Holiday rentals in Leonardtown
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Top-rated holiday rentals in Leonardtown
Guests agree: these stays are highly rated for location, cleanliness and more.
Guest suite in Lusby
4.99 out of 5 average rating, 299 reviewsRiverfront Chalet Kayak/Canoe, pier, breakfast!
This is a two room above the garage apartment with a dedicated side entrance for guests separate from the main house by screens down and a barn door up. Once upstairs you have your own completely private space. Your mini fridge will always be stocked with an assortment of beverages and snacks as well as breakfast items. Enjoy, our kayaks, fire pit or sunset viewing on the pier. Lots of hiking and water sports abound in the area. A short drive south is beautiful Solomon’s island. Boaters welcome!
25 Feb – 4 Mar
Cottage in Leonardtown
4.93 out of 5 average rating, 193 reviewsPotomac River Freedom Cottage
Welcome to the Freedom Cottage! We hope you will have a wonderful relaxing stay. Guest access will be provided via a keycode which will be emailed prior to arrival, spare key hanging inside. Guests will have access to the entire house and grounds (front and rear yard, stretching down to the beach/water). I won't be there for check-in/out but guests are encouraged to call/text during their stay if any questions arise. **Off-season long term rentals available, please contact me to discuss.
19–26 Apr
Tiny home in Saint Inigoes
4.98 out of 5 average rating, 292 reviewsHistoric St.Mary's City at the Lazy Bear Cottage
Inquire first on pets, there is a 40 lb. weight limit total, can be split up between 2 small dogs or 1 at 40lbs 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.
13–20 Oct
Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for Leonardtown holiday rentals
Other great holiday rentals in Leonardtown
Guest suite in Colonial Beach
4.97 out of 5 average rating, 257 reviewsBayview Bungalow
9–16 Jun
Cabin in Lusby
4.91 out of 5 average rating, 203 reviewsPeaceful Waterfront Retreat on The Bay
22–29 Oct
Flat in Lexington Park
4.93 out of 5 average rating, 187 reviewsPrivate apartment with kitchenette
16–23 Nov
Home in Lusby
5.0 out of 5 average rating, 110 reviewsHistoric Rousby Hall, Waterfront, Patuxent River
20–27 Oct
Home in Montross
4.92 out of 5 average rating, 144 reviewsTranquil River Home
17–24 Nov
Guest suite in Leonardtown
4.87 out of 5 average rating, 190 reviewsHappy Guesthouse! Located waterfront
12–19 Feb
Cottage in Saint Leonard
4.99 out of 5 average rating, 101 reviewsCaptain Jack's Bay Hideaway
3–10 Sep
Flat in Leonardtown
4.94 out of 5 average rating, 33 reviewsRetreat at Fenwick
29 Sep – 6 Oct
Home in Leonardtown
4.95 out of 5 average rating, 39 reviewsOld Bay Inn
25 Sep – 2 Oct
Home in Leonardtown
5.0 out of 5 average rating, 19 reviewsWater's Edge Cottage | Luxury Retreat
18–25 Sep
Flat in Leonardtown
4.92 out of 5 average rating, 13 reviewsBeech Creek Farm Apt
4–11 Apr
Home in Leonardtown
5.0 out of 5 average rating, 10 reviewsWaterfront Cottage w/ Incredible Views
19–26 May
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