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.
Ramada Plaza by Wyndham Portland
Nasons Corner
Price was $736, price is now $595 per person
$595
per person
Oct 5 - Oct 9
found 2 days ago
Roundtrip flight included
Chicago (ORD) to Portland (PWM)
Book a stay at this business-friendly hotel in Portland. Enjoy free WiFi, free parking, and 2 restaurants. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Thompson's Point and Maine Mall are located nearby.
there was no complimentary breakfast the bathroom did not have any safety bars in case of falls plus it was so small the staff was very friendly and professional the hotel was clean
Reviewed on Aug 2, 2026
Ogunquit River Inn & Suites
Moody
Price was $895, price is now $619 per person
$619
per person
Oct 5 - Oct 9
found 2 days ago
Roundtrip flight included
Chicago (ORD) to Portland (PWM)
Book a stay at this business-friendly hotel in Ogunquit. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Ogunquit Beach and Moody Beach are located nearby.
What a nice place to stay- clean, great views, updated rooms and bathrooms. Would definitely stay here again
Reviewed on Aug 3, 2026
The Meadowmere Resort
Save 100% on your flight
Price was $999, price is now $713 per person
$713
per person
Oct 5 - Oct 9
found 2 days ago
Roundtrip flight included
Chicago (ORD) to Portland (PWM)
Stay at this hotel in Ogunquit. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Ogunquit Beach and Marginal Way are located nearby.
The Docent's Collection at 178 Middle Street
Downtown Portland
Save 100% on your flight
Price was $2,670, price is now $2,202 per person
$2,202
per person
Sep 21 - Sep 26
found 20 hours ago
Roundtrip non-stop flight included
Tulsa (TUL) to Portland (PWM)
Stay at this hotel in Portland. Enjoy free WiFi, parking (surcharge), and a 24-hour front desk. Popular attractions Cross Insurance Arena and Casco Bay Lines Ferry Terminal are located nearby.
The apartment itself was lovely but unfortunately when I showered in the morning it became clear from the alarming abundance of body hair in the shower that it had not been (even sort of) cleaned. That’s a serious choice to make when people are paying just shy of $400 a night.
Reviewed on Jul 30, 2026
Newagen Seaside Inn
Price was $846, price is now $711 per person
$711
per person
Oct 5 - Oct 9
found 2 days ago
Roundtrip flight included
Chicago (ORD) to Portland (PWM)
Book a stay at this family-friendly hotel in Southport. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Coastal Maine Botanical Gardens and Southport Memorial Library are located nearby.
Old Orchard Beach Inn
Price was $818, price is now $696 per person
$696
per person
Sep 21 - Sep 26
found 20 hours ago
Roundtrip non-stop flight included
Tulsa (TUL) to Portland (PWM)
Stay at this B&B in Old Orchard Beach. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Palace Playland and Old Orchard Beach are located nearby.
This was our favorite stay on our road trip through New England. The hotel itself is stunning with its antiques and quaintness in every room. Our actual bedroom was beautiful and very comfortable! The breakfast that was included was delicious and much more than we had expected! Perfect location from the beach and shops. I would highly recommend this hotel and we are looking forward to returning at a later time!
Reviewed on Aug 2, 2026
Top Hotel Deals
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 ...
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 ...
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. ...
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 ...
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 ...
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 ...
Comfort Inn South Portland Airport
90 Maine Mall Rd South Portland ME
33.34 km from city center
Book a stay at this business-friendly hotel in South Portland. Enjoy free breakfast, free WiFi, and a free airport shuttle. Our guests praise the breakfast and ...
Ocean Surf at York Beach
780 York Street (Rte 1A) York Beach ME
26.85 km from city center
Book a stay at this beach motel in York Beach. Enjoy free WiFi, breakfast (surcharge), and parking (surcharge). Our guests praise the pool and the helpful staff ...
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 ...
Waves Oceanfront Resort
87 W Grand Ave Old Orchard Beach ME
19.28 km from city center
Book a stay at this beach hotel in Old Orchard Beach. Enjoy free parking, an outdoor pool, and a beach locale. Our guests praise the helpful staff and the clean ...
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 WiFi, free parking, and an outdoor pool. Our guests praise the breakfast and the pool 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 River Inn & Suites
17 Post Road Ogunquit ME
13.24 km from city center
Book a stay at this business-friendly hotel in Ogunquit. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
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.
Thu, Sep 3 - Thu, Sep 10
MCO
Orlando Intl.
PSM
Portsmouth Intl.
$184 Roundtrip, found 5 days ago
$184
Roundtrip
found 5 days ago
Mon, Aug 31 - Tue, Sep 1
RDU
Raleigh - Durham Intl.
PWM
Portland Intl. Jetport
$233 Roundtrip, found 2 days ago
$233
Roundtrip
found 2 days ago
Thu, Oct 8 - Fri, Oct 16
EWR
Newark Liberty Intl. Airport
PWM
Portland Intl. Jetport
$237 Roundtrip, found 14 hours ago
$237
Roundtrip
found 14 hours ago
Mon, Aug 31 - Tue, Sep 1
RDU
Raleigh - Durham Intl.
PWM
Portland Intl. Jetport
$258 Roundtrip, found 2 days ago
$258
Roundtrip
found 2 days ago
Mon, Aug 31 - Tue, Sep 1
RDU
Raleigh - Durham Intl.
PWM
Portland Intl. Jetport
$267 Roundtrip, found 2 days ago
$267
Roundtrip
found 2 days ago