Kennebunk Vacations
Build a Flight + Hotel Bundle & Save up to $536 On Your Vacation*
Kennebunk Flight + Hotel packages
Price found within the past 48 hours. Click for updated prices.
Portland Regency Hotel & Spa
Downtown Portland
Price was $1,180, price is now $1,020 per person
$1,020
per person
Dec 28 - Jan 2
found 17 hours 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.
Favorite hotel in old port. Great location for walking the whole area. Staff is are all great. Valet parking always goes smoothly... there is a public lot a coulpeof blocks inland and to the right if you prefer self parking.
Excellent breakfast. Nice dinner lounge below and whiskey lounge in the evenings.
3rd time staying there and will many more times. Very well run hotel.
Reviewed on Nov 2, 2026
Blind Tiger Portland - Danforth Street.
West End
Price was $2,560, price is now $1,975 per person
$1,975
per person
Dec 28 - Jan 2
found 17 hours 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 State Theatre and Cross Insurance Arena are located nearby.
The Docent's Collection at 121 Middle Street
Downtown Portland
Price was $1,705, price is now $1,413 per person
$1,413
per person
Dec 28 - Jan 2
found 17 hours ago
Roundtrip flight included
Chicago (ORD) to Portland (PWM)
Stay at this hotel in Portland. Enjoy free WiFi, parking (surcharge), and premium TV channels. Popular attractions State Theatre and Thompson's Point are located nearby.
Inn By The Sea
Price was $1,548, price is now $1,295 per person
$1,295
per person
Dec 28 - Jan 2
found 17 hours ago
Roundtrip flight included
Chicago (ORD) to Portland (PWM)
Book a stay at this luxury hotel in Cape Elizabeth. Enjoy free valet parking, a full-service spa, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. Popular attractions Crescent Beach State Park and Crescent Beach are located nearby.
The Docent's Collection at 178 Middle Street
Downtown Portland
Price was $1,921, price is now $1,626 per person
$1,626
per person
Dec 28 - Jan 2
found 17 hours ago
Roundtrip flight included
Chicago (ORD) to Portland (PWM)
Stay at this hotel in Portland. Enjoy free WiFi, parking (surcharge), and a 24-hour front desk. Popular attractions State Theatre and Thompson's Point are located nearby.
room was very modern, however some areas did not look well cleaned (edge if the bed had some dried white liquid). the surrounding area has nice shops but is very sketchy at night. did not feel comfortable with the parking situation. also at 6am sounded like maintenance or cleaning crew was constantly in and out of the elevator making tons of noise. was good for a night but wouldnt stay again.
Reviewed on Oct 27, 2026
The Weldon Hotel
Downtown Portland
Price was $1,646, price is now $1,447 per person
$1,447
per person
Dec 28 - Jan 2
found 17 hours 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 Cross Insurance Arena and State Theatre are located nearby.
Top Hotel Deals
Port Inn & Suites Kennebunk, an Ascend Collection Hotel
55 York St Kennebunk ME
0.67 km from city center
Stay at this motel in Kennebunk. Enjoy free breakfast, an outdoor pool, and WiFi (surcharge). Our guests praise the helpful staff and the clean rooms in our ...
The Beach House Inn
211 Beach Avenue Kennebunk ME
5.96 km from city center
Book a stay at this beach hotel in Kennebunk. Enjoy free WiFi, free parking, and free bicycles on site. Our guests praise the helpful staff and the clean rooms ...
White Barn Inn & Spa, Auberge Collection
37 Beach Ave Kennebunk ME
6.17 km from city center
Book a stay at this luxury hotel in Kennebunk. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Dock Square and Kennebunkport Village ...
Kings Port Inn
18 Western Ave Kennebunk ME
5.82 km from city center
Stay at this hotel in Kennebunk. Enjoy free breakfast, cable TV channels, and housekeeping. Our guests praise the breakfast and the helpful staff in our reviews. ...
Kennebunk Gallery Motel & Cottages
65 York Street Kennebunk ME
0.84 km from city center
Stay at this motel in Kennebunk. Enjoy free WiFi, free parking, and daily housekeeping. Our guests praise the helpful staff in our reviews. Popular attractions ...
Quality Inn & Suites South Portland
738 Main Street South Portland ME
32.21 km from city center
Book a stay at this business-friendly hotel in South Portland. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
Casco Bay Hotel Portland Airport - Maine Mall, an Ascend Collection Hotel
80 John Roberts Rd. South Portland ME
32.37 km from city center
Book a stay at this business-friendly hotel in South Portland. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
Ocean Sands at York Beach
277 Long Beach Avenue York Beach ME
26.05 km from city center
Book a stay at this beach motel in York Beach. Enjoy an outdoor pool, parking (surcharge), and a garden. Our guests praise the pool and the helpful staff in ...
Spark by Hilton Portland Airport Maine Mall
461 Maine Mall Rd South Portland ME
32.07 km from city center
Book a stay at this business-friendly hotel in South Portland. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the ...
Ogunquit - The Milestone
687 Main Street Ogunquit ME
13.87 km from city center
Book a stay at this business-friendly motel in Ogunquit. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the pool in our ...
Grand Beach Inn
198 East Grand Avenue Old Orchard Beach ME
22.19 km from city center
Stay at this hotel in Old Orchard Beach. Enjoy free WiFi, free parking, and room service. Our guests praise the restaurant and the helpful staff in our reviews. ...
Clarion Pointe South Portland
675 Main Street I-95 South Portland ME
32.49 km from city center
Book a stay at this business-friendly hotel in South Portland. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Maine Mall and Thompson's ...
Anchorage Inn and Resort
265 Long Beach Avenue York Beach ME
25.88 km from city center
Book a stay at this beach hotel in York Beach. Enjoy free WiFi, free parking, and 2 indoor pools. Our guests praise the pool and the helpful staff in our reviews. ...
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.
Wed, Dec 9 - Sat, Dec 12
JFK
John F. Kennedy Intl.
PWM
Portland Intl. Jetport
$207 Roundtrip, found 5 hours ago
$207
Roundtrip
found 5 hours ago
Thu, Nov 12 - Sun, Nov 15
DCA
Ronald Reagan Washington National
PWM
Portland Intl. Jetport
$349 Roundtrip, found 5 days ago
$349
Roundtrip
found 5 days ago
Thu, Nov 12 - Sun, Nov 15
DCA
Ronald Reagan Washington National
PWM
Portland Intl. Jetport
$457 Roundtrip, found 5 days ago
$457
Roundtrip
found 5 days ago
Sat, Nov 14 - Sun, Nov 22
RDU
Raleigh - Durham Intl.
PSM
Portsmouth Intl.
$510 Roundtrip, found 21 hours ago
$510
Roundtrip
found 21 hours ago