Drayden Vacation Rentals

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Our top choices for Drayden vacation rentals

9.8 out of 10, Exceptional, (40 reviews)
"The cozy cabin had everything needed for a comfortable stay. It was in a very private setting with the beach access a few houses away. You can hear the Chesapeake bay lapping at the shore and catch a glimpse of sail boats going by. We enjoyed our time at the home."
United States
Mary G.
$243 nightly
The price is $257
Jan 25 - Jan 26
Total with taxes and fees
Soul Oasis - home on the Chesapeake Bay
9.4 out of 10, Exceptional, (10 reviews)
"The cottage was clean and welcoming. The location can't be beat. It is right on the water, quiet and nearby point lookout. Great place to visit and walk our dogs. The property owners were responsive and gave us a nice list of things to do around the area. Would definitely stay again!"
United States
Adam P.
$286 nightly
The price is $316
Jan 25 - Jan 26
Total with taxes and fees
Cozy Sunrise Waterfront 2-bedroom Cottage & Dock. Serene Point Lookout/Scotland

Cabin in Hague

Coles Point Marina
2.0 star property
$344 nightly
The price is $375
Jan 23 - Jan 24
Total with taxes and fees
Coles Point Marina

Vacation Home in Montross

Luxury Modern Waterfront Retreat
9.6 out of 10, Exceptional, (14 reviews)
"Very nice inside, love all the windows"
United States
Elizabeth S.
$430 nightly
The price is $468
Feb 1 - Feb 2
Total with taxes and fees
Luxury Modern Waterfront Retreat
3.0 star property
$754 nightly
The price is $837
Jan 25 - Jan 26
Total with taxes and fees
Lakefront Log Cabin Retreat w/ Hot tub + Kayaks!

Vacation Home in Leonardtown

Potomac Vista Cottage
2.0 star property
$351 nightly
The price is $353
Jan 25 - Jan 26
Total with taxes and fees
Potomac Vista Cottage
10.0 out of 10, Exceptional, (5 reviews)
"Everything was very clean and well put together. Loved the view!"
United States
Minji S.
$361 nightly
The price is $363
Feb 2 - Feb 3
Total with taxes and fees
Waterfront Escape | Family-Friendly | Remodeled Home | Epic Sunset Views | Decks
10.0 out of 10, Exceptional, (30 reviews)
"Great spot"
United States
SHAWN W.
$424 nightly
The price is $461
Jan 25 - Jan 26
Total with taxes and fees
Easthaven | Game-Themed Waterfront Retreat
2.0 star property
$268 nightly
The price is $292
Jan 23 - Jan 24
Total with taxes and fees
2 Bedroom Cottage at Coles Point Marina
10.0 out of 10, Exceptional, (5 reviews)
"We enjoyed this house fully for our Thanksgiving stay! We even took the canoes out for a spin. Nice walks around the development and the beach area is lovely. "
United States
Julie I.
$370 nightly
The price is $403
Jan 25 - Jan 26
Total with taxes and fees
Modern Waterfront Home with Kayak, Firepit, Gameroom, Pool+Beaches, Dog & EV OK

Vacation Home in Solomons

4-BR Waterfront Turret Home
2.0 star property
10.0 out of 10, Exceptional, (7 reviews)
"Beautiful house. Beautiful scenery. Everything was perfect. "
United States
Thomas S.
$680 nightly
The price is $751
Jan 24 - Jan 25
Total with taxes and fees
4-BR Waterfront Turret Home
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.
$308 nightly
The price is $326
Jan 23 - Jan 24
Total with taxes and fees
Riverside Lodge Bed & Breakfast on the Honga River UNIT C
10.0 out of 10, Exceptional, (1 review)
"We loved our stay! Lovely home, beautiful view"
United States
Sarah R.
$868 nightly
The price is $874
Jan 27 - Jan 28
Total with taxes and fees
Waterfront home on Mill Creek-5BR-3bath-Hot tub, Kayaks & private dock
10.0 out of 10, Exceptional, (1 review)
"Beautiful newly renovated space with all new appliances, furniture and kitchenware. Comfortable beds, and super clean rooms. Large outside area with new Weber grill, fire pit, and three kayaks. Nice easy to access dock. "
United States
Kit C.
$519 nightly
The price is $573
Jan 23 - Jan 24
Total with taxes and fees
Charming Waterfront 3-bedroom house in Piney Point
9.2 out of 10, Wonderful, (5 reviews)
"Nice place to stay. Perfect location for our needs. Suggest noting the hot and cold water flip upstairs, and to add a mirror in the hallway by outlet for blow dryer."
United States
Lauren A.
$547 nightly
The price is $579
Jan 25 - Jan 26
Total with taxes and fees
Anne & Fred`s Leonardtown Home W/ Arcade room!

Apartment in Mechanicsville

Come relax yourself a while
$532 nightly
The price is $587
Jan 23 - Jan 24
Total with taxes and fees
Come relax yourself a while
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

Everything you need to know about Drayden vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Drayden vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Drayden vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Drayden vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Drayden. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Drayden in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $257 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Drayden rentals

At Expedia, we put the best Drayden vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Drayden rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Drayden vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Drayden. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

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?

Spacious Waterfront Home secluded on 60 ac with Beach and Boat Ramp: This Drayden vacation home rental is located on the beach and has a balcony, a garden, 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 and your friends and family can relax into your vacation with amenities like a selection of games.

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.