Point Lookout Vacations from $189
Book a Hotel + Flight or Car together to unlock savings
Your Point Lookout Vacation
Make planning your travels easy by creating a vacation package to Point Lookout. We'll look after the finer points, so you can concentrate on enjoying everything this neighborhood has to offer. Give yourself enough time to get to leading nearby attractions like Confederate Memorial Park during your trip to Point Lookout. No matter your travel goals or the size of your budget, booking a perfect Point Lookout vacation is quick and easy with Expedia.
The Latest Point Lookout Vacation Packages
Price found within the past 48 hours. Click for updated prices.
Point Lookout Hotel Deals
Hideaway in Hays Beach: Western Sandy Shore of Chesapeake Bay and 5g WiFi!
Scotland MD
10/10 Exceptional! (139 reviews)
"We loved our time staying here. Such a beautiful and thoughtfully appointed home. Highly recommended."
Reviewed on Sep 6, 2026
π©π¨π πΊπ°π«π¬ πΉπ¬π»πΉπ¬π¨π», ON THE SANDS OF THE ππππππππππ πππ
Scotland MD
10/10 Exceptional! (141 reviews)
"This is the 2nd year Iβve rented this home on the Chesapeake, and Iβll definitely be back! Missy has thought of every comfort and convenience! The home is clean, spotless, bright and welcoming! The kitchen has all youβd ever need! The view is breathtaking; I was up every morning before sunrise to ..."
Reviewed on Sep 14, 2026
Cozy Sunrise Waterfront 2-bedroom Cottage & Dock. Serene Point Lookout/Scotland
Scotland MD
$392 nightly
$433 total
Oct 13 - Oct 14
Total with taxes and fees
9.4/10 Exceptional! (18 reviews)
"Great communication. Scenic , quiet spot. Unfortunately the small beach area shown in the pics is no longer there and we were really hoping to use that. Beautiful wildlife and only 100 yds from state park."
Reviewed on Sep 12, 2026
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.
Stay near popular Point Lookout attractions
Point Lookout State Park
8.6/10 (134 reviews)
You can take time to visit Point Lookout State Park during your travels to Scotland. Wander the beautiful beaches in this relaxing area.
Confederate Memorial Park
You can find out about the history of Scotland with a stop at Confederate Memorial Park. Wander the beautiful beaches in this relaxing area.
Swimming Beach
Why not spend a lazy afternoon at Swimming Beach during your trip to Scotland?
Point Lookout Light
After visiting Point Lookout Light, make a plan to see the other sights and activities in Scotland.
Lake Conoy
Commune with nature and explore the great outdoors at Lake Conoy during your travels in Scotland.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.