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Holiday homes in Leonardtown

Enjoy your stay and find the best Holiday homes in Leonardtown at affordable prices

Searching for a holiday home in Leonardtown (Maryland)? Explore a great selection of vacation homes in Leonardtown to find the one that best fits to your needs, starting from $149 per night. Holiday homes offer a relaxing escape, providing a cozy retreat for vacationers seeking a home away from home.

Holiday-homes in Leonardtown and region (50 miles)
Waterfront Potomac River Gem with Kayaks and Dock! in Montross, USA

Waterfront Potomac River Gem with Kayaks...

Holiday home in Montross near Leonardtown, Maryland
Situated 38 km from George Washington Birthplace National Monument and 39 km from Memorial House, Waterfront Potomac River Gem with Kayaks and Dock! f...
  • Parking
  • Pets allowed
  • Outdoor pool
  • Swimming pool
  • Swimming Pool

no reviews

from $249.33 Show details »

Montross Home with Private Pool and Yard! in Montross, USA

Montross Home with Private Pool and Yard...

Holiday home in Montross near Leonardtown, Maryland
Montross Home with Private Pool and Yard! offers accommodation in Montross, 22 km from Memorial House.
  • Parking
  • Pets allowed
  • Outdoor pool
  • Swimming pool
  • Swimming Pool

no reviews

from $248.00 Show details »

Montross Retreat with Private Boat Dock! in Montross, USA

Montross Retreat with Private Boat Dock!

Holiday home in Montross near Leonardtown, Maryland
Montross Retreat with Private Boat Dock! offers accommodation in Montross, 35 km from Memorial House.
  • Parking
  • Pets allowed

no reviews

from $149.00 Show details »

Waterfront Montross Home with Private Boat Slip! in Montross, USA

Waterfront Montross Home with Private Bo...

Holiday home in Montross near Leonardtown, Maryland
Featuring a spa bath, Waterfront Montross Home with Private Boat Slip! is set in Montross.
  • Parking
  • Bath
  • Hairdryer
  • Iron
  • Balcony

no reviews

from $248.14 Show details »

Tranquil Port Republic Home with Water Views! in Prince Frederick, USA

Tranquil Port Republic Home with Water V...

Holiday home in Prince Frederick near Leonardtown, Maryland
Located in Prince Frederick, 18 km from New Carrollton and 22 km from Annmarie Garden, Tranquil Port Republic Home with Water Views! provides accommod...
  • Parking
  • Pets allowed

no reviews

from $465.67 Show details »

Isle Have Another - 1 Block to Colonial Beach! in Colonial Beach, USA

Isle Have Another - 1 Block to Colonial...

Holiday home in Colonial Beach near Leonardtown, Maryland
Set in Colonial Beach, 18 km from George Washington Birthplace National Monument and 19 km from Memorial House, Isle Have Another - 1 Block to Colonia...
  • Parking

Exceptional 2 Reviews 10.0

from $236.00 Show details »

The Blue Crab Cottage - 3 Blocks From The Beach! in Colonial Beach, USA

The Blue Crab Cottage - 3 Blocks From Th...

Holiday home in Colonial Beach near Leonardtown, Maryland
Situated in Colonial Beach, 19 km from George Washington Birthplace National Monument, 19 km from Memorial House and 32 km from Aqua-Land Marina, The ...
  • Parking
  • Pets allowed
  • Shower
  • TV
  • Air conditioning

Superb 9 Reviews 9.3

from $157.00 Show details »

Chic Cottage with Private Yard Steps to Beach! in Colonial Beach, USA

Chic Cottage with Private Yard Steps to...

Holiday home in Colonial Beach near Leonardtown, Maryland
Situated in Colonial Beach, 20 km from George Washington Birthplace National Monument and 20 km from Memorial House, Chic Cottage with Private Yard St...
  • Parking
  • Pets allowed

no reviews

from $191.33 Show details »

Colonial Beach House with Patio 2 Blocks to Beach! in Colonial Beach, USA

Colonial Beach House with Patio 2 Blocks...

Holiday home in Colonial Beach near Leonardtown, Maryland
Comfy Colonial Beach House, 2 Blocks to Beach! enjoys a location in Colonial Beach, just 18 km from Memorial House and 32 km from Aqua-Land Marina.
  • Parking
  • Pets allowed

Exceptional 9 Reviews 10.0

from $189.00 Show details »

Private 5BR Home 4 Min Walk to Colonial Beach, VA! in Colonial Beach, USA

Private 5BR Home 4 Min Walk to Colonial...

Holiday home in Colonial Beach near Leonardtown, Maryland , 221 Madison Street
Private 5BR Home 4 Min Walk to Colonial Beach, VA! is located in Colonial Beach, 18 km from George Washington Birthplace National Monument, and provid...
  • Parking
  • Pets allowed
  • Family rooms

no reviews

from $300.20 Show details »

Waterfront Cottage with Private Beach and Deck! in Colonial Beach, USA

Waterfront Cottage with Private Beach an...

Holiday home in Colonial Beach near Leonardtown, Maryland
Waterfront Cottage with Private Beach and Deck! is a beachfront property located in Colonial Beach, 15 km from George Washington Birthplace National M...
  • Parking

Fabulous 2 Reviews 9.0

from $421.00 Show details »

Sunrise Waterfront Cottage with Dock & Kayaks! in Scotland, USA

Sunrise Waterfront Cottage with Dock & K...

Holiday home in Scotland near Leonardtown, Maryland , 14511 East Way
Boasting lake views, Sunrise Waterfront Cottage with Dock & Kayaks! offers accommodation with water sports facilities and a patio, around 11 km from C...
  • Parking
  • Family rooms

no reviews

from $352.33 Show details »

Delightful Pet Friendly Family Home In Great Location! home in Huntingtown, USA

Delightful Pet Friendly Family Home In G...

Holiday home in Huntingtown near Leonardtown, Maryland
Situated in Huntingtown in the Maryland region, Delightful Pet Friendly Family Home In Great Location! home has a garden.
  • Parking
  • Pets allowed

no reviews

from $233.38 Show details »

JuJus Place Warsaw House with Deck and Tree Swings! in Warsaw, USA

JuJus Place Warsaw House with Deck and T...

Holiday home in Warsaw near Leonardtown, Maryland
JuJus Place Warsaw House with Deck and Tree Swings! enjoys a location in Warsaw, just 32 km from George Washington Birthplace National Monument and 32...
  • Parking
  • Refrigerator
  • Fan
  • Toilet
  • Microwave

Exceptional 6 Reviews 9.7

from $304.33 Show details »

Historic Hoopersville Getaway on Chesapeake Bay! in Fishing Creek, USA

Historic Hoopersville Getaway on Chesape...

Holiday home in Fishing Creek near Leonardtown, Maryland
Located in Fishing Creek in the Maryland region, Historic Hoopersville Getaway on Chesapeake Bay! features a patio.
  • Parking
  • Pets allowed

Disappointing 1 Reviews 4.0

from $565.33 Show details »

Heathsville Home with Sunroom Less Than 10 Mi to Beach! in Heathsville, USA

Heathsville Home with Sunroom Less Than...

Holiday home in Heathsville near Leonardtown, Maryland
Offering free WiFi, Heathsville Home with Sunroom Less Than 10 Mi to Beach! is set on the beachfront in Heathsville.
  • Parking
  • Pets allowed

Exceptional 2 Reviews 10.0

from $217.33 Show details »

Adorable Beach Cottage with Hot Tub and Tropical Bar! in Chesapeake Beach, USA

Adorable Beach Cottage with Hot Tub and...

Holiday home in Chesapeake Beach near Leonardtown, Maryland
Situated in Chesapeake Beach, Adorable Beach Cottage with Hot Tub and Tiki Bar! features accommodation with a balcony and free WiFi.
  • Parking

no reviews

from $303.67 Show details »

Waterfront Cottage with Fishing Dock and Fireplace! in Heathsville, USA

Waterfront Cottage with Fishing Dock and...

Holiday home in Heathsville near Leonardtown, Maryland
Located in Heathsville, Northern Neck Waterfront Home with Dock and View! provides accommodation with a balcony and free WiFi.
  • Parking
  • Pets allowed
  • Internet facilities
  • Shower
  • Hairdryer

no reviews

from $456.00 Show details »

Private 2BR Luxe Suite Natl Harbor DC MD VA in Waldorf, USA

Private 2BR Luxe Suite Natl Harbor DC MD...

Holiday home in Waldorf near Leonardtown, Maryland , 10781 Cheryl Turn
Located in Waldorf, 30 km from National Harbor and 33 km from Alexandrias Christ Church, Private 2BR Luxe Suite Natl Harbor DC MD VA provides accommod...
  • Family rooms

Exceptional 40 Reviews 9.7

from $281.33 Show details »

Riverfront Retreat on 4 Acres with Private Dock in Heathsville, USA

Riverfront Retreat on 4 Acres with Priva...

Holiday home in Heathsville near Leonardtown, Maryland
Riverfront Retreat on 4 Acres with Private Dock is set in Heathsville.
  • Parking
  • Pets allowed

no reviews

from $472.33 Show details »

North Beach Cottage - Walk to Chesapeake Bay in North Beach, USA

North Beach Cottage - Walk to Chesapeake...

Holiday home in North Beach near Leonardtown, Maryland
North Beach Cottage - Walk to Chesapeake Bay is situated in North Beach, 400 metres from North Beach, and features a patio, garden, and free WiFi.
  • Parking

no reviews

from $286.00 Show details »

North Beach Blue Heron Bungalow with Backyard in North Beach, USA

North Beach Blue Heron Bungalow with Bac...

Holiday home in North Beach near Leonardtown, Maryland
Situated in North Beach, 1.2 km from North Beach and 45 km from Addison Road-Seat Pleasant, North Beach Blue Heron Bungalow with Backyard provides acc...
  • Parking
  • Pets allowed

no reviews

from $286.00 Show details »

Updated North Beach Cottage Pet Friendly! in Deale, USA

Updated North Beach Cottage Pet Friendly...

Holiday home in Deale near Leonardtown, Maryland
Situated in Deale, Updated North Beach Cottage Pet Friendly! features accommodation with a patio and free WiFi.
  • Parking
  • Pets allowed
  • Outdoor pool
  • Swimming pool
  • Swimming Pool

no reviews

from $321.33 Show details »

Waterfront North Beach Home about 2 Mi to Beach! in Deale, USA

Waterfront North Beach Home about 2 Mi t...

Holiday home in Deale near Leonardtown, Maryland
Waterfront North Beach Home about 2 Mi to Beach! offers accommodation in Deale, 45 km from Annapolis Harbor.
  • Parking
  • Pets allowed

no reviews

from $375.67 Show details »

Rivers Edge Retreat with Kayaks and River Access! in Reedville, USA

Rivers Edge Retreat with Kayaks and Rive...

Holiday home in Reedville near Leonardtown, Maryland
Set in Reedville in the Virginia region, Rivers Edge Retreat with Kayaks and River Access! features a balcony and garden views.
  • Parking
  • Pets allowed

Very good 1 Reviews 8.0

from $497.33 Show details »

Number of Holiday homes in Leonardtown 37
Number of guest ratings 96
Average price per night $380.76
Lowest price per night $149.00
Highest price per night $938.33

Most popular Holiday-homes in Leonardtown

The most popular Holiday-homes in Leonardtown based on average guest rating (Top 10).

Cheapest Holiday-homes in Leonardtown

The cheapest Holiday-homes in Leonardtown based on room rate per night (Top 10).

Most booked Holiday-homes in Leonardtown

The most booked Holiday-homes in Leonardtown based on popularity with guests (Top 10).

Holiday homes in Leonardtown (Maryland), comfortable and familiar

Staying in a holiday or vacation home in Leonardtown can be a great alternative to a hotel or resort. They can range from small cottages to luxurious villas, and are often located in popular tourist destinations such as beaches or mountains. One of the main benefits is the privacy and flexibility that comes with having your own space. Unlike a hotel room, a holiday home provides you with a living area, kitchen, and sometimes even outdoor space, allowing you to cook your own meals, relax in comfort, and enjoy the company of your friends or family without the interruptions of other guests.

Holiday homes often offer more space than a hotel room. This can be particularly useful for families or groups of friends traveling together, who may need more than one room or want to avoid the cramped feeling of a single hotel room. They can also provide a more authentic travel experience, allowing guests to immerse themselves in the local culture and lifestyle. This can be particularly appealing for those who prefer to stay in quieter, residential areas away from the hustle and bustle of tourist hotspots.

Find the best Holiday home in Leonardtown for your needs

Holiday homes should offer a comfortable and enjoyable stay, providing all the necessary amenities and conveniences to make your vacation experience memorable. At a minimum, your holiday home in Leonardtown should offer a clean and well-maintained living space with comfortable furnishings, adequate lighting, and climate control.

In addition to basic amenities such as a fully equipped kitchen, comfortable bedding, and clean linens and towels, holiday homes should also offer modern conveniences such as Wi-Fi, cable or streaming TV, and laundry facilities. A private outdoor space, such as a balcony or terrace, can also add to the overall enjoyment. They can also offer additional features such as a swimming pool, hot tub, or outdoor grill. Location is also important, for example, close to popular tourist attractions, restaurants and shopping areas.

Accommodation data and pictures provided by Booking.com