Point Lookout holiday lettings

We found 27 holiday rentals — enter your dates for availability

Select from 18 homes, 13 cottages and other holiday rentals in Point Lookout to find one that's perfect for your trip. Holiday rentals provide the amenities that you need and want for your stay with friends, family or just your pet, such as Wi-Fi and parking. You'll be able to choose a property to rent that has what everyone needs, including places that are non-smoking or accessible.

Find spaces that suit your style

  • Peace of mind

    Our Book with Confidence Guarantee gives you 24/7 support

  • More quality time

    From booking to staying, the whole process is simple and enjoyable

  • All the privacy of home

    Enjoy full kitchens, pools, gardens and more

  • More for less

    More space, more privacy, more amenities — more value

Frequently asked questions

How much does it cost to rent a holiday home in Point Lookout?
Prices for holiday rentals in Point Lookout vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're traveling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in Point Lookout to more spacious homes. To get the best value, book early and take advantage of Vrbo's free rewards program.
Are there any discounts for Point Lookout holiday house rentals?
You can find great discounts on house rentals in Point Lookout on Vrbo, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for Last minute bookings, and Early bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Are there any Point Lookout holiday rentals with parking?
Vrbo offers a wide selection of holiday rentals in Point Lookout with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details on Vrbo and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
Can I find long-stay holiday rentals in Point Lookout?
A long-stay holiday rental in Point Lookout is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your travel dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
When is the best time to visit Point Lookout for a holiday rental?
The best time to book a holiday rental in Point Lookout is during the peak season from June to August, with July being particularly popular. This vibrant time of year draws families and beachgoers eager to enjoy the warm summer weather and the beautiful beaches along the Chesapeake Bay. Visitors can relish various outdoor activities such as swimming, fishing, and hiking, all while soaking in the stunning coastal views.

During these summer months, temperatures typically range from 20 to 30 degrees Celsius, providing the ideal climate for sun-soaked days and evening strolls along the shore. The lively option is complemented by local events and activities, making it an excellent choice for those looking to engage with the community and experience the best of what Point Lookout has to offer.

For those seeking a more budget-friendly option, consider visiting in December. While this month may be quieter, it presents a unique opportunity to enjoy the serene beauty of Point Lookout in winter. The peaceful surroundings can be superb for a tranquil getaway, with the chance to explore the area's historical sites and enjoy some solitude.

Ultimately, your choice of when to visit Point Lookout will depend on whether you prefer the energetic buzz of summer or the calm, reflective nature of a winter retreat.
How early should I book a Point Lookout holiday rental?
Book your Point Lookout holiday rental at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your holiday rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
What are the top attractions in Point Lookout, Maryland, United States of America?
In Point Lookout, visitors can explore several great attractions that highlight the area's natural beauty and historical significance. The Point Lookout State Park is a key feature, offering a blend of scenic landscapes, hiking trails, and opportunities for fishing and birdwatching. The park is also home to the remnants of a Civil War-era fort, which adds a layer of historical interest for those keen on exploring the past.

Another highlight is the Point Lookout Lighthouse, an iconic structure that has guided mariners for over a century. The lighthouse and its surrounding area offer picturesque views of the Chesapeake Bay and are superb for photography or simply enjoying the coastal scenery.

Additionally, nearby, the serene beaches provide an excellent spot for sunbathing, swimming, and relaxing by the water.
Can I change or cancel my Point Lookout home rental booking on Vrbo?
To find Point Lookout holiday rentals with free cancellation, just use Vrbo's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Vrbo makes it easy to book with confidence.
Why should I join Vrbo as a host?
Joining Vrbo as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Vrbo makes it easy to list, manage, and succeed. Whether it's a cosy cabin or a beach house, you can turn your space into a standout destination, become a host and let Vrbo handle the heavy lifting to help you thrive.

Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.
Are all fees included in the Point Lookout holiday rental prices shown on Vrbo?
Vrbo provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
What is VrboCare™ and how does it work?
Vrbo's mission is to help guests relax, reconnect, and enjoy precious time together. With VrboCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable.

If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
What can I expect from Vrbo customer service and VrboCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, VrboCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to support you every step of the way.

Vrbo also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
Can I plan a group trip on Vrbo?
Vrbo's Trip Planner makes organising group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favorites, and build the perfect itinerary together.

More holiday ideas