Woolwich Holidays

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Woolwich Flight & Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Hampton Inn Portland Downtown - Waterfront

Hampton Inn Portland Downtown - Waterfront

Downtown Portland
S$1,563
per person
9 Oct - 12 Oct
found 1 day ago
Return direct flight included
Raleigh (RDU) to Portland (PWM)
8.8/10 Excellent! (1,020 reviews)
Pet friendly

Reviewed on 8 Aug, 2026

Evalina Hotel

Evalina Hotel

Downtown Portland
Save 100% on your flight
S$1,857
per person
9 Oct - 12 Oct
found 1 day ago
Return direct flight included
Raleigh (RDU) to Portland (PWM)
10/10 Exceptional! (7 reviews)
It was our first time visiting Portland, and the Evalina exceeded our expectations. The location is perfect, right on Commercial Street, with plenty of restaurants and shops nearby. The ferry and cruise ports are also just a 5–10 minute walk away, making it easy to visit the different islands. The suite was comfortable and thoughtfully equipped with everything we could need, including an umbrella for rainy days, coffee and a French press, tea, a washer and dryer, and so much more. Communication was excellent throughout our stay as well. We truly enjoyed our visit, and the next time we’re in Portland, the Evalina will be our first choice!

Reviewed on 8 Aug, 2026

The Docent's Collection at 121 Middle Street

The Docent's Collection at 121 Middle Street

Downtown Portland
S$1,703
per person
9 Oct - 12 Oct
found 1 day ago
Return direct flight included
Raleigh (RDU) to Portland (PWM)
9.6/10 Exceptional! (365 reviews)
Fantastic and always accommodating staff!

Reviewed on 7 Aug, 2026

The Docent's Collection at 178 Middle Street

The Docent's Collection at 178 Middle Street

Downtown Portland
S$1,994
per person
9 Oct - 12 Oct
found 1 day ago
Return direct flight included
Raleigh (RDU) to Portland (PWM)
9.8/10 Exceptional! (45 reviews)
Portland Harbor Hotel

Portland Harbor Hotel

Downtown Portland
S$1,869
per person
9 Oct - 12 Oct
found 1 day ago
Return direct flight included
Raleigh (RDU) to Portland (PWM)
9.2/10 Wonderful! (1,792 reviews)
We had a shower that leaked all the way out to the foyer. We called and reported it. They sent a repair person. They caulked around the edge which helped but didn’t fix the whole problem. It still leaked, just not as bad. No one followed up to see if it was fixed. They have a pantry on each floor with fruit infused water snacks, fresh fruit, cookies, canned sparkling water and ice for free. But it was mostly depleted most of the time we were there. There was a sign advertising live music at the front of the hotel. But when we asked where it was, the hotel attendant said they were not having live music after all. No one went to take the sign down. It was still there the next day. We checked out. Hope the musician showed up that night.

Reviewed on 7 Aug, 2026

Top hotels in Woolwich

Flagship Inn and Suites

Flagship Inn and Suites

200 Townsend Avenue Boothbay Harbor ME
S$233
2 Sept - 3 Sept
includes taxes & fees
8/10 Very good! (1,015 reviews)
"Location, appearance, cleanliness, breakfast"

Reviewed on 9 Aug, 2026

Flagship Inn and Suites
The Freeport Hotel, an Ascend Collection Hotel

The Freeport Hotel, an Ascend Collection Hotel

506 Us Route 1 Freeport ME
Fully refundable
S$137
30 Aug - 31 Aug
includes taxes & fees
The Freeport Hotel, an Ascend Collection Hotel
Holiday Inn Express Hotel & Suites Freeport by IHG

Holiday Inn Express Hotel & Suites Freeport by IHG

450 U.S. Route 1 Freeport ME
Fully refundable
S$195
1 Sept - 2 Sept
includes taxes & fees
Holiday Inn Express Hotel & Suites Freeport by IHG
See all 1,930 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.

Stay near popular Woolwich attractions

Montsweag Flea Market

8.0/10 (2 reviews)
Maine's largest outdoor flea market since 1977, showcasing 125+ tables of antiques, collectibles, and local treasures. Arrive early Wednesdays for "Antique Dealer Day" featuring vendors' finest curated selections.
See properties

Frequently asked questions

How much does a Woolwich holiday package cost?
You'll find cheap prices from S$1,563 on Expedia for your Woolwich getaway. However, factors like the hotel choice, length of stay and season will influence how much your holiday to Woolwich costs.
What are the cheapest months to go to Woolwich?
To score cheap Woolwich holiday packages, plan your trip outside of peak times such as public holidays. You'll typically find lower prices and better availability when it's less busy.
How many days is enough for Woolwich?
With a well-organised travel plan, you can easily hit the most popular Woolwich sights in a few days. But if you want to venture off the beaten track or take day trips, consider booking your Woolwich holiday for longer.
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 holiday package well in advance.
Is it cheaper to book a Woolwich holiday as a package?
You can enjoy significant savings on your Woolwich escape by booking a personalised holiday 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 holiday 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.
How to plan a trip to Woolwich?
  1. Choose when to go: Check your calendar and get your bags packed. Your favourite time of year and the type of activities on offer will also help you decide when to visit Woolwich.
  2. Set a budget: Consider costs such as flights, food and transportation when calculating how much to set aside for your trip to Woolwich. Then, select a property that fits your budget, whether that's a wallet-friendly stay or a swankier getaway.
  3. Decide how many days away: Start by listing all the activities and sights you want to get to in Woolwich. Then, estimate how long you'll need at each, including any travel time.
  4. Bundle your airfare and accommodation: Once you've settled on your dates and duration, lock in the ideal Woolwich holiday 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. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.