Durham Vacations
Build a Flight + Hotel Bundle & Save up to $536 On Your Vacation*
Durham Flight + Hotel packages
Price found within the past 48 hours. Click for updated prices.
Portland Harbor Hotel
Downtown Portland
$1,120
per person
Nov 11 - Nov 16
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Portland (PWM)
Book a stay at this business-friendly hotel in Portland. Enjoy free WiFi, 3 coffee shops/cafes, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Maine Mall and Cross Insurance Arena are located nearby.
Blind Tiger Portland - Danforth Street.
West End
$1,457
per person
Nov 11 - Nov 16
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Portland (PWM)
Stay at this B&B in Portland. Enjoy free breakfast, free WiFi, and parking (surcharge). Popular attractions Thompson's Point and Portland Head Light are located nearby.
Perfect location & beautiful stay! Very unique property. Great recommendations & lovely hospitality. We will definitely come back the next time we’re in Portland!
:)
Reviewed on Aug 23, 2026
The Weldon Hotel
Downtown Portland
$1,260
per person
Nov 11 - Nov 16
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Portland (PWM)
Book a stay at this luxury aparthotel in Portland. Enjoy free WiFi, a 24-hour fitness center, and parking (surcharge). Popular attractions Maine Mall and Cross Insurance Arena are located nearby.
The unit was great. The kitchen and it's utensils are excellent.
The turntable record player gives a classic wonderful back in time.
We would suggest more soaking towels under the sink. And keep the corner of the rug not in the living room not slippery.
Other than that it was a wonderfully clean and high end place to stay close to the Old Port.
Reviewed on Aug 24, 2026
Blind Tiger Portland – Carleton Street
West End
$1,303
per person
Nov 11 - Nov 16
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Portland (PWM)
Stay at this B&B in Portland. Enjoy free breakfast, free WiFi, and daily housekeeping. Popular attractions State Theatre and Cross Insurance Arena are located nearby.
Evalina Hotel
Downtown Portland
$1,511
per person
Nov 11 - Nov 16
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Portland (PWM)
Stay at this aparthotel in Portland. Enjoy free WiFi, parking (surcharge), and in-room washers/dryers. Popular attractions Thompson's Point and Portland Head Light are located nearby.
Great location! Fun space! Comfortable and clean!
Reviewed on Aug 17, 2026
Portland Regency Hotel & Spa
Downtown Portland
$1,210
per person
Nov 11 - Nov 16
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Portland (PWM)
Book a stay at this 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 in our reviews. Popular attractions State Theatre and Thompson's Point are located nearby.
The staff was really lovely and helpful. A lovely, very well located historic property. The spa was very nice!
Reviewed on Aug 25, 2026
Top Hotel Deals
Portland Regency Hotel & Spa
20 Milk Street Portland ME
Book a stay at this 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 in ...
Cambria Hotel Portland Downtown-Old Port
25 HANCOCK STREET Portland ME
Book a stay at this business-friendly hotel in Portland. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the restaurant ...
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 ...
Hilton Garden Inn Portland Downtown Waterfront
65 Commercial St Portland ME
Book a stay at this business-friendly hotel in Portland. Enjoy free WiFi, breakfast (surcharge), and a fitness center. Our guests praise the helpful staff and ...
Oceanfront Studio w/ Private Dock in Harpswell!
Harpswell ME
Stay at this apartment in Harpswell. Enjoy patios, an in-room coffeemaker, and air conditioning. Popular attractions Mitchell Field and Bailey Island Bridge ...
AC Hotel Portland Downtown/Waterfront, ME
158 Fore St Portland ME
Book a stay at this business-friendly hotel in Portland. Enjoy free WiFi, breakfast (surcharge), and a free airport shuttle. Our guests praise the helpful staff ...
The Press Hotel, Marriott Autograph Collection
119 Exchange Street Portland ME
Book a stay at this business-friendly hotel in Portland. Enjoy free WiFi, 2 bars/lounges, and breakfast (surcharge). Our guests praise the helpful staff in our ...
The Freeport Hotel, an Ascend Collection Hotel
506 Us Route 1 Freeport ME
Book a stay at this business-friendly motel in Freeport. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff ...
Travelers Inn
130 Pleasant St Brunswick ME
Book a stay at this business-friendly motel in Brunswick. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
Residence Inn Portland Downtown/Waterfront
145 Fore Street Portland ME
Book a stay at this business-friendly hotel in Portland. Enjoy free breakfast, free WiFi, and a free airport shuttle. Our guests praise the helpful staff and ...
Holiday Inn Express Hotel & Suites Freeport by IHG
450 U.S. Route 1 Freeport ME
Book a stay at this business-friendly hotel in Freeport. Enjoy free breakfast, free parking, and a fitness center. Our guests praise the breakfast and the helpful ...
Best Western Freeport Inn
31 US Route 1 Freeport ME
Stay at this hotel in Freeport. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff and the clean rooms in our reviews. Popular ...
The Brunswick Hotel
4 Noble St Brunswick ME
Book a stay at this business-friendly hotel in Brunswick. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff in our ...
Spark by Hilton Brunswick
199 Pleasant St Brunswick ME
Book a stay at this business-friendly hotel in Brunswick. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
The Harraseeket Inn & Event House Freeport Downtown
162 Main St Freeport ME
Book a stay at this business-friendly hotel in Freeport. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff ...
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
These prices were available within the past 7 days. Prices quoted are per person, round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.
Sun, Oct 4 - Fri, Oct 9
EWR
Newark Liberty Intl. Airport
PWM
Portland Intl. Jetport
$217
Roundtrip
found 6 hours ago
Fri, Oct 30 - Mon, Nov 2
RDU
Raleigh - Durham Intl.
PWM
Portland Intl. Jetport
$222
Roundtrip
found 1 day ago
Tue, Oct 27 - Mon, Nov 2
TPA
Tampa Intl.
PWM
Portland Intl. Jetport
$237
Roundtrip
found 4 days ago
Fri, Oct 30 - Mon, Nov 2
RDU
Raleigh - Durham Intl.
PWM
Portland Intl. Jetport
$245
Roundtrip
found 1 day ago
Sat, Sep 26 - Wed, Sep 30
DCA
Ronald Reagan Washington National
PWM
Portland Intl. Jetport
$257
Roundtrip
found 19 hours ago
Best points of interest in Durham
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