Woolwich Vacations from $468

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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.
84 Main

84 Main

4 out of 5
Price was $633, price is now $468 per person
$468
per person
Apr 30 - May 3
found 3 hours ago
Roundtrip flight included
New York (JFK) to Portland (PWM)
9.8/10 Exceptional! (56 reviews)
Very spacious and relaxing. Nice view of Kennebunk quaint ice rink and Main Street. Coffee shop at Street level was a fantastic add! Beds and bedding were comfortable. Will visit again! Nothing lacking with respect to amenities.

Reviewed on Dec 29, 2025

Portland Harbor Hotel

Portland Harbor Hotel

4 out of 5
Downtown Portland
Save 100% on your flight
Price was $1,900, price is now $1,328 per person
$1,328
per person
May 17 - May 24
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Portland (PWM)
9.2/10 Wonderful! (1,776 reviews)
Very nice room, hotel was clean, staff kind and attentive. The location of thos hotel is great.

Reviewed on Mar 24, 2026

The Docent's Collection at 121 Middle Street

The Docent's Collection at 121 Middle Street

3.5 out of 5
Downtown Portland
Save 100% on your flight
Price was $2,119, price is now $1,493 per person
$1,493
per person
May 17 - May 24
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Portland (PWM)
9.6/10 Exceptional! (275 reviews)
So spacious, decor is modern yet warm. Staff super friendly and helpful. Perfect location for concerts at Merrill, short walk.

Reviewed on Mar 28, 2026

Cliff House Maine

Cliff House Maine

4.5 out of 5
Bald Head
Save 100% on your flight
Price was $1,380, price is now $1,030 per person
$1,030
per person
Apr 30 - May 3
found 1 hour ago
Roundtrip flight included
New York (JFK) to Portland (PWM)
9.4/10 Exceptional! (1,007 reviews)
Gorgeous room in a gorgeous setting. Norman the lead bartender is a treasure. Hector was great as well. Everything was outstanding.

Reviewed on Mar 25, 2026

Ogunquit River Inn & Suites

Ogunquit River Inn & Suites

3 out of 5
Price was $1,524, price is now $1,174 per person
$1,174
per person
May 17 - May 24
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Portland (PWM)
9/10 Wonderful! (1,000 reviews)
The room was very clean!

Reviewed on Oct 31, 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

SpringHill Suites by Marriott Freeport Brunswick

SpringHill Suites by Marriott Freeport Brunswick

2 out of 5
500 US-1 Freeport ME
Fully refundableReserve now, pay when you stay
$84 nightly
The price is $92 total per night from Apr 3 to Apr 4
$92 total
Apr 3 - Apr 4
Total with taxes and fees
8.8/10 Excellent! (228 reviews)
Clean, comfortable hotel. Easy access from I-295 and a quick drive to downtown Freeport.

Reviewed on Mar 17, 2026

SpringHill Suites by Marriott Freeport Brunswick
Holiday Inn Express Hotel & Suites Freeport by IHG

Holiday Inn Express Hotel & Suites Freeport by IHG

2.5 out of 5
450 U.S. Route 1 Freeport ME
Fully refundable
$85 nightly
The price is $93 total per night from Apr 5 to Apr 6
$93 total
Apr 5 - Apr 6
Total with taxes and fees
8.6/10 Excellent! (1,001 reviews)
Very friendly staff! Room was very clean, breakfast was good, super comfy beds! A little noisy with the highway traffic, but the room fan noise helped to minimize that noise.

Reviewed on Mar 28, 2026

Holiday Inn Express Hotel & Suites Freeport by IHG
Residence Inn Bath Brunswick Area

Residence Inn Bath Brunswick Area

3 out of 5
139 Richardson St. Bath ME
Fully refundableReserve now, pay when you stay
$152 nightly
The price is $166 total per night from Apr 5 to Apr 6
$166 total
Apr 5 - Apr 6
Total with taxes and fees
9.6/10 Exceptional! (389 reviews)
everything was great

Reviewed on Mar 10, 2026

Residence Inn Bath Brunswick Area
See all 1,694 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 $468 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.