Kennebunkport Vacations
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Kennebunkport Flight + Hotel packages
Price found within the past 48 hours. Click for updated prices.
Portland Regency Hotel & Spa
Downtown Portland
$1,021
per person
Nov 12 - Nov 19
found 12 hours ago
Roundtrip non-stop flight included
Dayton (DAY) 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 Cross Insurance Arena and Maine Mall are located nearby.
Great location! Was not impressed with the desk clerk who checked us in. We asked about parking and were told only valet offered. When I asked about other options we were told that it was unsafe other than valet. We had never been to Portland before so walking to dinner didn’t know if we were safe after that comment.
Reviewed on Oct 13, 2026
Blind Tiger Portland - Danforth Street.
West End
$2,133
per person
Nov 12 - Nov 19
found 12 hours ago
Roundtrip non-stop flight included
Dayton (DAY) to Portland (PWM)
Stay at this B&B in Portland. Enjoy free breakfast, free WiFi, and parking (surcharge). Popular attractions Cross Insurance Arena and Maine Mall are located nearby.
Wonderful staff, convenient location, fun stay in an old building. So much character with modern amenities and a neighborhood feel. We thoroughly enjoyed our stay and will return. Off-street parking was a huge bonus and the light breakfast had a wide spread. Such a wonderful property.
Reviewed on Oct 11, 2026
The Docent's Collection at 121 Middle Street
Downtown Portland
$1,303
per person
Nov 12 - Nov 19
found 12 hours ago
Roundtrip non-stop flight included
Dayton (DAY) to Portland (PWM)
Stay at this hotel in Portland. Enjoy free WiFi, parking (surcharge), and premium TV channels. Popular attractions Cross Insurance Arena and Maine Mall are located nearby.
Evalina Hotel
Downtown Portland
$1,757
per person
Nov 12 - Nov 19
found 12 hours ago
Roundtrip non-stop flight included
Dayton (DAY) to Portland (PWM)
Stay at this aparthotel in Portland. Enjoy free WiFi, parking (surcharge), and in-room washers/dryers. Popular attractions Cross Insurance Arena and Maine Mall are located nearby.
Centrally located in the Old Port, with views of the harbor, this was a last minute — therefore pricey — excellent find for a fall weekend getaway. Stylish, elegant rehab of 19th century granite industrial building. Whimsical decor notes referring to 19th century owner Evalina Fox. Nicely appointed kitchenette — though if you came to Portland for the foodie scene, you might end up just using it for breakfast, as we did. Only sour note was the disco music (coming in via the ventilation system?) from a nearby establishment audible during business hours. Well, if you pick a hotel in the middle of things, you get the noise and bustle that comes from being in the middle of things. That said, we’d come again, but shoot for a penthouse/upper floor unit farther from the street-level mania.
Reviewed on Oct 5, 2026
The Weldon Hotel
Downtown Portland
$1,309
per person
Nov 12 - Nov 19
found 12 hours ago
Roundtrip non-stop flight included
Dayton (DAY) 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 Maine Mall are located nearby.
This was the best accommodation in Portland that we have stayed at—by a wide margin. The building and unit itself are a dream. Spacious, quiet, elevated, fresh, clean, thoughtful touches, quality finishes and materials, comfortable, inviting, secure…I have nothing but praise for this property. My spouse and I waxed lyrical about it for the entire stay, “Oh my goodness, I wish we lived here.”, and “we’re home!”. Of course we were happy to get back to our real home back in Boston after our time at the Weldon came to a close, but it was sincerely a “home away from home” experience top to bottom. Book this place—you’ve found the one.
Reviewed on Oct 9, 2026
The Francis
Parkside
$1,353
per person
Nov 12 - Nov 19
found 12 hours ago
Roundtrip non-stop flight included
Dayton (DAY) to Portland (PWM)
Stay at this hotel in Portland. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular attractions Cross Insurance Arena and Maine Mall are located nearby.
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View all tripsKennebunkport Vacation Packages
Trying to save both time and money on your upcoming holiday to Kennebunkport? The AARP Travel Center Powered by Expedia® can help you do both. We can assist you with hotel bookings, flights, car rentals and more. You can get almost everything you need here to make your trip to Kennebunkport perfect. In just a few clicks, you can choose the best Kennebunkport vacation package for you. AARP Travel Center has an amazing selection of flights and hotels, and local endeavors to choose from.
Kennebunkport Hotels
Our listings include lodgings that are close to all the Kennebunkport points of interest, and some that are just outside the city center for a peaceful retreat.
From Kennebunkport hotels with pools and on-site restaurants, to boutique accommodations that add all the thoughtful amenities, you'll find a hotel here that will make your trip one to remember. With AARP Travel Center's Kennebunkport hotel packages, you not only get a great rate on your flight, but also a wonderful place to stay.
Things to do in Kennebunkport
Kennebunkport is the perfect spot when you need to get away from it all. With only around 3,567 people living here year-round, this hidden-gem is perfect for a quiet vacation. If you want to take walk through the past, then you are in luck as Kennebunkport has a rich historic district. There are several great things to do and see in and around Kennebunkport that will make trip a bit of an adventure. Not sure where to begin? Here are a several things that the area is known for:
- St. Ann's Church
- St. Anthony's Monastery and Franciscan Guest House
- Seashore Trolley Museum
- Kittery Outlets
If you are looking for more, then head over to our "Things to Do" tab for more inspiration or to reserve an activity in Kennebunkport.
Book Together and Save
With so much happening in Kennebunkport, you'll be wanting to plan your outings, not devoting time to searching for the cheapest hotel. The AARP Travel Center Powered by Expedia® allows you to quickly book everything you need, and save money at the same time. You can coordinate your entire vacation, including activities in Kennebunkport from just one place. So what are you waiting for? Book today and save!
Top Hotel Deals
The Colony Hotel
140 Ocean Ave Kennebunkport ME
Book a stay at this business-friendly hotel in Kennebunkport. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff in our ...
The Lodge at Turbat's Creek
7 Turbat's Creek Road Kennebunkport ME
Stay at this motel in Kennebunkport. Enjoy free breakfast, an outdoor pool, and premium TV channels. Our guests praise the helpful staff and the clean rooms ...
Kennebunkport Captains Collection
6 Pleasant Street Kennebunkport ME
Book a stay at this luxury hotel in Kennebunkport. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in ...
AWOL Kennebunkport
34 Maine St Kennebunkport ME
Stay at this hotel in Kennebunkport. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. ...
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 helpful staff and the clean ...
Clarion Hotel Portland Airport ME
1230 Congress St Portland ME
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 ...
Fireside Inn & Suites Portland
81 Riverside St Portland ME
Book a stay at this business-friendly hotel in Portland. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff and the clean ...
Quality Inn & Suites South Portland
738 Main Street South Portland ME
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
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 ...
Clarion Pointe South Portland
675 Main Street I-95 South Portland ME
Book a stay at this business-friendly hotel in South Portland. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Maine Mall and Cross Insurance ...
Inn at St John Portland In-Town
939 Congress St Portland ME
Stay at this B&B in Portland. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular ...
Casco Bay Hotel Portland Airport - Maine Mall, an Ascend Collection Hotel
80 John Roberts Rd. South Portland ME
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 ...
Portland Harbor Hotel
468 Fore Street Portland ME
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 ...
Ogunquit - The Milestone
687 Main Street Ogunquit ME
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 ...
Anchorage Inn and Resort
265 Long Beach Avenue York Beach ME
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, Jan 20 - Sat, Jan 23
TPA
Tampa Intl.
PWM
Portland Intl. Jetport
$142
Roundtrip
found 21 hours ago
Mon, Nov 2 - Mon, Nov 9
JFK
John F. Kennedy Intl.
PWM
Portland Intl. Jetport
$207
Roundtrip
found 3 days ago
Sat, Oct 31 - Sun, Nov 1
JFK
John F. Kennedy Intl.
PWM
Portland Intl. Jetport
$227
Roundtrip
found 3 days ago
Wed, Jan 20 - Tue, Jan 26
TPA
Tampa Intl.
PWM
Portland Intl. Jetport
$237
Roundtrip
found 19 hours ago
Wed, Jan 20 - Tue, Jan 26
TPA
Tampa Intl.
PWM
Portland Intl. Jetport
$237
Roundtrip
found 19 hours ago
Best neighborhoods in Kennebunkport
Best points of interest in Kennebunkport
- Dock Square Vacations
- Kennebunkport Village Green Vacations
- Colony Beach Vacations
- Walker's Point Vacations
- Seashore Trolley Museum Vacations
- St. Ann’s Episcopal Church Vacations
- Cape Arundel Golf Club Vacations
- Goat Island Lighthouse Vacations
- Vaughn's Island Preserve Vacations
- First Families Kennebunkport Museum Vacations
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More Types of Hotels
- Hotels with Complimentary Breakfast in Kennebunkport
- Hotels with Air Conditioning in Kennebunkport
- Beach Hotels in Kennebunkport
- Hotels with WiFi in Kennebunkport
- Hotel with wifi in Kennebunkport
- Family Hotels in Kennebunkport
- Smoke Free Hotels in Kennebunkport
- Hotels with Bars in Kennebunkport
- Hotels with a Pool in Kennebunkport
- Hotels with Balconies in Kennebunkport
- Luxury Hotels in Kennebunkport
- Hotel with a Concierge in Kennebunkport
- Hotels with Fireplaces in Kennebunkport
- Resorts & Hotels with Spas in Kennebunkport
- Hotels with Hot Tubs in Kennebunkport
- Cheap Hotels in Kennebunkport
- Oceanfront Hotels in Kennebunkport
- Pet-friendly Hotels in Kennebunkport
- Hotels on the River in Kennebunkport
- Lakefront Hotels in Kennebunkport
- Hotels with smoking rooms in Kennebunkport
- Hotels with an Indoor Pool in Kennebunkport