Portland Luxury Holidays
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
Better together
Save up to NZ$616 when you book a flight and hotel together*
Find the right fit
With over 300,000 hotels worldwide, it's easy to create a perfect package
Rest easy
Plan, book, and manage your trip all in one place
Top Luxury Portland Hotels
Breakwater Inn
127 Ocean Avenue, Kennebunkport, ME
Stay at this 4.5-star luxury hotel in Kennebunkport. Enjoy free WiFi, free parking, and free bicycles on site. Our guests praise the helpful staff in our reviews. ...
8.4/10 Very Good! (32 reviews)
"Ice view of the tidel river and a sort walk to a beautiful beach"
Reviewed on 22 Aug. 2025
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 ...
9.4/10 Exceptional! (1,379 reviews)
"Charming, beautifully maintained, historic hotel located in former Armory of the Maine national guard. Lovely outdoor summer dining in a small garden setting across a small rotunda, as well as within the he hotel itself. Service excellent and gracious and cleanliness seems to be impeccable. To me, ..."
Reviewed on 20 Aug. 2025
Ramada Plaza by Wyndham Portland
155 Riverside St, Portland, ME
Stay at this 3-star business-friendly hotel in Portland. Enjoy free WiFi, free parking, and 2 hot tubs. Our guests praise the restaurant and the helpful staff ...
7.8/10 Good! (1,045 reviews)
"Property is good . Nice area and convenient"
Reviewed on 22 Aug. 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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.