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A calm lake with a buoy in the center, surrounded by a dense forest and a misty shoreline.

Waldoboro Vacations from $516

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The Latest Waldoboro Vacation Packages

Price found within the past 48 hours. Click for updated prices.
  • Lobby
    Aug 26 - Aug 31

    Grand Summit Hotel + Flight

    Newry
    5 nights
    3.0 star property
    8.4/10 - Very Good (385 reviews)
    "Tout etait parfait!"
    Reviewed July 14, 2026
    Roundtrip • New York (JFK) - Augusta (AUG)
    JFK - BOS • Nonstop BOS - JFK • Nonstop
    $672
    $516
    per traveler
    found 5 hours ago
    Grand Summit Hotel
  • Exterior
    Aug 26 - Aug 31

    Jordan Hotel + Flight

    Newry
    5 nights
    3.0 star property
    8.8/10 - Excellent (544 reviews)
    "The best experience all around."
    Reviewed July 13, 2026
    Roundtrip • New York (JFK) - Augusta (AUG)
    JFK - BOS • Nonstop BOS - JFK • Nonstop
    $695
    $533
    per traveler
    found 5 hours ago
    Jordan Hotel
  • Windward Premium Harbor View King | Premium bedding, Tempur-Pedic beds, minibar, iron/ironing board
    Aug 22 - Aug 24

    Topside Inn + Flight

    Boothbay Harbor
    2 nights
    3.0 star property
    10/10 - Exceptional (126 reviews)
    Roundtrip • New York (NYC) - Augusta (AUG)
    JFK - BOS • Nonstop BOS - JFK • Nonstop
    Save 100% on your flight
    $1,024
    $798
    per traveler
    found 1 day ago
    Topside Inn
  • Reception
    Sep 8 - Sep 13

    Hampton Inn Augusta + Flight

    Augusta
    5 nights
    2.5 star property
    9.4/10 - Exceptional (820 reviews)
    "Our check in was quick. The room was clean and comfortable. We did not have time to use the amenities but would have either more time. Breakfast provided a decent choice ."
    Reviewed July 14, 2026
    Roundtrip • Cleveland (CLE) - Augusta (AUG)
    CLE - BOS • 1 stop BOS - CLE • 1 stop
    $927
    $730
    per traveler
    found 3 hours ago
    Hampton Inn Augusta
  • Apartment, Ensuite (St Moritz) | Hypo-allergenic bedding, bed sheets
    Sep 8 - Sep 13

    Evergreen Valley Inn by Coolvacay + Flight

    Stoneham
    5 nights
    3.0 star property
    8.2/10 - Very Good (185 reviews)
    "Super clean and friendly people at the desk"
    Reviewed October 28, 2025
    Roundtrip • Cleveland (CLE) - Augusta (AUG)
    CLE - BOS • 1 stop BOS - CLE • 1 stop
    $682
    $551
    per traveler
    found 3 hours ago
    Evergreen Valley Inn by Coolvacay

Waldoboro Hotel Deals

House (3 Bedrooms) | Front of property

Near Lakes, Bay & Trails! Historic Waldoboro Gem

Near Lakes, Bay & Trails! Historic Waldoboro Gem
3.0 star property
3.7 mi from Waldoboro
10.0 out of 10, Exceptional, (2 reviews)
"This home is such a gem! A historic home that is updated with many modern conveniences. We’ve been to MANY AirB&B’s and this home was probably the best equipped we’ve been in! Convenient to Boothbay and lots of downeast inlets and harbors. Very quiet, but close to groceries, food and farm stands. Our only regret was not staying longer- we would have loved to grill and use the fire pit!"
$450 nightly
The price is $491
Aug 9 - Aug 10
Total with taxes and fees
Near Lakes, Bay & Trails! Historic Waldoboro Gem
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.
See all properties in Waldoboro

Frequently Asked Questions

How much does a Waldoboro vacation package cost?

You'll find cheap prices from $516 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.