Tall Timbers holiday lettings

We found 86 holiday rentals — enter your dates for availability

Discover a selection of holiday rentals in Tall Timbers that are perfect for your trip. Whether you're staying in a holiday rental with family, friends or just your furry companion, you'll have the amenities that you expect and more, which might include parking and a washer and dryer. You'll be sure to find a property to rent to meet everyone's needs, including places that are non-smoking or accessible.

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Find the perfect holiday rental for your Tall Timbers getaway

Learn about the unique charm of Tall Timbers with a stay in a holiday home rental. This city has something for everyone. If you need more space to accommodate a family holiday or a trip with friends, rental homes often come with separate dining areas and spacious living rooms.

Activities and attractions in and around Tall Timbers

Are you looking for things to do while you're in town? Although it can be tempting to stay in your comfortable holiday rental, you'll want to check out everything that makes Tall Timbers a fun place to get away to. Here are some of the most popular attractions to put on your list, all within 30 miles (48.2 km) of the city centre:

  • Michael P. O'Brien Athletics and Recreation Center (6.6 mi / 10.7 km)
  • Hague Winery (8.9 mi / 14.4 km)
  • Breton Bay Golf Course (9.7 mi / 15.5 km)
  • Port of Leonardtown Winery (11.1 mi / 17.9 km)
  • General's Ridge Vineyard and Winery (11.6 mi / 18.6 km)
  • Chesapeake Hills Golf Course (16 mi / 25.8 km)

Exploring the natural landscape of Tall Timbers

Whether you're an outdoor enthusiast or just want to appreciate the scenery, you'll be sure to find the perfect setting for your holiday in Tall Timbers. Here are some of the area’s noteworthy natural features, all within 30 miles (48.2 km) of the city centre:

  • Piney Point Beach (2.4 mi / 3.8 km)
  • Saint George Island Beach (4.9 mi / 8 km)
  • St. Mary's River State Park (6.4 mi / 10.3 km)
  • Sandy Point Beach (6.5 mi / 10.5 km)
  • Elms Beach Park (9.9 mi / 15.9 km)
  • St. Clement's Island State Park (11.4 mi / 18.3 km)

Frequently asked questions

What is the best area to stay in Tall Timbers when booking a holiday rental?
When considering a holiday rental in Tall Timbers, Maryland, the best area to stay is close to the scenic waterfront, which offers a tranquil atmosphere and stunning views. This charming community is located along the banks of the Potomac River, providing easy access to a variety of outdoor activities such as kayaking and fishing.

In terms of attractions, the nearby St. George Island State Park is a highlight, featuring beautiful sandy beaches and opportunities for hiking and birdwatching. Another point of interest is the historic Point Lookout Lighthouse, which adds a touch of history to your stay while offering picturesque views of the surrounding waters.

While the number of properties in this area can vary, you can typically find a selection of charming cottages and waterfront homes that cater to different group sizes and preferences.
How much does it cost to rent a holiday home in Tall Timbers?
Prices for holiday rentals in Tall Timbers 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 Tall Timbers 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 Tall Timbers holiday house rentals?
You can find great discounts on house rentals in Tall Timbers 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.
What is the most popular type of holiday rental accomodation in Tall Timbers?
In Tall Timbers, cottages are the most popular type of holiday rental, with several options available throughout the area. These charming properties typically feature cosy interiors, fully equipped kitchens, and outdoor spaces that often include decks or patios for enjoying the natural surroundings. Nestled in serene locations, they provide a great getaway for those looking to relax in a peaceful setting.
Are there any family house rentals in Tall Timbers?
In Tall Timbers, Maryland, there are several family-friendly house rentals available, making it a lovely spot for those travelling with children. The area is known for its natural beauty and tranquil surroundings, providing a superb backdrop for family getaways. Many of these homes come equipped with spacious living areas, full kitchens for preparing family meals, and outdoor spaces ideal for children to play safely.

Visitors will appreciate amenities such as Wi-Fi and air conditioning, ensuring a comfortable stay. Additionally, the locale offers easy access to local attractions, including scenic hiking trails and opportunities for water activities on nearby lakes and rivers.
Can I rent a holiday home with a pool or hot tub in Tall Timbers?
In Tall Timbers, Maryland, several holiday homes are available for rent that feature pools and hot tubs, making it a delightful option for travellers seeking relaxation and recreation. The area is known for its serene natural surroundings, providing a peaceful escape. Many of these properties offer amenities such as private pools, outdoor seating areas, and fully equipped kitchens, ideal for families or groups looking to enjoy quality time together. Some rentals may also include hot tubs, great for unwinding after a day of exploring the scenic beauty of the region.
Can I find long-stay holiday rentals in Tall Timbers?
A long-stay holiday rental in Tall Timbers 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.
Are there pet-friendly house rentals in Tall Timbers?
In Tall Timbers, Maryland, there are several pet-friendly house rentals available, making it a great choice for travellers with furry companions. Many of these holiday homes come equipped with essential amenities such as fully stocked kitchens, spacious living areas, and outdoor spaces where pets can roam.

The surrounding area offers access to beautiful natural settings, including nearby parks and trails that are great for long walks with your pet. The tranquil atmosphere of Tall Timbers allows for a relaxing getaway while still providing opportunities for outdoor activities.
Are there any remote work holiday rentals in Tall Timbers?
In Tall Timbers, Maryland, there are several remote work holiday rentals available, providing a conducive environment for those looking to combine work and leisure. Many of these properties come equipped with essential amenities such as free Wi-Fi, dedicated workspaces with desk chairs, and some even offer printers for added convenience.

The area is known for its tranquil surroundings, making it an ideal spot for focusing on work while enjoying the beauty of nature. With access to nearby recreational activities, such as hiking or fishing, these rentals provide a great balance of productivity and relaxation. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Tall Timbers holiday rentals with parking?
Vrbo offers a wide selection of holiday rentals in Tall Timbers 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.
What are popular rental amenities in Tall Timbers?
In Tall Timbers, popular rental amenities include kitchens equipped for meal preparation, allowing guests to enjoy home-cooked meals during their stay. Many properties also feature comfortable living areas with fireplaces, creating a cosy atmosphere, especially on cooler evenings. Outdoor spaces such as decks or patios are common, providing a lovely setting for relaxation or al fresco dining. Families will appreciate the availability of books for children, making these rentals suitable for guests of all ages.
How early should I book a Tall Timbers holiday rental?
Book your Tall Timbers 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 Tall Timbers?
In Tall Timbers, Maryland, visitors can immerse themselves in the natural beauty of the area, particularly within the nearby scenic landscapes of the Chesapeake Bay. The region is known for its tranquil setting, making it an ideal spot for outdoor activities like kayaking and birdwatching.

The nearby Point Lookout State Park offers historical significance, with remnants of a Civil War-era fort and lovely hiking trails that provide stunning views of the bay. Additionally, the waters surrounding Tall Timbers are popular for fishing, and there are opportunities for boating and sailing, especially in the Potomac River area.

For those interested in local culture, the nearby town of Leonardtown features quaint shops, restaurants, and galleries, showcasing the charm of Southern Maryland.
Can I change or cancel my Tall Timbers home rental booking on Vrbo?
To find Tall Timbers 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 Tall Timbers 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.

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