Holiday rentals near Port of Leonardtown Winery
We found 353 holiday rentals — enter your dates for availability
If you are looking to stay near Port of Leonardtown Winery, take a look at holiday rentals to find the perfect home base for your trip. Whether you’re staying in a holiday home with your children or with friends, you'll find the amenities that you need and want, which might include parking and a washer and dryer. No matter what you're looking for, you're sure to find a property to rent that has what everyone needs, including a place that is accessible or non-smoking.
Holiday rentals with weekly discounts - Port of Leonardtown Winery
Showing deals for:10 Oct - 17 Oct
Image gallery for 7 mins to the beach! Fire Pit, BBQ, Games, Fully Equipped Kitchen & Beach Gear
9.69.6 out of 10 rating
Exceptional
(5 reviews)
7 mins to the beach! Fire Pit, BBQ, Games, Fully Equipped Kitchen & Beach Gear
Colonial Beach, VA
8% off
Price is NZ$3,843
NZ$3,843
NZ$549 per night
includes taxes & fees
Image gallery for Quiet Woodland cottage near St. Leonard's Creek
9.89.8 out of 10 rating
Exceptional
(20 reviews)
Quiet Woodland cottage near St. Leonard's Creek
Lusby, MD
7% off
Price is NZ$1,255
NZ$1,255
NZ$179 per night
includes taxes & fees
Image gallery for Terrace Suite · Terrace Suite - Private Flat in Historic Manor.
9.89.8 out of 10 rating
Exceptional
(29 reviews)
Terrace Suite · Terrace Suite - Private Flat in Historic Manor.
Lusby, MD
9% off
Price is NZ$1,767
NZ$1,767
NZ$252 per night
includes taxes & fees
Image gallery for Enjoy the beach & the woods while you relax & unwind at Wandering Woods Bungalow
1010 out of 10 rating
Exceptional
(8 reviews)
Enjoy the beach & the woods while you relax & unwind at Wandering Woods Bungalow
Montross, VA
7% off
Price is NZ$1,940
NZ$1,940
NZ$277 per night
includes taxes & fees
Image gallery for Courtyard Studio at Bancroft Manor. Cozy Retreat!
1010 out of 10 rating
Exceptional
(23 reviews)
Courtyard Studio at Bancroft Manor. Cozy Retreat!
Lusby, MD
11% off
Price is NZ$1,970
NZ$1,970
NZ$281 per night
includes taxes & fees
Image gallery for Cottage on The Point! Bring your bikes & golf cart, and your pets!
1010 out of 10 rating
Exceptional
(27 reviews)
Cottage on The Point! Bring your bikes & golf cart, and your pets!
Colonial Beach, VA
8% off
Price is NZ$2,065
NZ$2,065
NZ$295 per night
includes taxes & fees
Image gallery for Garden Cottage · Garden Cottage - Fire Pit and Grill near Beaches
1010 out of 10 rating
Exceptional
(30 reviews)
Garden Cottage · Garden Cottage - Fire Pit and Grill near Beaches
Lusby, MD
8% off
Price is NZ$2,091
NZ$2,091
NZ$299 per night
includes taxes & fees
Image gallery for Potomac River Crabbing & Fishing Paradise
9.69.6 out of 10 rating
Exceptional
(20 reviews)
Potomac River Crabbing & Fishing Paradise
Leonardtown, MD
16% off
Price is NZ$2,099
NZ$2,099
NZ$300 per night
includes taxes & fees
Image gallery for Waterfront Solomons Apartment
9.49.4 out of 10 rating
Exceptional
(9 reviews)
Waterfront Solomons Apartment
Solomons, MD
12% off
Price is NZ$2,134
NZ$2,134
NZ$305 per night
includes taxes & fees
Image gallery for Harbor Cottage at the Chesapeake Bay - Dog Friendly Beach
9.89.8 out of 10 rating
Exceptional
(154 reviews)
Harbor Cottage at the Chesapeake Bay - Dog Friendly Beach
St. Leonard, MD
5% off
Price is NZ$2,166
NZ$2,166
NZ$309 per night
includes taxes & fees
Image gallery for Stunning sunsets Leonardtown apartment
1010 out of 10 rating
Exceptional
(6 reviews)
Stunning sunsets Leonardtown apartment
Leonardtown, MD
8% off
Price is NZ$2,240
NZ$2,240
NZ$320 per night
includes taxes & fees
Image gallery for Quiet Clean Cozy Whole Home Sleeps 8 ~ Walk to Water ~ Fast Wi-fi ~ Hike Nearby!
1010 out of 10 rating
Exceptional
(13 reviews)
Quiet Clean Cozy Whole Home Sleeps 8 ~ Walk to Water ~ Fast Wi-fi ~ Hike Nearby!
Colonial Beach, VA
7% off
Price is NZ$2,256
NZ$2,256
NZ$322 per night
includes taxes & fees
Image gallery for Waterfront with spectacular view, close to restaurants and bars
1010 out of 10 rating
Exceptional
(38 reviews)
Waterfront with spectacular view, close to restaurants and bars
Colonial Beach, VA
15% off
Price is NZ$2,306
NZ$2,306
NZ$329 per night
includes taxes & fees
Image gallery for Where peace is sitting by the moonlight
9.89.8 out of 10 rating
Exceptional
(89 reviews)
Where peace is sitting by the moonlight
Kinsale, VA
8% off
Price is NZ$2,364
NZ$2,364
NZ$338 per night
includes taxes & fees
Image gallery for Cozy Virginia Potomac Riverfront Cottage
9.69.6 out of 10 rating
Exceptional
(35 reviews)
Cozy Virginia Potomac Riverfront Cottage
Hague, VA
8% off
Price is NZ$2,398
NZ$2,398
NZ$343 per night
includes taxes & fees
Image gallery for Waterfront cottage for paddle boarding, kayaking, crabbing, and fishing
9.89.8 out of 10 rating
Exceptional
(136 reviews)
Waterfront cottage for paddle boarding, kayaking, crabbing, and fishing
Newburg, MD
8% off
Price is NZ$2,543
NZ$2,543
NZ$363 per night
includes taxes & fees
Image gallery for Waterfront 3-Bed Oasis Perfect for City Getaway
1010 out of 10 rating
Exceptional
(11 reviews)
Waterfront 3-Bed Oasis Perfect for City Getaway
Montross, VA
7% off
Price is NZ$2,811
NZ$2,811
NZ$402 per night
includes taxes & fees
Image gallery for Waterfront home with private dock
9.89.8 out of 10 rating
Exceptional
(13 reviews)
Waterfront home with private dock
Lusby, MD
15% off
Price is NZ$2,816
NZ$2,816
NZ$402 per night
includes taxes & fees
Image gallery for The Hidaway on the Patuxent River<br>Children allowed and welcomed to stay.
9.29.2 out of 10 rating
Wonderful
(9 reviews)
The Hidaway on the Patuxent River<br>Children allowed and welcomed to stay.
Prince Frederick, MD
8% off
Price is NZ$2,827
NZ$2,827
NZ$404 per night
includes taxes & fees
Image gallery for Peace & Tranquile waterfront home, Colonial Beach
9.89.8 out of 10 rating
Exceptional
(16 reviews)
Peace & Tranquile waterfront home, Colonial Beach
Colonial Beach, VA
8% off
Price is NZ$3,127
NZ$3,127
NZ$447 per night
includes taxes & fees
Image gallery for Welcome to Solymar Coastal Living.
1010 out of 10 rating
Exceptional
(6 reviews)
Welcome to Solymar Coastal Living.
Colonial Beach, VA
8% off
Price is NZ$3,185
NZ$3,185
NZ$455 per night
includes taxes & fees
Image gallery for Waterfront retreat with dock, kayaks, and outdoor living. Bring the boat!
1010 out of 10 rating
Exceptional
(7 reviews)
Waterfront retreat with dock, kayaks, and outdoor living. Bring the boat!
Montross, VA
8% off
Price is NZ$3,204
NZ$3,204
NZ$458 per night
includes taxes & fees
Image gallery for Potomac Rvr Woodland Cottage, Polite Pets welcomed, Central Air, Stunning Sunset
9.89.8 out of 10 rating
Exceptional
(53 reviews)
Potomac Rvr Woodland Cottage, Polite Pets welcomed, Central Air, Stunning Sunset
Tall Timbers, MD
23% off
Price is NZ$3,220
NZ$3,220
NZ$460 per night
includes taxes & fees
Image gallery for The Little Blue Cottage on the Crick.
1010 out of 10 rating
Exceptional
(14 reviews)
The Little Blue Cottage on the Crick.
Hollywood, MD
8% off
Price is NZ$3,390
NZ$3,390
NZ$484 per night
includes taxes & fees
Find spaces that suit your style
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Find the best place to stay - Port of Leonardtown Winery
Chesapeake Bay Waterfront View
Sleeps 7 · 3 bedrooms · 2+ bathrooms
9.89.8 out of 10
Exceptionalexceptional
River Refresh - Waterfront with Spa on Placid Bay
Sleeps 8 · 3 bedrooms · 3 bathrooms
1010 out of 10
Exceptionalexceptional
14 reviews(14 reviews)
Waterfront Cottage with Pier & Boatlift on the Beautiful Potomac River
Sleeps 8 · 2 bedrooms · 2 bathrooms
1010 out of 10
Exceptionalexceptional
12 reviews(12 reviews)
2 Mi to Lighthouse: Waterfront Home w/ Dock!
Sleeps 9 · 4 bedrooms · 2 bathrooms
9.09.0 out of 10
Wonderfulwonderful
33 reviews(33 reviews)
Peace of mindOur Book with Confidence guarantee gives you 24/7 support
More quality timeFrom booking to staying, the whole process is simple and enjoyable
All the privacy of homeEnjoy full kitchens, laundry, pools, gardens and more
More for lessMore space, more privacy, more amenities — more value