Downtown Portland Vacations from $329
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to $1,045 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.
The Docent’s Collection – Thompson Block
Downtown Portland
Price was $707, price is now $574 per person
$574
per person
Apr 10 - Apr 12
found 18 hours ago
Roundtrip flight included
Baltimore (BWI) to Portland (PWM)
9.6/10 Exceptional! (249 reviews)
Room was very clean, neat vibe, tons of space! Made coming back from
Reviewed on Jan 23, 2026
Cliff House Maine
Bald Head
Price was $1,120, price is now $910 per person
$910
per person
Apr 17 - Apr 19
found 12 hours ago
Roundtrip flight included
Columbus (CMH) to Portland (PWM)
9.4/10 Exceptional! (1,001 reviews)
Phenomenal service and food with stunning east coast views. A favorite for sure.
Reviewed on Jan 23, 2026
84 Main
Price was $695, price is now $569 per person
$569
per person
Mar 27 - Mar 30
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Portland (PWM)
10/10 Exceptional! (52 reviews)
Very spacious and relaxing. Nice view of Kennebunk quaint ice rink and Main Street. Coffee shop at Street level was a fantastic add! Beds and bedding were comfortable. Will visit again! Nothing lacking with respect to amenities.
Reviewed on Dec 29, 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
The price is $108 total per night from Feb 26 to Feb 27
$108 total
per night
Feb 26 - Feb 27
8.8/10 Excellent! (1,005 reviews)
The room was clean and comfortable. Thr hotel itself was beautiful
Reviewed on Feb 4, 2026
Portland Harbor Hotel
468 Fore Street Portland ME
Fully refundableReserve now, pay when you stay
The price is $163 total per night from Feb 18 to Feb 19
$163 total
per night
Feb 18 - Feb 19
9.2/10 Wonderful! (1,751 reviews)
Wonderful stay!
Reviewed on Feb 7, 2026
Portland Regency Hotel & Spa
20 Milk Street Portland ME
Fully refundableReserve now, pay when you stay
The price is $141 total per night from Mar 1 to Mar 2
$141 total
per night
Mar 1 - Mar 2
9.4/10 Exceptional! (1,578 reviews)
The room was impeccable, the restaurant was delicious and perfect location
Reviewed on Jan 29, 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.
Discover the most popular places to visit in Downtown Portland
State Theatre
4.5/5(88 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
4.5/5(255 reviews)
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
4/5(78 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.
Things to do
Portland Smartphone Audio Tour: Self-Guided Drive
$17
per traveler
Downtown Portland: Coastal Vibe and Old Mansions with In-Add Audio Tour
$10
per traveler
Ultimate Portland Self-Guided Driving GPS Audio Tour
$17
per traveler
100% of travellers recommend
Explore a world of travel with Expedia
- Portland Hotels
- Hotels near Old Port
- Cheap Hotels in Portland
- Oceanfront Hotels in Portland
- Hotels with Free Airport Shuttle in Portland
- B&B in Portland
- Hotels near Cross Insurance Arena
- Cheap Hotels in Old Port
- Hotels with Free Parking in Old Port
- Pet-friendly Hotels in Old Port
- Hotels with Hot Tubs in Old Port
- Boutique Hotels in Old Port
- Hotels with Fireplaces in Old Port
- Family Hotels in Old Port
- Hotels with Balconies in Old Port
- Resorts & Hotels with Spas in Old Port
- 4 Star Hotels in Old Port
- Oceanfront Hotels in Old Port
- Hotels with Connecting Rooms in Old Port
- Hotel Wedding Venues Hotels in Old Port
- Romantic Hotels in Old Port
- Hotels with an Outdoor Pool in Old Port
- Luxury Hotels in Old Port
- Historic Hotels in Old Port
- Hotels with a Pool in Old Port
- Hotels with an Indoor Pool in Old Port
- 5 Star Hotels in Old Port
- Hotels with Free Airport Shuttle in Old Port
- Hotels with Free Breakfast in Old Port
- Adults Only Resorts & in Old Port
- Hotels with Laundry Facilities in Old Port
- Hotels with Restaurants in Old Port
- Hotels with Bars in Old Port
- 3 Star Hotels in Old Port
- Hotels with a Gym in Old Port
- Hotel with a Concierge Hotels in Old Port
- Golf Hotels in Old Port
- Honeymoon Resorts & in Old Port
- Pet-friendly Hotels in Portland
- Hotels near N.W. Barrett Gallery
- Hotels near Monument Square
- Motels in Portland
- Hotels near Portland Arts District
- Hotels near Maine Historical Society
- Hotels near Wadsworth-Longfellow House
- Cabin Rentals in Portland
- 4 Star Hotels in Portland Arts District
- Historic Hotels in Portland Arts District
- Hotels with Free Airport Shuttle in Portland Arts District
- Hotels near Port City Music Hall
- Luxury Hotels in Portland
- Hotels near Merrill Auditorium
- Hotels near Maine College of Art
- Hotels near Institute of Contemporary Art
- Hotels with an Indoor Pool in Portland
- Hotels near Space Gallery
- Resorts & Hotels with Spas in Portland
- Boutique Hotels in Portland
- Best Western Hotels in Portland
- Hotels near Casco Bay Lines Ferry Terminal
- Hotels with an Outdoor Pool in Portland
- 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.