Portland Holidays

Book a Hotel + Flight or Car together to unlock savings

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

5 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

Ramada Plaza by Wyndham Portland

Ramada Plaza by Wyndham Portland

3 out of 5
155 Riverside St, Portland, ME
Fully refundableReserve now, pay when you stay
The price is 3.432.329 ₫ per night from 1 Sept to 2 Sept
3.432.329 ₫
3.797.325 ₫ total
1 Sept - 2 Sept
includes taxes & fees
7.6/10 Good! (1,038 reviews)
"I would have like to have the hotel provide a continental breakfast. There was a restaurant attached to the hotel called "Stacks" that was a rip off they charged me for the milk in my tea."

Reviewed on 7 Aug 2025

Ramada Plaza by Wyndham Portland
The Westin Portland Harborview

The Westin Portland Harborview

4 out of 5
157 High St, Portland, ME
Fully refundableReserve now, pay when you stay
The price is 5.322.863 ₫ per night from 1 Sept to 2 Sept
5.322.863 ₫
5.977.581 ₫ total
1 Sept - 2 Sept
includes taxes & fees
8.8/10 Excellent! (1,000 reviews)
"Nice property could add some vending machines by ice machines for soft drinks and snacks."

Reviewed on 24 Jul 2025

The Westin Portland Harborview
Clarion Hotel Portland

Clarion Hotel Portland

2.5 out of 5
1230 Congress St, Portland, ME
Fully refundableReserve now, pay when you stay
The price is 3.988.156 ₫ per night from 18 Aug to 19 Aug
3.988.156 ₫
4.412.495 ₫ total
18 Aug - 19 Aug
includes taxes & fees
7.8/10 Good! (1,001 reviews)
"Great location and convenience for concert at Thompson’s Point. Easy walk!"

Reviewed on 6 Aug 2025

Clarion Hotel Portland
See all 481 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.

Popular places to visit

State Theatre featuring street scenes as well as an individual female

State Theatre

You can get tickets for a performance at State Theatre during your stay in Portland. Experience the area's acclaimed theatre scene and entertainment choices.

State Theatre
Portland Museum of Art featuring art and interior views as well as a small group of people

Portland Museum of Art

4/5(2 reviews)

You can spend time browsing the exhibits at Portland Museum of Art during your travels in Portland. Stroll along the area's waterfront or experience its great live music.

Portland Museum of Art
Eastern Promenade which includes a bay or harbour and general coastal views as well as a small group of people

Eastern Promenade

Eastern Promenade is just one of the places to see in Portland, so why not enjoy the other things to explore during your travels? Amble around the area's waterfront or attend a sporting event.

Eastern Promenade

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.