Holiday rentals in Westmoreland County

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Top-rated holiday rentals in Westmoreland County

Guests agree: these stays are highly rated for location, cleanliness and more.

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Top guest favourite
A serene private dock overlooks a calm cove, with vibrant kayaks stacked nearby. A simple bench provides seating, surrounded by lush greenery and mist rising from the water's surface, inviting relaxation and peaceful reflections.
Cottage in Montross
4.93 out of 5 average rating, 123 reviews

Lakefront/Dock, Cove, Boats, HotTub, Woods & Beach

Welcome to the Butterfly Effect! Recharge at this tranquil getaway. 2.5 wooded acres with a private dock and cove, a short paddle away from the lake beach with a swimming dock and sandy beach! Fishing, swimming, and floating all on the protected freshwater lake. We have boats for your use, theater space & hot tub to wind down at night after dining on our deck. Picnic at our private Shark Tooth Beach, watch Osprey & Eagles fish the Potomac, and collect 15-million-year-old fossilized shark teeth!

Top guest favourite
Cottage in Leonardtown
4.96 out of 5 average rating, 262 reviews

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.

Top guest favourite
Cottage in Cobb Island
4.97 out of 5 average rating, 95 reviews

*Waterfront island escape.*

YOUR WATERFRONT OASIS AWAITS! If you are looking for a true getaway, look no further. Tucked away on a small, peaceful island, this hidden gem is uniquely surrounded by 3 bodies of water: The Potomac River, the Wicomico River, and Neale Sound. This quiet island oasis offers the perfect place to step away from the busy world! This cottage is incredibly special to us. For four generations, it has been a sanctuary for our family-filled with love, laughter, and countless memories.

Guest favourite
A single-story home is situated on a grassy area with trees in the foreground. The house features a covered porch with multiple windows that reflect the colorful sunset over the water in the background, creating a serene lakeside atmosphere.
Home in Montross
4.91 out of 5 average rating, 55 reviews

Enjoy the Sunset at Nomini Bay

Enjoy the peace and serenity of Nomini Bay. The home is located right on the water! With expansive water views and your own private boat dock, the house has plenty of space to gather as a family and enjoy game nights but is also cozy enough for a peaceful couple's getaway. Comfortably and stylishly furnished, this home will provide everything you and your family need for your visit. Located 10 minutes from the town of Montross, come enjoy the sunset happy hours at this lovely home.

Guest favourite
A contemporary cottage rests by tranquil water, surrounded by trees. A spacious deck with white railings adjoins the home, leading down to the water’s edge. A small blue kayak is positioned nearby, complementing the serene landscape reflected in the water.
Home in Colonial Beach
4.99 out of 5 average rating, 134 reviews

Waterfront Cottage in Colonial Beach at Placid Bay

Luxury Cottage with private water views full of natural wildlife. You will love the open floor plan with a chef's kitchen stocked with All the essentials including beverages and coffee. Sleep late with private bedrooms that include luxurious bedding Enjoy the expansive outdoor space complete with Patio, Pergola, Fire Pit, and large deck with outdoor kitchen. Walk down to the 28ft foot dock where you can fish, relax in the sun or take the Kayaks for a ride Close to DC and NOVA

Top guest favourite
A private dock extends into the calm water, featuring a wooden platform and seating areas. A vibrant blue paddleboard rests on the grassy shoreline, while an in-ground trampoline is seen nearby. The scene is framed by trees under a clear blue sky.
Home in Montross
4.97 out of 5 average rating, 105 reviews

Waterfront home, private dock

Relax right next to the water in this tranquil Montross getaway. Fish, crab, kayak, paddleboard, or just sit on the swing and watch dolphins, eagles, herons, and stingrays from your private dock. Dine outdoors on the spacious deck, spend some some quality family time with an in-ground trampoline, tree swing, cornhole, bocce ball, spikeball, and a unique custom-built treehouse. Or just stay inside, relax, and enjoy the views, with an indoor electric fireplace and jacuzzi bathtub.

Top guest favourite
A view from the property shows a grassy area leading to the water. A screened porch is visible, providing a tranquil space. The river reflects the blue sky and fluffy clouds, with trees lining the opposite bank. A wooden dock extends into the water.
Guest house in Bushwood
4.93 out of 5 average rating, 181 reviews

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.

Guest favourite
Home in Montross
4.98 out of 5 average rating, 152 reviews

Waterfront, Pool + Beach, Dock + Kayaks, Potomac

Relax - Star Gaze - Kayaks/Paddleboard - Hike - Fish - Swim - Beach & more! ☀️ Waterfront w/Dock 👨‍🍳 Gas griddle 🛶 Kayaks/Paddleboard 🔥 Fire pit ⛱️ 3 Community Beaches 🎯 Gameroom 🐶 Dogs OK (Max 2) ⚡️EV Outlet The Riverside Retreat in Montross, VA is the perfect spot to relax and connect with nature. We offer a peaceful sanctuary that families & small groups love to visit! Book your getaway today or ❤️ us for next time!

Superhost
A hot tub is set within a private deck area, surrounded by lush greenery. Soft lighting creates a warm ambiance as steam rises gently from the water, and a scenic view of trees can be seen in the background at twilight.
Home in Colonial Beach
4.88 out of 5 average rating, 108 reviews

The Lake Oasis Retreat *cozy, serene, relaxing*

Escape to The Lovers’ Lake Oasis, a cozy four-season retreat designed for romance and relaxation. Soak in the hot tub under soft twilight lighting, take in peaceful Placid Lake views, or unwind in the secluded backyard. On warmer days, walk five minutes to the dock and launch a kayak. For a special touch, add our romantic decor package with roses, candles, chocolates, and bubbly ($320) to enjoy while stargazing from the hot tub. Serenity awaits. 🍾🥂❣️

Guest favourite
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.
Home in Montross
4.86 out of 5 average rating, 98 reviews

Potomac River Getaway

Discover an incredible escape at our cliffside gem on the Potomac! This 3BR, 2.5BA retreat has airy living spaces and panoramic river vistas from the wraparound deck. Enjoy your coffee as eagles soar above, and unwind in a private hot tub beneath star-filled skies, all while soaking in breathtaking riverside sunsets. Perfect for family and friend getaways, with historical sites close by. Montross’s small-town charm awaits your exploration—enjoy!

Top guest favourite
A spacious open-concept living area features large windows offering unobstructed views of the water and sunset. A comfortable sectional sofa is positioned near the windows, with a dining table visible in the background. Natural light fills the space, enhancing the tranquil setting.
Home in Leonardtown
4.99 out of 5 average rating, 134 reviews

Water's Edge Cottage | Luxury Retreat

We are thrilled to host guests at the newly renovated Water's Edge Cottage -- a serene oasis offering what may be the best views on the Potomac. The rural charm of St. Mary’s County is among Maryland’s best kept secrets -- 90 minutes but a world away from Washington DC (with no Bay Bridge traffic!). We are near historic Leonardtown, boasting one of Maryland’s few remaining town squares (we affectionately call it “Mayberry”).

Top guest favourite
A cozy outdoor seating area is showcased with a propane fire pit surrounded by decorative stones. Two cushioned chairs and a spacious sofa are positioned nearby. A bright red umbrella stands tall, adding a splash of color against the darkening sky and tree silhouettes.
Cottage in Montross
4.99 out of 5 average rating, 211 reviews

Waterfront Escape w/ Private Dock & Fire Pit

Escape to Mallard Cottage, our renovated home nestled along the picturesque Nomini Creek. Step onto the private dock for direct water access, where you can launch one of our paddleboards or kayaks for a day of exploration. Highlights include: ✔ 4 Outdoor Decks ✔ High-Speed Wi-Fi ✔ Central Heating & Air Conditioning ✔ Game Room ✔ Free Parking ✔ No Cleaning Fee!

Popular amenities for Westmoreland County holiday rentals