Vacation rentals in Tall Timbers

4.97 out of 5 average rating, 162 reviews

Home in Hague

Osprey's roost: Spring and summer 2025

Hidden treasure! Come join the osprey along the Potomac River in the Northern Neck of Virginia! This 4 bedroom/3 bath custom home is at the end of a quiet lane and sits on a point of land between the Potomac River and Blackbeard’s Pond, making for magnificent river views from sunrise to sunset. Enjoy swimming, canoeing, Bocce on the lawn, barbecue on the deck! Osprey’s Roost is the perfect retreat to rest and recharge, ideal for a romantic week away, a girls’ weekend or a family gathering!

Tiny home in Saint Inigoes

4.98 out of 5 average rating, 349 reviews

Historic St.Mary's City at the Lazy Bear Cottage

Inquire first on pets, there is a 50 lb. weight limit total, can be split up between 2 small dogs or 1 at 50lbs or less,must be house broken and friendly. Close to Saint Mary's historic city, Pt. Lookout State Park, Sotterley Plantation. Great hiking trails, restored colonial village,a replica of the Maryland Dove. Tour a lighthouse. Great restaurants , or spend a day over in Solomons Island, about 20 miles from us. Peaceful settings for relaxing right on the water,or kayak on the river.

4.96 out of 5 average rating, 191 reviews

A charming cottage sits at the water's edge, surrounded by lush greenery. A wooden staircase leads down from an elevated deck to the sandy beach. Two blue chairs are positioned on the deck, inviting relaxation as the sun sets in the background.

Cottage in Leonardtown

Beach Front and 'Perfectly Placed'

Escape to our charming Potomac River waterfront cottage, complete with 2 cozy bedrooms, 1 tastefully appointed bathroom, and stunning river views. Enjoy a comfortable living area with large windows, a fully equipped kitchen, and an outdoor picnic table. Perfect for small families or friends seeking a peaceful retreat, our cottage is conveniently located just a short drive from local restaurants and shopping. Come relax, unwind, and make unforgettable memories on the beautiful Potomac River.

Apartment in Lexington Park

A person in colonial attire is shown feeding pigs in a rural setting. The focus is on a large pig approaching for food, with wooden fencing partially visible in the foreground. The background features trees and sparse underbrush, reflecting a historical farming scene.

4.97 out of 5 average rating, 568 reviews

Historic St. Mary's City, MD

1,000 square foot two-bedroom, one bath waterfront apartment features separate entrance and a screened-in porch overlooking the St. Mary’s River. Property has a large dock and a small private beach. Jellyfish, crabs, and oysters make swimming challenging, although many swim off the dock in the deeper water. No Diving! Dogs are welcome. We just ask that they be on a leash. The apartment is attached to part of the house where we reside, although it is sealed off and nothing is shared.

4.89 out of 5 average rating, 122 reviews

A winding stone pathway is lined with landscaped greenery and accentuated by soft lighting. The path is framed by a white fence and features a mixture of rocks and plants, creating a tranquil outdoor space beside the cottage.

Home in Tall Timbers

Old World Cottage/Fabulous Sunsets/Polite Pets OK

Immaculate cottage with old world detail and large stone patio. Easement to water to enjoy the fantastic Southern Maryland sunsets dipping beyond the Potomac River. Situated in St Mary’s County near Piney Point and St George’s Island. A short walk to Tall Timbers Marina. Boats and polite pets are welcome with prior approval. Central heat & air conditioning, Front-yard fire-pit, Fast Internet, Smart TVs, Cable 2 Plastic Kayaks Fully stocked Kitchen, and bedding Crab net Fish Table

5 out of 5 average rating, 110 reviews

Home in Piney Point

Living on Island Time

Relax with the whole family and spend life on Island Time. Full bar set up with ice maker and wine refrigerator. Private pier, paddle boards and firepit. Unwind on St Goerge Island or head out to one of the local eateries for some southern Maryland faire. Inside you have 2 spacious rooms, 2 bathrooms. A massive island for cooking, card playing or just great conversations with endless views. Crabbing, fishing. The Neighbors have 2 Great Danes and a cat that you may see occasionally

5 out of 5 average rating, 117 reviews

A bright sun porch is highlighted by large windows offering views of the waterfront. Comfortable seating is arranged around a central coffee table, while decorative cushions add a touch of color. Natural light enhances the serene ambiance, creating an inviting space for relaxation.

Home in Leonardtown

White Point Cottage -- Quiet Waterfront Getaway

Welcome to White Point Cottage on the beautiful Potomac — 90 minutes from Washington, DC, but a world away. The renovated 2 bedroom, 1 bath cottage sits on nearly an acre of south-facing waterfront property, affording a sense of privacy along with sunrise and sunset views. We’ve owned in the same neighborhood in St. Mary's County since 2005 and are eager to show guests why we love it here. More on IG @whitepointcottage, and be sure to visit our sister property, Water's Edge Cottage.

4.98 out of 5 average rating, 135 reviews

A serene outdoor seating area is framed by lush greenery and colorful flowers, leading to an expansive view of Breton Bay. A decorative lantern hangs from the pergola, enhancing the tranquil atmosphere of this inviting garden space.

Apartment in Leonardtown

Stunning Sunsets on Breton Bay, Seaside apartment

Charming efficiency apartment decorated with a coastal theme overlooks Breton Bay. Use of pier for hanging out... or crabbing and fishing. Apartment is in the second floor of detached garage on the premises of a private home. Beautiful serene surroundings 5 min. from downtown Leonardtown with shopping, restaurants and events. Area offers historical sites, wonderful parks, a large Mennonite and Amish community, great restaurants and friendly people! 25 minutes from Solomons Island.

4.93 out of 5 average rating, 160 reviews

A screened porch features a clear view of the water, framed by lush greenery. Two chairs and a small table are positioned on the wooden deck, allowing for leisurely seating amidst nature. The sky above is partly cloudy, contributing to the serene ambiance.

Guesthouse in Bushwood

Little House by the water

Serenity - Privacy - Beauty - This little house by the water has it all. New Sealy queen size mattress, well equipped kitchen, Cuisinart coffee maker, full oven, glass topped stove, new refrigerator, and fully screened porch with water view. Perfect for 1 or 2 adults looking to get off the grid and recharge. In St. Mary's County,MD, just 90 minutes south of Washington DC. However, the space is small and it is really a studio apartment as I think the pictures make evident.

Apartment in Lexington Park

5 out of 5 average rating, 383 reviews

Adorable Waterfront Apartment Weekend Getaway

Bright & cheery 1 bedroom waterfront apartment nestled on the banks of the St. Mary's River. Amazing, dreamy views. It's a sweet spot to relax and enjoy a quiet get-away or launch a kayak, take a walk, enjoy great food cuisine. We sit next to St. Mary's College of MD and Historic St. Mary's City. You may see college sailing races, crew teams rowing, or the historic Maryland Dove sailing down the river. It's lovely here fall, winter, spring, summer! SUNSETS!

4.99 out of 5 average rating, 156 reviews

Cottage in Hague

Potomac River cheerful cottage

Embark on a journey to the serenity of nature and the gentle lullaby of the Potomac River at the cottage. Escape the hustle and let the timeless embrace of water and tranquility rejuvenate your mind and soul. The private sandy beach (no public access) is steps away and awaits your footprints. Delight in the serene surroundings of the Northern Neck countryside. Two hours from DC, Richmond and Maryland.

Aerial view of the serene shoreline, revealing sandy beaches bordered by golden grasses. The calm waters extend into the distance, with gentle waves lapping at the shore. Rocky sections are visible, along with a scattering of trees and distant homes along the water's edge.

4.98 out of 5 average rating, 106 reviews

Waterfront Retreat| Kayak+Beaches+Pool | Gameroom

Relax ✧ Kayak ✧ Paddleboard ✧ Hike ✧ Fish ✧ Swim ✧ Beach & more at the Riverside Retreat in Montross! ☀️ Welcome to our modern waterfront sanctuary with kayaks + paddleboard 🏊‍♀️ 3 community beaches + pool (open Memorial to Labor Day) 👨‍🍳 Gas griddle for cooking a delicious meal 🔥 Fire pit + Gameroom (ping pong, arcade, & more!) 🐶 Dogs Welcome ⚡️EV Charging Book today or ❤️ us for next time

Vacation rentals for every style

Get the amount of space that is right for you

Hotels

Stylish accommodations and amenities

Unique stays

Spaces that are more than just a place to sleep

Homes

Comfortable places with all the essentials

Popular amenities for Tall Timbers vacation rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Other great vacation rentals in Tall Timbers

4.94 out of 5 average rating, 16 reviews

A spacious porch is showcased, featuring a swing and rocking chairs under a covered ceiling. Lush greenery surrounds the area, with a well-maintained yard visible in the background, complete with a gravel path leading into a natural landscape.

Home in Kinsale

Nature's Retreat

JessicaRating, 5 stars1 month ago

Was looking for a nice and relaxing getaway and this place delivered! It was clean and I was impressed that the kitchen had everything stocked. Check-in was easy and the hosts were communicative.

4.87 out of 5 average rating, 55 reviews

Home in Drayden

Spacious and peaceful w/ private beach & boat ramp

JulissaRating, 5 stars2 months ago

Loved it so much great view and everything!

4.96 out of 5 average rating, 47 reviews

An aerial view captures the shoreline of Historic St. George’s Island, showcasing sandy beaches, calm waters, and piers extending into the Lower Potomac. Lush greenery and occasional residences are visible along the coast, framed by gentle water currents under a partly cloudy sky.

Cottage in Piney Point

Quaint fishing retreat on the lower Potomac Piney

ElizabethRating, 5 stars1 month ago

Fantastic stay! Quiet getaway which was exactly what I was looking for. House was fully stocked with all the amenities listed and so much better in person! The sunsets were epic! Cam was very helpful with providing things to do in the area which was fun to explore! I will certainly be back again.

A window frame is visible, showcasing a scenic view of the Potomac River. A telescope is positioned within the frame, aimed towards the tranquil waters. The horizon features trees and a distant shoreline, while a wooden fence adds a touch of structure to the foreground.

4.91 out of 5 average rating, 22 reviews

Potomac River Getaway

SkyRating, 5 stars1 week ago

Had a great weekend in the Northern Neck here! We watched a pod of dolphins and stingrays from the backyard, enjoyed easy access to nearby parks, and had a great time cooking in the kitchen. This is seemingly a very recently renovated house, and all the towels, sheets, beds, etc. seemed brand new as well. It was super clean, super comfy, and the hosts were very responsive! I liked that the property was surrounded on one side by forest as well—it was nice and quiet and secluded. Finally, they have a super cute collection of board games disguised as old timey books. I'd definitely stay here again!

Superhost

Two piers extend into the calm water, reflecting hues of orange and pink from the sunset in the background. The wooden beams of the piers create a rustic look against the serene bay, framed by lush greenery along the shoreline.

Home in Leonardtown

4.91 out of 5 average rating, 32 reviews

Abells Wharf Cottage - Natural Splendor Getaway

BrianRating, 5 stars8 months ago

We enjoyed our stay at Jan's cottage. Very clean, spacious and very good amenities. Jan was very responsive and informative on local places to visit/eat. The property is beautiful and peaceful. Just what we needed to have a relaxing weekend. Will visit again, Highly recommend!

A spacious deck area is surrounded by vibrant autumn foliage, featuring modern outdoor furniture arranged for relaxation. Large windows provide views into the house, while a gas grill and firepit enhance the outdoor dining experience. A quiet, wooded backdrop creates a tranquil setting.

4.95 out of 5 average rating, 66 reviews

Luxury Modern Waterfront Retreat

MalikRating, 5 stars2 weeks ago

Kelly and Thomas were amazing host. Very responsive and accommodating The home was very clean and the location was great.. 10/10. Definitely would book again!

A stainless steel sink is filled with crabs, surrounded by water, while water is running from the faucet. The countertop features a speckled granite surface, and a red dish rack is visible in the background, adding a practical touch to the setting.

4.96 out of 5 average rating, 76 reviews

Waterfront home, private dock

ShufanRating, 5 stars2 weeks ago

We had a wonderful vacation here. Although it rained during our stay, we found the treehouse to be a great place just for listening the rain drops and having some inner peace.