Portland Vacations from ￥178,700

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The Latest Portland Vacation Packages

Price found within the past 48 hours. Click for updated prices.
The Windrifter Resort

The Windrifter Resort

2.5 out of 5
per person
Feb 24 - Mar 3
found 4 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Portland (PWM)
9/10 Wonderful! (263 reviews)
View of Lake Winnipesaukee from balcony of bedroom suite!!

Reviewed on Dec 1, 2024

The Wolfeboro Inn

The Wolfeboro Inn

3.5 out of 5
per person
Feb 24 - Mar 3
found 4 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Portland (PWM)
8.2/10 Very Good! (472 reviews)
Weloved our stsy. Once again...things get better with each visit! The staff is great...MOST comfortable bed, and live the revived libby. This time we were thrilled with the new breakfasts amd the cafe. Absolutely delucious! Cant wait to teturn in the Spring!

Reviewed on Dec 9, 2024

Purity Spring Resort

Purity Spring Resort

2 out of 5
per person
Feb 24 - Mar 3
found 4 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Portland (PWM)
8.6/10 Excellent! (138 reviews)
It seemed extremely pleasant, but we were only there for a very short time

Reviewed on Oct 30, 2024

Days Inn by Wyndham Tamworth

Days Inn by Wyndham Tamworth

2.5 out of 5
per person
Feb 24 - Mar 3
found 4 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Portland (PWM)
7.2/10 Good! (463 reviews)
Average hotel. Inside is much better than the outside. Staff was professional. The Indoor pool was very cold and sauna was out of order

Reviewed on Nov 18, 2024

Where to stay in Portland

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

Downtown Portland

4 out of top 10 points of interest in this area
4.5/5(326 area reviews)

Downtown Portland is known for its captivating waterfront views, and with sights like Cross Insurance Arena and Fore Street Gallery, you won't get bored spending a day wandering around this part of Portland.

Find hotels in Downtown Portland

Find the Best Portland Vacation Packages

Portland Hotel Deals

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 ￥15,318 per night from Jan 8 to Jan 9
￥15,318
￥17,179 total
includes taxes & fees
Jan 8 - Jan 9, 2025
8.6/10 Excellent! (1,002 reviews)
"I had an incredible stay! This was my first time at the Westin Harborview. Upon check-in I was awarded “Guest of the Day” status with a top floor upgrade. It was such a sweet surprise and a wonderful experience. The harbor view is quite lovely and the next morning I watched a couple of cargo ships ..."

Reviewed on Dec 18, 2024

The Westin Portland Harborview
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 ￥14,615 per night from Dec 29 to Dec 30
￥14,615
￥16,170 total
includes taxes & fees
Dec 29 - Dec 30
7.6/10 Good! (1,009 reviews)
"This was a great place to stay at. Very easy to locate and close enough to everything. The room was very clean and stocked perfectly. It was a breeze to check in and out. There are 2 hot tubs on site. Definately a great place to stay especially for the money."

Reviewed on Dec 14, 2024

Ramada Plaza by Wyndham 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 ￥17,392 per night from Dec 25 to Dec 26
￥17,392
￥25,181 total
includes taxes & fees
Dec 25 - Dec 26
9/10 Wonderful! (1,421 reviews)
"I liked having the pantry for water and snacks."

Reviewed on Dec 16, 2024

Portland Harbor Hotel
See all 437 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 vacation package cost?
You’ll find cheap prices from ￥178,700 on Expedia for your Portland break. However, factors like your choice of hotel, the season and length of stay will determine how much your vacation 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 vacation packages and you could score some great off-season discounts.
How many days is enough for Portland?
We recommend booking a Portland vacation 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 neighborhoods like Downtown Portland and Old Port. You might even be able to make time for a day trip (or two) outside of Portland.
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 vacation as a package?
You can enjoy significant savings on your Portland retreat by booking a personalized vacation 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 vacation 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, favorite 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 customized Portland vacation package.

Discover the most popular places to visit in Portland

Eastern Promenade showing a bay or harbor and general coastal views as well as a small group of people

Eastern Promenade

5/5(1 review)

Built on an old rail corridor along the easternmost portion of Portland’s peninsula, this waterfront trail offers stunning views of the harbor and Atlantic Ocean.

Eastern Promenade

What to do in Portland

Portland Downtown Highlights: "The Golden Adventure" Exploration Game

Downtown Golden Adventure Quest Experience in Portland

￥1,584
per adult
Downtown Golden Adventure Quest Experience in Portland
Downtown Portland: Coastal Vibe and Old Mansions with In-Add Audio Tour

Downtown Portland: Coastal Vibe and Old Mansions with In-Add Audio Tour

￥1,347
per traveler
Downtown Portland: Coastal Vibe and Old Mansions with In-Add Audio Tour
Portland, Maine: Local Brewery & Spirits Bus Tour

Portland, Maine: Local Brewery & Spirits Bus Tour

￥14,850
per adult
100% of travellers recommend
Portland, Maine: Local Brewery & Spirits Bus Tour
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.