Drayden Vacation Rentals

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Our top choices for Drayden vacation rentals

Soul Oasis - home on the Chesapeake Bay

Soul Oasis - home on the Chesapeake Bay
Lusby
10.0 out of 10, Exceptional, (49 reviews)
"Gorgeous. Host is very welcoming and available. Clear instructions, which are super helpful. Peaceful and stunning location. Thank you, Teresa!"
United States
Carver Z.
The price is CA $198
CA $422 total
includes taxes & fees
May 28 - May 29
Soul Oasis - home on the Chesapeake Bay

Waterfront Reset—Games, Views, Kayaks & Total Calm

Waterfront Reset—Games, Views, Kayaks & Total Calm
Montross
10.0 out of 10, Exceptional, (34 reviews)
"Great spot"
United States
SHAWN W.
The price is CA $412
CA $832 total
includes taxes & fees
Jun 4 - Jun 5
Waterfront Reset—Games, Views, Kayaks & Total Calm

Cozy Sunrise Waterfront 2-bedroom Cottage & Dock. Serene Point Lookout/Scotland

Cozy Sunrise Waterfront 2-bedroom Cottage & Dock. Serene Point Lookout/Scotland
Point Lookout
9.6 out of 10, Exceptional, (14 reviews)
"Hosts were very helpful. The cottage is adorable and well maintained. "
United States
William L.
The price is CA $324
CA $628 total
includes taxes & fees
Jun 1 - Jun 2
Cozy Sunrise Waterfront 2-bedroom Cottage & Dock. Serene Point Lookout/Scotland

Coles Point Marina

Coles Point Marina
2.0 star property
Hague
The price is CA $322
CA $478 total
includes taxes & fees
Jun 1 - Jun 2
Coles Point Marina

Riverside Lodge Bed & Breakfast on the Honga River UNIT C

Riverside Lodge Bed & Breakfast on the Honga River UNIT C
Fishing Creek
10.0 out of 10, Exceptional, (11 reviews)
"Peggy and Gary are the perfect hosts: welcoming, friendly, attentive and respectful of your preferences. Wonderful views of the Bay and River via the lodge -- including the cupola -- and walking around the majestic property."
United States
Thomas S.
The price is CA $373
CA $449 total
includes taxes & fees
May 30 - May 31
Riverside Lodge Bed & Breakfast on the Honga River UNIT C

Rustic 3BR Waterfront Cabin with Firepit + Dock Access

Rustic 3BR Waterfront Cabin with Firepit + Dock Access
Hague
The price is CA $224
CA $276 total
includes taxes & fees
Jun 1 - Jun 2
Rustic 3BR Waterfront Cabin with Firepit + Dock Access

Riverfront Home w/Dock · Fire Pit · Kids Play Area

Riverfront Home w/Dock · Fire Pit · Kids Play Area
Montross
9.6 out of 10, Exceptional, (15 reviews)
"Very nice inside, love all the windows"
United States
Elizabeth S.
The price is CA $268
CA $717 total
includes taxes & fees
Jun 2 - Jun 3
Riverfront Home w/Dock · Fire Pit · Kids Play Area

Anne & Fred`s Leonardtown Home W/ Arcade room!

Anne & Fred`s Leonardtown Home W/ Arcade room!
Leonardtown
9.4 out of 10, Exceptional, (6 reviews)
"Amazing place to stay. Very Very clean ! Great location. Definitely will book this place again "
United States
Christy C.
The price is CA $280
CA $737 total
includes taxes & fees
May 31 - Jun 1
Anne & Fred`s Leonardtown Home W/ Arcade room!

Waterfront Retreat, Private Pier, Remodeled, Epic Views, Sunsets on the River

Waterfront Retreat, Private Pier, Remodeled, Epic Views, Sunsets on the River
Lexington Park
10.0 out of 10, Exceptional, (9 reviews)
"Everything was very clean and well put together. Loved the view!"
United States
Minji S.
The price is CA $255
CA $546 total
includes taxes & fees
Jun 1 - Jun 2
Waterfront Retreat, Private Pier, Remodeled, Epic Views, Sunsets on the River

Charming Waterfront 3-bedroom house in Piney Point

Charming Waterfront 3-bedroom house in Piney Point
Piney Point
10.0 out of 10, Exceptional, (3 reviews)
"Loved it! Wish we had more time to spend in the lovely rental. "
United States
Hilary B.
The price is CA $425
CA $820 total
includes taxes & fees
Jun 1 - Jun 2
Charming Waterfront 3-bedroom house in Piney Point

Waterfront 3BR/3BA Getaway: Beach, Dock, Firepit! AMAZING Sweeping VIEWS!

Waterfront 3BR/3BA Getaway: Beach, Dock, Firepit! AMAZING Sweeping VIEWS!
Heathsville
9.6 out of 10, Exceptional, (33 reviews)
"We loved the tranquility of the place, beautiful views, and the unique design of the house. The host was very responsive. It was a very relaxing stay. I am sure we will be coming back soon."
United States
Liudmila U.
The price is CA $287
CA $873 total
includes taxes & fees
Jun 2 - Jun 3
Waterfront 3BR/3BA Getaway: Beach, Dock, Firepit! AMAZING Sweeping VIEWS!

4-BR Waterfront Turret Home

4-BR Waterfront Turret Home
Solomons
10.0 out of 10, Exceptional, (7 reviews)
"Beautiful house. Beautiful scenery. Everything was perfect. "
United States
Thomas S.
The price is CA $829
CA $1,524 total
includes taxes & fees
Jun 22 - Jun 23
4-BR Waterfront Turret Home

2 Bedroom Cottage at Coles Point Marina

2 Bedroom Cottage at Coles Point Marina
Hague
The price is CA $476
CA $590 total
includes taxes & fees
Jun 1 - Jun 2
2 Bedroom Cottage at Coles Point Marina

Peaceful Waterfront Retreat for Bird Lovers- Close to DC

Peaceful Waterfront Retreat for Bird Lovers- Close to DC
Leonardtown
10.0 out of 10, Exceptional, (5 reviews)
"Beautiful property in a peaceful neighborhood. Great location! "
United States
R. L.
The price is CA $407
CA $792 total
includes taxes & fees
Jun 1 - Jun 2
Peaceful Waterfront Retreat for Bird Lovers- Close to DC

Come relax yourself a while

Come relax yourself a while
Mechanicsville
The price is CA $342
CA $818 total
includes taxes & fees
Jun 3 - Jun 4
Come relax yourself a while

Riverside Lodge Bed & Breakfast on the Honga River UNIT E

Riverside Lodge Bed & Breakfast on the Honga River UNIT E
Fishing Creek
10.0 out of 10, Exceptional, (1 review)
"We stayed Sunday - Wednesday at Riverside Lodge. The Lodge was beautiful. Breakfast was absolutely fantastic and Hooper Island was breath taking. We were able to take a boat ride to tour around the island and grad a little history and enjoy the stories. If you looking for a place to relax and renew... this is the place. "
United States
Robin E.
The price is CA $373
CA $449 total
includes taxes & fees
May 30 - May 31
Riverside Lodge Bed & Breakfast on the Honga River UNIT E

Waterfront home on Mill Creek-5BR-3bath-Hot tub, Kayaks & private dock

Waterfront home on Mill Creek-5BR-3bath-Hot tub, Kayaks & private dock
Lusby
10.0 out of 10, Exceptional, (1 review)
"We loved our stay! Lovely home, beautiful view"
United States
Sarah R.
The price is CA $668
CA $1,405 total
includes taxes & fees
Jun 3 - Jun 4
Waterfront home on Mill Creek-5BR-3bath-Hot tub, Kayaks & private dock
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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Top Drayden Hotel Reviews

Find out more about Drayden

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Drayden. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

Frequently asked questions

Can I find a vacation rental in Drayden?

Yes, we give you a choice of vacation rentals near popular points of interest in Drayden, or you can choose a more remote option if you'd like a relaxing place to stay. Drayden is known for its waterfront.

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

The Beach Retreat is a cozy beach Villa with Hottub overlooking a private beach.: Visitors like this Drayden vacation home rental. It is located on a river and has an outdoor pool, a patio, and a barbecue grill 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 you can cook with friends or family. You can relax into your vacation with a garden and a hot tub.

What can I see and do in Drayden?

Explore the area and family-friendly sights such as Michael P. O'Brien Athletics and Recreation Center, or get out into nature at a spot like Piney Point Beach. In the larger area, you’ll find Dennis Point Marina and Historic St. Mary's City.

What are vacation rentals like in Drayden?

Vacation rentals are private properties you can reserve for a short or long stay in Drayden. Vacation rentals feature extras such as kitchens and laundry facilities so you'll have everything you want. If you're concerned about a clean environment, a vacation rental can offer a sense of security away from public hotel elevators and busy concierge desks while still allowing you the enjoyment of travel. You'll also get more space in a vacation rental than in a standard hotel, which is another reason why a vacation rental is a popular choice for family gatherings.