Woolwich Vacations from $523
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Your Woolwich Vacation
Let our vacation packages to Woolwich inspire your next great adventure. There's lots to like about this captivating city, starting with the neighborhood of Harpswell, which is good for nature and culture. If your trip to Woolwich includes a little sightseeing, take in renowned attractions like Chocolate Church, Waterfront Park and Maine Maritime Museum. Whatever your travel plans or budget, putting together the ultimate tailored Woolwich vacation is a walk in the park with Expedia.
The Latest Woolwich vacation packages
Price found within the past 48 hours. Click for updated prices.
The Meadowmere Resort
$523
per person
Nov 5 - Nov 8
found 1 day ago
Roundtrip flight included
New York (NYC) to Portland (PWM)
8.6/10 Excellent! (1,010 reviews)
Clean room, paid breakfast, front office staff very efficient, very limited items even in paid breakfast section.check in time 4 pm and check out 11 am.
Reviewed on Sep 2, 2026
The Wolfeboro Inn
$725
per person
Oct 2 - Oct 5
found 1 day ago
Roundtrip flight included
New York (NYC) to Portland (PWM)
8.2/10 Very Good! (631 reviews)
Just returned from a several-day stay at the Wolfeboro Inn. It was absolutely delightful! Clearly an older establishment, but well-maintained and very clean, cozy, and comfortable. The staff was especially friendly and helpful. Very welcoming! Sweet location right on the lake & close to the lovely downtown - so pretty! Extra kudos also to the tavern…the food is excellent at great prices!
👏🤗👏
Reviewed on Sep 1, 2026
Stay near popular Woolwich attractions
Montsweag Flea Market
8.0/10 (2 reviews)
Maine's largest outdoor flea market since 1977, showcasing 125+ tables of antiques, collectibles, and local treasures. Arrive early Wednesdays for "Antique Dealer Day" featuring vendors' finest curated selections.
Woolwich Hotel Deals
The Freeport Hotel, an Ascend Collection Hotel
506 Us Route 1 Freeport ME
Fully refundable
$98 nightly
$107 total
Sep 9 - Sep 10
Total with taxes and fees
7.6/10 Good! (1,004 reviews)
"The rooms were as clean as the staff could manage, I'm sure. By that I mean, nice clean bedding and towels; clean bathroom. But there was a mustiness that seemed to have permeated the rooms; perhaps the carpeting? Parking was fine and very available. The breakfast was so-so, but it was "you get what ..."
Reviewed on Aug 31, 2026
Flagship Inn and Suites
200 Townsend Avenue Boothbay Harbor ME
$129 nightly
$141 total
Sep 3 - Sep 4
Total with taxes and fees
8/10 Very Good! (1,003 reviews)
"Breakfast was great!"
Reviewed on Sep 1, 2026
Best Western Freeport Inn
31 US Route 1 Freeport ME
Fully refundableReserve now, pay when you stay
$101 nightly
$111 total
Sep 7 - Sep 8
Total with taxes and fees
7.6/10 Good! (1,008 reviews)
"The check in attendant was kind and helpful. The room was clean and comfortable. We liked the close location of the hotel to Freeport shopping outlets."
Reviewed on Sep 2, 2026
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 Woolwich Vacation Packages
Woolwich Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Closest Airport | Augusta State Airport (AUG) |
Population | 2,900 |
Top Sights | Popham Beach, Reid State Park and Hunnewell Beach |
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Frequently asked questions
How much does a Woolwich vacation package cost?
You'll find cheap prices from $523 on Expedia for your Woolwich getaway. However, factors like the hotel choice, length of stay and season will influence how much your vacation to Woolwich costs.
What are the cheapest months to go to Woolwich?
You're likely to find reduced prices and greater availability in January, April and December. Explore our cheap Woolwich vacation packages and you could score some great off-season discounts.
How many days is enough for Woolwich?
Usually, a handful of days is enough to tick off the main attractions during your Woolwich vacation. However, if you prefer to have some time to chill out or take day tours, think about extending your itinerary.
How to find the best Woolwich package deals?
Use Expedia's filters to find some terrific Woolwich package deals. When you begin your search, simply set your maximum budget and then sort the results by "Price: low to high." If you're looking to save, plan your trip for midweek, or look for Woolwich package deals in the off-season. Play around with your travel dates and you may score even better discounts. As a rule of thumb, it's usually best to book your vacation package well in advance.
Is it cheaper to book a Woolwich vacation as a package?
You can enjoy significant savings on your Woolwich escape by booking a personalized vacation package. Click on the "Package" heading, then enter your travel dates and destination to see some great hotel and flight prices. Bundle everything into a great-value package and you can save hundreds of dollars. Consider adding a car rental and you may land a better deal.
When to book a vacation package to Woolwich?
If you're planning a spur-of-the-moment Woolwich adventure, browse our last-minute deals that can be booked up to a week before you take off. Prefer not to wait until the last minute? You can land sensational deals on your hotels and flights by booking well in advance.
Does Expedia offer Book Now, Pay Later Woolwich vacation packages?
Secure your perfect escape to Woolwich with Expedia's Book Now, Pay Later vacations. There's no need to save like crazy or wait for your next paycheck — we've joined forces with online lender Affirm to give you flexibility and choice. Our vacation packages with payment plans mean you can spread the cost over 3, 6 or 12 months. With no late payment fees or extra charges, it's a breeze to stick to your budget and snap up bargains before they disappear.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
