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Drayden Vacation Rentals

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Our top choices for Drayden vacation rentals

Coles Point Marina

Coles Point Marina
2.0 star property
Hague
The price is CA $266
CA $421 total
includes taxes & fees
Jul 7 - Jul 8
Coles Point Marina

Lakefront Log Cabin Retreat w/ Hot tub + Kayaks!

Lakefront Log Cabin Retreat w/ Hot tub + Kayaks!
3.0 star property
Lusby
The price is CA $778
CA $1,625 total
includes taxes & fees
Jul 20 - Jul 21
Lakefront Log Cabin Retreat w/ Hot tub + Kayaks!

Soul Oasis - home on the Chesapeake Bay

Soul Oasis - home on the Chesapeake Bay
Lusby
10.0 out of 10, Exceptional, (53 reviews)
"Everything was great! Just read the book about the property and amenities…some crucial details about heat and hiking around the neighborhood. Definitely would stay again!"
United States
Chris G.
The price is CA $217
CA $453 total
includes taxes & fees
Jul 8 - Jul 9
Soul Oasis - home on the Chesapeake Bay

2 Bedroom Cottage at Coles Point Marina

2 Bedroom Cottage at Coles Point Marina
Hague
The price is CA $490
CA $607 total
includes taxes & fees
Jul 6 - Jul 7
2 Bedroom Cottage at Coles Point Marina

Hideaway in Hays Beach: Western Sandy Shore of Chesapeake Bay and 5g WiFi!

Hideaway in Hays Beach: Western Sandy Shore of Chesapeake Bay and 5g WiFi!
Point Lookout
10.0 out of 10, Exceptional, (133 reviews)
"Hideaway at Hayes Beach was amazing It was a wonderful place to spend Christmas with our family. We were lucky enough to get snow! My husband and I enjoy walking so it was a prefect place to for it. Would definitely recommend this place"
United States
April T.
The price is CA $497
CA $941 total
includes taxes & fees
Jul 19 - Jul 20
Hideaway in Hays Beach: Western Sandy Shore of Chesapeake Bay and 5g WiFi!

'The Bayside Escape' Remote Chesapeake Bay Estate

'The Bayside Escape' Remote Chesapeake Bay Estate
Fishing Creek
The price is CA $570
CA $1,346 total
includes taxes & fees
Jul 29 - Jul 30
'The Bayside Escape' Remote Chesapeake Bay Estate

Lakefront Cabin near Solomons Island w/ Hot Tub

Lakefront Cabin near Solomons Island w/ Hot Tub
Lusby
10.0 out of 10, Exceptional, (1 review)
"We had such a wonderful stay at Diana’s lake house! The view of the lake is absolutely beautiful waking up to that peaceful scenery every morning was one of the highlights of our trip.The property has a charming rustic feel while still offering all the amenities you could need. It felt cozy and comfortable, yet fully equipped for a relaxing getaway. We especially loved being able to kayak right from the area such a perfect way to enjoy the water and the surroundings.Diana was an exceptional...
United States
rakesh s.
The price is CA $660
CA $1,650 total
includes taxes & fees
Jul 6 - Jul 7
Lakefront Cabin near Solomons Island w/ Hot Tub

Waterfront Retreat | New Private Pier | Remodeled | Epic Sunset Views

Waterfront Retreat | New Private Pier | Remodeled | Epic Sunset Views
Lexington Park
10.0 out of 10, Exceptional, (10 reviews)
"We had a wonderful stay! Beautiful waterfront home with a brand new pier overlooking the river and a perfect sunset. Quiet location, perfectly appointed and great location next to parks, St Mary’s City and campus. Highly recommend!"
United States
Kurt O.
The price is CA $253
CA $551 total
includes taxes & fees
Jul 27 - Jul 28
Waterfront Retreat | New Private Pier | Remodeled | Epic Sunset Views

Lakefront A-Frame: Private Dock, Kayaks & Sauna – Sleeps 12, Chesapeake Bay

Lakefront A-Frame: Private Dock, Kayaks & Sauna – Sleeps 12, Chesapeake Bay
Lusby
9.6 out of 10, Exceptional, (12 reviews)
"The home was lovely and very quiet location. My sister and I were caring for our mom after discharge from hospital and it was very convenient. Would stay there again. "
United States
Tova A.
The price is CA $656
CA $1,225 total
includes taxes & fees
Jul 8 - Jul 9
Lakefront A-Frame: Private Dock, Kayaks & Sauna – Sleeps 12, Chesapeake Bay

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 $383
CA $462 total
includes taxes & fees
Jul 8 - Jul 9
Riverside Lodge Bed & Breakfast on the Honga River UNIT C

'the Bayside Escape' Remote Chesapeake Bay Estate

'the Bayside Escape' Remote Chesapeake Bay Estate
3.0 star property
Fishing Creek
The price is CA $648
CA $1,297 total
includes taxes & fees
Jul 1 - Jul 2
'the Bayside Escape' Remote Chesapeake Bay Estate

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

Anne & Fred`s Leonardtown Home W/ Arcade room!
Leonardtown
9.2 out of 10, Wonderful, (7 reviews)
"Amazing place to stay. Very Very clean ! Great location. Definitely will book this place again "
United States
Christy C.
The price is CA $287
CA $753 total
includes taxes & fees
Jul 8 - Jul 9
Anne & Fred`s Leonardtown Home W/ Arcade room!

4-BR Waterfront Turret Home

4-BR Waterfront Turret Home
Solomons
10.0 out of 10, Exceptional, (8 reviews)
"Beautiful house. Beautiful scenery. Everything was perfect. "
United States
Thomas S.
The price is CA $710
CA $1,389 total
includes taxes & fees
Jul 1 - Jul 2
4-BR Waterfront Turret Home

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, (34 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 $295
CA $898 total
includes taxes & fees
Jul 1 - Jul 2
Waterfront 3BR/3BA Getaway: Beach, Dock, Firepit! AMAZING Sweeping VIEWS!

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 $383
CA $462 total
includes taxes & fees
Jul 8 - Jul 9
Riverside Lodge Bed & Breakfast on the Honga River UNIT E

Charming Waterfront 3-bedroom house in Piney Point

Charming Waterfront 3-bedroom house in Piney Point
Piney Point
10.0 out of 10, Exceptional, (4 reviews)
"This property was perfect for our night visiting St. Mary's! Spacious, right on the water, and quiet. Thank you!"
United States
Meira
The price is CA $487
CA $919 total
includes taxes & fees
Jul 13 - Jul 14
Charming Waterfront 3-bedroom house in Piney Point

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)
"Everything about this stay was FANTASTIC. The host was amazing, the condo was in excellent condition and the view is AMAZING! Enjoyed everything about this stay!"
United States
N C.
Riverfront Home w/Dock · Fire Pit · Kids Play Area

Waterfront Reset: Views, Games, Boats & Total Calm

Waterfront Reset: Views, Games, Boats & Total Calm
Montross
10.0 out of 10, Exceptional, (36 reviews)
"Great spot"
United States
SHAWN W.
The price is CA $676
CA $1,159 total
includes taxes & fees
Jul 28 - Jul 29
Waterfront Reset: Views, Games, Boats & Total Calm

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, (2 reviews)
"We loved our stay! Lovely home, beautiful view"
United States
Sarah R.
The price is CA $687
CA $1,445 total
includes taxes & fees
Jul 1 - Jul 2
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?

Belle of the Chesapeake Bay: Visitors like this Drayden vacation home rental. It offers a patio, an arcade game room, and air-conditioning to help you feel perfectly comfortable in your new surroundings. It has 4 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family.

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.