Downtown Portland Vacations from $711
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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 Meadowmere Resort
$1,142
per person
Dec 27 - Jan 3
found 22 hours ago
Roundtrip flight included
Tampa (TPA) to Portland (PWM)
8.6/10 Excellent! (1,008 reviews)
Great mid-price range option! Still walking distance to most things you’ll want to do in ogunquit and they let you check in early just to park even if your room isn’t ready yet, which is valuable in of itself. The outdoor horrible was very spacious and the up keep of the entire property was very nice. Free continental breakfast too
Reviewed on Oct 11, 2026
Blind Tiger Portland - Danforth Street.
West End
$1,246
per person
Dec 30 - Jan 4
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Portland (PWM)
9.6/10 Exceptional! (193 reviews)
Wonderful staff, convenient location, fun stay in an old building. So much character with modern amenities and a neighborhood feel. We thoroughly enjoyed our stay and will return. Off-street parking was a huge bonus and the light breakfast had a wide spread. Such a wonderful property.
Reviewed on Oct 11, 2026
The Docent's Collection at 121 Middle Street
Downtown Portland
$1,109
per person
Dec 24 - Dec 28
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Portland (PWM)
9.6/10 Exceptional! (400 reviews)
The Docent’s Collection at 121 Middle Street is a very good hotel. The room is clean and roomy with all amenities provided even though we didn’t use many of the kitchen utensils or cook ware. The staff was responsive and provided fast service and gave us a big water every day. The only thing that I knocked off one star from the review is the hotel doesn’t have a service staff on premise full time. Some late request was delayed until the staff comes to the premise at 8AM. The parking is pretty expensive at $60/day but we just parked the car in the 2 nearby public parking structures for either $20/day or $38/day. It was only 5 min walk from the parking structure to the hotel.
Reviewed on Oct 11, 2026
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
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.
West End
Distinguished by its well-preserved Victorian architecture, this downtown Portland neighborhood boasts the scenic Western Promenade park, offering views of the White Mountains, and several historic structures, such as the Gothic House and Morrill Mansion.
Portland Arts District
The ample dining options and captivating waterfront views are top of the list for many visitors to Portland Arts District. A stop by Cross Insurance Arena or Portland Museum of Art might round out your trip.
West Bayside
If you're looking for some top things to see and do in West Bayside and surrounding area, you can visit Merrill Auditorium and Cross Insurance Arena.
East Bayside
Bordered by Franklin Street and Washington Avenue, East Bayside offers a community arts venue, Mayo Street Arts, and the relaxing green space of Kennedy Park. Explore nearby Old Port and Munjoy Hill.
Downtown Portland Hotel Deals
The Westin Portland Harborview
157 High St Portland ME
Fully refundableReserve now, pay when you stay
$127 nightly
$141 total
Nov 11 - Nov 12
Total with taxes and fees
Portland Harbor Hotel
468 Fore Street Portland ME
Fully refundableReserve now, pay when you stay
$214 nightly
$236 total
Nov 1 - Nov 2
Total with taxes and fees
Holiday Inn Portland-By the Bay by IHG
88 Spring St Portland ME
Fully refundable
$102 nightly
$112 total
Nov 1 - Nov 2
Total with taxes and fees
9/10 Wonderful! (1,664 reviews)
"We were in Portland for three (3) days on the tail end of our 2-week east coast trip. While the hotel is showing some signs of age, it did not disappoint and fully met our needs. The breakfast was great, especially the cook to order omelets. The hotel is not in the Old Port area but is still a comfortable ..."
Reviewed on Oct 11, 2026
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.
Stay near popular Downtown Portland attractions
State Theatre
8.8/10 (392 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.
Portland Museum of Art
9.2/10 (610 reviews)
Maine’s largest and oldest art institution showcases three centuries of American art and European masters in its architecturally impressive museum complex.
Photo by Tim Thomas
Maine College of Art
10.0/10 (2 reviews)
You can spend an afternoon browsing the exhibits at Maine College of Art during your trip to Portland. Experience the area's acclaimed theater scene and great live music.
Wadsworth-Longfellow House
8.6/10 (119 reviews)
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.
Cross Insurance Arena
8.6/10 (275 reviews)
Catch an event at Cross Insurance Arena during your trip to Portland. Stroll along the area's waterfront or experience its great live music.
Merrill Auditorium
8.8/10 (107 reviews)
You can enjoy a show at Merrill Auditorium during your trip to Portland. Stroll along the area's waterfront or experience its entertainment choices.
Fore Street Gallery
You can spend an afternoon studying the exhibits at Fore Street Gallery during your trip to Portland. Experience the area's entertainment choices and great live music.
Port City Music Hall
9.6/10 (12 reviews)
You can get tickets for a performance at Port City Music Hall during your stay in Portland. Experience the area's entertainment choices and acclaimed theater scene.
Things to do
Sunset Windjammer Cruise Along the Coast of Portland Maine
$77
per adult
90% of travellers recommend
Portland: Casco Bay Morning Lighthouse Cruise
$59
per adult
80% of travellers recommend
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- Victoria Mansion
- Bug Light
- Old Port Vacations
- Portland Museum of Art
- Casco Bay Bridge
- Ll Bean Flagship Store
- Mclellan-Sweat Mansion
- Charles Q. Clapp House
- Fitzpatrick Stadium
- Higgins Beach
- Two Lights State Park
- Eastern Promenade
- International Cryptozoology Museum
- Casco Bay Lines Ferry Terminal
- Port City Music Hall
- Merrill Auditorium
- Wadsworth-Longfellow House
- Maine Sports Hall of Fame
- State Street Church
- Visit Bailey Island
- State Theatre
- Fort Preble
- Portland Head Light
- Spring Point Ledge Lighthouse
- Maine College of Art
- Fort Williams Park
- East End Beach
- Visit Portland
- Southworth Planetarium
- Maine Jewish Museum
- Maine Historical Society
- Mclellan-Sweat House
- Visit Old Port
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.