Search Deals onDowntown Portland Vacation Packages
Downtown Portland Flight + Hotel packages
Price found within the past 48 hours. Click for updated prices.
Clarion Hotel Portland
Price was $602, price is now $513 per person
$513
per person
Dec 4 - Dec 12
found 20 hours ago
Roundtrip non-stop flight included
Chicago (ORD) to Portland (PWM)
Book a stay at this business-friendly hotel in Portland. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Thompson's Point and Maine Mall are located nearby.
The Docent's Collection - New Opening
Downtown Portland
Save 100% on your flight
Price was $1,551, price is now $1,089 per person
$1,089
per person
Dec 4 - Dec 12
found 20 hours ago
Roundtrip non-stop flight included
Chicago (ORD) to Portland (PWM)
Stay at this hotel in Portland. Enjoy free WiFi, parking (surcharge), and daily housekeeping. Popular attractions Thompson's Point and Maine Mall are located nearby.
Portland Harbor Hotel
Downtown Portland
Price was $1,010, price is now $746 per person
$746
per person
Dec 4 - Dec 12
found 20 hours ago
Roundtrip non-stop flight included
Chicago (ORD) to Portland (PWM)
Stay at this 4-star business-friendly hotel in Portland. Enjoy free WiFi, 3 coffee shops/cafes, and breakfast (surcharge). Our guests praise the bar and the helpful staff in our reviews. Popular attractions Thompson's Point and Maine Mall are located nearby.
Inn By The Sea
Save 100% on your flight
Price was $3,518, price is now $2,637 per person
$2,637
per person
Dec 4 - Dec 12
found 20 hours ago
Roundtrip non-stop flight included
Chicago (ORD) to Portland (PWM)
Stay at this 4-star luxury hotel in Cape Elizabeth. Enjoy free valet parking, a full-service spa, and a beach locale. Our guests praise the helpful staff in our reviews. Popular attractions Crescent Beach State Park and Crescent Beach are located nearby.
Hampton Inn Portland Downtown - Waterfront
Downtown Portland
Price was $1,019, price is now $780 per person
$780
per person
Dec 4 - Dec 12
found 20 hours ago
Roundtrip non-stop flight included
Chicago (ORD) to Portland (PWM)
Book a stay at this business-friendly hotel in Portland. Enjoy free breakfast, free WiFi, and a 24-hour fitness center. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Thompson's Point and Maine Mall are located nearby.
The Docent's Collection
Downtown Portland
Save 100% on your flight
Price was $1,381, price is now $1,074 per person
$1,074
per person
Dec 4 - Dec 12
found 20 hours ago
Roundtrip non-stop flight included
Chicago (ORD) to Portland (PWM)
Stay at this 3.5-star hotel in Portland. Enjoy free WiFi, parking (surcharge), and a 24-hour front desk. Popular attractions Thompson's Point and Maine Mall are located nearby.
The Weldon Hotel
Downtown Portland
Price was $1,358, price is now $1,138 per person
$1,138
per person
Dec 4 - Dec 12
found 20 hours ago
Roundtrip non-stop flight included
Chicago (ORD) to Portland (PWM)
Stay at this 4.5-star luxury aparthotel in Portland. Enjoy free WiFi, a 24-hour fitness center, and parking (surcharge). Popular attractions Thompson's Point and Maine Mall are located nearby.
Admiral Peary Inn
Price was $954, price is now $813 per person
$813
per person
Dec 24 - Dec 28
found 20 hours ago
Roundtrip non-stop flight included
Atlanta (ATL) to Portland (PWM)
Stay at this 3-star B&B in Fryeburg. Enjoy free WiFi, free parking, and a garden. Popular attractions Fryeburg Public Library and Bradley Memorial Park are located nearby.
3-4 Night Vacations in Downtown Portland
Price found within the past 48 hours. Click for updated prices.
5-7 Night Vacations in Downtown Portland
Price found within the past 48 hours. Click for updated prices.
Cheap Hotel Deals in Downtown Portland
Portland Harbor Hotel
468 Fore Street, Portland, ME
Stay at this 4-star business-friendly hotel in Portland. Enjoy free WiFi, 3 coffee shops/cafes, and breakfast (surcharge). Our guests praise the bar and the ...
Portland Regency Hotel & Spa
20 Milk Street, Portland, ME
Stay at this 3.5-star spa hotel in Portland. Enjoy free WiFi, a full-service spa, and 2 bars/lounges. Our guests praise the helpful staff and the clean rooms ...
Holiday Inn Portland-By the Bay by IHG
88 Spring St, Portland, ME
Stay at this 3-star business-friendly hotel in Portland. Enjoy free WiFi, breakfast (surcharge), and a free airport shuttle. Our guests praise the helpful staff ...
Save an average of 15% on thousands of hotels when you're signed in
Hyatt Place Portland Downtown - Old Port Square
433 Fore St, Portland, ME
Stay at this 3-star business-friendly hotel in Portland. Enjoy free WiFi, breakfast (surcharge), and a free airport shuttle. Our guests praise the breakfast ...
Hampton Inn Portland Downtown - Waterfront
209 Fore St, Portland, ME
Book a stay at this business-friendly hotel in Portland. Enjoy free breakfast, free WiFi, and a 24-hour fitness center. Our guests praise the breakfast and the ...
Canopy by Hilton Portland Waterfront
9 Center Street, Portland, ME
Stay at this 4-star hotel in Portland. Enjoy free WiFi, 2 restaurants, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in ...
Hilton Garden Inn Portland Downtown Waterfront
65 Commercial St, Portland, ME
Stay at this 3-star business-friendly hotel in Portland. Enjoy free WiFi, breakfast (surcharge), and a fitness center. Our guests praise the helpful staff and ...
The Westin Portland Harborview
157 High St, Portland, ME
Book a stay at this spa hotel in Portland. Enjoy free WiFi, a full-service spa, and breakfast (surcharge). Our guests praise the bar and the helpful staff in ...
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.
Top Flight Deals
Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.
Wed, Nov 19 - Wed, Dec 3
MCO
Orlando Intl.
PWM
Portland Intl. Jetport
$172 Roundtrip, found 17 hours ago
$172
Roundtrip
found 17 hours ago
Mon, Nov 10 - Sat, Nov 15
JFK
John F. Kennedy Intl.
PWM
Portland Intl. Jetport
$182 Roundtrip, found 4 days ago
$182
Roundtrip
found 4 days ago
Thu, Jan 15 - Mon, Jan 19
DCA
Ronald Reagan Washington National
PWM
Portland Intl. Jetport
$189 Roundtrip, found 3 days ago
$189
Roundtrip
found 3 days ago
Thu, Nov 27 - Wed, Dec 3
TPA
Tampa Intl.
PWM
Portland Intl. Jetport
$212 Roundtrip, found 2 days ago
$212
Roundtrip
found 2 days ago
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