House vacation rentals in Saint Leonard

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Top-rated house rentals in Saint Leonard

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Guest favourite

Home in Church Creek

4.78 out of 5 average rating, 161 reviews

Waterview cottage on Chesapeake Bay

(The crabs will be running soon, it getting warmer. Great view of the Chesapeake Bay. The Access to the Bay through canal behind the house. Private beach just five minute kayak ride from the house. Bring your own kayaks or rental them from Blackwater Adventures ask for Matt . There floating dock for a kayak launch. Now easy for you to get in and out of your kayak. New picnic table on porch that seat 6 people and two new beds. Two crab traps set for you and also a holding pen on the property.

Nov. 23 – 30

$250 CAD per night

Guest favourite

Home in Lusby

4.99 out of 5 average rating, 114 reviews

Coastal Oasis On The Chesapeake, King Bd sleeps 12

Coastal Oasis On The Chesapeake (PARTY & 4•20 FREE zone) is where you come to: RELAX, DECOMPRESS and RE-CHARGE! You'll experience all the tranquility & majestic beauty of PEACEFUL living on the Chesapeake Bay. You'll awaken to breathtaking & alluring sunrises while also being surrounded by nature's wooded bliss of starry nights. Located 4 miles from Solomon's Island. Contact host for pre-approval of pets, pet fee applies. Unregistered: guests/pets & smoking including marijuana will incur fines!

Aug. 28 – Sep. 4

$841 CAD per night

Guest favourite

Home in Cambridge

4.99 out of 5 average rating, 142 reviews

Sunset Breezes - quiet waterfront retreat

Enjoy our waterfront home styled after historic bay lighthouses. Relax by the water in a hammock under the tall pines. Gather with family and friends around the fire pit. Take in the beautiful water sights while paddling in a kayak, canoe, or paddleboard. Laugh with family and friends while playing corn hole, croquet, or bocce ball waterside. Photograph abundant wildlife - bald eagles, blue herons, osprey, deer, turkey and numerous waterfowl. Dine on the deck while enjoying beautiful sunsets.

Mar. 28 – Apr. 4

$636 CAD per night

Guest favourite

Home in Lusby

4.94 out of 5 average rating, 157 reviews

Waterfront Home on the Chesapeake Bay-Pvt Beach

A commanding view of the Chesapeake Bay. Enjoy walking the beach to Calvert Cliffs, bike to parks, art and cultural events. Enjoy the private beach with plenty of fine sand and gentle waves, great for teaching little one's water skills, playing with your canine companion or fishing/crabbing off the beach. You’ll love this waterfront hideaway because of the location, views, and the ambiance. My place is suburb for couples, solo adventurers, business travelers, families, and canine friends.

Apr. 22 – 29

$597 CAD per night

Guest favourite

Home in St. Leonard

4.91 out of 5 average rating, 162 reviews

Cozy Cottage on the Chesapeake Bay

Tranquility supreme. Sit on the terrace and gaze at the Chesapeake Bay. Sandy beach -- just 50 steps from front door; quiet residential area; nearby antiquing & fishing; Only 75 min. from DC. Finish your book or just replenish your spirit. Enjoy. Oh, one more thing — looking for the perfect place for a retreat for your small DC team? Strategic planning will be even more creative and enjoyable when you have the Chesapeake Bay as your muse. Note: This property is for non-smokers.

Oct. 21 – 28

$368 CAD per night

Guest favourite

Home in Chesapeake Beach

4.91 out of 5 average rating, 111 reviews

Indoor pool/spa nestled in Southern Md. woods.

Contemporary all-brick French manor nestled within 16-acres of secluded woodlands. Indoor pool/spa with waterfall inside a stunning, sunlit atrium. Three bedrooms and three bathrooms accommodate 6-8 people. Centrally located near the Chesapeake Bay where quaint towns include restaurants, antiques, sandy beaches and fishing boat rentals. Centrally located for trips in all directions: Washington, D.C. (35 miles); Annapolis (30 miles) Baltimore (50 miles) and Ocean City (139 miles).

Jul. 12 – 19

$1,159 CAD per night

Guest favourite

Home in Woolford

4.93 out of 5 average rating, 118 reviews

Waterfront Getaway with Dock

Bicyclist's and outdoorsman's dream! Beautiful rancher on two waterfront acres just 4 miles from Blackwater Wildlife Refuge and Harriet Tubman National Park. 10 minute drive from downtown, the Hyatt, and the Ironman starting point as well. Ironman and Eagleman races actually pass right by! Bright, sunny, and newly renovated, it's a great place to hang your hat after a day of hunting, fishing, bicycling, or triatholon-ing! Or just take a weekend to relax on the water!

Oct. 21 – 28

$325 CAD per night

Guest favourite

Home in Lexington Park

4.96 out of 5 average rating, 140 reviews

Private beach retreat in historic St. Mary's City

Nestled next to historic St Mary's City and a lovely state park, your Lucas Cove Beach home awaits you with your own private sandy beach and pier with vast views of the water, new salt water hot tub steps away from the beach, four beautifully furnished bedrooms with Casper mattresses, an upstairs deck with adirondack chairs to take in the water views and amazing sunrises while sipping a beverage or just relaxing, high speed Wi-Fi. Kayaks avail for rent.

Mar. 23 – 30

$670 CAD per night

Guest favourite

Home in Lusby

5.0 out of 5 average rating, 135 reviews

Cove Point Beach Home 1 &1/2 blocks to Beach

"Welcome to our Beach House, located in the unique peaceful private beach community of Cove Point. You'll enjoy the tranquility and the beauty of living less than a 2 min walk to the sandy beach and just a few away from Solomon's Island, MD. Our home was just renovated and is ready for your family to enjoy, offering beach necessities (wagon, chairs, umbrella, & toys) and recreational equipment (bikes & kayaks). This will be your home away from home.

Oct. 4 – 11

$346 CAD per night

Guest favourite

Home in Cambridge

4.92 out of 5 average rating, 180 reviews

Guest House: Farm homestead

Quiet country guest house with 1 BR/ 1 BA, queen sleeper sofa and fully stocked kitchen. Coffee/creamer/sugar provided. Come relax & enjoy the row boat and paddle boat, fishing in the ponds (C&R, No Pond Access from August 24 thru January 30 annually), grill on the deck, watch the bikers roll by (Ironman course) or finish your day by the fire-pit with s'mores! All this and only 3 miles to town and on the Eagle Man and Iron Man race course.

Jun. 28 – Jul. 5

$186 CAD per night

Guest favourite

Home in Lusby

4.99 out of 5 average rating, 175 reviews

Cove Point Cottage with Chesapeake Bay views

Cozy beach house just one block from the sandy Cove Point Beach on the Chesapeake Bay. Grab the beach wagon from the shed, load up with beach chairs, towels and your cooler and take a short stroll to enjoy a day at the beach searching for sharks teeth, shells and swimming in the bay. Rinse off in our outdoor shower and enjoy a relaxing evening by the fireplace, reading in the sunroom overlooking the bay or on the outdoor shady patio

Nov. 7 – 14

$396 CAD per night

Guest favourite

Home in Cambridge

4.9 out of 5 average rating, 146 reviews

Jewell on the Chesapeake

626 Hills Point on Brannocks Bay off of the Chesapeake Bay is one of the most peaceful beautiful places on the Eastern shore. Our recently renovated 3 bedroom single bath home sits on 3 acres of pristine waterfront with a new 80 ft private dock, with 300 ft of Chesapeake shoreline. The perfect place for kayaking, paddle boarding, fishing, crabbing, boating or just relaxing watching the wildlife.

Jul. 28 – Aug. 4

$286 CAD per night