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.
Ramada Plaza by Wyndham Portland

Ramada Plaza by Wyndham Portland

3 out of 5
Nasons Corner
per person
Oct 17 - Oct 20
found 7 hours ago
Roundtrip non-stop flight included
Calgary (YYC) to Portland (PWM)
7.8/10 Good! (1,044 reviews)
Hotel did not look full, I had made my reservation back in April , beginning of, and they stuck us in a room next to the exit of the highway, it was Jake brakes all night from truckers. You’d think that 3-1/2 months in advance hotel reservations, they’d put you in a room away from the exit.. not a good night sleep, having to be at airport at 5 AM, and listening to traffic all night

Reviewed on Aug. 12, 2025

The Docent's Collection

The Docent's Collection

3.5 out of 5
Downtown Portland
per person
Sep 11 - Sep 14
found 3 hours ago
Roundtrip flight included
Toronto (YTO) to Portland (PWM)
9.6/10 Exceptional! (219 reviews)
Property is modern and clean and a great choice if staying more than one night. The 5:00 check in time is inconvenient and the additional rates for early check in are ridiculous. Our room was ready early even though the information given before check in stated early check in was not available, so we appreciated that. Bed was okay comfort-wise, but the pillows are awful. The biggest gripe I had was being woken by a very loud family with screaming kids well before 7:30 am on a day we looked forward to sleeping in. If this matters to you, the walls and floors are not very soundproof. This was a very unpleasant way to start the second day of a two-day trip. On a positive note, the staff was available via text and responded to our questions quickly and professionally. One suggestion-an exterior sign. The loft was hard to find, with only small signage on the entry doors which is not easily visible from the street. Overall we were happy and would stay again.

Reviewed on Aug. 11, 2025

Portland Harbor Hotel

Portland Harbor Hotel

4 out of 5
Downtown Portland
per person
Oct 17 - Oct 20
found 7 hours ago
Roundtrip non-stop flight included
Calgary (YYC) to Portland (PWM)
9.2/10 Wonderful! (1,542 reviews)
Great hotel love the area

Reviewed on Aug. 11, 2025

Chebeague Island Inn

Chebeague Island Inn

4 out of 5
per person
Sep 22 - Sep 29
found 8 hours ago
Roundtrip non-stop flight included
Calgary (YYC) to Portland (PWM)
8.8/10 Excellent! (76 reviews)
Great place to go and relax for a few days.

Reviewed on Jul. 20, 2025

Hampton Inn Portland Downtown - Waterfront

Hampton Inn Portland Downtown - Waterfront

2.5 out of 5
Downtown Portland
per person
Oct 17 - Oct 20
found 7 hours ago
Roundtrip non-stop flight included
Calgary (YYC) to Portland (PWM)
8.8/10 Excellent! (1,005 reviews)
The hotel had everything you needed to enjoy your stay in Portland.

Reviewed on Aug. 11, 2025

Ready to book your vacation to Woolwich?

 

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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
The price is CA $166 per night from Aug 13 to Aug 14
CA $166
CA $181 total
Aug 13 - Aug 14
includes taxes & fees
8.2/10 Very Good! (1,009 reviews)
"It was a nice quiet place close to anything you want to do. One thing we really appreciated was how clean the room was. The price was also reasonable for this time of year. We would definitely come back."

Reviewed on Aug. 8, 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
The price is CA $170 per night from Aug 31 to Sep 1
CA $170
CA $186 total
Aug 31 - Sep 1
includes taxes & fees
7.8/10 Good! (1,006 reviews)
"We had a nice stay at the Best Western. It was very nice to be able to stay somewhere conveniently located with our dog and it was great to have a room on the first floor to easily take him outside."

Reviewed on Aug. 10, 2025

Best Western Freeport Inn
Ocean Gate Resort

Ocean Gate Resort

3 out of 5
70 Ocean Gate Rd, Southport, ME
Fully refundableReserve now, pay when you stay
The price is CA $191 per night from Sep 1 to Sep 2
CA $191
CA $242 total
Sep 1 - Sep 2
includes taxes & fees
8.4/10 Very Good! (1,004 reviews)
"The beds are very comfortable, the view was lovely from our room, staff was friendly and helpful, no gluten-free options for breakfast. The pool was lovely and inviting, but there was no hot tub. Did you want that or you were just covering up?"

Reviewed on Aug. 8, 2025

Ocean Gate Resort
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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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Frequently asked questions

How much does a Woolwich vacation package cost?
Offering great value package deals from CA $568 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.