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Compare 145 Vacation Homes in Drayden with updated reviews, rates, and availability.

Large RENOVATED 6 bedroom 5 bath private home with LOTS of space!
The driveway allows for plenty of parking for guests!

Large RENOVATED 6 bedroom 5 bath private home with LOTS of space!

9.6 out of 10, Exceptional, (29)
"This was our third year celebrating our family Thanksgiving in this home. Three generations coming from three different states. Location offers an easy drive for everyone, and the home is large enough for us spread out yet gather for meals. The host listened to our comments from previous years and addressed all of our concerns. Will be returning again."
Large RENOVATED 6 bedroom 5 bath private home with LOTS of space!
Waterfront Scotland Beach Retreat w/ Private Beach
Ridge Vacation Rental | 4BR | 4.5BA | 3,000 Sq Ft | 5 Steps Required to Access

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
Waterfront Relaxing Getaway
Property grounds

Waterfront Relaxing Getaway

9.8 out of 10, Exceptional, (19)
"Nice house, beautiful waterfront property, great host. No complaints whatsoever, highly recommend. "
Waterfront Relaxing Getaway
Sea Glass Beach House! Large sand beach, dock and hot tub! Pets welcome!
Sunrise on your private beach

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

10.0 out of 10, Exceptional, (15)
"House is perfect for families to get together for a holiday. Has pretty much everything you need."
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
Sit on the patio and enjoy your coffee in the morning.

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

9.8 out of 10, Exceptional, (19)
"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
Stylish & Modern Waterfront retreat, Serene and with great views,1Hr to DC
living room, there is TV with netflix/ prime streaming.

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
Stove top with a View !

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
18-Acre Waterfront Sanctuary: Peace & Privacy
Aerial view

18-Acre Waterfront Sanctuary: Peace & Privacy

9.6 out of 10, Exceptional, (5)
"Lots to do and very quiet."
18-Acre Waterfront Sanctuary: Peace & Privacy
Waterfront Maryland Vacation Home: Private Beach!
Ridge Vacation Rental | 3BR | 3BA | 1,779 Sq Ft | Access Only By Stairs

Waterfront Maryland Vacation Home: Private Beach!

10.0 out of 10, Exceptional, (8)
"We had such a peaceful stay! We felt the love you put into your family’s farmhouse! It was perfect! You didn’t miss a detail! The view was beautiful and we enjoyed the beach as well! Thank you for providing the kayaks and bikes! Our experience truly was heaven on earth! We look forward to coming back!"
Waterfront Maryland Vacation Home: Private Beach!
Secluded River Front Cottage
Property grounds

Secluded River Front Cottage

9.4 out of 10, Exceptional, (3)
"The home and property are exactly as advertised. I loved being five minutes away from Point Lookout, the sunset views, and the waterfront. "
Secluded River Front Cottage
Beachy Maryland A-Frame: Steps to Chesapeake Bay!
Scotland Vacation Rental | 3BR | 2BA | Stairs Required | 1,644 Sq Ft

Beachy Maryland A-Frame: Steps to Chesapeake Bay!

9.8 out of 10, Exceptional, (9)
"I loved this sweet A frame home! Celebrated my 48th birthday with a girls' trip and we all loved it. Enjoyed fires and Christmas movies each night. House has a lot of space and is so comfortable. Loved the views of the Bay, particularly from the sunroom and porch. Found quite a bit of sea glass on the neighborhood beach, as well as at the house beach during low tide. Owner was incredibly responsive and went above and beyond. Great place. Would highly recommend. "
Beachy Maryland A-Frame: Steps to Chesapeake Bay!
Luxury Modern Waterfront Retreat
★ Coziness & Outdoor ★ Gas fire-pit to enjoy your evening or wood fire-pit if you prefer the wood crackling sounds

Luxury Modern Waterfront Retreat

9.8 out of 10, Exceptional, (9)
"A little had to trailer a boat to house but nice other then that "
The price is SAR 597
SAR 1,753 total
includes taxes & fees
6 Jan - 7 January 2025
Luxury Modern Waterfront Retreat
Bay Estate by AvantStay | Waterfront, Private Pond
Pier.

Bay Estate by AvantStay | Waterfront, Private Pond

10.0 out of 10, Exceptional, (1)
"Such a beautiful house, very nice for family or friends get together."
Bay Estate by AvantStay | Waterfront, Private Pond
Riverside House w/ Kayaks, Piano & Fireplace
California Vacation Rental | 5BR | 2.5BA | 2,300 Sq Ft | Stairs Required

Riverside House w/ Kayaks, Piano & Fireplace

9.0 out of 10, Wonderful, (12)
"This house is well-maintained and my business associates enjoy staying here. We will book this house every time it comes available."
Riverside House w/ Kayaks, Piano & Fireplace
Cottage on the Bay
Exterior

Cottage on the Bay

9.8 out of 10, Exceptional, (6)
"Clean and accommodating host. Has many of the necessities for the home, including washer/dryer , soaps , trash bags , cleaning essentials , plates/bowls/cups, kitchen gadgets , and more. Home feels safe away from predator animals . Couple deers around. Bring insect repellent."
Cottage on the Bay
Beautiful Beach Boutique 2 Beaches, 1 lake, mature trees for beauty and privacy
Interior

Beautiful Beach Boutique 2 Beaches, 1 lake, mature trees for beauty and privacy

9.4 out of 10, Exceptional, (3)
"We were in town for a reunion and this was a nice alternative to the local hotels. Updates to the house were nicely done and I love that checkout was simplified to two to three tasks, not a whole laundry list. If I had two suggestions, one would be that the plug-ins were too many and too strong - we considered opening a window for some relief but did not since we were out at the reunion most of the day. But only one per floor would likely be enough although the house is so clean (five stars!)...
Beautiful Beach Boutique 2 Beaches, 1 lake, mature trees for beauty and privacy
Waterfront Leonardtown Retreat w/ Dock Access!
Leonardtown Vacation Rental | 4BR | 4BA | 6,500 Sq Ft | Steps Required

Waterfront Leonardtown Retreat w/ Dock Access!

10.0 out of 10, Exceptional, (1)
"We had a wonderful time. My husband spent the days crabbing from the pier, my brother fishing from the pier. We all went out kayaking. Beautiful sunsets. Enjoyed a crazy night of ping pong, playing cards and online Jackbox games. Plenty of space and loved the large kitchen and bathroom for every bedroom. None of us wanted to leave."
Waterfront Leonardtown Retreat w/ Dock Access!
Waterfront Beauty on the Bay
Exterior

Waterfront Beauty on the Bay

Waterfront Beauty on the Bay
3 Bedrooms Relaxing Rustic House on Saint Thomas CreeK
Property grounds

3 Bedrooms Relaxing Rustic House on Saint Thomas CreeK

3 Bedrooms Relaxing Rustic House on Saint Thomas CreeK
Riverside Dreams -golfcart-views-screened porch-
Screened porch and river view.

Riverside Dreams -golfcart-views-screened porch-

2.0 star property
The price is SAR 434
SAR 1,234 total
includes taxes & fees
6 Jan - 7 January 2025
Riverside Dreams -golfcart-views-screened porch-
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 property types in Drayden

Spacious Waterfront Home secluded on 60 ac with Beach and Boat Ramp
Pier next to main beach

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

9.8 out of 10, Exceptional, (57)
"My friend and I stayed for the weekend and had a lovely time. The property is quiet and secluded, and the beach area is very cute. Dog friendly is also a plus."
Spacious Waterfront Home secluded on 60 ac with Beach and Boat Ramp
Large RENOVATED 6 bedroom 5 bath private home with LOTS of space!
The driveway allows for plenty of parking for guests!

Large RENOVATED 6 bedroom 5 bath private home with LOTS of space!

9.6 out of 10, Exceptional, (29)
"This was our third year celebrating our family Thanksgiving in this home. Three generations coming from three different states. Location offers an easy drive for everyone, and the home is large enough for us spread out yet gather for meals. The host listened to our comments from previous years and addressed all of our concerns. Will be returning again."
Large RENOVATED 6 bedroom 5 bath private home with LOTS of space!
Waterfront Relaxing Getaway
Property grounds

Waterfront Relaxing Getaway

9.8 out of 10, Exceptional, (19)
"Nice house, beautiful waterfront property, great host. No complaints whatsoever, highly recommend. "
Waterfront Relaxing Getaway
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.