Drayden Holiday Rentals

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Holiday Rentals in Drayden

Spacious Waterfront Home secluded on 60 ac with Beach and Boat Ramp

9.8 out of 10, Exceptional, (56)
"Our group of 6 guys who have been friends since elementary school (all 60+ years old now) enjoyed another great annual visit to Cove House. Fish and crabs were biting. Sunsets and rainbows lit up the sky. And good friends reconnected, laughed, and enjoyed being away from the world for a bit. We will be calling again!"
Spacious Waterfront Home secluded on 60 ac with Beach and Boat Ramp

Soul Oasis - home on the Chesapeake Bay

9.8 out of 10, Exceptional, (17)
"Beautiful and quiet in the fall. A great place for relaxing. Clean, great communication. End of the street with views of the bay. "
The price is AU$483
includes taxes & fees
1 Dec - 2 Dec
Soul Oasis - home on the Chesapeake Bay

Waterfront Relaxing Getaway

9.8 out of 10, Exceptional, (18)
"Nice house, beautiful waterfront property, great host. No complaints whatsoever, highly recommend. "
Waterfront Relaxing Getaway

Belle of the Chesapeake Bay

9.6 out of 10, Exceptional, (9)
"This was a great place to stay in a quiet neighborhood, a short drive from Calvert Cliffs State Park. Plenty of space for four adults. We could have stayed longer and would not hesitate to book again."
Belle of the Chesapeake Bay

Waterfront Scotland Beach Retreat w/ Private Beach

10.0 out of 10, Exceptional, (41)
"The house is lovely and very comfortable for our group of 8 friends. We would highly recommend!"
Waterfront Scotland Beach Retreat w/ Private Beach

Cozy Virginia Potomac Riverfront Cottage

9.8 out of 10, Exceptional, (34)
"This is a nice little cottage, tucked away from everything right on the river. I was looking for some peace and quiet, and that’s exactly what I got. Even though the weather wasn’t great, the sunroom still let me enjoy the views. "
Cozy Virginia Potomac Riverfront Cottage

El Camino

10.0 out of 10, Exceptional, (31)
"Nice short getaway with the wife at this lovely cabin. Very relaxing and peaceful in a great setting. Only downside was not being able to enjoy the dock as there was another family with kids that occupied it most of the time that was staying at the other cabin on the property. Also, not a clear view of the water from the porch due to the trees but all in all it was a great stay. "
El Camino

Waterfront Cottage in Beautiful Hoopers Island

10.0 out of 10, Exceptional, (63)
"My boyfriend and I needed to get away. This house and location was just what we needed. Beautiful scenery, cozy home. We started a full week and I was sad to go at the end of our trip. We look forward to visiting again in the future! "
Waterfront Cottage in Beautiful Hoopers Island

The Schultz Estate

8.8 out of 10, Excellent, (14)
"What a wonderful stay we had! The house was so comfortable with plenty of space for everyone to relax and enjoy each other's company. We enjoyed the brisk mornings on the porch and the gorgeous sunsets in the evenings. Very comfortable beds and linens. The scenery and landscape in the area are breathtaking. Every turn provided another incredible view of the water. Fishing Creek is close to so many beautiful, quaint towns along the Chesapeake Bay. Highly recommend!"
The Schultz Estate

Waterfront House with Dock, Kayaks, & Sailboat!

9.0 out of 10, Wonderful, (30)
"We stayed for a motorcross race (son was racing). We didnt do much at the house. Its nestled back in a quiet point on the water. Easy commute to and from to the grocery/simple shopping stores. Starbucks right down the street for you coffee lovers. The interior decor is simple and antique."
Waterfront House with Dock, Kayaks, & Sailboat!

Maryland Vacation Rental w/ Private Pool & Dock

10.0 out of 10, Exceptional, (6)
"We needed a house for a quick stay in Lusby. The hosts have thought of everything to make the stay easy. They communicated ahead of our trip and were easy to work with. "
Maryland Vacation Rental w/ Private Pool & Dock

Private Beach Front Getaway at The Sunshine Beach Cottage.

9.8 out of 10, Exceptional, (63)
"Beautifully appointed cottage. Literally right on the water. Quiet, serene and relaxing. Loved it and will be back!"
Private Beach Front Getaway at The Sunshine Beach Cottage.

Off-season prices! Waterfront Cottage on Hoopers Island. Pet friendly. 🏝️🦀🎣

10.0 out of 10, Exceptional, (46)
"Great experience, wonderful cozy cottage with thoughtful touches throughout. Remote, peaceful location with excellent fishing and crabbing all around you. Fantastic eating at Old Salty's less than a couple of miles away. Very dog friendly cottage and lovely screened in porch area to sit and watch the sunsets. We will be booking again next year."
Off-season prices! Waterfront Cottage on Hoopers Island. Pet friendly. 🏝️🦀🎣

Stunning secluded Luxury waterfront cottage with private deep water pier!

10.0 out of 10, Exceptional, (72)
"Great location. Spacious and clean. Easy checking in and communicate with owner."
Stunning secluded Luxury waterfront cottage with private deep water pier!

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

10.0 out of 10, Exceptional, (14)
"I was in charge of booking my very first family vacation and I really wanted to be near water and trees. This location was perfect as the kids loved being on the beach (and utilizing the Kayaks, Life Jackets, and Floaties provided by the host) and the adults loved the serenity of the area. The host was very quick to respond to any questions I had which definitely set the tone for me before even arriving! "
Sea Glass Beach House! Large sand beach, dock and hot tub! Pets welcome!

Stunning Water Front Home 90 minutes from DC with Deepwater Dock.Bring your boat

9.8 out of 10, Exceptional, (18)
"The house was very comfortable and well stocked! It has everything you need for a relaxing time. "
Stunning Water Front Home 90 minutes from DC with Deepwater Dock.Bring your boat

Bay view from Calvert Cliffs, Solomons Island & State Park nearby

10.0 out of 10, Exceptional, (39)
"Awesome home wnd location! Would stay again!"
Bay view from Calvert Cliffs, Solomons Island & State Park nearby

Stylish & Modern Waterfront retreat, Serene and with great views,1Hr to DC

10.0 out of 10, Exceptional, (10)
"Great place to stay while in the area. Thank you!"
Stylish & Modern Waterfront retreat, Serene and with great views,1Hr to DC

Pine Shore Beach House on the Chesapeake Bay w/ 170ft pier

10.0 out of 10, Exceptional, (36)
"We wanted a family vacation and looked for a place on Chesapeake Bay. My son and daughter found this place and we reserved it. The house is beautiful. Has everything one would want. The location is great although it’s a bit of a drive to anywhere. Our plan was to spend most of the time at the house and in the bay. However that didn’t happen. First the weather didn’t cooperate as it rained most of the week. In addition there was an invasion of jellyfish. They were terrible! My grandchildren were...
Pine Shore Beach House on the Chesapeake Bay w/ 170ft pier

**FAMILY FRIENDLY CREEKSIDE GETAWAY - HIDEAWAY AND ENJOY THE FAMILY MOMENTS**

10.0 out of 10, Exceptional, (182)
"We had a very relaxing weekend celebrating my 60th birthday. Ray was such a terrific host. Everything about the property and the owner was spectacular!!"
**FAMILY FRIENDLY CREEKSIDE GETAWAY - HIDEAWAY AND ENJOY THE FAMILY MOMENTS**
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Other types of properties in Drayden you may be interested in

Spacious Waterfront Home secluded on 60 ac with Beach and Boat Ramp

9.8 out of 10, Exceptional, (56)
"Our group of 6 guys who have been friends since elementary school (all 60+ years old now) enjoyed another great annual visit to Cove House. Fish and crabs were biting. Sunsets and rainbows lit up the sky. And good friends reconnected, laughed, and enjoyed being away from the world for a bit. We will be calling again!"
Spacious Waterfront Home secluded on 60 ac with Beach and Boat Ramp

La Quinta Inn & Suites by Wyndham Lexington Park - Patuxent

2.5 star property
7.6 out of 10, Good, (1076)
"Very nice rooms but the breakfast is average. "
The price is AU$151
includes taxes & fees
30 Nov - 1 Dec
La Quinta Inn & Suites by Wyndham Lexington Park - Patuxent

Holiday Inn Express & Suites Lexington Park-California, an IHG Hotel

2.5 star property
9.2 out of 10, Wonderful, (519)
"Great service "
The price is AU$190
includes taxes & fees
19 Dec - 20 Dec
Holiday Inn Express & Suites Lexington Park-California, an IHG Hotel
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Beautiful view of the beach with palm trees

Black Friday: Members save 30%+

Members save 30%+ on selected hotels until 4 Dec (property time) with our Black Friday deals. Stay by 15 Dec 2025.

Frequently asked questions

Can I find a holiday rental in Drayden?

Yes, there are holiday rentals close to the most popular sights in Drayden, or you can select a more secluded option if you're looking for a relaxing stay. Drayden is known for its waterfront.

What are some of the best holiday rentals that Drayden has to offer?

Spacious Waterfront Home secluded on 60 ac with Beach and Boat Ramp: This highly rated holiday home rental in Drayden is located on a river, and has a fireplace, a balcony and a BBQ to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You can relax into your holiday with a garden and a selection of games.

What can I see and do in Drayden?

Explore the area and family-friendly sights such as Kinsale Museum, or get out into nature at a spot like Piney Point Beach. In the wider area, you’ll find Dennis Point Marina and St. Mary's College of Maryland.

What are holiday rentals like in Drayden?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Drayden. Holiday rentals feature extras such as patios, hot tubs and fire pits so you'll have a home away from home. If you're concerned about a sanitised environment, holiday rentals can offer a sense of privacy away from public hotel lifts and busy reception areas while still allowing you the enjoyment of travel. You'll also find more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is a great option for a family trip.