Downtown Portland Vacations from $680
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to $2,000 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
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.
Nautical Mile
$680
per person
Dec 4 - Dec 8
found 21 hours ago
Roundtrip flight included
Chicago (ORD) to Portland (PWM)
8.6/10 Excellent! (24 reviews)
I've stayed at the Nautical Mile many times! The rooms are perfect for a get-away! The pool is always ready to cool off in and the people, both working at the Nautical Mile and guests are very friendly.
Reviewed on Sep 8, 2026
Evalina Hotel
Downtown Portland
$1,133
per person
Nov 13 - Nov 16
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Portland (PWM)
10/10 Exceptional! (11 reviews)
This is a very nice hotel in a great location. It’s new and wonderfully appointed. Everything about it is first class.
Reviewed on Sep 24, 2026
The Docent's Collection at 121 Middle Street
Downtown Portland
$733
per person
Dec 3 - Dec 6
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Portland (PWM)
9.6/10 Exceptional! (382 reviews)
The loft was wonderful! Really great location for old port! Really enjoyed our stay! Felt homely! We relaxed and felt so comfortable there! Would recommend!
Reviewed on Sep 24, 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.
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.
Parkside
While visiting Parkside, you might make a stop by sights like Neal S. Dow House and Fitzpatrick Stadium.
Downtown Portland Hotel Deals
Portland Harbor Hotel
468 Fore Street Portland ME
$277 nightly
$306 total
Oct 25 - Oct 26
Total with taxes and fees
Holiday Inn Portland-By the Bay by IHG
88 Spring St Portland ME
$227 nightly
$251 total
Oct 26 - Oct 27
Total with taxes and fees
The Westin Portland Harborview
157 High St Portland ME
Fully refundableReserve now, pay when you stay
$220 nightly
$243 total
Oct 25 - Oct 26
Total with taxes and fees
9/10 Wonderful! (1,008 reviews)
"The room was clean, the hotel is spacious, and well located in the city. The interior has multiple flights of stairs to drag suitcases which made it somewhat difficult. It was difficult to navigate the wifi in the room and the off site parking requires that they accurately enter your license plate ..."
Reviewed on Sep 24, 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.
State Street Church
Portland’s history of religious tolerance finds its place in a Gothic Revival building at the city center, perfect for attending religious services while on vacation.
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.
International Cryptozoology Museum
You can spend time browsing the exhibits at International Cryptozoology Museum in Portland. Stroll along the area's waterfront or experience its great live music.
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
Explore a world of travel with Expedia
- Old Port Hotels
- Cape Elizabeth Hotels
- Freeport Hotels
- South Portland Hotels
- Oceanfront Hotels in Old Orchard Beach
- Hotels with Free Airport Shuttle in Portland
- Scarborough Hotels
- Kennebunkport Hotels
- Hotels near Portland Intl. Jetport
- Portland Hotels
- Wells Hotels
- Pet-Friendly Hotels in Portland
- Oceanfront Hotels in Portland
- Old Orchard Beach Hotels
- B&B in Portland
- Cheap Hotels in Portland
- Ogunquit Hotels
- Downtown Portland Hotels
- Motels in Portland
- Flights from Tampa (TPA) to Portland (PWM)
- Flights from New York (JFK) to Portland (PWM)
- Flights from Tucson (TUS) to Portland (PWM)
- Flights from Salt Lake City (SLC) to Portland (PWM)
- Flights from Nashville (BNA) to Portland (PWM)
- Flights from Buffalo (BUF) to Portland (PWM)
- Flights from Orlando (MCO) to Portland (PWM)
- Flights from Fort Lauderdale (FLL) to Portland (PWM)
- Flights from New York (LGA) to Portland (PWM)
- Flights from Boston (BOS) to Portland (PWM)
- Flights from Miami (MIA) to Portland (PWM)
- Flights from Dallas (DFW) to Portland (PWM)
- Flights from Atlanta (ATL) to Portland (PWM)
- Flights from Washington (IAD) to Portland (PWM)
- Flights from Portland (PDX) to Portland (PWM)
- Flights from Seattle (SEA) to Portland (PWM)
- Flights from Cleveland (CLE) to Portland (PWM)
- Flights from San Francisco (SFO) to Portland (PWM)
- Flights from Los Angeles (LAX) to Portland (PWM)
- Flights from Minneapolis (MSP) to Portland (PWM)
- Flights from St. Louis (STL) to Portland (PWM)
- Flights from Jacksonville (JAX) to Portland (PWM)
- Flights to Portland
- Flights from Raleigh (RDU) to Portland (PWM)
- Flights from Pittsburgh (PIT) to Portland (PWM)
- Flights from Phoenix (PHX) to Portland (PWM)
- Flights from Chicago (ORD) to Portland (PWM)
- Flights from Detroit (DTW) to Portland (PWM)
- Flights from Hartford (BDL) to Portland (PWM)
- Flights from Austin (AUS) to Portland (PWM)
- Flights from Cincinnati (CVG) to Portland (PWM)
- Flights from New York (NYC) to Portland (PWM)
- Flights from Indianapolis (IND) to Portland (PWM)
- Flights from White Plains (HPN) to Portland (PWM)
- Flights from Columbus (CMH) to Portland (PWM)
- Flights from Newark Liberty Intl. Airport (EWR) to Portland (PWM)
- Flights from Washington (DCA) to Portland (PWM)
- Flights from Portland Intl. Jetport
- Flights from Charlotte (CLT) to Portland (PWM)
- Flights from Philadelphia (PHL) to Portland (PWM)
- Flights from Denver (DEN) to Portland (PWM)
- Flights from Richmond (RIC) to Portland (PWM)
- Flights from Houston (IAH) to Portland (PWM)
- Flights from Baltimore (BWI) to Portland (PWM)
- 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.