Woolwich Vacation Packages

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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.

Top Woolwich Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Inn at Diamond Cove

Inn at Diamond Cove

3.5 out of 5
Price was CA $1,511, price is now CA $1,168 per person
CA $1,168
per person
Sep 24 - Sep 27
found 20 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) 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
Price was CA $1,790, price is now CA $1,252 per person
CA $1,252
per person
Aug 14 - Aug 17
found 14 hours ago
Roundtrip flight included
Ottawa (YOW) to Portland (PWM)
9/10 Wonderful! (1,017 reviews)
Everything was good!

Reviewed on Jul 2, 2026

The Weldon Hotel

The Weldon Hotel

4.5 out of 5
Downtown Portland
Price was CA $3,078, price is now CA $2,529 per person
CA $2,529
per person
Aug 17 - Aug 21
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) 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

Portland Harbor Hotel

Portland Harbor Hotel

4 out of 5
Downtown Portland
Price was CA $2,256, price is now CA $1,874 per person
CA $1,874
per person
Aug 17 - Aug 21
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Portland (PWM)
9.4/10 Exceptional! (1,771 reviews)
Great room. Excellent location nice courtyard for food and drinks with firepit

Reviewed on Jul 1, 2026

Blind Tiger Portland - Danforth Street.

Blind Tiger Portland - Danforth Street.

3.5 out of 5
West End
Price was CA $2,858, price is now CA $2,376 per person
CA $2,376
per person
Aug 17 - Aug 21
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) 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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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
The price is CA $211 per night from Jul 14 to Jul 15
CA $211
CA $289 total
Jul 14 - Jul 15
includes taxes & fees
8/10 Very good! (1,003 reviews)
"The Flagship Inn was surprisingly great. The room was clean and had a sweet retro fridge and microwave. The staff was just lovely and responded immediately to a request for more towels. Kids loved the pool and the free breakfast was good. Especially for the kids. It was very convenient to the botanical ..."

Reviewed on Jul 1, 2026

Flagship Inn and Suites
Ocean Gate Inn

Ocean Gate Inn

3 out of 5
70 Ocean Gate Rd Southport ME
The price is CA $351 per night from Jul 14 to Jul 15
CA $351
CA $402 total
Jul 14 - Jul 15
includes taxes & fees
8.6/10 Excellent! (1,006 reviews)
"We really enjoyed our brief stay at the Ocean Gate Inn. The staff was friendly and helpful and the on-site amenities were plentiful. We especially enjoyed our morning kayak adventure where we saw a couple gray seals and a lobster boat out checking their traps. The breakfast buffet was good not great ..."

Reviewed on Jul 1, 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
The price is CA $158 per night from Jul 6 to Jul 7
CA $158
CA $172 total
Jul 6 - Jul 7
includes taxes & fees
7.8/10 Good! (1,000 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 1,765 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.
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Stay near popular Woolwich attractions

Montsweag Flea Market

8.0/10 (2 reviews)
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.
See properties

Frequently asked questions

How much does a Woolwich vacation package cost?
Offering great value package deals from CA $1,168 on Expedia, you'll be pleasantly surprised at how much a vacation to Woolwich costs! Our packages make travel planning easier and save you more.
What are the cheapest months to go to Woolwich?
Plan your getaway for the off-peak season and you're likely to find cheap Woolwich vacation packages. Keep in mind that public holidays and local events and festivals can impact prices, so do a little research before you go.
How many days is enough for Woolwich?
The ideal length for your Woolwich vacation depends on what you'd like to do. Typically, a few days to a week will give you enough time to tick off all the leading attractions and discover some hidden treasures along the way.
How to find the best Woolwich package deals?
Finding a cheap Woolwich package deal is a cinch with Expedia. After you've entered your travel dates and destination under our "Packages" tab, set your maximum budget, add a few filters and see what's available. You can tailor your search by "Amenities," "Property type," "Guest rating" and more. Sort the results by "Price: low to high" to view the most wallet-friendly Woolwich package deals. Want a simple trick to get even more savings? Have some flexibility with your departure dates and consider travelling on a weekday, when prices are usually lower.
Is it cheaper to book a Woolwich vacation as a package?
Expedia vacation packages are designed to help you keep more cash in your pocket. Bundle your car rental, hotel and flight into one great-value price and you could save hundreds of dollars. You'll generally snag a better deal than booking each component separately. And you'll still enjoy the flexibility to create a customized Woolwich vacation by choosing your favourite accommodation type, airline and car class.
When to book a vacation package to Woolwich?
If you've got your Woolwich travel dates confirmed, book early to score some incredible deals. With Expedia, you can typically reserve some flights up to one year in advance. Prefer spur-of-the-moment adventures? Our last-minute deals are great for setting off on a whim.
How to plan a trip to Woolwich?

  1. Pick the perfect time to travel: Your schedule, favourite season and the type of weather you enjoy can all impact your decision on when to go to Woolwich.
  2. Set a budget: Factor in expenses like flights, food and transportation when working out how much to set aside for your trip to Woolwich. Then, pick a hotel that matches your budget, whether that's an economical stay or a more upscale getaway.
  3. Work out your trip length: Consider how much time you want to spend exploring Woolwich. Plan your days so you can get to all the attractions and experiences you're interested in at a leisurely pace.
  4. Combine your airfare and accommodations: Once you've nailed down your trip dates and duration, lock in the right Woolwich vacation package for you.

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.