Tall Timbers vacation rentals

We found 86 vacation rentals — enter your dates for availability

Discover a selection of vacation rentals in Tall Timbers that are perfect for your trip. Whether you're staying in a vacation rental with friends, family, or even just your pets, you'll find the amenities you need and want, including parking and a TV. You'll be able to choose a rental that has what everyone needs, including places that are non-smoking or accessible.

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Find out more about Tall Timbers

Why visit Tall Timbers

  • Stunning natural scenery: Tall Timbers offers breathtaking landscapes with unspoiled wilderness and beautiful pines.
  • Diverse outdoor activities: Ideal for both relaxation and adventure, enjoy hiking, beach outings, and exploring urban parks.
  • Family-friendly environment: A welcoming destination for families, providing numerous activities that cater to all ages.
  • Quaint neighborhoods: Discover charming local areas perfect for leisurely strolls and unique excursions.
  • Variety of accommodations: Choose from cozy cottages, private vacation homes, or rustic cabin rentals for a memorable stay.

Popular types of accommodation in Tall Timbers

If you're looking for the perfect getaway in Tall Timbers, you're in the right place. Our most popular accommodations include houses, cozy cottages, and comfortable apartments. Whether you’re dreaming of a peaceful vacation cabin rental or a rustic cabin experience, we have something for everyone. Plus, you can explore options like the Tall Timbers bed, camp, and resort to make your stay unforgettable.

  • Houses: These are the top choice for travelers seeking spacious and comfortable accommodations perfect for families or groups.
  • Cottages: Offering a quaint and cozy atmosphere, cottages are ideal for those looking for a charming getaway experience.
  • Apartments: A versatile option, apartments provide convenient living spaces for couples or solo travelers wanting flexibility.
  • Cabins: Perfect for nature enthusiasts, cabins offer a rustic escape surrounded by the beauty of the outdoors.
  • Caravan Parks: A budget-friendly option, caravan parks are great for those looking for a unique outdoor experience.**

Top attractions near Tall Timbers

Tall Timbers, Maryland, is perfect for outdoor enthusiasts and beach lovers alike, offering stunning scenery and family-friendly activities. Visitors can explore urban parks, sandy beaches, and nearby military installations, making it an ideal destination for a diverse range of experiences. Whether you're seeking relaxation or adventure, Tall Timbers has something to offer for every traveler looking to enjoy the great outdoors and local attractions.

  • Patuxent River Naval Air Station: Explore this military installation that offers family-friendly excursions. It's a hub for aviation enthusiasts, featuring exhibits and opportunities to learn about naval aviation history and technology.
  • Historic St. Mary's City: Immerse yourself in this historic village that showcases the rich culture and heritage of Maryland. With archaeological sites and interactive exhibits, it provides a fascinating glimpse into colonial life.
  • Piney Point Beach: Relax at this beautiful beach, just a short distance away. Enjoy sunbathing, swimming, and stunning views of the Potomac River in a serene setting.

Things to do recommended for couples

For a romantic getaway in Tall Timbers, explore the serene waters of the Potomac River with a sunset kayak tour. Enjoy a cozy picnic at Point Lookout State Park, or savor a candlelit dinner at a charming local restaurant, surrounded by stunning views and tranquil nature.

Things to do recommended for families

In Tall Timbers, families can explore the scenic beauty of Point Lookout State Park, enjoy kayaking in the Patuxent River, or visit the nearby historic St. Mary’s City for interactive learning. The area offers a blend of outdoor adventure and educational experiences perfect for all ages.

Things to do recommended for groups

Explore the scenic beauty of the Patuxent River while kayaking with your group or visit the historic St. George Island, where you can enjoy a picnic and watch the sunset. Don't miss the chance to try local seafood at nearby restaurants for a true taste of the region.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

What do I need to keep in mind when booking a vacation in Tall Timbers

If you're traveling with a group, family, or pets, or if you're interested in extended stays, be sure to prioritize your filters accordingly. Here are some helpful Vrbo booking tips to assist you.

  • Traveling to Tall Timbers with a group: Think about how many bedrooms you require, as well as any additional features like a full kitchen or outdoor area for group activities. Luckily, you can easily apply filters for these options and more on Vrbo.
  • Traveling to Tall Timbers with young kids: Traveling with young kids can be a bit tricky. It's important to prioritize their comfort and safety, along with finding age-appropriate amenities like a private swimming pool. Additionally, considering how close you are to family-friendly attractions can enhance your travel experience.
  • Taking your pets with you to Tall Timbers: For many families, a vacation just wouldn't be the same without their furry companion. If this resonates with you, explore Vrbo listings that welcome pets. Most of these pet-friendly properties come equipped with feeding bowls and beds, ensuring that everyone feels comfortable and at home.
  • Planning for a long term stay visiting Tall Timbers: If you're searching for vacation rentals with discounts for extended stays of a month or more, you've come to the right spot. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. Don't forget to include features like a parking space, a well-equipped kitchen, or a private pool in your search.

Where to stay near Tall Timbers

Experience the charm of Tall Timbers, Maryland, where unspoiled wilderness meets natural beauty. This family-friendly destination offers a variety of outdoor activities amid beautiful pines and scenic landscapes. Nearby, explore quaint neighborhoods and enjoy excursions that highlight the area's relaxing atmosphere. Whether you're seeking adventure or a peaceful retreat, Tall Timbers and its surroundings promise a memorable vacation filled with friendly people and breathtaking scenery.

  • California: Located 9 miles from Tall Timbers, California, Maryland, offers a vibrant outdoor experience surrounded by stunning scenery. This city is a haven for adventure seekers, with activities ranging from motor racing to exploring recreational areas. Visitors can enjoy thrilling events at the local racetrack, while the nearby cliffs and bay provide opportunities for breathtaking views and leisurely walks. California is perfect for those looking to combine excitement with natural beauty.
  • Lexington Park: Situated 8 miles from Tall Timbers, Lexington Park is a blend of outdoor adventure, scenic charm, and cultural experiences. The city is known for its rich educational institutions, including a historic college university, making it a great spot for those interested in culture and history. Outdoor enthusiasts can explore the beautiful bay and participate in motor racing and other recreational activities. Lexington Park's vibrant atmosphere is sure to captivate visitors looking for a mix of fun and learning.
  • Leonardtown: Just 10 miles from Tall Timbers, Leonardtown is a picturesque city that invites tourists to unwind with its outdoor and beach experiences. The scenic bay, sandy beaches, and serene lakes create a perfect backdrop for relaxing days by the water. Visitors can engage in motor racing or take advantage of the recreational areas for a day filled with fun. Leonardtown's charming atmosphere makes it an ideal destination for those who appreciate nature and leisure activities.

Best time to go to Tall Timbers

If you're planning a trip to Tall Timbers, it's a good idea to check both the weather and property rates. The warmest month is July. Peak season runs from June to August, while off-peak times, like December to February tend to have fewer bookings and better deals.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January37.2°F (2.9°C)Light RainMostly SunnyLowSlightly Low
February39.7°F (4.3°C)Light RainMostly SunnyLowSlightly Low
March45.9°F (7.7°C)Light RainMostly SunnyAverageSlightly Low
April55.9°F (13.3°C)Light RainMostly SunnyAverageAverage
May64.9°F (18.3°C)Light RainMostly SunnyAverageAverage
June73.6°F (23.1°C)Light RainMostly SunnyHighSlightly High
July78.6°F (25.9°C)Light RainMostly SunnyHighSlightly High
August77.2°F (25.1°C)Light RainMostly SunnyHighSlightly High
September71.6°F (22.0°C)Light RainMostly SunnyAverageAverage
October61.5°F (16.4°C)Light RainMostly SunnyAverageAverage
November50.2°F (10.1°C)Light RainMostly SunnyAverageAverage
December43.0°F (6.1°C)Light RainMostly SunnyLowAverage

Booking with Vrbo is simple

Are you hoping to save on your upcoming trip? Being flexible with your travel dates can make a difference, as prices often fluctuate. Additionally, booking a longer stay can lead to substantial savings. To discover a Vrbo property that meets your budget, simply use our filters to sort by price, location, and type of vacation rental. We're here to help you find the perfect option for your travel needs.

Vrbo Trips: Planning as easy as it gets

Vrbo's unique Trip Board offers you a convenient way to plan your travels, allowing you to start new trips, pick up where you left off, or manage your existing plans. You can easily access properties you've saved or booked by checking the sections for Potential, Upcoming, or Current Trips. To explore Trip Boards, simply visit: https://www.vrbo.com/trips.

**Based on Vrbo properties bookings.

Find the perfect vacation rental for your Tall Timbers getaway

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

Activities and attractions in and around Tall Timbers

Are you hoping to find attractions to see in the area? Venture out of your cozy vacation rental and check out everything that makes Tall Timbers a one-of-a-kind vacation spot. Here are some of the major attractions to explore, all within 30 miles (48.2 km) of the city center:

  • Michael P. O'Brien Athletics and Recreation Center (6.6 mi / 10.7 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)
  • Hague Winery (8.9 mi / 14.4 km)
  • Chesapeake Hills Golf Course (16 mi / 25.8 km)

Exploring the natural landscape of Tall Timbers

Whether you're looking for adventure or just want to take in the scenery, Tall Timbers is a great place to spend some time outside. Here are a few of the area's most stunning natural features, all within 30 miles (48.2 km) of the city center:

  • 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

How much does it cost to rent a vacation home in Tall Timbers?
Prices for vacation 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 vacation 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 vacation rental accomodation in Tall Timbers?
In Tall Timbers, cottages are the most popular type of vacation rental, with several available throughout the area. These charming properties are often situated in serene, wooded settings, providing a peaceful escape for travelers. Most cottages feature cozy living spaces, fully equipped kitchens for self-catering, and outdoor areas where guests can enjoy nature. They are ideal for those looking to unwind and experience the tranquil beauty of Maryland's landscape.
Are there any family house rentals in Tall Timbers?
In Tall Timbers, Maryland, there are several family-friendly house rentals available, making it a great option for a family getaway. Visitors can find homes that offer spacious living areas, well-equipped kitchens, and outdoor spaces where children can play and explore. Many properties also come with amenities like Wi-Fi and air conditioning to enhance comfort during your stay.

The area is surrounded by natural beauty, with opportunities for outdoor activities such as hiking and fishing nearby. Families can enjoy the peaceful atmosphere while being close to local attractions, ensuring an enjoyable and memorable experience for all ages.
Can I rent a vacation home with a pool or hot tub in Tall Timbers?
In Tall Timbers, Maryland, there are several vacation homes available for rent that feature pools and hot tubs. This serene area, located along the banks of the Potomac River, provides a tranquil setting for guests seeking relaxation. Many of the rentals come equipped with private pools, hot tubs, and spacious outdoor areas ideal for gatherings or family fun. Inside, travelers can expect amenities like fully equipped kitchens, comfortable living spaces, and often multiple bedrooms, making these homes great for families or groups.
Can I find long-stay vacation rentals in Tall Timbers?
A long-stay vacation rental in Tall Timbers is the best way to experience local living. Plus, you can make the most of long-stay discounts. For month-long stays, save an average of 19%, and for week-long bookings you can save an average of 10%.* Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
Are there pet-friendly house rentals in Tall Timbers?
In Tall Timbers, Maryland, there are several vacation rentals that welcome pets, making it a great destination for travelers looking to enjoy a getaway with their furry companions. Many of these rentals are equipped with amenities such as spacious living areas, fully stocked kitchens, and outdoor spaces where pets can roam and play.

The area is known for its serene natural surroundings, providing opportunities for outdoor activities such as hiking and fishing. Nearby points of interest include the scenic shores of the Potomac River, superb for leisurely strolls with pets, and various parks where you can enjoy nature.
Are there any remote work vacation rentals in Tall Timbers?
In Tall Timbers, Maryland, there are several vacation rentals that cater to remote work needs. Many of these properties offer amenities such as free Wi-Fi, dedicated workspaces with desks and chairs, and even printing facilities, ensuring that guests can stay productive while enjoying their time away. The serene surroundings of Tall Timbers provide a peaceful backdrop for remote work, with opportunities for outdoor activities during breaks. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Tall Timbers vacation rentals with parking?
Vrbo offers a wide selection of vacation rentals in Tall Timbers with parking available—perfect for families or travelers 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 cater to a cozy and family-friendly experience, with many vacation rentals featuring essential comforts. Most properties include a fully equipped kitchen, allowing guests to prepare meals together. Outdoor spaces such as decks or patios are common, providing a great spot for relaxation or enjoying meals al fresco. Many rentals also feature a fireplace, superb for cozy evenings. Additionally, families will value the availability of books for children, ensuring entertainment for younger guests.
How early should I book a Tall Timbers vacation rental?
Book your Tall Timbers vacation 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 vacation 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, Maryland, United States of America?
In Tall Timbers, Maryland, visitors can enjoy the natural beauty and outdoor activities of the surrounding area. The nearby Potomac River offers opportunities for kayaking, fishing, and boating, making it a popular spot for water enthusiasts. The Chesapeake and Ohio Canal National Historical Park is also close by, providing scenic trails for hiking and biking along the historic canal.

For those interested in birdwatching, the area is renowned for its diverse wildlife, particularly in the wetlands and forests surrounding Tall Timbers. Additionally, the local community often hosts events and festivals that celebrate the rich maritime culture and history of the region, allowing visitors to engage with the local lifestyle.
Can I change or cancel my Tall Timbers home rental booking on Vrbo?
To find Tall Timbers vacation 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 rentals give you the privacy of having the entire place to yourself, and for extra flexibility, some travelers can choose to pay over time with Affirm. Whether you're adjusting your plans or looking for flexible payment options, 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 travelers 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 cozy cabin or a beach condo, 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 vacation 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 like last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to help resolve problems quickly and effectively.

Vrbo also offers support via live chat through our Help Center, 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 organizing 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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