Downtown Portland Vacations from $580
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Your Downtown Portland Vacation
Book your vacation package to Downtown Portland and get ready to enjoy its markets and more. Whether you're searching for adventure or relaxation, you'll find it in this appealing neighborhood. Some popular nearby attractions to check out during your trip to Downtown Portland include Portland Museum of Art, University of Southern Maine and Victoria Mansion. Expedia is here to help put your travel plans into action. Book your perfect Downtown Portland vacation today.
The Latest Downtown Portland Vacation Packages
Price found within the past 48 hours. Click for updated prices.
The Docent's Collection
Downtown Portland
Price was $835, price is now $580 per person
$580
per person
Oct 20 - Oct 23
found 1 day ago
Roundtrip non-stop flight included
Cleveland (CLE) to Portland (PWM)
9.6/10 Exceptional! (219 reviews)
This property was beyond expectation. As long as you are comfortable using the app, check in was super easy and so was getting into our suite. The kitchen had everything we could have possibly needed, and having a living space was a great lift from a normal hotel room.
Reviewed on Aug 16, 2025
The Weldon Hotel
Downtown Portland
Save 100% on your flight
Price was $1,219, price is now $759 per person
$759
per person
Oct 20 - Oct 23
found 1 day ago
Roundtrip non-stop flight included
Cleveland (CLE) to Portland (PWM)
9.8/10 Exceptional! (68 reviews)
The space was so sparkling clean and the layout was super comfortable. We enjoyed our stay very much!
Reviewed on Aug 17, 2025
Cliff House Maine
Save 100% on your flight
Price was $2,129, price is now $1,473 per person
$1,473
per person
Sep 23 - Sep 28
found 23 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Portland (PWM)
9.4/10 Exceptional! (1,005 reviews)
We had an amazing stay at Cliffhouse and were pleasantly surprised by how beautiful it is. The only minor issues we encountered were that the pullout couch was quite uncomfortable for our kids, and it was frustrating that children aren’t allowed in the main pool—everyone with kids ends up crowded around a small pool off to the side. Aside from that, everything else was fantastic!
Reviewed on Aug 9, 2025
Inn By The Sea
Save 100% on your flight
Price was $1,374, price is now $1,004 per person
$1,004
per person
Oct 20 - Oct 23
found 1 day ago
Roundtrip non-stop flight included
Cleveland (CLE) to Portland (PWM)
9.6/10 Exceptional! (275 reviews)
We chose Inn by the Sea because it was advertised as a “pet-friendly” property with beach access for pets, which was a key factor in our decision. Unfortunately, our experience didn’t quite align with those expectations.
We arrived on a Sunday around noon and, as expected, our room wasn’t ready (check-in is at 4:00pm). However, unlike many hotels, we were not offered anything while we waited — no welcome drink, light refreshment, or even an early check-in estimate — despite having to wait the full four hours.
Once we checked in, we were told our assigned room was not pet-friendly, and we would be charged for any accidents — despite booking under the premise that this was a pet-friendly stay. Additionally, the restaurant only allows pets in the outdoor seating area, and the pool area is not pet-friendly at all. So while the hotel does accommodate pets in some areas, it’s misleading to call it fully pet-friendly when the main guest amenities are off-limits.
That said, the property is beautiful and most of the staff were friendly and professional, which we appreciated. But overall, if you’re traveling with a pet and hoping for a truly integrated experience, this may not be the best fit.
Reviewed on Aug 18, 2025
The McKernan Inn
Save 100% on your flight
Price was $802, price is now $587 per person
$587
per person
Sep 21 - Sep 24
found 1 day ago
Roundtrip flight included
New York (JFK) to Portland (PWM)
9/10 Wonderful! (47 reviews)
Quiet and peaceful with views of the Bay. Easy to access and close to downtown Portland
Reviewed on Aug 18, 2025
Where to stay in Downtown Portland
Find the best Downtown Portland areas and neighborhoods for the activities you enjoy most. Learn more about Downtown Portland
Old Port
4.5/5(473 area reviews)
Cobblestone streets, 19th-century brick buildings, and fishing piers define this district, offering boutiques, restaurants, and bars. Explore Post Office Park, Tommy's Park with its large mural, and stroll the Eastern Promenade Trail to East End Beach.
Downtown Portland Hotel Deals
The Westin Portland Harborview
157 High St, Portland, ME
Fully refundableReserve now, pay when you stay
$223 nightly
The price is $247 total per night from Sep 1 to Sep 2
$247 total
Sep 1 - Sep 2
Total includes taxes and fees
8.8/10 Excellent! (1,005 reviews)
"Excellent room, gorgeous location, and phenomenal staff!"
Reviewed on Aug 18, 2025
Portland Harbor Hotel
468 Fore Street, Portland, ME
Fully refundableReserve now, pay when you stay
$340 nightly
The price is $376 total per night from Sep 1 to Sep 2
$376 total
Sep 1 - Sep 2
Total includes taxes and fees
9.2/10 Wonderful! (1,545 reviews)
"The decor and private garden were nice, as was the self-service pantry on the 2nd floor. The destination fee was a little annoying on top of the proxy room rate, as the credit for the bar was not useful for one member of our party who does not drink. Very convenient to Old Port."
Reviewed on Aug 17, 2025
Holiday Inn Portland-By the Bay by IHG
88 Spring St, Portland, ME
Fully refundable
$149 nightly
The price is $165 total per night from Sep 1 to Sep 2
$165 total
Sep 1 - Sep 2
Total includes taxes and fees
8.8/10 Excellent! (1,331 reviews)
"We had an enjoyable time. The hotel was in a nice location to restaurants & shopping. We were very appreciative of the shuttle guys!!"
Reviewed on Aug 19, 2025
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 Downtown Portland
State Theatre
The beautiful mix of architectural styles, from Art Deco to Moorish, makes this newly renovated performing arts venue one of New England’s best.
Portland Museum of Art
Maine’s largest and oldest art institution showcases three centuries of American art and European masters in its architecturally impressive museum complex.
Wadsworth-Longfellow House
As you tour this historic brick home, trace three generations of Maine family history and learn about the cultural and political impact of its family members.
Things to do
Downtown Golden Adventure Quest Experience in Portland
$7
per adult
Afternoon Windjammer Cruise Along the Coast of Portland Maine
$67
per adult
Sunset Lighthouse Cruise Tour from Casco Bay
$59
per adult
90% of travellers recommend
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- Portland Vacations
- Visit Old Port
- Old Port Vacations
- Cross Insurance Arena
- N.W. Barrett Gallery
- Casco Bay Lines Ferry Terminal
- Victoria Mansion
- Wadsworth-Longfellow House
- Museum of African Culture
- Maine Historical Society
- Center for Maine History
- Maine Sports Hall of Fame
- Maine College of Art
- Merrill Auditorium
- Space Gallery
- Portland Museum of Art
- Charles Q. Clapp House
- McLellan-Sweat Mansion
- McLellan-Sweat House
- State Theatre
- Maine Jewish Museum
- Portland Fire Museum
- Visit Portland
- Cathedral Church of Saint Luke
- International Cryptozoology Museum
- State Street Church
- Center for Cultural Exchange
- Maine Narrow Gauge Railroad Company and Museum
- Visit Portland Arts District
- Casco Bay Bridge
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.