Tall Timbers holiday rentals

We found 80 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.

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, laundry, pools, gardens and more
  • More for less
    More space, more privacy, more amenities — more value

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:

  • Port of Leonardtown Winery (11.1 mi / 17.9 km)
  • Hague Winery (8.9 mi / 14.4 km)
  • Breton Bay Golf Course (9.7 mi / 15.5 km)
  • General's Ridge Vineyard and Winery (11.6 mi / 18.6 km)
  • Vault Field Vineyards (11.4 mi / 18.4 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)
  • 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)
  • Drum Point Lake (12.6 mi / 20.3 km)

Frequently asked questions

What is the most popular type of holiday home 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. Stayz has holiday homes 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 holiday home in Tall Timbers?
The average price for a holiday 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 cosy 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 holiday home 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 Stayz 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 holiday homes 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 holiday homes on Stayz. Simply enter your travel dates and destination, then check our “Pets allowed” filter box.
What are popular home amenities in Tall Timbers?
Some of the most popular home amenities people search for in Tall Timbers are a barbecue grill, a garden and a fireplace. Whether you’re holidaying with your besties, family or even pets, Stayz holiday properties include the best amenities for starting a new adventure with your loved ones.
Are there holiday homes in Tall Timbers that welcome kids?
Tall Timbers has two family-friendly holiday 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 holiday homes with air conditioning in Tall Timbers?
There are two holiday homes 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 holiday home in Tall Timbers?
The minimum age permitted can differ across properties on Stayz, so be sure to check the rules of the holiday home in Tall Timbers you’re considering. But typically, it’s 16, 18 or 21.
How long can I rent a holiday home 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 Stayz’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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