Portland Vacations from $401
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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.
The Latest Portland vacation packages
Price found within the past 48 hours. Click for updated prices.
Dormir
Price was $485, price is now $401 per person
$401
per person
Jan 4 - Jan 7
found 6 hours ago
Roundtrip flight included
Philadelphia (PHL) to Portland (PWM)
9/10 Wonderful! (1,004 reviews)
I love this place. This is the 2nd time I've stayed here. It's clean, quiet, well located. The staff is friendly and helpful. I would recommend it to anyone.
Reviewed on Nov 3, 2026
Waldo Emerson Inn
Price was $660, price is now $549 per person
$549
per person
Jan 4 - Jan 7
found 6 hours ago
Roundtrip flight included
Philadelphia (PHL) to Portland (PWM)
8.8/10 Excellent! (357 reviews)
Our stay at the Waldo Emerson was nothing short of exceptional! From the moment we arrived, Amelia welcomed us with warm hospitality, and every detail of this charming property made us feel right at home.
The accommodations were comfortable and full of character, and the property itself is absolutely beautiful. Each morning, we looked forward to a delicious, fresh, and thoughtfully prepared breakfast that was the perfect start to our day.
What truly made our experience special were the wonderful sightseeing and dinner recommendations. Amelia and Ron are phenomenal hosts who go above and beyond to ensure their guests have a memorable stay. Their genuine warmth, local knowledge, and attention to detail made our visit to Kennebunkport even more enjoyable.
The Waldo Emerson is an outstanding choice for anyone looking for a charming bed and breakfast in Kennebunkport. We thoroughly enjoyed our stay and would gladly return. We highly recommend it to anyone seeking the perfect combination of comfort, charm, exceptional hospitality, and relaxation!
**A truly wonderful experience from start to finish!**
Reviewed on Oct 18, 2026
Where to stay in Portland
Find the best Portland areas and neighborhoods for the activities you enjoy most. Learn more about Portland
Downtown Portland
5 out of top 10 points of interest in this area
Known for its culinary delights, inspiring art and live music, the heart of Maine’s largest city is an exciting location.
Stay near popular Portland attractions
What to do in Portland
Vintage Fire Truck Sightseeing Tour of Portland Maine
$45
per adult
98% of travellers recommend
Portland, Maine: Tour in Vintage Fire Engine
$45
per adult
90% of travellers recommend
Portland, Maine: Hidden Histories Guided Walking Tour
$54
per adult
Portland Hotel Deals
The Westin Portland Harborview
157 High St Portland ME
Fully refundableReserve now, pay when you stay
$108 nightly
The price is $119 total per night from Nov 22 to Nov 23
$119 total
Nov 22 - Nov 23
Total with taxes and fees
9/10 Wonderful! (1,005 reviews)
"Good stay"
Reviewed on Nov 3, 2026
Clarion Hotel Portland Airport ME
1230 Congress St Portland ME
Fully refundable
$81 nightly
The price is $89 total per night from Nov 10 to Nov 11
$89 total
Nov 10 - Nov 11
Total with taxes and fees
8.2/10 Very Good! (1,843 reviews)
"The hotel is a little run down, and it needs to be updated. Overall clean. The noise was brutal, there were some laud guests."
Reviewed on Nov 3, 2026
Fireside Inn & Suites Portland
81 Riverside St Portland ME
Fully refundableReserve now, pay when you stay
$87 nightly
The price is $96 total per night from Nov 16 to Nov 17
$96 total
Nov 16 - Nov 17
Total with taxes and fees
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.
Find the Best Portland Vacation Packages
Portland Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Closest Airport | Portland Intl. Jetport Airport (PWM) |
Population | 66,900 |
Max Temp Winter | 30ºF |
Max Temp Summer | 75ºF |
Top Sights | State Theatre, Higgins Beach and East End Beach |
More vacations you might like
Frequently asked questions
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- Hotels near Downtown Portland
- Hotels near Old Port
- Hotels near Cathedral of the Immaculate Conception
- Hotels near Merrill Auditorium
- Hotels near Maine Jewish Museum
- Hotels near N.W. Barrett Gallery
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- Cheap Hotels in Old Port
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- Honeymoon Resorts & in Old Port
- Hotels with Hot Tubs in Downtown Portland
- Hotels near Casco Bay Lines Ferry Terminal
- Hotels with Balconies in Downtown Portland
- Hotels with Connecting Rooms in Downtown Portland
- Pet-Friendly Hotels in Downtown Portland
- Oceanfront Hotels in Downtown Portland
- Luxury Hotels in Downtown Portland
- Hotel Wedding Venues Hotels in Downtown Portland
- Cheap Hotels in Downtown Portland
- Historic Hotels in Downtown Portland
- Hotels with Free Airport Shuttle in Downtown Portland
- Hotels with Free Parking in Downtown Portland
- Hotels with Fireplaces in Downtown Portland
- 3 Star Hotels in Downtown Portland
- Family Hotels in Downtown Portland
- Romantic Hotels in Downtown Portland
- Hotels with Laundry Facilities in Downtown Portland
- Hotels with an Outdoor Pool in Downtown Portland
- Hotels with Free Breakfast in Downtown Portland
- Hotels with an Indoor Pool in Downtown Portland
- Hotels with a Pool in Downtown Portland
- Maine Jewish Museum
- Merrill Auditorium
- Casco Bay Lines Ferry Terminal
- Visit Old Port
- N.w. Barrett Gallery
- Maine Sports Hall of Fame
- Old Port Vacations
- Wadsworth-Longfellow House
- Downtown Portland Vacations
- Maine Historical Society
- Center for Maine History
- Cross Insurance Arena
- Museum of African Culture
- Maine College of Art
- Space Gallery
- Maine Narrow Gauge Railroad Company and Museum
- Victoria Mansion
- Portland Museum of Art
- Charles Q. Clapp House
- East End Beach
- State Theatre
- Mclellan-Sweat Mansion
- Mclellan-Sweat House
- International Cryptozoology Museum
- Eastern Promenade
- Portland Fire Museum
- State Street Church
- Cathedral Church of Saint Luke
- Center for Cultural Exchange
- Visit Downtown Portland
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
