like Medomak, which is good for walking. Fill your trip to Waldoboro with tours of its top attractions. First stop? Don't miss Fawcetts Antique Toy and Art Museum. Whatever your travel plans or budget, organizing your ultimate tailored Waldoboro vacation is a piece of cake with Expedia.

The Latest Waldoboro vacation packages

Price found within the past 48 hours. Click for updated prices.
Harborline Hotel

Harborline Hotel

3 out of 5
Price was $469, price is now $372 per person
$372
per person
Oct 23 - Oct 26
found 1 day ago
Roundtrip non-stop flight included
Philadelphia (PHL) to Rockland (RKD)
7.6/10 Good! (124 reviews)
Great location and friendly staff

Reviewed on Aug 22, 2025

Greenleaf Inn

Greenleaf Inn

2 out of 5
Save 100% on your flight
Price was $1,046, price is now $687 per person
$687
per person
Oct 4 - Oct 7
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Augusta (AUG)
9.4/10 Exceptional! (9 reviews)
The location and view of this property was excellent. The staff gave good dining recommendations. The fire pit at night with s’mores was nice. We were given a nice bouquet of flowers at time of check in. The morning breakfast was a bit different. The kitchen was stocked with eggs, cream cheese, yogurt and condiments and pastries. You were responsible to make your own breakfast in the kitchen.

Reviewed on Jul 23, 2025

Grand Summit Hotel

Grand Summit Hotel

3 out of 5
Save 100% on your flight
Price was $980, price is now $742 per person
$742
per person
Oct 25 - Nov 1
found 1 day ago
Roundtrip flight included
Minneapolis (MSP) to Augusta (AUG)
8.2/10 Very Good! (274 reviews)
We love staying here every year for the TMC. It’s clean, comfortable, and friendly. The pool is great! The restaurant in the hotel, however, is always a disappointment. Food is ok, but service is poor.

Reviewed on Aug 20, 2025

Trade Winds on the Bay

Trade Winds on the Bay

3.5 out of 5
Price was $545, price is now $431 per person
$431
per person
Oct 12 - Oct 15
found 1 day ago
Roundtrip flight included
Minneapolis (MSP) to Rockland (RKD)
8.4/10 Very Good! (250 reviews)
It was very hands off-- you go, retrieve your key from the lock box and let yourself in. But it is a gorgeous old building built like a fancy plantation - castle, in the middle of a small coastal town in pristine Maine, with a pool and a fitness center. I didn't realize it at first, but my room had a hallway to another living room area, with a balcony to sit and watch the sunrise from. Wow! Yeah, it's a great place.

Reviewed on Aug 14, 2025

Topside Inn

Topside Inn

3 out of 5
Price was $1,236, price is now $981 per person
$981
per person
Oct 4 - Oct 7
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Augusta (AUG)
10/10 Exceptional! (38 reviews)
A perfect stay for our mother-daughter trip! We look forward to a future stay.

Reviewed on Aug 19, 2025

Don't see what you're looking for?
See all available trips from Columbus to Waldoboro
View all trips

Discover the most popular places to visit in Waldoboro

Morse's Sauerkraut

Enjoy an outing to Morse's Sauerkraut during your stay in Waldoboro. Wander the forest or discover the area's sunrises.

Morse's Sauerkraut

Fawcett's Antique Toy and Art Museum

You can spend time studying the exhibits at Fawcett's Antique Toy and Art Museum in Waldoboro. Amble around this relaxing area's waterfront or experience its museums.

Fawcett's Antique Toy and Art Museum

Waldoboro Hotel Deals

Ocean Gate Resort

Ocean Gate Resort

3 out of 5
70 Ocean Gate Rd, Southport, ME
Fully refundableReserve now, pay when you stay
$177 nightly
The price is $191 total per night from Sep 1 to Sep 2
$191 total
Sep 1 - Sep 2
Total with taxes and fees
8.4/10 Very Good! (1,000 reviews)
"Gorgeous views, peaceful and very friendly"

Reviewed on Aug 22, 2025

Ocean Gate Resort
Harborline Hotel

Harborline Hotel

3 out of 5
6 Park Drive, Rockland, ME
Fully refundableReserve now, pay when you stay
$138 nightly
The price is $150 total per night from Aug 27 to Aug 28
$150 total
Aug 27 - Aug 28
Total with taxes and fees
7.6/10 Good! (134 reviews)
"Great location and friendly staff"

Reviewed on Aug 22, 2025

Harborline Hotel
Flagship Inn and Suites

Flagship Inn and Suites

2.5 out of 5
200 Townsend Avenue, Boothbay Harbor, ME
$149 nightly
The price is $163 total per night from Sep 21 to Sep 22
$163 total
Sep 21 - Sep 22
Total with taxes and fees
8.2/10 Very Good! (1,011 reviews)
"It was a nice place to stay! Quiet and clean. Agreeable personnel!"

Reviewed on Aug 20, 2025

Flagship Inn and Suites
See all 1,819 properties in Waldoboro
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.

More vacations you might like

All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Kid Friendly Vacations
Kid Friendly Vacations

Frequently asked questions

How much does a Waldoboro vacation package cost?
You'll find cheap prices from $372 on Expedia for your Waldoboro escape. However, factors like your choice of hotel, the season and length of stay will determine how much your vacation to Waldoboro costs.
What are the cheapest months to go to Waldoboro?
October, November and December are the best times to search for cheap Waldoboro vacation packages. Opting to travel in quieter periods means you can typically find lower prices on flights and hotels.
How many days is enough for Waldoboro?
The ideal length for your Waldoboro vacation depends on what you'd like to do. Typically, a handful of days to a week will give you time to go to all the top sights and discover some hidden gems along the way.
How to find the best Waldoboro package deals?
Use Expedia's filter tool to help you find some great Waldoboro package deals. When you start your search, simply set your maximum budget and then sort the results by "Price: low to high." If you want to save, plan your trip for midweek, or browse for Waldoboro package deals in the off-season. Switch up your travel dates and you may score even better 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 Waldoboro vacation as a package?
You can enjoy significant savings on your next Waldoboro getaway by booking a personalized vacation package. Click on the "Package" heading, then select your destination and travel dates to browse the best airfares and hotel prices. Bundle everything into a neat package and you can save hundreds of dollars. Consider adding a car rental and you may score a better deal.
When to book a vacation package to Waldoboro?
If you're planning a spontaneous Waldoboro trip, check out our last-minute deals that can be booked up to one week before you go. Prefer not to wait until the last minute? You can score terrific deals on your flights and hotels by booking ahead.
Does Expedia offer Book Now, Pay Later Waldoboro vacation packages?
Set off on your perfect trip to Waldoboro with help from our Book Now, Pay Later vacations. No need to scrimp and save or wait until your next payday — we've teamed up with online lender Affirm to give you more flexibility with your finances. Our vacation packages with payment plans let you spread the cost over 3, 6 or 12 months. With no hidden charges or late payment fees, it's easy to stay on budget and snap up cheap deals while they last.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.