Woolwich Vacation Packages

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    Save up to CA $4,200 when you book a flight and hotel together*

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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.
USA Inn

USA Inn

2.5 out of 5
Price was CA $992, price is now CA $843 per person
CA $843
per person
Sep 12 - Sep 18
found 1 day ago
Roundtrip flight included
Montreal (YUL) to Portland (PWM)
8/10 Very good! (802 reviews)

The Meadowmere Resort

The Meadowmere Resort

2.5 out of 5
Price was CA $1,964, price is now CA $1,370 per person
CA $1,370
per person
Sep 12 - Sep 18
found 1 day ago
Roundtrip flight included
Montreal (YUL) to Portland (PWM)
8.6/10 Excellent! (1,000 reviews)
Great location and close to downtown plus beach 🏖️

Reviewed on Jul 20, 2026

Ogunquit River Inn & Suites

Ogunquit River Inn & Suites

3 out of 5
Moody
Price was CA $2,078, price is now CA $1,574 per person
CA $1,574
per person
Aug 20 - Aug 23
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Portland (PWM)
9/10 Wonderful! (1,020 reviews)

Inn at Diamond Cove

Inn at Diamond Cove

3.5 out of 5
Price was CA $1,952, price is now CA $1,516 per person
CA $1,516
per person
Aug 20 - Aug 23
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Portland (PWM)
8.8/10 Excellent! (200 reviews)
Unusual place to stay; in a renovated former army base. Huge rooms, gorgeous recent renovation/reconstruction.Expensive!

Reviewed on Jul 12, 2026

Blind Tiger Portland - Danforth Street.

Blind Tiger Portland - Danforth Street.

3.5 out of 5
West End
Price was CA $2,106, price is now CA $1,735 per person
CA $1,735
per person
Sep 14 - Sep 17
found 15 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Portland (PWM)
9.6/10 Exceptional! (188 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 $167 per night from Jul 26 to Jul 27
CA $167
CA $237 total
Jul 26 - Jul 27
includes taxes & fees
Flagship Inn and Suites
Ocean Gate Inn

Ocean Gate Inn

3 out of 5
70 Ocean Gate Rd Southport ME
The price is CA $445 per night from Aug 3 to Aug 4
CA $445
CA $509 total
Aug 3 - Aug 4
includes taxes & fees
8.6/10 Excellent! (1,003 reviews)
"Scenic property run “family lodge” style. No upcharge for canoes, kayaks. Excellent value in a beautiful area. We stayed in a dog-friendly unit - clean and spacious. Some areas dated but all safe and clear the property is being updated carefully."

Reviewed on Jul 19, 2026

Ocean Gate Inn
Clarion Hotel Lewiston

Clarion Hotel Lewiston

3 out of 5
490 Pleasant St Lewiston ME
Fully refundable
The price is CA $143 per night from Aug 17 to Aug 18
CA $143
CA $156 total
Aug 17 - Aug 18
includes taxes & fees
6.8/10 (38 reviews)
"Very clean room and a well kept property. We felt very comfortable and enjoyed our stay."

Reviewed on Jul 19, 2026

Clarion Hotel Lewiston
See all 1,936 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 $843 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.

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