Search Vacation Homes in Drayden

  • Plan, book, stay with confidence
  • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    today icon
    Change your mind
    Book hotels with free cancellation

Compare 149 Vacation Homes in Drayden with updated reviews, rates, and availability.

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

Beachy Maryland A-Frame: Steps to Chesapeake Bay!

9.8 out of 10, Exceptional, (7)
"Comfortable home and a great place to get away for a chance to exhale and unwind. Host was great! Sunrises, night sky and water front makes this a wonderful relaxing getaway!"
Beachy Maryland A-Frame: Steps to Chesapeake Bay!

Riverside House w/ Kayaks, Piano & Fireplace

9.0 out of 10, Wonderful, (11)
"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

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

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!

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

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

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

Sunrise Views: Waterfront Lusby Home w/ Deck!

9.6 out of 10, Exceptional, (7)
"The house was lovely and clean. Loved the location right on the water. Sunrises were spectacular. We would definitely rent this house again. "
Sunrise Views: Waterfront Lusby Home w/ Deck!

Your private beach retreat in historic St. Mary's

10.0 out of 10, Exceptional, (20)
"We had a wonderful stay at this property. The house was in mint condition and had all the amenities we needed. Enjoyed the hot tub, kayaks, the fire pit, and the dock. Great place to spend a relaxing long weekend. "
Your private beach retreat in historic St. Mary's

Seascair at Scotland Yards

9.6 out of 10, Exceptional, (104)
"Perfect spot to unwind with incredible sunrises and the beach is so nice. While others walk through, it otherwise is a private beach. Kitchen is stocked with nearly everything you need. It’s one of our favorite places. "
Seascair at Scotland Yards

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

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

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!

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

Waterfront Beauty on the Bay
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.
Don't see what you're looking for?
See all available properties in Drayden
Save an average of 15% on thousands of hotels when you're signed in

Other property types 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 SAR 563
SAR 1,178 total
includes taxes & fees
26 Nov - 27 Nov
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
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.