Woolwich Vacations from $327

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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 $458, price is now $327 per person
$327
per person
Apr 19 - Apr 22
found 1 hour ago
Roundtrip flight included
New York (NYC) to Portland (PWM)
10/10 Exceptional! (52 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

The Weldon Hotel

The Weldon Hotel

4.5 out of 5
Downtown Portland
Save 100% on your flight
Price was $1,455, price is now $989 per person
$989
per person
May 28 - Jun 1
found 1 day ago
Roundtrip flight included
Chicago (CHI) to Portland (PWM)
9.8/10 Exceptional! (93 reviews)
Location is excellent. Short walking distance to every good restaurant and shop. The property was very nice and clean. The kitchen is very well equipped. The gym is very good sized for the size of the apartment building with 13 units in it. The management’s communication was prompt and friendly and responded to all of our wishes. However, the place is advertised as a hotel, but don’t expect services as in a hotel. It resembles more a short term rental home - no cleaning service and no lobby. Otherwise everything was very nice in the apartment and we had a great time.

Reviewed on Jan 3, 2026

Portland Harbor Hotel

Portland Harbor Hotel

4 out of 5
Downtown Portland
Save 100% on your flight
Price was $1,126, price is now $780 per person
$780
per person
May 28 - Jun 1
found 1 day ago
Roundtrip flight included
Chicago (CHI) to Portland (PWM)
9.2/10 Wonderful! (1,765 reviews)
Business facilities were perfect. Front desk man Roman was an all star helping us out. Whole stay was 100/100

Reviewed on Mar 4, 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 $1,357, price is now $1,001 per person
$1,001
per person
May 28 - Jun 1
found 1 day ago
Roundtrip flight included
Chicago (CHI) to Portland (PWM)
9.6/10 Exceptional! (175 reviews)
The whole was cozy! Well curated style and knowledgeable staff.

Reviewed on Jan 5, 2026

Cliff House Maine

Cliff House Maine

4.5 out of 5
Bald Head
Save 100% on your flight
Price was $1,550, price is now $1,161 per person
$1,161
per person
May 7 - May 10
found 5 hours ago
Roundtrip flight included
Minneapolis (MSP) to Portland (PWM)
9.4/10 Exceptional! (1,001 reviews)
Great hotel with super nice views!

Reviewed on Mar 1, 2026

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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

Maine waterfront home, with hot tub and dock access, 1 mile from downtown Bath

Maine waterfront home, with hot tub and dock access, 1 mile from downtown Bath

Woolwich ME
10/10 Exceptional! (114 reviews)
Such a beautiful home and state of the art Kitchen! The views are incredible! Saw a few eagles and watched the majestic sun risesEvery morning! As the owner told me “treasure the sun rise”. Will be back next year and bringing more family!

Reviewed on Dec 9, 2025

Get rates
Maine waterfront home, with hot tub and dock access, 1 mile from downtown Bath
The Federal

The Federal

3.5 out of 5
10 Water St Brunswick ME
Fully refundableReserve now, pay when you stay
$118 nightly
The price is $129 total per night from Mar 8 to Mar 9
$129 total
Mar 8 - Mar 9
Total with taxes and fees
9.6/10 Exceptional! (580 reviews)
Extremely cute and decor perfect for its era. Decorated for Christmas elegant. Comfy bed, amazing shower. Plenty of options for eating out in the area. Definitely want to visit again!

Reviewed on Mar 4, 2026

The Federal
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
$87 nightly
The price is $95 total per night from Mar 8 to Mar 9
$95 total
Mar 8 - Mar 9
Total with taxes and fees
9/10 Wonderful! (221 reviews)
Clean comfortable and quiet

Reviewed on Mar 1, 2026

SpringHill Suites by Marriott Freeport Brunswick
See all 1,713 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 $327 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.