Waldoboro Vacation Packages

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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.

Top Waldoboro Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Trade Winds on the Bay

Trade Winds on the Bay

3.5 out of 5
Price was CA $1,420, price is now CA $1,307 per person
CA $1,307
per person
Dec 28 - Jan 2
found 19 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Rockland (RKD)
8.6/10 Excellent! (519 reviews)

Harborline Hotel

Harborline Hotel

3 out of 5
Price was CA $1,508, price is now CA $1,307 per person
CA $1,307
per person
Dec 28 - Jan 2
found 19 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Rockland (RKD)
7.4/10 Good! (448 reviews)

Snow Cap Inn

Snow Cap Inn

2.5 out of 5
Price was CA $2,499, price is now CA $2,281 per person
CA $2,281
per person
Dec 20 - Dec 26
found 1 day ago
Roundtrip flight included
Montreal (YUL) to Augusta (AUG)
9/10 Wonderful! (546 reviews)

Pressey House Lakeside Bed & Breakfast

Pressey House Lakeside Bed & Breakfast

3 out of 5
Price was CA $1,807, price is now CA $1,664 per person
CA $1,664
per person
Dec 28 - Jan 1
found 21 hours ago
Roundtrip flight included
Toronto (YTO) to Augusta (AUG)
10/10 Exceptional! (1 review)
Very charming place with great breakfast and beautiful lake

Reviewed on Oct 4, 2026

Ready to book your vacation to Waldoboro?

 

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Waldoboro Hotel Deals

Applecroft Cabin No. 3 - Modern off-grid cabin deep in the woods.

Applecroft Cabin No. 3 - Modern off-grid cabin deep in the woods.

Waldoboro ME
The price is CA $203 per night from Oct 29 to Oct 30
CA $203
CA $254 total
Oct 29 - Oct 30
includes taxes & fees
Applecroft Cabin No. 3 - Modern off-grid cabin deep in the woods.
Harborline Hotel

Harborline Hotel

3 out of 5
6 Park Drive Rockland ME
Fully refundableReserve now, pay when you stay
The price is CA $134 per night from Nov 17 to Nov 18
CA $134
CA $164 total
Nov 17 - Nov 18
includes taxes & fees
Harborline Hotel
Trade Winds on the Bay

Trade Winds on the Bay

3.5 out of 5
2 Park Dr Rockland ME
Fully refundableReserve now, pay when you stay
The price is CA $163 per night from Nov 15 to Nov 16
CA $163
CA $177 total
Nov 15 - Nov 16
includes taxes & fees
Trade Winds on the Bay
See all 1,941 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.
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Stay near popular Waldoboro attractions

Morse's Sauerkraut

10.0/10 (4 reviews)
Enjoy an outing to Morse's Sauerkraut during your stay in Waldoboro. Wander the forest or discover the area's sunrises.
See properties

Frequently asked questions

How much does a Waldoboro vacation package cost?
You can pick up a vacation package to this top destination from CA $1,307 on Expedia. But how much your vacation to Waldoboro costs will depend on factors like the season, length of stay and hotel choice.
What are the cheapest months to go to Waldoboro?
Plan your trip for the off-peak season and you're likely to score cheap Waldoboro vacation packages. Keep in mind that public holidays and major local events can impact prices, so do some research before you go.
How many days is enough for Waldoboro?
With a well-planned schedule, you can easily visit the main Waldoboro attractions in a few days. But if you'd like to explore off the beaten track or take day trips, think about booking your Waldoboro vacation for longer.
How to find the best Waldoboro package deals?
Begin your search for a Waldoboro package deal by entering your destination and travel dates under our "Packages" tab. Then add some filters, like "Guest rating" and "Property type," to fine-tune the results to your exact style. You can also sort by "Package discount" and browse offers that come with irresistible savings. If you don't find the perfect Waldoboro package deal straight away, simply change your dates and search again. Keep in mind that deals are only available for a limited time, so book early and get your Waldoboro escape underway.
Is it cheaper to book a Waldoboro vacation as a package?
An Expedia vacation package could land you significant savings when compared to booking accommodations and flights individually. Better still, you can customize your Waldoboro trip to fit your exact style. Choose your preferred flight time, select the hotel type and add a car rental. Browse our great deals to see how much you can save.
When to book a vacation package to Waldoboro?
If you've got your Waldoboro vacation dates confirmed, book as soon as you can to grab some awesome deals. With Expedia, you can generally reserve some flights up to one year ahead of time. Prefer spontaneous getaways? Our last-minute deals are ideal for quick escapes.
How to plan a trip to Waldoboro?

  1. Pick your travel dates: The things you'd like to do in Waldoboro and your favourite season will help you decide when to go.
  2. Set a budget: Factor in costs such as flights, food and transportation when working out how much to put aside for your trip to Waldoboro. Then, select a property that fits your budget, whether that's an economical stay or a lavish retreat.
  3. Decide how many days away: Start by compiling a list of the activities and attractions you'd like to get to in Waldoboro. Then, estimate how long you'll need for each, including any travel time.
  4. Combine your airfare and accommodations: After you've nailed down your dates and duration, lock in the right Waldoboro vacation package for you.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.