House vacation rentals in Saint Leonard

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Top-rated house rentals in Saint Leonard

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Guest favorite

A bright and airy living space features two comfortable armchairs and a dark sofa, arranged around a round coffee table. Large windows allow for expansive views of the river and landscape. Sheer curtains gently filter the light, enhancing the serene ambiance.

Home in Mechanicsville

4.93 out of 5 average rating, 14 reviews

Modern luxury waterfront retreat, 1 hr to DC

Expansive river views from every room and on your bed! A luxurious waterfront retreat. Relax in a full marble tiled, oversized rainfall shower, rich cotton sheets and pillowtop bed. Full kitchen with Nespresso and tea. Cul-de-sac house, on a cliff with private deck/dock. High ceilings and massive windows let in lots of light. Easy access to dining, wineries, farms, beaches, and historic sites. DC/VA easy 1 hr drive away. *Host lives in adjoining building, attached guest house is fully private.

Guest favorite

Aerial view of a waterfront home situated at the edge of Carr's Creek. Lush greenery surrounds the property, with serene water stretching towards the Chesapeake Bay. Boating docks are visible, along with trees displaying autumn colors along the shoreline.

Home in Deale

4.97 out of 5 average rating, 29 reviews

Beautiful Waterfront Escape w/ Gorgeous Views

Escape to this stunning waterfront home on lovely Carr's Creek in Deale, MD. It offers four bedrooms and full bathrooms, two spacious living areas, two sunrooms, and a large fully stocked kitchen. You can birdwatch from the balcony, snuggle by the fireplace, soak in the hot tub, kayak, canoe, or play games and grill outdoors. Nearby, you can take a charter on the Chesapeake, kayak or hike at the Smithsonian Environmental Research Center, and enjoy local seafood restaurants and antique shopping.

Guest favorite

A classic historic cottage features white siding and a steeply pitched roof. An American flag hangs from the front door, which is framed by a small porch and decorative elements. Lush greenery and a white picket fence enhance the welcoming facade.

Home in Saint Michaels

4.85 out of 5 average rating, 121 reviews

Premier St Michaels Cottage- In Town Location

The truly special and restored historic Thomas Blades house is centrally located in the Town of St. Michaels on a quiet st. Shops, restaurants, museums and the Town park with its magnificent water views are steps away. It is a 2 bedroom 1.5 bath cottage with a large paneled family room and a large screened porch. Ideal for a small family or two couples, or a romantic getaway for two. Rate varies by day of the week and season. Discounts for stays of a week or more, or for "last minute" bookings.

Superhost

A spacious waterfront house is shown surrounded by lush trees, with multiple balconies and large windows. A sandy area extends toward the water's edge, and smooth stones form a barrier along the shore, reflecting the natural beauty of the Chesapeake Bay.

Home in Shady Side

4.88 out of 5 average rating, 181 reviews

Cattail Landing- Photographer's Waterfront Retreat

Accepting 2025 bookings as of June 1st.... "Cattail Landing" Spring is here, with beautiful sunsets, new foliage on the trees, and our nest of Bald Eagles! Take our kayaks to explore, or go fishing off our landing. In the afternoon enjoy the magnificent sunsets, a drink on the deck, our outdoor hot tub and/or fireplace. A waterfront retreat on 2 acres in a spacious, charming house on the Western Shore of the Chesapeake Bay. Great for a couples getaway, family reunion, or work from home.

Guest favorite

A modern two-story house features multiple large windows and balconies, allowing for ample natural light. The deck showcases orange lounge chairs positioned for outdoor relaxation, while the well-maintained lawn is bordered by trees displaying autumn colors.

Home in Deale

4.88 out of 5 average rating, 100 reviews

Chesapeake Paradise Lite 4-5 Br 3 Ba Vacation Home

Fabulous 4-5 bedroom 3-bath house with spectacular views on a lush, waterfront point! Shady waterfront lawns & sunny pier, breezy open spaces, sparkling views, & wildlife. Hidden but close to services. Couples & groups love our wonderful, nature-filled spot, a fun, relaxing, serene retreat on the WEST shore of the Chesapeake (close proximity to D.C., Annapolis, Baltimore)! Crabbing, kayaks, fire pit on two country-like acres. See “NEW Amazing” for whole 6-7 bed 4 ba listing of same house.

Superhost

The house is positioned among leafy trees, featuring numerous large windows that brighten the interior. A spacious deck is visible, along with a hot tub. A stone fire pit surrounded by wooden chairs is located in the foreground, inviting outdoor gatherings.

Home in Montross

4.88 out of 5 average rating, 233 reviews

Lakefront/Dock, Woods, 3 Beaches, Kayaks, Hot tub

Our 3 bed/2 full bath+loft house sits in the woods surrounding a beautiful freshwater lake in a neighborhood on the stunning Potomac River! Come enjoy the nearby attractions or simply do nothing at all! We have kayaks/boats for your use right off the private dock. The community has 3 beaches: a private sandy lake beach with a swimming dock, a river-front sandy beach with 15 million+ old shark teeth, and a fossil cliff beach. Fishing! Hot tub on the patio! Bald eagle sightings! Theater Room!

Guest favorite

A spacious backyard features a circular fire pit surrounded by Adirondack chairs. A picnic table sits to one side, and a hot tub is partially shielded by evergreen trees and a wooden fence, providing a serene outdoor retreat.

Home in Cambridge

4.94 out of 5 average rating, 135 reviews

Peaceful Historic House Near Water, with Hot Tub!

Peaceful 3 bedroom/1.5 bath Victorian house near the water. Located in Historic West End, this 1900 house has been recently renovated to accentuate its historic charm while delivering all the modern comforts. Just a short walk from Long Wharf Park, the Choptank River Lighthouse, and downtown Cambridge with great restaurants and shops. Amenities include air conditioning/heating, a hot tub, WIFI, a back deck and grill, front porch with rocking chairs, and a fire pit with Adirondack chairs.

Guest favorite

A private beach area is depicted with soft, sandy ground, featuring two beach chairs under a blue umbrella. Calm waters extend to the horizon, complemented by a wooden dock and a distant view of the opposite shore under a clear, blue sky.

Home in Montross

4.93 out of 5 average rating, 203 reviews

The Glebe

This 3br 2ba home with own private beach is nestled off of the Potomac River and boasts serene and expansive views. Sunbathe on the private beach, cool off in the water, go fishing/crabbing from the dock, or just listen to the waves crash. Whatever it is, you’ll find it absolutely relaxing. Be sure to explore local wineries, breweries, shops and enjoy the community pool and tennis court. It's the perfect getaway house for couples/families or anyone looking for a serene weekend.

Guest favorite

Aerial view of a spacious house surrounded by lush greenery, with a private pier extending into the water. The house features a large, wrap-around porch and several trees dotting the landscape, creating a natural and serene setting by the water.

Home in Scotland

4.91 out of 5 average rating, 130 reviews

Spacious Gorgeous Waterfront Home with Sunset View

Dreamy weekends on the water, the perfect getaway for the entire family and friends in the southern tip of St Mary’s peninsula. This gorgeous newly remodeled house with 5 Bedroom 3.5 Bath sleeps 10 very comfortably. Wake up with amazing water views and access to the water with your own private pier. Spend your day crabbing, fishing, kayaking, or paddle boarding. Amazing beaches at Point Lookout State Park, just a few minutes away. High speed internet, WiFi, and cable.

Top guest favorite

A charming blue cottage is depicted with a gabled roof and white columns framing the entrance. Lush green bushes line the pathway, providing an inviting approach. Clear blue skies and tall trees are visible in the background, enhancing the peaceful setting.

Home in Saint Michaels

4.98 out of 5 average rating, 101 reviews

SM’s Premier Rental Heated Pool opens 4/11/2025

Harbor Hideaway's in- town location and now featuring a PRIVATE POOL is a rare find. Steps away from everything that SM's has to offer. HH is a 1940’s - 1 1/2 story cottage loaded with thoughtful amenities. Airy and appointed with modern/ comfortable furnishings, resort quality linens, a well stocked kitchen; this 2 bdrm /2 B cottage is sure to please! Perfect for 1 to 2 couples, girls' wknds, small family, or anyone just in need of a relaxing getaway.

Guest favorite

Four white Adirondack chairs are arranged on a grassy area, facing the tranquil waterfront. A wooden pier extends into the calm river, surrounded by lush greenery and a single tree providing shade. The clear blue sky complements the serene setting.

Home in Cambridge

4.98 out of 5 average rating, 127 reviews

Waterfront Getaway w/ Pier - Sleeps 10, 4 bedrooms

Escape to our charming & serene waterfront retreat, perfectly situated on the picturesque Choptank River. This 4-bedroom home accommodates 10 guests w/ 7 comfortable beds & offers the ideal blend of relaxation & adventure. Our property comes fully equipped with bikes, kayaks, paddleboards & yard games for endless fun. Unwind and relax on the new pier. The river offers gorgeous sunrises and sunsets. Your perfect waterfront getaway awaits you!

Top guest favorite

The exterior of a renovated home is showcased, featuring a welcoming front porch with seating and adorned by landscaped greenery. A stone pathway leads to the entrance, surrounded by ornamental plants and a patio space. Blue skies and scattered clouds add to the inviting ambiance.

Home in Colonial Beach

5 out of 5 average rating, 30 reviews

Greystone Manor-Magnificently restored! Sleeps 10

Enjoy this magnificently renovated home in the center of town in Colonial Beach. Every inch of this house has been renovated and re-styled with a mix of the past and present. This home boasts 3 large bedrooms (1 King bed with ensuite, 2 Queen beds) and a large loft with 4 twin beds that would make every tweenager delighted! Each bedroom and living space has smart-TV's, and there is plenty of room to entertain and enjoy the outdoor spaces.