Old Port Vacations from $402
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Your Old Port Vacation
Planning your next adventure just got easier with a vacation package to Old Port. Take in the best this neighborhood has to offer while creating wonderful memories that will last forever. Wondering where to go during your trip to Old Port? Nearby attractions like Portland Museum of Art, University of Southern Maine and Victoria Mansion are excellent places to start. Stop daydreaming and start doing. When it's time to book your dream vacation to Old Port, Expedia is here to help.
The Latest Old Port Vacation Packages
Price found within the past 48 hours. Click for updated prices.
Portland Harbor Hotel
Downtown Portland
Save 100% on your flight
Price was $556, price is now $402 per person
$402
per person
Dec 30 - Jan 3
found 3 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Portland (PWM)
18.4/10 Exceptional! (1,668 reviews)
Hotel is so centrally located, you can't beat it. The bar is welcoming and perfect to play cards near the fireplace. Have stayed here a couple times now, and it's the new favorite. Parking is convenient, but a bit pricey at $45/night - but worth the access. Staff are kind and accommodating, rooms are clean and updated.
Reviewed on Nov 20, 2025
The Docent’s Collection – Thompson Block
Downtown Portland
Save 100% on your flight
Price was $745, price is now $443 per person
$443
per person
Dec 30 - Jan 3
found 3 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Portland (PWM)
19.2/10 Exceptional! (249 reviews)
This is in a great location and room was very spacious. Blind in bedroom was broken in down position so it was always dark in there.
You are supposed to download an app that requires “always on” connection to Bluetooth to get in, but someone was available to give us card keys instead.
Reviewed on Nov 16, 2025
Blind Tiger Portland - Danforth Street.
West End
Save 100% on your flight
Price was $1,108, price is now $677 per person
$677
per person
Dec 30 - Jan 3
found 3 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Portland (PWM)
19.2/10 Exceptional! (161 reviews)
Wish they had a liquor license and could do a cocktail hour in addition to a breakfast service. Wish they had just a tad more breakfast options. Really wish they had a key pad and front door access! LOVED the fire places in every room. Property manager was lovely and friendly. Loved the snacks available and variety.
Reviewed on Oct 27, 2025
Blind Tiger Portland – Carleton Street
West End
Save 100% on your flight
Price was $949, price is now $662 per person
$662
per person
Dec 30 - Jan 3
found 3 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Portland (PWM)
19.2/10 Exceptional! (119 reviews)
Adorable spot in Portland, great location, really cool concept. Felt like an upgraded vacation rental. You don’t have the whole place to yourself but it basically feels like it. Check in and everything was seamless. The local recommendations, games, and snacks were a nice touch. We loved plays scrabble and drinking wine in the parlor. We do wish some items were a bit nicer given the cost. The bathroom could've had nicer facilities (cheap toilet seat, low water pressure) our bed was a rickety. The breakfast delivered was a nice touch but the contents itself kinda fell flat, not as curated as the website made it seem. Overall we still enjoyed our stay and the concept, but the website may have upsold it a bit.
Reviewed on Nov 11, 2025
Portland Regency Hotel & Spa
Downtown Portland
Save 100% on your flight
Price was $593, price is now $430 per person
$430
per person
Dec 30 - Jan 3
found 3 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Portland (PWM)
18.8/10 Exceptional! (1,512 reviews)
Everything! We love the charm of this place. Even down to the gold key standard. Location , sevice , design…perfect. Been coming for years and will always return .
Reviewed on Nov 22, 2025
Where to stay in Old Port
Find the best Old Port areas and neighborhoods for the activities you enjoy most. Learn more about Old Port
Downtown Portland
4 out of top 10 points of interest in this area
4.5/5(326 area reviews)
Known for its culinary delights, inspiring art and live music, the heart of Maine’s largest city is an exciting location.
Old Port Hotel Deals
Portland Harbor Hotel
468 Fore Street Portland ME
Fully refundableReserve now, pay when you stay
$139 nightly
The price is $154 total per night from Nov 24 to Nov 25
$154 total
Nov 24 - Nov 25
Total with taxes and fees
9.2/10 Wonderful! (1,676 reviews)
Excellent location, helpful front desk, quiet, clean, well-appointed room.
Reviewed on Nov 18, 2025
Hyatt Place Portland Downtown - Old Port Square
433 Fore St Portland ME
Fully refundableReserve now, pay when you stay
$109 nightly
The price is $121 total per night from Nov 24 to Nov 25
$121 total
Nov 24 - Nov 25
Total with taxes and fees
8.8/10 Excellent! (1,257 reviews)
Rooms very clean. Daily turnover service. Friendly staff. Good breakfast choices with attentive attendant. Highly recommend.
Reviewed on Nov 20, 2025
Portland Regency Hotel & Spa
20 Milk Street Portland ME
Fully refundableReserve now, pay when you stay
$130 nightly
The price is $144 total per night from Nov 24 to Nov 25
$144 total
Nov 24 - Nov 25
Total with taxes and fees
9.4/10 Exceptional! (1,527 reviews)
Room was spacious and so comfortable. Booked this specifically for the spa though and it closed right when I got there. I went the next morning but the steam room smelled so strongly of cleaning solution I had to leave, the sauna door wouldn’t close all the way and the whirlpool was out of ...
Reviewed on Nov 21, 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 Old Port
Cross Insurance Arena
Catch an event at Cross Insurance Arena during your trip to Portland. Stroll along the area's waterfront or experience its entertainment choices.
Casco Bay Lines Ferry Terminal
Explore the waterfront in Portland with a trip to Casco Bay Lines Ferry Terminal. Discover the top-notch restaurants and great live music in this family-friendly area.
Maine Sports Hall of Fame
You can spend an afternoon studying the exhibits at Maine Sports Hall of Fame during your travels in Portland. Stroll along the area's waterfront or experience its acclaimed theater scene.
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
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- Portland Vacations
- N.W. Barrett Gallery
- Downtown Portland Vacations
- Casco Bay Lines Ferry Terminal
- Maine Sports Hall of Fame
- Cross Insurance Arena
- Merrill Auditorium
- Wadsworth-Longfellow House
- Victoria Mansion
- Maine Historical Society
- Museum of African Culture
- Center for Maine History
- Maine College of Art
- Space Gallery
- Maine Jewish Museum
- Portland Museum of Art
- Charles Q. Clapp House
- Visit Portland
- McLellan-Sweat Mansion
- McLellan-Sweat House
- State Theatre
- Visit Downtown Portland
- Portland Fire Museum
- Maine Narrow Gauge Railroad Company and Museum
- Cathedral Church of Saint Luke
- International Cryptozoology Museum
- State Street Church
- Center for Cultural Exchange
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- Car rental Portland Airport (PWM)
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.