Woolwich Vacations from $840

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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.
Inn at Diamond Cove

Inn at Diamond Cove

3.5 out of 5
Save 100% on your flight
Price was $1,243, price is now $840 per person
$840
per person
Sep 13 - Sep 18
found 1 day ago
Roundtrip non-stop flight included
Denver (DEN) to Portland (PWM)
8.8/10 Excellent! (196 reviews)
We had a really wonderful visit at the Inn at Diamond Cove. It was a special adventure and the staff tried to work with us to help us enjoy our visit after arriving very late at night for a one night /one day stay. We knew nothing about the inn or the island's history so it was a leap of faith and well worth it.

Reviewed on Jun 29, 2026

Ogunquit River Inn & Suites

Ogunquit River Inn & Suites

3 out of 5
Moody
Save 100% on your flight
Price was $1,430, price is now $899 per person
$899
per person
Aug 20 - Aug 24
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Portland (PWM)
9/10 Wonderful! (1,017 reviews)
Clean rooms and surroundings…helpful staff

Reviewed on Jun 28, 2026

The Meadowmere Resort

The Meadowmere Resort

2.5 out of 5
Save 100% on your flight
Price was $1,593, price is now $1,035 per person
$1,035
per person
Aug 20 - Aug 24
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Portland (PWM)
8.6/10 Excellent! (1,003 reviews)
Price was good for the amenities offered and location. Our room was just recently renovated.

Reviewed on Jun 22, 2026

The Weldon Hotel

The Weldon Hotel

4.5 out of 5
Downtown Portland
Save 100% on your flight
Price was $2,094, price is now $1,454 per person
$1,454
per person
Sep 14 - Sep 18
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Portland (PWM)
9.8/10 Exceptional! (101 reviews)
Lovely suite! Comfy king bed, everything spotless, Great location. Would stay here again

Reviewed on Apr 23, 2026

Blind Tiger Portland - Danforth Street.

Blind Tiger Portland - Danforth Street.

3.5 out of 5
West End
Save 100% on your flight
Price was $1,410, price is now $1,025 per person
$1,025
per person
Aug 16 - Aug 19
found 1 day ago
Roundtrip non-stop flight included
Dallas (DAL) to Portland (PWM)
9.6/10 Exceptional! (185 reviews)
We were only there for 1 night, but the innkeeper made a great suggestion for dinner. Overall a great place and would stay again.

Reviewed on Jun 26, 2026

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Stay near popular Woolwich attractions

Montsweag Flea Market

8.0/5 (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.
See properties

Woolwich Hotel Deals

Flagship Inn and Suites

Flagship Inn and Suites

2.5 out of 5
200 Townsend Avenue Boothbay Harbor ME
Fully refundableReserve now, pay when you stay
$193 nightly
The price is $211 total per night from Jul 8 to Jul 9
$211 total
Jul 8 - Jul 9
Total with taxes and fees
8/10 Very Good! (1,002 reviews)
"We stayed overnight and found the staff to be very helpful, the room clean and spacious, and the complementary breakfast buffet was very good."

Reviewed on Jun 29, 2026

Flagship Inn and Suites
Ocean Gate Inn

Ocean Gate Inn

3 out of 5
70 Ocean Gate Rd Southport ME
$267 nightly
The price is $291 total per night from Jul 1 to Jul 2
$291 total
Jul 1 - Jul 2
Total with taxes and fees
8.6/10 Excellent! (1,004 reviews)
"Loved kayaking in the bay"

Reviewed on Jun 30, 2026

Ocean Gate Inn
Best Western Freeport Inn

Best Western Freeport Inn

3 out of 5
31 US Route 1 Freeport ME
Fully refundableReserve now, pay when you stay
$111 nightly
The price is $121 total per night from Jul 5 to Jul 6
$121 total
Jul 5 - Jul 6
Total with taxes and fees
7.8/10 Good! (1,004 reviews)
"The room was fine, but we hadn’t expected to have to walk up stairs to get to our room in a three floor facility. Although it was only a half flight, it was inconvenient. Also, breakfast was not included in the price. There was a good breakfast available near by."

Reviewed on Jun 29, 2026

Best Western Freeport Inn
See all 1,770 properties in Woolwich
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 $840 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.