Tall Timbers vacation rentals

We found 78 vacation rentals — enter your dates for availability

your current months are April, 2024 and May, 2024.
April 2024
May 2024
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 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:

  • Hague Winery (8.9 mi / 14.4 km)
  • Port of Leonardtown Winery (11.1 mi / 17.9 km)
  • Vault Field Vineyards (11.4 mi / 18.4 km)
  • General's Ridge Vineyard and Winery (11.6 mi / 18.6 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)
  • Point Lookout State Park (14.6 mi / 23.5 km)
  • St. Mary's River State Park (6.4 mi / 10.3 km)
  • Elms Beach Park (9.9 mi / 15.9 km)
  • Jefferson Patterson Park and Museum (16.2 mi / 26 km)
  • Sandy Point Beach (6.5 mi / 10.5 km)

Frequently asked questions

What is the most popular type of vacation rental accommodation in Tall Timbers?

Based on our research, houses are the most popular type of property in Tall Timbers. But of course, everyone's idea of an awesome stay is bound to be different. Vrbo has vacation rentals in a variety of sizes and shapes, and we'll help you find the perfect fit for you.

How much does it cost to rent a vacation rental in Tall Timbers?

The average price for a vacation home in Tall Timbers can vary depending on factors like property type, length of stay and season. Whether you're in search of a sprawling villa with lots of space or a cozy cabin for just you and your sweetheart, just enter your travel dates to discover stays with terrific value.

How much does it cost to rent a beach house in Tall Timbers?

The average price for a vacation rental by the beach in Tall Timbers depends on when you'll be there and the style and size of property you want. You can find prices quickly and easily on Vrbo by entering your destination and preferred travel dates. Then use the filters to pick the number of bedrooms and amenities that you prefer, such as air conditioning, a pool and WiFi.

Are there pet-friendly vacation rentals in Tall Timbers?

Pack a travel bag for your pooch because Tall Timbers has two stays that roll out the welcome mat to pets. Let your four-legged pal join in with the family fun at one of our pet-friendly vacation rentals on Vrbo. Simply enter your travel dates and destination, then check our "Pets allowed" filter box.

What are popular rental amenities in Tall Timbers?

Some of the most popular rental amenities people search for in Tall Timbers are a barbecue grill, a garden and a fireplace. Whether you're vacationing with your besties, family or even pets, Vrbo vacation properties include the best amenities for starting a new adventure with your loved ones.

Are there vacation rentals in Tall Timbers that welcome kids?

Tall Timbers has two family-friendly vacation homes to choose from. And tracking down a stay that welcomes kids is a breeze with our "Properties good for families" filter. Besides having the entire place to yourselves, you'll get access to conveniences and perks like dining rooms, private pools and yards.

What are the top attractions for families in Tall Timbers?

There are plenty of awesome things to see and do with the family in Tall Timbers, including:

  • Patuxent River Naval Air Museum
  • St. Marys River State Park
  • Historic St. Marys City

How can I find vacation rentals with air conditioning in Tall Timbers?

There are two vacation rentals with air conditioning in Tall Timbers providing that cooling breeze and extra level of comfort. Just enter your dates of travel and then take advantage of our filters to look for stays with air conditioning.

How old do you have to be to rent a vacation rental in Tall Timbers?

The minimum age permitted can differ across properties on Vrbo, so be sure to check the rules of the vacation home in Tall Timbers you're considering. But typically, it's 16, 18 or 21.

How long can I rent a vacation rental in Tall Timbers for?

It's down to the Tall Timbers property. To look over a list of options offering extended stays, simply type your dates and number of people into Vrbo's search page. Enjoy having the property to yourself, along with home comforts like air conditioning, a kitchen and a backyard to run around in. Keep your eyes peeled for long-term stays that offer weekly or monthly discounts.

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