Tall Timbers holiday rentals

We found 84 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.

Holiday rentals with weekly discounts – Tall Timbers

Showing deals for:6 Nov - 13 Nov

Property grounds
Property grounds
Living area
Dining
Exceptional
(24 reviews)

WATERFRONT 3000 SQFT HOME W/ PIER, WRAP PORCH, KAYAK, PADDLE BOARD, FIRE PIT

Piney Point

7% off
AU$5,484
for 7 nights, 1 home
AU$783 per night
includes taxes & fees
WATERFRONT 3000 SQFT HOME W/ PIER, WRAP PORCH, KAYAK, PADDLE BOARD, FIRE PIT
Exterior
White sand beach
Exterior
Dining
Exceptional
(58 reviews)

Beach & River Retreat. Spectacular house with private sand beach and hot tub!

Montross

8% off
AU$7,747
for 7 nights, 1 home
AU$1,107 per night
includes taxes & fees
Beach & River Retreat. Spectacular house with private sand beach and hot tub!
Exterior
Exterior
Exterior
Exterior
Exceptional
(8 reviews)

An amazing large group vacation home with elevator and breathtaking views.

Montross

8% off
AU$10,714
for 7 nights, 1 home
AU$1,531 per night
includes taxes & fees
An amazing large group vacation home with elevator and breathtaking views.
Exterior
Sunrise on your private beach
Exterior
Aerial view
Exceptional
(35 reviews)

Sea Glass Beach House! Large sand beach, dock and hot tub! Pets welcome!

Hague

7% off
AU$3,710
for 7 nights, 1 home
AU$530 per night
includes taxes & fees
Sea Glass Beach House! Large sand beach, dock and hot tub! Pets welcome!
Renovated kitchen
Views from the waterfront
St George's Island
Full sized kitchen stocked with essentials: oil/vinegar, salt & pepper, spices, coffee maker, toaster oven, microwave, pots & pans, dishwashing pods + laundry detergent, etc.
Exceptional
(60 reviews)

Quaint fishing retreat on the lower Potomac Piney Pt

Piney Point

9% off
AU$1,995
for 7 nights, 1 home
AU$285 per night
includes taxes & fees
Quaint fishing retreat on the lower Potomac Piney Pt
Beach
Exterior
Beach
Beach
Exceptional
(43 reviews)

The Beach Retreat is a cozy beach Villa with Hottub overlooking a private beach.

Montross

7% off
AU$2,744
for 7 nights, 1 home
AU$392 per night
includes taxes & fees
The Beach Retreat is a cozy beach Villa with Hottub overlooking a private beach.
Most items you would expect to find in a well provisioned kitchen. Pack cloths.
Located across  the road from lNational Water Trail
A dining room table expands to 12 seats with a view.  Two extensions not show.
Just beyond the counter is a 2nd teak dinning room Table for puzzles and layout.
Exceptional
(65 reviews)

Potomac Rvr Woodland Cottage, Polite Pets welcomed, Central Air, Stunning Sunset

Tall Timbers

16% off
AU$2,174
for 7 nights, 1 cottage
AU$311 per night
includes taxes & fees
Potomac Rvr Woodland Cottage, Polite Pets welcomed, Central Air, Stunning Sunset
  • 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:

  • Michael P. O'Brien Athletics and Recreation Center (6.6 mi / 10.7 km)
  • Breton Bay Golf Course (9.7 mi / 15.5 km)
  • General's Ridge Vineyard and Winery (11.6 mi / 18.6 km)
  • Hague Winery (8.9 mi / 14.4 km)
  • Port of Leonardtown Winery (11.1 mi / 17.9 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)
  • Jimmy Island (6 mi / 9.6 km)
  • St. Mary's River State Park (6.4 mi / 10.3 km)
  • Elms Beach Park (9.9 mi / 15.9 km)
  • Confederate Memorial Park (12.9 mi / 20.8 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.

More holiday ideas