Portland Holidays

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Where to stay in Portland

Find the best Portland areas and neighborhoods for the activities you enjoy most. Learn more about Portland
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Downtown Portland

4 out of top 10 points of interest in this area
3.5/5(2 area reviews)

A noteworthy feature of Downtown Portland is its captivating waterfront views. While you're in town, be sure to stop and check out Cross Insurance Arena and Merrill Auditorium.

Find hotels in Downtown Portland

Top hotels in Portland

Portland Harbor Hotel
Portland Harbor Hotel
4 out of 5
468 Fore Street, Portland, ME
Fully refundableReserve now, pay when you stay
The price is S$226 per night from 22 Jan to 23 Jan
S$226
includes taxes & fees
22 Jan - 23 Jan
9/10 Wonderful! (1,445 reviews)
"Perfect hotel for a weekend get away!"

Reviewed on 18 Jan,2025

Portland Harbor Hotel
Canopy by Hilton Portland Waterfront
Canopy by Hilton Portland Waterfront
4 out of 5
9 Center Street, Portland, ME
Fully refundableReserve now, pay when you stay
The price is S$205 per night from 27 Jan to 28 Jan
S$205
includes taxes & fees
27 Jan - 28 Jan
9.2/10 Wonderful! (897 reviews)
"We had a wonderful time staying here. The rooms were clean, staff helpful. Restaurant and bar on site were amazing!! Perfect location to walk and explore the city."

Reviewed on 15 Jan,2025

Canopy by Hilton Portland Waterfront
Holiday Inn Portland-By the Bay, an IHG Hotel
Holiday Inn Portland-By the Bay, an IHG Hotel
3 out of 5
88 Spring St, Portland, ME
Fully refundable
The price is S$148 per night from 22 Jan to 23 Jan
S$148
includes taxes & fees
22 Jan - 23 Jan
8.8/10 Excellent! (1,106 reviews)
"All good!"

Reviewed on 14 Jan,2025

Holiday Inn Portland-By the Bay, an IHG Hotel
See all 433 properties in Portland
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.

Frequently asked questions

How much does a Portland holiday package cost?
You’ll find cheap prices on Expedia for your Portland break. However, factors like your choice of hotel, the season and length of stay will determine how much your holiday to Portland costs.
What are the cheapest months to go to Portland?
You’re likely to find lower rates and greater availability in January, February and March. Explore our cheap Portland holiday packages and you could score some great off-season discounts.
How many days is enough for Portland?
We recommend booking a Portland holiday for at least 2 days. This will allow you plenty of time to tick off top sights including East End Beach and Sand Beach, as well as explore neighbourhoods like Downtown Portland and Old Port. You might even be able to make time for a day trip (or two) outside of Portland.
Is it worth booking a holiday package to Portland?
During your Portland holiday, you can count on experiencing some top-notch walking trails and culture. Leave enough time in your itinerary to discover major sights like Thompson’s Point and State Theatre.
How to find the best Portland package deals?
Start your search for a Portland package deal by entering your destination and travel dates under our “Packages” tab. Then select a few filters, like “Popular locations” and “Amenities,” to fine-tune the results to your exact style. You can also sort by “Package discount” and discover offers that come with irresistible savings. If you don’t find the ideal Portland package deal right away, simply change your dates and search again. Remember that deals are only available for a limited time, so book early and get your Portland escape off to a flying start.
Is it cheaper to book a Portland holiday as a package?
You can enjoy significant savings on your Portland retreat by booking a personalised holiday package. Check the “Package” heading, then select your destination and travel dates to browse the best airfares and hotel prices. Bundle everything into a neat package and you can save hundreds of dollars. Consider adding a rental car and you may land a better deal.
When to book a holiday package to Portland?
Secure fantastic discounts by booking your flights early with Expedia. If being spontaneous is more your thing, take advantage of our last-minute deals for an impromptu Portland escape.
How to plan a trip to Portland?

  1. Pick the ideal time to travel: Your schedule, favourite season and the type of weather you enjoy can all influence your decision on when to travel to Portland.
  2. Figure out your budget: Ensure you have enough money to cover everything from food and transportation to activities and airfares. Your hotel will likely be the largest expense during your trip to Portland.
  3. Decide your trip length: Think about how much time you’d like to spend discovering Portland. Plan your itinerary so you can get to all the attractions and activities you’re interested in at a comfortable pace.
  4. Bundle your bookings: With your travel dates in order, you can combine your hotels, car rental, flights and more into a customised Portland holiday package.

Popular places to visit

Thompson's Point

Commune with nature and explore the great outdoors at Thompson's Point during your travels in Portland. Stroll along the waterfront or attend a sporting event in the area.

Thompson's Point

What to do in Portland

Portland Downtown Highlights: "The Golden Adventure" Exploration Game

Downtown Golden Adventure Quest Experience in Portland

S$14
per adult
Downtown Golden Adventure Quest Experience in Portland
Portland, Maine: Local Brewery & Spirits Bus Tour

Portland, Maine: Local Brewery & Spirits Bus Tour

S$133
per adult
100% of travellers recommend
Portland, Maine: Local Brewery & Spirits Bus Tour
Private Professional Vacation Photoshoot in Portland

Private Professional Vacation Photoshoot in Portland

S$224
per adult
Private Professional Vacation Photoshoot in Portland
See all activities in Portland

* 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.