Point Lookout Holidays

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Your Point Lookout Holiday

Make planning your travels easy by creating a holiday package to Point Lookout. We'll look after the finer points, so you can concentrate on enjoying everything this neighbourhood 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 holiday is quick and easy with Expedia.

Our pick of the best Point Lookout Hotel Deals

𝑩𝑨𝒀 𝑺𝑰𝑫𝑬 𝑹𝑬𝑻𝑹𝑬𝑨𝑻, ON THE SANDS OF THE 𝐂𝐇𝐄𝐒𝐀𝐏𝐄𝐀𝐊𝐄 𝐁𝐀𝐘

𝑩𝑨𝒀 𝑺𝑰𝑫𝑬 𝑹𝑬𝑻𝑹𝑬𝑨𝑻, ON THE SANDS OF THE 𝐂𝐇𝐄𝐒𝐀𝐏𝐄𝐀𝐊𝐄 𝐁𝐀𝐘

Scotland MD
10/10 Exceptional! (129 reviews)
"Relaxing Stay in a Perfect Location! Before we arrived, Missy was so helpful and provided a lot of information about our stay. After arriving, we loved the cottage and its Frontline view of the bay. The sound of the waves was relaxing and we spent a lot of time on the back deck just enjoying them ..."

Reviewed on 26 May 2026

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𝑩𝑨𝒀 𝑺𝑰𝑫𝑬 𝑹𝑬𝑻𝑹𝑬𝑨𝑻, ON THE SANDS OF THE 𝐂𝐇𝐄𝐒𝐀𝐏𝐄𝐀𝐊𝐄 𝐁𝐀𝐘
Private Beach Front Getaway at The Sunshine Beach Cottage.

Private Beach Front Getaway at The Sunshine Beach Cottage.

Scotland MD
9.8/10 Exceptional! (80 reviews)
"Waking up to the rising sun on the Bay was spectacular. So peaceful and rejuvenating. Make sure you checkout out Calvert Cliffs State Park too. You’ll get a workout on the multiple trails and a beautiful shoreline at the end to find some natural treasures!! Sunshine Cottage was well equipped and ..."

Reviewed on 24 Oct 2025

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Private Beach Front Getaway at The Sunshine Beach Cottage.
FAMILY FRIENDLY CREEKSIDE GETAWAY - HIDEAWAY AND ENJOY THE FAMILY MOMENTS

FAMILY FRIENDLY CREEKSIDE GETAWAY - HIDEAWAY AND ENJOY THE FAMILY MOMENTS

Ridge MD
10/10 Exceptional! (199 reviews)
"Ray and Mary were extremely nice and welcoming. Our dogs loved the trip. Weather did not cooperate , but we still had a nice time. Water view from the house is great."

Reviewed on 25 May 2026

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FAMILY FRIENDLY CREEKSIDE GETAWAY - HIDEAWAY AND ENJOY THE FAMILY MOMENTS
See all 384 properties in Point Lookout
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.
All Inclusive Holidays
All Inclusive Holidays
All Inclusive Holidays
Cheap Holidays
Cheap Holidays
Cheap Holidays
beach holidays
Beach Holidays
Beach Holidays

Frequently asked questions

How much does a Point Lookout holiday package cost?
Choose from any combination of flights, hotels and car rentals, and you can be holidaying in Point Lookout from just . And the more you bundle, the more cash you save. Your dream escape has never been more affordable.
How do I get a cheap travel package to Point Lookout?
One of the easiest ways to save dollars (and time) is to combine your bookings with Expedia. Flights, rental cars, hotels and activities — we've got them all. Pick and choose the combination that best fits you and see your savings grow. We know a travel package is never a one-size-fits-all. That's why we offer more than 550 airlines and 1 000 000 hotel options worldwide, which lets you customize your Point Lookout holiday.
Where should I stay in Point Lookout?
Point Lookout features a number of interesting places to see, including Point Lookout State Park. Secure a room in a hotel near this attraction and make sightseeing simple.
What are the top hotels in Point Lookout?
Secure a room at Bay Watch - At Point Lookout On Beautiful Hays Beach In Scotland Maryland. It's one of the area's most sought-after hotels. Another top option in Point Lookout is Private Beach Front Getaway At The Sunshine Beach Cottage.
How far in advance should I book my Point Lookout holiday?
Browse Expedia to compare flights as early as possible. In many cases, you can purchase a ticket up to 12 months prior to departure. If you don't see your preferred carrier, or you've left things to the last minute, don't despair. Cheap fares to Point Lookout sometimes appear just weeks before departure.
What does an Expedia Point Lookout travel package include?
It comes down to what kind of escape you're planning. Point Lookout holiday deals can include hotels, flights and car rentals. You can mix and match to find the package that works for you! You can also add on activities and experiences after you've booked to score even bigger discounts.
What should I know before booking a Point Lookout travel package?
A travel package can be more affordable than separately booking everything you need for your trip. For example, combine your hotels, flights and rental cars and score big savings. Whatever kind of holiday you're planning, there's sure to be a package that suits your budget.
Can I choose my airline with a Point Lookout Expedia holiday package?
You certainly can. We have more than 550 airline partners across the globe, so fly with the carrier that fits your travel preferences.
If I'm not able to travel, can I cancel my Point Lookout holiday package?
Yes, it's possible to cancel your Point Lookout booking if your plans have been upended. Whether you'll incur a fee or not depends on your hotel, airline or car rental company. You may be able to change or cancel free of charge if you booked in the last 24 hours. Head to our Customer Service Portal to find out more.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.