Portland Vacation Packages

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Your Portland Vacation

When a break in the city is calling, answer it with a vacation package to Portland. The neighborhood of Parkside, which is great for festivals, markets and walking, makes a fantastic base for your adventures. Fill your free time with tours of Portland Head Light, University of Southern Maine and Portland Museum of Art, some of the top attractions you just have to see during your trip to Portland. Don't put off your visit to this destination any longer. Your perfect Portland vacation is just a few clicks away with Expedia.

Top Portland Vacation Deals

Prices and availability subject to change. Additional terms may apply.
River View Resort

River View Resort

2.5 out of 5
per person
Jun. 17 - Jun. 24
Roundtrip flight included
Toronto (YYZ) to Portland (PWM)
8.8/10 Excellent! (254 reviews)
This property was very clean with modern updates. The staff was kind and helpful, pool and hot tub were amazing. Highly recommend River View.

Reviewed on Mar. 11, 2024

Portland Harbor Hotel

Portland Harbor Hotel

4 out of 5
Downtown Portland
Save 100% on your flight
per person
Jun. 5 - Jun. 11
Roundtrip flight included
Toronto (YTO) to Portland (PWM)
9/10 Wonderful! (1,135 reviews)
Loved the spacious rooms and atmosphere

Reviewed on Apr. 24, 2024

Admiral Peary Inn Bed and Breakfast

Admiral Peary Inn Bed and Breakfast

2 out of 5
per person
Jun. 5 - Jun. 11
Roundtrip flight included
Toronto (YTO) to Portland (PWM)
No reviews
Portland Regency Hotel & Spa

Portland Regency Hotel & Spa

3.5 out of 5
Downtown Portland
per person
Jun. 5 - Jun. 11
Roundtrip flight included
Toronto (YTO) to Portland (PWM)
9.2/10 Wonderful! (1,075 reviews)
Great spot, nice people

Reviewed on Apr. 22, 2024

Inn at Diamond Cove

Inn at Diamond Cove

3.5 out of 5
per person
Jun. 5 - Jun. 11
Roundtrip flight included
Toronto (YTO) to Portland (PWM)
9/10 Wonderful! (134 reviews)
Beautiful hotel on the island! Staff were warm and welcoming!

Reviewed on Oct. 1, 2023

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

5 out of top 10 points of interest in this area
4.5/5(11 area reviews)

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

Find hotel + flight trips in Downtown Portland

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 CA $123 per night from Apr. 28 to Apr. 29
CA $123
CA $136 total
includes taxes & fees
Apr 28 - Apr 29
7.4/10 Good! (1,002 reviews)
"Always clean and esy check in and out"

Reviewed on Apr. 24, 2024

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 CA $243 per night from May 6 to May 7
CA $243
CA $276 total
includes taxes & fees
May 6 - May 7
8.4/10 Very Good! (1,059 reviews)
Best location in Portland
"Fantastic (the best for comparable hotels) location. The room can feel dated compared to something like AC hotel, which is on the water but not central. Service is great, the Windows have interesting visitas. Bathrooms are dated and rooms are tighter than comparable."

Reviewed on Apr. 18, 2024

The Westin Portland Harborview
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 CA $243 per night from May 1 to May 2
CA $243
CA $269 total
includes taxes & fees
May 1 - May 2
9/10 Wonderful! (1,160 reviews)
"The hotel’s decor truly captured the vibe of coastal Maine. Valet parking at the hotel was easy and efficient. Every employee was happy and helpful. I would stay here again."

Reviewed on Apr. 23, 2024

Portland Harbor Hotel
See all 413 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.

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Frequently asked questions

How much does a Portland vacation package cost?
Get set to book, because a getaway to Portland starts from only CA $1,293. When you bundle your flights, hotels and car rentals into a vacation package, you’ll enjoy the best bargains.
How do I get a cheap travel package to Portland?
Combining your flight and hotel with Expedia won’t just save you time — it’ll save you cash too. A Portland vacation package makes it a breeze to create the perfect trip. With more than 550 airlines across the world to pick from, finding flights that suit your busy schedule won’t be difficult. On top of that, we’ve got over 1,000,000 properties globally to choose from. Now that’s what you call choice. Whatever your budget, Expedia will help show you the world.
Where should I stay in Portland?
Downtown Portland is an area of Portland that no one should miss. If exploring Portland Museum of Art and Wadsworth-Longfellow House is one of your priorities, booking a hotel in this neighborhood could be a great idea. Another option is Portland Arts District. From here, it’ll be easy for you to get to Portland Museum of Art and Wadsworth-Longfellow House.
What are the top hotels in Portland?
If you intend to stay in the Munjoy Hill neighborhood, some top options are The Westin Portland Harborview and La Quinta Inn & Suites by Wyndham Portland. East End is also a well-known Portland area. We recommend Portland Harbor Hotel or Embassy Suites by Hilton Portland Maine if you prefer this part of town.
How far in advance should I book my Portland vacation?
Smart travelers often reserve their seats as early as possible. You can normally compare international airfares on Expedia up to a year before your intended flight. If you’re booking last minute, don’t despair. Cheap prices sometimes become available in the last weeks before departure dates.
What does an Expedia Portland travel package include?
It comes down to what kind of getaway you’re thinking about. Portland vacation deals can include hotels, flights and car rentals. You can mix and match to find the travel package that suits your needs. You can also add on activities and experiences after you’ve booked to get even bigger discounts.
What should I know before booking a Portland travel package?
You can save big by bundling your airfares, hotels and rental cars. Once you’ve created your package, you can add on tours and activities. Your next awesome adventure is only a couple of clicks away.
Can I choose my airline with a Portland Expedia vacation package?
Yes, and with more than 550 airlines to choose from worldwide, you have loads of choice. Scroll through the available options and find out which airline fits your budget and needs.
If I'm not able to travel, can I cancel my Portland vacation package?
You can. We understand that things don’t always go to plan, so we’re happy to help if you have to make changes to your Portland vacation package. You may be able to cancel or change your itinerary at no cost if you’ve booked within 24 hours. Your hotel, airline or car rental company may impose a fee if you booked more than 24 hours ago. Head to our Customer Service Portal for more information. Also, check your itinerary for the nitty-gritty on change fees.

Discover the most popular places to visit in Portland

Image for State Theatre

State Theatre

4.5/5(5 reviews)

The beautiful mix of architectural styles, from Art Deco to Moorish, makes this newly renovated performing arts venue one of New England’s best.

State Theatre
Image for Portland Museum of Art

Portland Museum of Art

5/5(5 reviews)

Maine’s largest and oldest art institution showcases three centuries of American art and European masters in its architecturally impressive museum complex.

Portland Museum of Art
Image for Victoria Mansion

Victoria Mansion

4/5(9 reviews)

Visit the remarkably preserved 19th-century manor house, located in downtown Portland. Get an authentic impression of life during that era.

Victoria Mansion

What to do in Portland

Image for Portland: Old Port Seafood Lovers Tour

Portland: Old Port Seafood Lovers Tour

CA $198
Per adult
Portland: Old Port Seafood Lovers Tour
Image for Portland, Maine: Old Port Brewery & Pub Walking Tour

Portland, Maine: Old Port Brewery & Pub Walking Tour

CA $121
Per adult
Portland, Maine: Old Port Brewery & Pub Walking Tour
Image for Self-Guided Driving & Walking Bundle of Portland Maine Tours

Self-Guided Driving & Walking Bundle of Portland Maine Tours

CA $23
Per adult
100% of travellers recommend
Self-Guided Driving & Walking Bundle of Portland Maine Tours
See all activities in Portland

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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.