Drayden holiday homes

We found 141 holiday rentals — enter your dates for availability
Discover a selection of holiday rentals in Drayden that are perfect for your trip. Whether you’re staying in a holiday home with your children and pets or just with friends, you'll find the amenities that you need and want, which might include parking and a fireplace. No matter what you're looking for, you'll be able to choose a property to rent for everyone's needs, including a place that's non-smoking or offers accessibility.

Holiday rentals with weekly discounts – Drayden

Showing deals for:18 Dec - 25 Dec

Room
Property grounds
Exterior
Dining
Exceptional
(9 reviews)

Houseboat on Solomons Island

Solomons

8% off
NZ$3,956
for 7 nights, 1 houseboat
NZ$565 per night
includes taxes & fees
Houseboat on Solomons Island
Exterior
White sand beach
Exterior
Dining
Exceptional
(61 reviews)

Beach & River Retreat. Spectacular house with private sand beach and hot tub!

Montross

8% off
NZ$9,469
for 7 nights, 1 home
NZ$1,353 per night
includes taxes & fees
Beach & River Retreat. Spectacular house with private sand beach and hot tub!
Enjoy morning coffee or evening drinks on the private waterfront deck
Wake up to serene water views from the primary suite
Private waterfront setting with direct access to the shoreline
Dine with panoramic waterfront views—perfect for unforgettable group meals
Exceptional
(21 reviews)

🏖Chesapeake Bay Retreat – Private Beach • Fire Pit • WiFi • 2 Homes in 1

Scotland

8% off
NZ$9,373
for 7 nights, 1 home
NZ$1,339 per night
includes taxes & fees
🏖Chesapeake Bay Retreat – Private Beach • Fire Pit • WiFi • 2 Homes in 1
Exterior
Sunrise on your private beach
Exterior
Aerial view
Exceptional
(36 reviews)

Sea Glass Beach House! Large sand beach, dock and hot tub! Pets welcome!

Hague

7% off
NZ$4,655
for 7 nights, 1 home
NZ$665 per night
includes taxes & fees
Sea Glass Beach House! Large sand beach, dock and hot tub! Pets welcome!
Dining
Private kitchen
Interior
Room
Exceptional
(24 reviews)

WATERFRONT 3000 SQFT HOME W/ PIER, WRAP PORCH, KAYAK, PADDLE BOARD, FIRE PIT

Piney Point

7% off
NZ$6,776
for 7 nights, 1 home
NZ$968 per night
includes taxes & fees
WATERFRONT 3000 SQFT HOME W/ PIER, WRAP PORCH, KAYAK, PADDLE BOARD, FIRE PIT
There is extra bedding for each room and it is all washed between each guest.
Piney Point Light House and underwater park with German U-Boat is 5 miles away.
Property grounds
A quiet and relaxing road with an abundance of deer, birds, squirrels, and crab.
Exceptional
(66 reviews)

Potomac River Woodland Cottage, Polite Pets welcome Central Air Stunning Sunset

Tall Timbers

12% off
NZ$3,582
for 7 nights, 1 cottage
NZ$512 per night
includes taxes & fees
Potomac River Woodland Cottage, Polite Pets welcome Central Air Stunning Sunset
Dining room showing steps to loft. Dining room seats 8-10
French doors from kitchen go to backyard wrap-around deck
Entryway from front door showing ramp and steps from living room to kitchen area
Ariel view of the house, pool, dock, lagoon and beautiful Chesapeake Bay.
Wonderful
(22 reviews)

Serenity Bay-Spacious House-Prv Pool-6 bdrms-5baths-Hot Tub-AskAbout 2NightStays

Lexington Park

5% off
NZ$8,986
for 7 nights, 1 home
NZ$1,284 per night
includes taxes & fees
Serenity Bay-Spacious House-Prv Pool-6 bdrms-5baths-Hot Tub-AskAbout 2NightStays
Exterior
Exterior
Exterior
Exterior
Exceptional
(12 reviews)

An amazing large group vacation home with elevator and breathtaking views.

Montross

7% off
NZ$10,913
for 7 nights, 1 home
NZ$1,559 per night
includes taxes & fees
An amazing large group vacation home with elevator and breathtaking views.
A wall of windows in main living area offers stunning panoramic Potomac views.
Deck view at dusk.
Dining room
Looking from kitchen and dining room to the primary bedroom.
Exceptional
(17 reviews)

Water's Edge Cottage -- Luxury Retreat -- 180 Degree Potomac Views

Leonardtown

8% off
NZ$5,245
for 7 nights, 1 home
NZ$749 per night
includes taxes & fees
Water's Edge Cottage -- Luxury Retreat -- 180 Degree Potomac Views
Beach
Exterior
Beach
Beach
Exceptional
(45 reviews)

The Beach Retreat is a cozy beach Villa with Hottub overlooking a private beach.

Montross

7% off
NZ$4,516
for 7 nights, 1 home
NZ$645 per night
includes taxes & fees
The Beach Retreat is a cozy beach Villa with Hottub overlooking a private beach.
Living room
Coffee, tea, cream, and sugar provided
Front porch
Side view
Exceptional
(16 reviews)

Two bedroom two bath home on charming Solomons Island

Solomons

8% off
NZ$4,244
for 7 nights, 1 apartment
NZ$606 per night
includes taxes & fees
Two bedroom two bath home on charming Solomons Island
The deck is for your use
View from driveway
Interior
Kitchen is stocked with pots pans, dishes etc
Exceptional
(17 reviews)

Solomons Island with views of harbor!

Solomons

8% off
NZ$2,610
for 7 nights, 1 apartment
NZ$373 per night
includes taxes & fees
Solomons Island with views of harbor!

  • Peace of mind

    Our Book with Confidence guarantee gives you 24/7 support

  • More quality time

    From booking to staying, the whole process is simple and enjoyable

  • All the privacy of home

    Enjoy full kitchens, laundry, pools, gardens and more

  • More for less

    More space, more privacy, more amenities — more value

Explore the waterfront setting in Drayden

Learn about the unique charm of Drayden with a stay in a holiday home rental. One of the city's many top draws is its boating. Whether you're planning a family holiday, romantic stay or trip with friends, holiday rentals offer features like full kitchens and laundry facilities for a more convenient stay.

Activities and attractions in Drayden

Do you want to discover attractions to see in the area? Although it can be tempting to stay in your comfortable holiday rental, you'll want to experience everything that makes Drayden a fun place to get away to. Here are some of the top attractions to put on your list, all within 30 miles (48.2 km) of the city centre:

  • Michael P. O'Brien Athletics and Recreation Center (3 mi / 4.8 km)
  • Breton Bay Golf Course (13 mi / 20.9 km)
  • General's Ridge Vineyard and Winery (14 mi / 22.5 km)
  • Hague Winery (11.8 mi / 19.1 km)
  • Port of Leonardtown Winery (14 mi / 22.5 km)
  • Chesapeake Hills Golf Course (15.2 mi / 24.5 km)

Exploring the natural landscape of Drayden

Whether you're looking for exciting outdoor activities or just want to spend some time taking in the scenery, Drayden is a great place to get outside. Here are a few of the area's noteworthy natural features, all within 30 miles (48.2 km) of the city centre:

  • Piney Point Beach (3.3 mi / 5.4 km)
  • Saint George Island Beach (3.4 mi / 5.4 km)
  • Elms Beach Park (6.1 mi / 9.8 km)
  • St. Mary's River State Park (8 mi / 12.9 km)
  • St. Clement's Island State Park (15.4 mi / 24.8 km)
  • Cove Point Beach (15.7 mi / 25.2 km)

Frequently asked questions

What is the best area to stay in Drayden when booking a holiday rental?
When considering a holiday rental in Drayden, Maryland, the nearby area of Leonardtown is an excellent choice. This charming town offers a delightful mix of historical charm and modern amenities, making it an inviting spot for visitors. You'll find a variety of properties available, from quaint cottages to spacious family homes, providing plenty of options to suit different needs.Leonardtown is known for its picturesque waterfront and vibrant arts scene, with attractions such as the St. Mary's County Historical Society and the scenic Leonardtown Wharf Park, where you can enjoy leisurely strolls or picnics by the water. The town also hosts various events throughout the year, adding to its lively option.Another appealing area is California, which is just a short drive away from Drayden. This neighbourhood features a range of rental properties that cater to both couples and families. Here, you can explore the nearby California Plaza, which offers shopping and dining options, and the beautiful Patuxent River, superb for outdoor activities like kayaking or fishing.
Where are the best areas for renting a beach house in Drayden?
For renting a beach house in Drayden, Maryland, the area along the Patuxent River is particularly appealing. This stretch offers scenic waterfront properties with direct access to the river, great for those looking to enjoy water activities like kayaking or fishing. Many of the beach houses in this region come with desirable amenities such as private docks, spacious decks for entertaining, and outdoor grills, making them ideal for families or groups looking to relax by the water.Additionally, the nearby St. Mary's River State Park provides opportunities for hiking and nature walks, with several rentals situated close to the park's entrance. Properties here often feature large backyards, fire pits, and modern kitchens to accommodate home-cooked meals after a day of outdoor adventures. The charming local community also offers quaint shops and restaurants, enhancing the overall experience for travellers seeking a peaceful retreat by the water.
What is the most popular type of holiday rental accomodation in Drayden?
In Drayden, holiday houses are the predominant type of holiday rental, with several available throughout the area. These properties typically provide ample space, featuring multiple bedrooms and fully equipped kitchens, making them suitable for families or larger groups. Many of these homes also include outdoor spaces such as gardens or patios, allowing guests to enjoy the natural surroundings.
Are there any family house rentals in Drayden?
In Drayden, Maryland, there are several family-friendly house rentals available, superb for a memorable getaway. The area is known for its serene surroundings and proximity to the water, making it an excellent choice for families looking to enjoy nature. Many of these homes offer spacious living areas for relaxation, fully equipped kitchens ideal for preparing family meals, and outdoor spaces where children can play or families can gather for a barbecue.Visitors can explore the nearby Patuxent River, which provides opportunities for fishing and kayaking, adding to the outdoor experience. Additionally, the locale is not far from attractions such as historic sites and nature reserves, offering a mix of leisure and adventure.
Are there pet-friendly house rentals in Drayden?
In Drayden, Maryland, there are several pet-friendly house rentals available, providing travellers with welcoming accommodations for their furry companions. Many of these properties come equipped with essential amenities such as fully equipped kitchens, spacious living areas, and outdoor spaces where pets can enjoy the fresh air.The area is surrounded by natural beauty, making it a great choice for pet owners who appreciate outdoor activities. Nearby, the St. Mary's River State Park offers scenic trails ideal for walking and exploring with pets, while the Potomac River provides opportunities for fishing and boating. The peaceful setting of Drayden allows for a relaxing getaway, with plenty of space for pets to roam and enjoy the surroundings.
Are there any remote work holiday rentals in Drayden?
In Drayden, Maryland, there are several remote work holiday rentals available, making it a suitable destination for those looking to combine work with a peaceful getaway. Many of these properties feature essential amenities for remote work, including reliable Wi-Fi and designated workspaces with desks and chairs. This allows guests to comfortably manage their work tasks while enjoying the tranquility of the area.The surroundings of Drayden offer a serene environment, great for relaxing after a day of work, with easy access to local parks and scenic views. To help narrow your search, insert your dates and apply the "WiFi" filter on Bookabach.
What are popular rental amenities in Drayden?
In Drayden, popular rental amenities include sofa beds, which provide additional sleeping space for guests, and balconies that offer a pleasant outdoor area to relax and enjoy the surroundings. Many properties are located near the beach, allowing easy access to the sandy shores and scenic views. Additionally, some rentals boast direct beach views, enhancing the overall experience for travellers seeking a coastal getaway.
What are the top attractions in Drayden?
In Drayden, Maryland, visitors can enjoy a tranquil escape with a focus on natural beauty and outdoor activities. The nearby Patuxent River provides opportunities for kayaking and fishing, making it a popular spot for those who appreciate water-based recreation. The surrounding area is rich in scenic landscapes, great for hiking and exploring.For a taste of local history, the St. Mary's County Historical Society is not far, offering insights into the region's past. Additionally, the idyllic landscape of the nearby St. Mary's City, with its historical sites and reconstructed historic buildings, is a great place to delve into early American history.The charming waterfront at Leonardtown, just a short drive away, has a selection of shops and restaurants, providing a lovely atmosphere for a leisurely day out.
Are all fees included in the Drayden holiday homes prices shown on Bookabach?
Bookabach provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
Are there any Drayden holiday homes with parking?
Bookabach offers a wide selection of holiday homes in Drayden with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
Are there any discounts for Drayden holiday homes?
You can find great discounts on holiday homes in Drayden on Bookabach, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for last-minute bookings, and early-bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Can I change or cancel my Drayden holiday home booking on Bookabach?
To find Drayden holiday rentals with free cancellation, just use Bookabach's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Whether you're adjusting your plans or looking for flexible payment options, Bookabach makes it easy to book with confidence.
Can I find long-stay holiday homes in Drayden?
A long-stay holiday home in Drayden is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Can I plan a group trip on Bookabach?
Bookabach's Trip Planner makes organising group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favourites, and build the perfect itinerary together.
How early should I book a Drayden holiday home?
Book your Drayden holiday home at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price. *Based on analysis of Bookabach booking and occupancy data for 2024 stays.
How much does it cost to rent a holiday home in Drayden?
Prices for holiday homes in Drayden vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're travelling solo, as a couple, with family, or in a group. Bookabach offers something for every taste and budget, from affordable homes in Drayden to more spacious homes.
What can I expect from Bookabach customer service and Bookabach Care™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, Bookabach Care™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, Bookabach customer service is available 24/7 to support you every step of the way. Bookabach also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
What is Bookabach Care™ and how does it work?
Bookabach's mission is to help guests relax, reconnect, and enjoy precious time together. With Bookabach Care™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable. If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
Why should I join Bookabach as a host?
Joining Bookabach as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Bookabach makes it easy to list, manage, and succeed. Whether it's a cosy cabin or a beach house, you can turn your space into a standout destination, become a host and let Bookabach handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.