Portland Holidays

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

    • payments icon

    Better together

    Save up to NZ$616 when you book a flight and hotel together*
    lob hotels icon

    Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
    lob packages icon

    Rest easy

    Plan, book, and manage your trip all in one place

Our guide on where to stay in Portland

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

Downtown Portland

5 out of top 10 points of interest in this area
4/5(1 area review)

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

Portland Holiday

Our pick of the best Portland Hotel Deals

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 NZ$247 per night from 1 Sept to 2 Sept
NZ$247
1 Sept - 2 Sept
includes taxes & fees
7.6/10 Good! (1,045 reviews)
"I thought it was clean and well maintained. The pool and hot tub were nice. The pillows were too small though and I would have liked a bigger comforter."

Reviewed on 4 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 NZ$386 per night from 1 Sept to 2 Sept
NZ$386
1 Sept - 2 Sept
includes taxes & fees
8.8/10 Excellent! (1,002 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 NZ$284 per night from 24 Aug to 25 Aug
NZ$284
24 Aug - 25 Aug
includes taxes & fees
7.8/10 Good! (1,009 reviews)
Solid hotel
"Front desk, friendly, and very helpful helping me make dinner plans in terms of recommendations. The rooms were clean nobody came in between the two days I was there. I’m not sure I was supposed to request it or not. It is easily accessible to downtown if you have a car."

Reviewed on 4 Aug. 2025

Clarion Hotel Portland
See all 508 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.

Discover the most popular places to visit in Portland

East End Beach showing general coastal views and a beach as well as a small group of people

East End Beach

Swim in the Atlantic Ocean, stroll along the sand-and-pebble shoreline or enjoy a picnic with unbeatable views at Portland’s public beach.

East End Beach

Thompson's Point

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

Thompson's Point

University of New England

Walk around the campus at University of New England during your visit to Portland. Stroll along the seaside or attend a sporting event in the area.

University of New England

What to do in Portland

Port City Light Cruise

Port City Lights Cruise

NZ$65
per adult
100% of travellers recommend
Port City Lights Cruise
Vintage Fire Engine Tours

Vintage Fire Truck Sightseeing Tour of Portland Maine

NZ$65
per adult
98% of travellers recommend
Vintage Fire Truck Sightseeing Tour of Portland Maine
Portland: Maine Lighthouses Sightseeing Cruise with Drinks

Portland: Maine Lighthouses Sightseeing Cruise with Drinks

NZ$115
per adult
Portland: Maine Lighthouses Sightseeing Cruise with Drinks
See all activities in Portland

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.

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