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 Secluded waterfront house to relax or enjoy water activities from private pier
9.89.8 out of 10 rating
Exceptional
(27 reviews)
Secluded waterfront house to relax or enjoy water activities from private pier
Cobb Island, MD
8% off
Price is NZ$5,729
NZ$5,729
NZ$818 per night
includes taxes & fees
Image gallery for NEW: Life on the River! Luxury estate with jacuzzi and private pier!
1010 out of 10 rating
Exceptional
(29 reviews)
NEW: Life on the River! Luxury estate with jacuzzi and private pier!
St. Leonard, MD
8% off
Price is NZ$5,630
NZ$5,630
NZ$804 per night
includes taxes & fees
Image gallery for Large RENOVATED 6 bedroom 5 bath private home with LOTS of space!
9.49.4 out of 10 rating
Exceptional
(32 reviews)
Large RENOVATED 6 bedroom 5 bath private home with LOTS of space!
St. Leonard, MD
8% off
Price is NZ$9,431
NZ$9,431
NZ$1,347 per night
includes taxes & fees
Image gallery for Stunning luxury waterfront beach house 90 minutes from the Nations Capital.
1010 out of 10 rating
Exceptional
(8 reviews)
Stunning luxury waterfront beach house 90 minutes from the Nations Capital.
Piney Point, MD
9% off
Price is NZ$9,454
NZ$9,454
NZ$1,351 per night
includes taxes & fees
Image gallery for Year-Round River Escape with Beach & Indoor Heated Pool, Hot Tub and more!
1010 out of 10 rating
Exceptional
(26 reviews)
Year-Round River Escape with Beach & Indoor Heated Pool, Hot Tub and more!
Hague, VA
8% off
Price is NZ$14,003
NZ$14,003
NZ$2,000 per night
includes taxes & fees
Image gallery for Cottage Located on the Patuxent River!
1010 out of 10 rating
Exceptional
(39 reviews)
Cottage Located on the Patuxent River!
Prince Frederick, MD
9% off
Price is NZ$4,080
NZ$4,080
NZ$583 per night
includes taxes & fees
Image gallery for 2 blocks from Bay! Private beach! Boat launch! Kayak! Hike! Fossil Hunt!
1010 out of 10 rating
Exceptional
(5 reviews)
2 blocks from Bay! Private beach! Boat launch! Kayak! Hike! Fossil Hunt!
Prince Frederick, MD
17% off
Price is NZ$3,706
NZ$3,706
NZ$529 per night
includes taxes & fees
Image gallery for 5 bedroom, 8 bed, 3 story house a block from beach
9.69.6 out of 10 rating
Exceptional
(15 reviews)
5 bedroom, 8 bed, 3 story house a block from beach
St. Leonard, MD
5% off
Price is NZ$4,892
NZ$4,892
NZ$699 per night
includes taxes & fees
Image gallery for Privacy and space with world class views
9.89.8 out of 10 rating
Exceptional
(85 reviews)
Privacy and space with world class views
Montross, VA
10% off
Price is NZ$4,624
NZ$4,624
NZ$661 per night
includes taxes & fees
Image gallery for Inviting and Serene Home on Monroe Bay Creek
1010 out of 10 rating
Exceptional
(71 reviews)
Inviting and Serene Home on Monroe Bay Creek
Colonial Beach, VA
12% off
Price is NZ$4,566
NZ$4,566
NZ$652 per night
includes taxes & fees
Image gallery for Bayview Breeze w/screened porch
1010 out of 10 rating
Exceptional
(11 reviews)
Bayview Breeze w/screened porch
Colonial Beach, VA
8% off
Price is NZ$4,776
NZ$4,776
NZ$682 per night
includes taxes & fees
Image gallery for Amazing Sunsets in Jackson Creek Waterfront Home
9.49.4 out of 10 rating
Exceptional
(12 reviews)
Amazing Sunsets in Jackson Creek Waterfront Home
Kinsale, VA
8% off
Price is NZ$3,424
NZ$3,424
NZ$489 per night
includes taxes & fees
Image gallery for Great River Views, walk to Beach !
9.89.8 out of 10 rating
Exceptional
(83 reviews)
Great River Views, walk to Beach !
Colonial Beach, VA
8% off
Price is NZ$4,497
NZ$4,497
NZ$642 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 House Right on the Potomac River - Great Sunrises & Sunsets
1010 out of 10 rating
Exceptional
(92 reviews)
House Right on the Potomac River - Great Sunrises & Sunsets
Hague, VA
8% off
Price is NZ$6,148
NZ$6,148
NZ$878 per night
includes taxes & fees
Image gallery for Blue Heron Retreat on the Water
1010 out of 10 rating
Exceptional
(11 reviews)
Blue Heron Retreat on the Water
Solomons, MD
8% off
Price is NZ$4,529
NZ$4,529
NZ$647 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 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 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 Stunning Water Front Home with Private Dock and Beach and Sunsets
1010 out of 10 rating
Exceptional
(24 reviews)
Stunning Water Front Home with Private Dock and Beach and Sunsets
Lusby, MD
7% off
Price is NZ$7,779
NZ$7,779
NZ$1,111 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 Modern 3-bedroom house in Colonial Beach with access to pool and private hot tub
1010 out of 10 rating
Exceptional
(5 reviews)
Modern 3-bedroom house in Colonial Beach with access to pool and private hot tub
Colonial Beach, VA
8% off
Price is NZ$3,944
NZ$3,944
NZ$563 per night
includes taxes & fees
Image gallery for Magnificent Water Front Property
9.09.0 out of 10 rating
Wonderful
(16 reviews)
Magnificent Water Front Property
Solomons, MD
12% off
Price is NZ$9,113
NZ$9,113
NZ$1,302 per night
includes taxes & fees
Image gallery for Unplug and unwind at your Leonardtown waterfront vacation home!
9.09.0 out of 10 rating
Wonderful
(6 reviews)
Unplug and unwind at your Leonardtown waterfront vacation home!
Leonardtown, MD
8% off
Price is NZ$4,186
NZ$4,186
NZ$598 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