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 favourite

Guest suite in Lusby

4.99 out of 5 average rating, 299 reviews

Riverfront 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

€ 138 per night
Guest favourite

Cottage in Leonardtown

4.93 out of 5 average rating, 193 reviews

Potomac 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

€ 211 per night
Guest favourite

Tiny home in Saint Inigoes

4.98 out of 5 average rating, 292 reviews

Historic 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

€ 86 per night

Popular amenities for Leonardtown holiday rentals

Stay near Leonardtown's top sights

Leonardtown Wharf Park14 locals recommend
The Front Porch23 locals recommend
Salsas Mexican Cafe3 locals recommend
Olde Town Pub11 locals recommend
The Slice House13 locals recommend
Social12 locals recommend

Other great holiday rentals in Leonardtown

Guest favourite

Guest suite in Colonial Beach

4.97 out of 5 average rating, 257 reviews

Bayview Bungalow

9–16 Jun

€ 134 per night
Guest favourite

Cabin in Lusby

4.91 out of 5 average rating, 203 reviews

Peaceful Waterfront Retreat on The Bay

22–29 Oct

€ 154 per night
Guest favourite

Flat in Lexington Park

4.93 out of 5 average rating, 187 reviews

Private apartment with kitchenette

16–23 Nov

€ 75 per night
Guest favourite

Home in Lusby

5.0 out of 5 average rating, 110 reviews

Historic Rousby Hall, Waterfront, Patuxent River

20–27 Oct

€ 758 per night
Superhost

Home in Montross

4.92 out of 5 average rating, 144 reviews

Tranquil River Home

17–24 Nov

€ 159 per night
Guest favourite

Guest suite in Leonardtown

4.87 out of 5 average rating, 190 reviews

Happy Guesthouse! Located waterfront

12–19 Feb

€ 135 per night
Guest favourite

Cottage in Saint Leonard

4.99 out of 5 average rating, 101 reviews

Captain Jack's Bay Hideaway

3–10 Sep

€ 161 per night
Guest favourite

Flat in Leonardtown

4.94 out of 5 average rating, 33 reviews

Retreat at Fenwick

29 Sep – 6 Oct

€ 131 per night
Guest favourite

Home in Leonardtown

4.95 out of 5 average rating, 39 reviews

Old Bay Inn

25 Sep – 2 Oct

€ 148 per night
Guest favourite

Home in Leonardtown

5.0 out of 5 average rating, 19 reviews

Water's Edge Cottage | Luxury Retreat

18–25 Sep

€ 378 per night
Guest favourite

Flat in Leonardtown

4.92 out of 5 average rating, 13 reviews

Beech Creek Farm Apt

4–11 Apr

€ 148 per night
Superhost

Home in Leonardtown

5.0 out of 5 average rating, 10 reviews

Waterfront Cottage w/ Incredible Views

19–26 May

€ 333 per night

Destinations to explore