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.
84 Main

84 Main

$580
per person
Nov 19 - Nov 23
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Portland (PWM)
9.8/10 Exceptional! (58 reviews)
The property was very spacious, well equipped, and well taken care of. There was lots of natural light and a very large outdoor deck accessible from all bedrooms and the living room.

Reviewed on Jul 17, 2026

The Meadowmere Resort

The Meadowmere Resort

Save 100% on your flight
$1,060
per person
Dec 7 - Dec 13
found 3 hours ago
Roundtrip flight included
New York (NYC) to Portland (PWM)
8.6/10 Excellent! (1,008 reviews)
Check in was a nightmare, the room I paid for in full before the stay was not available (over booked) downgraded to a queen room, young man at check in was rides fold me it was my fault bc used Expedia. Finally got a room key after that din exchange and walked into a lady in bed! So apparently all the rooms were ‘double booked’ the manager did come talk to us, he was very nice, he got us into the queen room and told us he’d comp a return night (hasn’t happened yet). The resort is lovely, clean and spa area is great. Walkable to in town restaurants. Beds are comfortable and rooms are clean and updated. If not for the horrible check in and attitude I’d give this stay 5 stars, but tough to do when you paid for something you didn’t get. Expedia declined to refund any of what we paid, they said the resort had to and the resort said they had to …

Reviewed on Oct 17, 2026

Cliff House Maine

Cliff House Maine

Bald Head
$1,127
per person
Dec 26 - Dec 29
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Portland (PWM)
9.4/10 Exceptional! (1,002 reviews)
Cliff House Maine – Spectacular Views, Beautiful Accommodations, and a Few Areas for Improvement Overall, our stay at Cliff House was excellent. The property is absolutely beautiful, and the ocean views are spectacular. The rooms are spacious, beautifully appointed, and extremely comfortable. The bedding was especially luxurious, and the sheets felt fabulous, although they unfortunately wouldn’t stay on the bed! The dining experience was somewhat disappointing compared to the rest of the property. The food was beautifully presented, but the flavors and overall quality were average. Given the Michelin recognition and expectations, we anticipated a more memorable culinary experience. The spa itself was amazing. Beautifully designed, luxurious, and exceptionally well appointed, it was one of the highlights of the property. The spa services were definitely above average and very enjoyable, although not quite exceptional. The staff throughout the property were lovely. Housekeeping and valet deserve special recognition for their outstanding service, friendliness, and attention to detail. The restaurant waitstaff were good and attentive, while the front desk service was adequate but didn’t quite match the warmth and polish we experienced elsewhere. Despite a few areas for improvement, Cliff House is a wonderful destination. The spectacular setting, beautiful accommodations, and exceptional spa facilities make it a memorable coastal Maine getaway. We thoroughly enjoyed our stay

Reviewed on Oct 18, 2026

Canopy by Hilton Portland Waterfront

Canopy by Hilton Portland Waterfront

Downtown Portland
$794
per person
Dec 30 - Jan 2
found 1 day ago
Roundtrip flight included
New York (NYC) to Portland (PWM)
9.4/10 Exceptional! (1,007 reviews)
White Barn Inn & Spa, Auberge Collection

White Barn Inn & Spa, Auberge Collection

$1,163
per person
Dec 30 - Jan 2
found 1 day ago
Roundtrip flight included
New York (NYC) to Portland (PWM)
9.6/10 Exceptional! (124 reviews)

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
A marina with boats docked, a wooden pier, and a red brick building with balconies.

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.

A lighthouse on a rocky shore with a sailboat in the distance.

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.

A large, cream-colored building with white columns and a white picket fence in front.

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.

An aerial view of a coastal town with houses, a parking lot, and a rocky shoreline.

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.

A red brick building with Gothic architectural features, including pointed arches and a cross on top.

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

The Westin Portland Harborview

157 High St Portland ME
Fully refundableReserve now, pay when you stay
$108 nightly
$119 total
Nov 18 - Nov 19
Total with taxes and fees
The Westin Portland Harborview
Portland Harbor Hotel

Portland Harbor Hotel

468 Fore Street Portland ME
Fully refundableReserve now, pay when you stay
$195 nightly
$216 total
Nov 18 - Nov 19
Total with taxes and fees
Portland Harbor Hotel
Holiday Inn Portland-By the Bay by IHG

Holiday Inn Portland-By the Bay by IHG

88 Spring St Portland ME
Fully refundable
$95 nightly
$106 total
Nov 19 - Nov 20
Total with taxes and fees
Holiday Inn Portland-By the Bay by IHG
See all 2,423 properties in Downtown Portland
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

A multi-story brick building with a large arched window and a sign that reads "STATE".

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.
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A historic building with a sign reading "Portland Museum of Art McLellan House."

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.
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A building with large windows and a 'STOP' sign in front.
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.
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A red brick building with green shutters, a white garage door, and a tree in the foreground.

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.
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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.
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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.
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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.
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Monument Square

8.0/10 (1 review)
Find out about the history of Portland when you spend time at Monument Square. Stroll along the area's waterfront or experience its acclaimed theater scene.
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Things to do

Vintage Fire Truck Sightseeing Tour of Portland Maine

Vintage Fire Truck Sightseeing Tour of Portland Maine

$45
per adult
98% of travellers recommend
Vintage Fire Truck Sightseeing Tour of Portland Maine
Afternoon Windjammer Cruise Along the Coast of Portland Maine

Afternoon Windjammer Cruise Along the Coast of Portland Maine

$69
per adult
96% of travellers recommend
Afternoon Windjammer Cruise Along the Coast of Portland Maine
Sunset Windjammer Cruise Along the Coast of Portland Maine

Sunset Windjammer Cruise Along the Coast of Portland Maine

$77
per adult
90% of travellers recommend
Sunset Windjammer Cruise Along the Coast of Portland Maine
See all activities in Portland

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