Tall Timbers Vacation Rentals

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Our top choices for Tall Timbers vacation rentals

9.8 out of 10, Exceptional, (40 reviews)
"The cozy cabin had everything needed for a comfortable stay. It was in a very private setting with the beach access a few houses away. You can hear the Chesapeake bay lapping at the shore and catch a glimpse of sail boats going by. We enjoyed our time at the home."
United States
Mary G.
$252 nightly
The price is $267
Feb 9 - Feb 10
Total with taxes and fees
Soul Oasis - home on the Chesapeake Bay
9.4 out of 10, Exceptional, (10 reviews)
"The cottage was clean and welcoming. The location can't be beat. It is right on the water, quiet and nearby point lookout. Great place to visit and walk our dogs. The property owners were responsive and gave us a nice list of things to do around the area. Would definitely stay again!"
United States
Adam P.
$286 nightly
The price is $316
Jan 25 - Jan 26
Total with taxes and fees
Cozy Sunrise Waterfront 2-bedroom Cottage & Dock. Serene Point Lookout/Scotland

Vacation Home in Montross

Luxury Modern Waterfront Retreat
9.6 out of 10, Exceptional, (14 reviews)
"Very nice inside, love all the windows"
United States
Elizabeth S.
$430 nightly
The price is $468
Feb 1 - Feb 2
Total with taxes and fees
Luxury Modern Waterfront Retreat

Vacation Home in Leonardtown

Potomac Vista Cottage
2.0 star property
$351 nightly
The price is $353
Jan 25 - Jan 26
Total with taxes and fees
Potomac Vista Cottage

Cabin in Hague

Coles Point Marina
2.0 star property
$344 nightly
The price is $375
Jan 24 - Jan 25
Total with taxes and fees
Coles Point Marina
10.0 out of 10, Exceptional, (5 reviews)
"We enjoyed this house fully for our Thanksgiving stay! We even took the canoes out for a spin. Nice walks around the development and the beach area is lovely. "
United States
Julie I.
$370 nightly
The price is $403
Jan 25 - Jan 26
Total with taxes and fees
Modern Waterfront Home with Kayak, Firepit, Gameroom, Pool+Beaches, Dog & EV OK
10.0 out of 10, Exceptional, (5 reviews)
"Everything was very clean and well put together. Loved the view!"
United States
Minji S.
$361 nightly
The price is $363
Feb 2 - Feb 3
Total with taxes and fees
Waterfront Escape | Family-Friendly | Remodeled Home | Epic Sunset Views | Decks
3.0 star property
$754 nightly
The price is $837
Jan 25 - Jan 26
Total with taxes and fees
Lakefront Log Cabin Retreat w/ Hot tub + Kayaks!
2.0 star property
$267 nightly
The price is $291
Jan 24 - Jan 25
Total with taxes and fees
2 Bedroom Cottage at Coles Point Marina

Vacation Home in Solomons

4-BR Waterfront Turret Home
10.0 out of 10, Exceptional, (7 reviews)
"Beautiful house. Beautiful scenery. Everything was perfect. "
United States
Thomas S.
$680 nightly
The price is $751
Jan 24 - Jan 25
Total with taxes and fees
4-BR Waterfront Turret Home
10.0 out of 10, Exceptional, (30 reviews)
"Great spot"
United States
SHAWN W.
$424 nightly
The price is $461
Jan 25 - Jan 26
Total with taxes and fees
Easthaven | Game-Themed Waterfront Retreat
10.0 out of 10, Exceptional, (1 review)
"Beautiful newly renovated space with all new appliances, furniture and kitchenware. Comfortable beds, and super clean rooms. Large outside area with new Weber grill, fire pit, and three kayaks. Nice easy to access dock. "
United States
Kit C.
$519 nightly
The price is $573
Jan 24 - Jan 25
Total with taxes and fees
Charming Waterfront 3-bedroom house in Piney Point
10.0 out of 10, Exceptional, (1 review)
"We loved our stay! Lovely home, beautiful view"
United States
Sarah R.
$868 nightly
The price is $874
Jan 27 - Jan 28
Total with taxes and fees
Waterfront home on Mill Creek-5BR-3bath-Hot tub, Kayaks & private dock
9.2 out of 10, Wonderful, (5 reviews)
"Nice place to stay. Perfect location for our needs. Suggest noting the hot and cold water flip upstairs, and to add a mirror in the hallway by outlet for blow dryer."
United States
Lauren A.
$547 nightly
The price is $579
Jan 25 - Jan 26
Total with taxes and fees
Anne & Fred`s Leonardtown Home W/ Arcade room!

Apartment in Mechanicsville

Come relax yourself a while
$532 nightly
The price is $587
Jan 24 - Jan 25
Total with taxes and fees
Come relax yourself a while
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Tall Timbers Hotel Reviews

Find out more about Tall Timbers

Everything you need to know about Tall Timbers vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Tall Timbers vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Tall Timbers vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Tall Timbers vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Tall Timbers. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Tall Timbers in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $267 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Tall Timbers rentals

At Expedia, we put the best Tall Timbers vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Tall Timbers rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Tall Timbers vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Tall Timbers. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Frequently asked questions

Can I find a vacation rental in Tall Timbers?

Yes, we offer vacation rentals near the most popular local attractions in Tall Timbers, or you can choose a secluded option if you're looking for a relaxing stay.

What's the top vacation rental in Tall Timbers?

All Year Retreat - Indoor Heated Pool, Beach, Game & Movie Cottage, Sleeps 21: This vacation home rental near Tall Timbers is located on a river and has an indoor pool, a fireplace, and a barbecue grill to put you at ease in your new surroundings. It has 8 bedrooms as well as a kitchen with a dishwasher, a fridge, and an oven, so you can cook with friends or family. It offers a patio, a selection of games, and a hot tub so you can immerse yourself in your vacation.

What’s there to see and do in Tall Timbers?

While exploring the area, visit family-friendly sights like Michael P. O'Brien Athletics and Recreation Center, or get outside and enjoy nature at Piney Point Beach. In the larger area, you’ll find Piney Point Lighthouse and Saint George Island Beach.

What’s a vacation rental in Tall Timbers like?

A vacation rental is a private property you can book for a few weeks or just a few days in Tall Timbers. Vacation rentals offer amenities such as laundry facilities and kitchens so you'll have a home away from home. If you're concerned about a clean environment, a vacation rental can provide a sense of security away from public hotel elevators and busy lobbies while still allowing you the experience of travel. You'll also get more space in a vacation rental than in a hotel, which is another reason why a vacation rental is a popular option for family gatherings.