Woolwich Vacations from $452

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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.
InnSeason Resorts The Falls at Ogunquit

InnSeason Resorts The Falls at Ogunquit

2.5 out of 5
Price was $537, price is now $452 per person
$452
per person
Jan 19 - Jan 23
found 15 hours ago
Roundtrip non-stop flight included
Tampa (TPA) to Portland (PWM)
9.4/10 Exceptional! (351 reviews)
Staff was great and room was exactly what we needed with lots of space!

Reviewed on Oct 19, 2025

Kennebunkport Captains Collection

Kennebunkport Captains Collection

4.5 out of 5
Price was $1,149, price is now $898 per person
$898
per person
Jan 16 - Jan 23
found 8 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Portland (PWM)
9.4/10 Exceptional! (634 reviews)
Our Bed and Breakfast was amazing! The bed was comfortable and we loved the salted chocolate chip cookies at night! The staff was so kind and hospitable!

Reviewed on Nov 2, 2025

Portland Harbor Hotel

Portland Harbor Hotel

4 out of 5
Downtown Portland
Price was $634, price is now $501 per person
$501
per person
Jan 16 - Jan 18
found 7 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Portland (PWM)
9.2/10 Wonderful! (1,621 reviews)
Clean room, staff was very helpful and nice!!

Reviewed on Nov 5, 2025

The Docent's Collection - New Opening

The Docent's Collection - New Opening

2 out of 5
Downtown Portland
Price was $725, price is now $605 per person
$605
per person
Jan 16 - Jan 18
found 7 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Portland (PWM)
No reviews
Really nice and clean new hotel!

Reviewed on Oct 27, 2025

84 Main

84 Main

4 out of 5
Price was $754, price is now $634 per person
$634
per person
Dec 19 - Dec 22
found 13 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Portland (PWM)
10/10 Exceptional! (51 reviews)
This property was absolutely beautiful and well maintained! Right in the heart of Kennebunk within walking distance to great restaurants!!

Reviewed on Oct 26, 2025

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Discover the most popular places to visit in Woolwich

Montsweag Flea Market

3/5(1 review)

You can find the perfect gifts to bring home at Montsweag Flea Market during your stay in Woolwich. While you're in the area, stroll along the waterfront.

Montsweag Flea Market

Woolwich Hotel Deals

Casco Bay Inn

Casco Bay Inn

2 out of 5
107 US Route 1, Freeport, ME
Fully refundableReserve now, pay when you stay
$89 nightly
The price is $97 total per night from Dec 1 to Dec 2
$97 total
Dec 1 - Dec 2
Total with taxes and fees
8/10 Very Good! (1,055 reviews)
Large rooms and a quiet location. A very basic hotel good for a one-night stay.

Reviewed on Oct 23, 2025

Casco Bay 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
$88 nightly
The price is $96 total per night from Nov 12 to Nov 13
$96 total
Nov 12 - Nov 13
Total with taxes and fees
7.6/10 Good! (1,030 reviews)
Parking easy Comfortable stay

Reviewed on Oct 28, 2025

Best Western Freeport Inn
Comfort Inn Brunswick

Comfort Inn Brunswick

2.5 out of 5
199 Pleasant St, Brunswick, ME
Fully refundableReserve now, pay when you stay
$89 nightly
The price is $97 total per night from Dec 1 to Dec 2
$97 total
Dec 1 - Dec 2
Total with taxes and fees
8.8/10 Excellent! (1,010 reviews)
Staff was very courteous

Reviewed on Nov 1, 2025

Comfort Inn Brunswick
See all 1,661 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 $452 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.