Tall Timbers Holiday Rentals

Start date: Check-in selected.
To Date
End date: Check-out

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
2 Jan - 4 Jan
In two months
13 Feb - 15 Feb
In three months
13 Mar - 15 Mar
In four months
10 Apr - 12 Apr

Our top choices for Tall Timbers holiday rentals

Exterior
Soul Oasis - home on the Chesapeake Bay

Cottage in Lusby

Soul Oasis - home on the Chesapeake Bay
9.8 out of 10, Exceptional, (39)
"Great stay. Teresa was very helpful, the house is fun, and the location is great - nice place to visit."
United States
Samuel W.
The price is HK$973
HK$2,186 total
includes taxes & fees
22 Dec - 23 Dec
Soul Oasis - home on the Chesapeake Bay
Dining
Cozy Sunrise Waterfront 2-bedroom Cottage & Dock. Serene Point Lookout/Scotland

Cottage in Point Lookout

Cozy Sunrise Waterfront 2-bedroom Cottage & Dock. Serene Point Lookout/Scotland
9.4 out of 10, Exceptional, (8)
"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.
The price is HK$1,113
HK$2,603 total
includes taxes & fees
5 Jan - 6 Jan 2026
Cozy Sunrise Waterfront 2-bedroom Cottage & Dock. Serene Point Lookout/Scotland
Fridge, microwave, oven, stovetop
Waterfront home where you can relax or enjoy the things the Northern Neck.

Holiday Home in Lottsburg

Waterfront home where you can relax or enjoy the things the Northern Neck.
10.0 out of 10, Exceptional, (11)
"Property was very nice! Very clean and I especially loved the dual coffee maker!"
United States
Tamara G.
The price is HK$1,167
HK$2,121 total
includes taxes & fees
2 Jan - 3 Jan 2026
Waterfront home where you can relax or enjoy the things the Northern Neck.
Interior
Lakefront Log Cabin Retreat w/ Hot tub + Kayaks!

Cottage in Lusby

Lakefront Log Cabin Retreat w/ Hot tub + Kayaks!
3.0 star property
The price is HK$3,323
HK$7,043 total
includes taxes & fees
30 Dec - 31 Dec
Lakefront Log Cabin Retreat w/ Hot tub + Kayaks!
Property grounds
Potomac Vista Cottage

Holiday Home in Leonardtown

Potomac Vista Cottage
2.0 star property
The price is HK$1,082
HK$3,033 total
includes taxes & fees
21 Dec - 22 Dec
Potomac Vista Cottage
Interior
Xmas Sale! Game Theme+Boats+King Bd+EV Chrgr+Solar

Holiday Home in Montross

Xmas Sale! Game Theme+Boats+King Bd+EV Chrgr+Solar
10.0 out of 10, Exceptional, (30)
"Great spot"
United States
SHAWN W.
The price is HK$1,601
HK$3,588 total
includes taxes & fees
6 Jan - 7 Jan 2026
Xmas Sale! Game Theme+Boats+King Bd+EV Chrgr+Solar
Dining
Charming 2-bedroom cottage in wonderful Newburg with WiFi, AC

Cottage in Newburg

Charming 2-bedroom cottage in wonderful Newburg with WiFi, AC
2.0 star property
The price is HK$1,401
HK$3,522 total
includes taxes & fees
21 Dec - 22 Dec
Charming 2-bedroom cottage in wonderful Newburg with WiFi, AC
Interior
Peaceful tiny home Saltara where you can realx and unwind

Holiday Home in Lexington Park

Peaceful tiny home Saltara where you can realx and unwind
2.0 star property
The price is HK$1,114
HK$1,402 total
includes taxes & fees
21 Dec - 22 Dec
Peaceful tiny home Saltara where you can realx and unwind
Smart TV, books
4-BR Waterfront Turret Home

Holiday Home in Solomons

4-BR Waterfront Turret Home
2.0 star property
10.0 out of 10, Exceptional, (7)
"Absolutely wonderful home with the best view of the water from nearly every window. It was clean and it had many comfortable bedrooms. Highly recommend this property!!"
United States
Rudy L.
The price is HK$2,723
HK$5,842 total
includes taxes & fees
1 Jan - 2 Jan 2026
4-BR Waterfront Turret Home
TV, fireplace, video games, books
Waterfront home on Mill Creek-5BR-3bath-Hot tub, Kayaks & private dock

Holiday Home in Lusby

Waterfront home on Mill Creek-5BR-3bath-Hot tub, Kayaks & private dock
10.0 out of 10, Exceptional, (1)
"We loved our stay! Lovely home, beautiful view"
United States
Sarah R.
The price is HK$2,568
HK$6,709 total
includes taxes & fees
6 Jan - 7 Jan 2026
Waterfront home on Mill Creek-5BR-3bath-Hot tub, Kayaks & private dock
Exterior
Charming Waterfront 3-bedroom house in Piney Point

Holiday Home in Piney Point

Charming Waterfront 3-bedroom house in Piney Point
10.0 out of 10, Exceptional, (1)
"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.
The price is HK$2,334
HK$4,443 total
includes taxes & fees
21 Dec - 22 Dec
Charming Waterfront 3-bedroom house in Piney Point
Interior
Waterfront Escape | Family-Friendly | Remodeled Home | Epic Sunset Views | Decks

Holiday Home in Lexington Park

Waterfront Escape | Family-Friendly | Remodeled Home | Epic Sunset Views | Decks
10.0 out of 10, Exceptional, (5)
"This was our second time staying at this beautiful home, and it was just as wonderful as we remembered. The house is impeccably maintained, tastefully decorated, and incredibly comfortable. The beds are cozy, and every detail has been thoughtfully considered—from the clear labels throughout the home to the fully stocked kitchen and amenities. It truly feels like a home away from home. We had a fantastic stay and are already looking forward to our next visit!"
United States
Lisa M.
The price is HK$2,334
HK$4,066 total
includes taxes & fees
3 Jan - 4 Jan 2026
Waterfront Escape | Family-Friendly | Remodeled Home | Epic Sunset Views | Decks
Fridge, microwave, oven, stovetop
Luxury Modern Waterfront Retreat

Holiday Home in Montross

Luxury Modern Waterfront Retreat
9.6 out of 10, Exceptional, (14)
"Very nice inside, love all the windows"
United States
Elizabeth S.
The price is HK$2,622
HK$5,367 total
includes taxes & fees
26 Dec - 27 Dec
Luxury Modern Waterfront Retreat
Fridge, microwave, oven, stovetop
Anne & Fred`s Leonardtown Home W/ Arcade room!

Apartment in Leonardtown

Anne & Fred`s Leonardtown Home W/ Arcade room!
9.2 out of 10, Wonderful, (5)
"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.
The price is HK$1,945
HK$4,490 total
includes taxes & fees
11 Jan - 12 Jan 2026
Anne & Fred`s Leonardtown Home W/ Arcade room!
Property grounds
Come relax yourself a while

Apartment in Mechanicsville

Come relax yourself a while
The price is HK$1,926
HK$4,567 total
includes taxes & fees
1 Jan - 2 Jan 2026
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Tall Timbers Hotel Reviews

Spacious Waterfront Home secluded on 60 ac with Beach and Boat Ramp

Spacious Waterfront Home secluded on 60 ac with Beach and Boat Ramp

10/10 Excellent
"Everything was great! The home and property were beautiful and the friendly feral kitties outside made our stay a million times better. The home is spacious and well-designed and the beach is stunning. "
Sugam M. 3-night trip
Posted 4 days ago
Spacious Waterfront Home secluded on 60 ac with Beach and Boat Ramp

Find out more about Tall Timbers

Search for holiday rentals in Tall Timbers on Expedia! You can easily find your home rentals, villas, holiday apartments in Tall Timbers using one of the methods below:

  • View our selection of featured holiday rentals in Tall Timbers
  • Use the map to find apartments and other holiday homes in the Tall Timbers neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Tall Timbers while they last

Look no further and take a look at our great range of rental properties in Tall Timbers!

Frequently asked questions

Can I find a holiday rental in Tall Timbers?

Yes, there are holiday rentals close to the most popular sights in Tall Timbers, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Tall Timbers has to offer?

Spacious Waterfront Home secluded on 60 ac with Beach and Boat Ramp: This holiday home rental outside of Tall Timbers is located on the beach, and has a balcony, a garden and a BBQ to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You and your friends and family can relax into your holiday with amenities such as a selection of games.

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 wider area, you’ll find Piney Point Lighthouse and Saint George Island Beach.

What’s a holiday rental in Tall Timbers like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Tall Timbers. Holiday rentals offer extras such as WiFi and washers and dryers so you'll feel right at home. If you're concerned about a clean environment, a holiday rental can provide a sense of security away from public hotel lifts and busy front desks while still allowing you a great travel experience. You'll also get more space in a holiday rental than in a hotel, which is another reason why a holiday rental is an attractive choice for family trips.