Drayden Vacation Rentals

    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

Vacation Rentals in Drayden

Spacious Waterfront Home secluded on 60 ac with Beach and Boat Ramp
10.0 out of 10, Exceptional, (51)
"What a fantastic property! We loved staying here and our family had such a great time exploring. Sadly it was a drizzly, dreary weekend but we had one nice day to go down to the beach and the kids enjoyed playing in the water. We loved the variety of porches to sit on and have different views and there was plenty of room for the kids to play indoors when it was raining. Overall a great experience. Thank you!"
Spacious Waterfront Home secluded on 60 ac with Beach and Boat Ramp
Waterfront Cottage in Beautiful Hoopers Island
10.0 out of 10, Exceptional, (54)
"We have stayed at this property twice and love it. Very peaceful, clean, and comfortable."
Waterfront Cottage in Beautiful Hoopers Island
Piney Point, private , Beach Front Cottage
10.0 out of 10, Exceptional, (76)
"This place is incredible!!!! What an amazing property and beautiful home."
Piney Point, private , Beach Front Cottage
Save an average of 15% on thousands of hotels when you're signed in
Private Beach Front Getaway at The Sunshine Beach Cottage.
9.8 out of 10, Exceptional, (47)
"Best location yet.Been to alot of Beach houses,this surpassed expectations."
Private Beach Front Getaway at The Sunshine Beach Cottage.
Maryland Vacation Rental w/ Private Pool & Dock
10.0 out of 10, Exceptional, (4)
"Had a great time fishing from the dock while we got out of the city for a weekend."
Maryland Vacation Rental w/ Private Pool & Dock
Soul Oasis - home on the Chesapeake Bay
10.0 out of 10, Exceptional, (6)
"Pleasant relaxing time. We were pleased and impress to locate this property"
The price is CA $179
CA $397 total
includes taxes & fees
Jun 17 - Jun 18
Soul Oasis - home on the Chesapeake Bay
Waterfront Relaxing Getaway
10.0 out of 10, Exceptional, (11)
"I was looking for a nice, quiet, and relaxing, vacation. This property did not disappoint. The house was comfortable, cozy, well stocked, and so clean. The view is incredible. Just sitting outside watching the river was so "Zen". I had one of the most restful vacations ever. I was there for a little over two weeks and I would have stayed longer if I could have, Kim, the host, was very friendly and helpful. I look forward to staying at this beautiful property again."
The price is CA $254
CA $578 total
includes taxes & fees
Jun 27 - Jun 28
Waterfront Relaxing Getaway
Bay view from Calvert Cliffs, Solomons Island & State Park nearby
10.0 out of 10, Exceptional, (29)
"👍👍"
Bay view from Calvert Cliffs, Solomons Island & State Park nearby
The Schultz Estate
9.6 out of 10, Exceptional, (5)
"This house is great for large groups with plenty of comfortable bedrooms, three bathrooms (note one is only a tub, no shower), and loads of outdoor seating and fire options. This is an old farmhouse, so quirks of an old wooden house on the Eastern shore come with that. Personal bug spray at this property is essential as the mosquitos are very intense. The owner did stop by to give us a lawn spray for them but we did not use it as I am a master naturalist and community garden manager who is...
The Schultz Estate
Cozy Virginia Potomac Riverfront Cottage
9.6 out of 10, Exceptional, (24)
"We had a wonderful stay. The house was just as described, a cozy cottage perfect for relaxing with beautiful riverfront views. The kitchen was stocked with everything we needed, the living room and main bedroom we used were comfortable, and the sun porch had great views where you could relax in the AC. The patio had a great dining table/umbrella, and the dock was perfect for fishing. Thank you for a lovely getaway cottage!"
Cozy Virginia Potomac Riverfront Cottage
Waterfront Lusby Retreat w/ Deep-Water Dock & Slip
10.0 out of 10, Exceptional, (4)
"We were in town for a friends wedding. This was the perfect location as it was right in between the Catholic Church for the nuptial mass and the reception site. This place certainly did not disappoint. There was plenty of space for our large family, the home was well equipped and stocked with the necessary items. It was a relatively short stay, but I wish we had a bit more time and better weather to enjoy the use of kayaks - our one free morning was a bit chilly for us Florida folks, and we had...
Waterfront Lusby Retreat w/ Deep-Water Dock & Slip
**FAMILY FRIENDLY CREEKSIDE GETAWAY - HIDEAWAY AND ENJOY THE FAMILY MOMENTS**
10.0 out of 10, Exceptional, (171)
"Groomsmen stayed here for wedding. Great experience in a beautiful location. Swimming and kayaking right out the back door. Owners were very kind and helpful. Definitely recommend this beautiful spot."
**FAMILY FRIENDLY CREEKSIDE GETAWAY - HIDEAWAY AND ENJOY THE FAMILY MOMENTS**
Spacious River Front Home - 90 minutes from DC with Dock, Kayaks & Paddleboards
9.8 out of 10, Exceptional, (15)
"We booked a long weekend for our daughter’s graduation from St Mary’s. The house was beautiful and so spacious for our adult children and grandchildren to all be in one location without feeling cramped. We loved having the fire pit and room to throw a football around. Thank you for sharing your home Victoria!"
Spacious River Front Home - 90 minutes from DC with Dock, Kayaks & Paddleboards
Relax & Renew in a WATERFRONT Cottage , private pier, kayaks, fishing, wineries.
10.0 out of 10, Exceptional, (37)
"Great place to stay with a fantastic view. Kids loved all the activities to do at the home and property manager was wonderful to deal with and even went over the top with the welcome sign with our name on it. Highly recommend!"
Relax & Renew in a WATERFRONT Cottage , private pier, kayaks, fishing, wineries.
Lakefront Maryland Cabin w/ Fire Pit, Grill & Deck
9.4 out of 10, Exceptional, (9)
"The cabin itself was lovely with a southwestern feel. Very clean when we arrived and met our expectations. The outside space was the best! Even though it was a rainy weekend, we were able to take the kayaks out on the lake during a break in the rain. Unfortunately the weather prohibited us from visiting the beach but the property was close to Solomon's Island where there is plenty of shopping and dining. My only complaint was the mattress in the master bedroom. It felt wore out and we kind of...
Lakefront Maryland Cabin w/ Fire Pit, Grill & Deck
Newly Renovated Secluded Luxury waterfront cottage with private deep water pier!
10.0 out of 10, Exceptional, (66)
"My family had a wonderful stay at Ivy Cove. We were in town for our niece’s wedding and it was close enough to participate in all family activities but far enough away to be a peaceful haven to relax. The house is beautiful. Beds were very comfortable. We really enjoyed the fire pit and game room. The owner was fantastic. We would absolutely stay again in this amazing home."
Newly Renovated Secluded Luxury waterfront cottage with private deep water pier!
Waterfront house with private beach and pier
9.8 out of 10, Exceptional, (12)
"An amazing, secluded property that is perfect for a family or friends getaway. The rooms are clean, comfortable, and there were plenty of bathrooms. The property could improve by having additional toilet paper, shower toiletries, and towels, but the kitchen was very well stocked and there was plenty of seating. It really is a great house."
Waterfront house with private beach and pier
Historic Hoopersville Getaway on Chesapeake Bay!
9.6 out of 10, Exceptional, (9)
"Our vacation on Chesapeake Bay was wonderful. The house was clean and comfortable. It is an older home, but we loved the character and charm. There is a very large yard for playing, bikes and some board games/puzzles that we enjoyed. The island was very quiet so made for a relaxing vacation. The home came with kayaks, and we had a blast kayaking with our 2 and 4 year old on the ocean. I would highly recommend this home for a big gathering or small family like our trip. We felt so rested after...
Historic Hoopersville Getaway on Chesapeake Bay!
Welcome to Hickory House on the Chesapeake Bay!
9.6 out of 10, Exceptional, (19)
"Had a great week! Cottage is adorable, clean and cozy. Host very welcoming with treats and bowls for our dogs. House is a couple weeks from the beach and a beach parking pass is included. The beach is private and very relaxing. It was very hot that week that we visited abd tge AC was excellent. Lots of extras in the house - games, hand soaps and even ballth salts! Very enjoyable visit!"
Welcome to Hickory House on the Chesapeake Bay!
The Beach Retreat is a cozy beach Villa with Hottub overlooking a private beach.
10.0 out of 10, Exceptional, (26)
"Quick weekend getaway from Annapolis and wanted to bring the pups. Very dog friendly with great access to the water."
The Beach Retreat is a cozy beach Villa with Hottub overlooking a private beach.
Don't see what you're looking for?
See all available properties in Drayden
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.

Other types of properties in Drayden you may be interested in

Spacious Waterfront Home secluded on 60 ac with Beach and Boat Ramp
10.0 out of 10, Exceptional, (51)
"What a fantastic property! We loved staying here and our family had such a great time exploring. Sadly it was a drizzly, dreary weekend but we had one nice day to go down to the beach and the kids enjoyed playing in the water. We loved the variety of porches to sit on and have different views and there was plenty of room for the kids to play indoors when it was raining. Overall a great experience. Thank you!"
Spacious Waterfront Home secluded on 60 ac with Beach and Boat Ramp
La Quinta Inn & Suites by Wyndham Lexington Park - Patuxent
2.5 star property
7.6 out of 10, Good, (1002)
"The front desk was very polite, responsibe and professional. When we first arrived our room was fine but the beds were made with dirty covers and they swiftly moved us to another room. The room was fine and a little on the smaller side (we are a family of 4 and we made it work) i did wake up with one single bite on my leg that is suspicious so well be steaming all of our things (we always try to do that anyway when we stay in any hotel. The pool was clean and the exercise room was great. The...
The price is CA $133
CA $148 total
includes taxes & fees
Jul 4 - Jul 5
La Quinta Inn & Suites by Wyndham Lexington Park - Patuxent
Hilton Garden Inn Solomons
3.0 star property
8.6 out of 10, Excellent, (530)
"The hotel and room was very nice, clean, and the staff is very friendly! It’s close to town and affordable. We will definitely be back!"
The price is CA $159
CA $177 total
includes taxes & fees
Jun 30 - Jul 1
Hilton Garden Inn Solomons
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.

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?

Spacious Waterfront Home secluded on 60 ac with Beach and Boat Ramp: This Drayden vacation home rental is located on a river and has a fireplace, a balcony, 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. It offers a garden, a selection of games, and a spa tub so you can immerse yourself in your vacation.

What can I see and do in Drayden?

Explore the area and family-friendly sights such as Kinsale Museum, or get out into nature at a spot like Piney Point Beach. In the larger area, you’ll find Dennis Point Marina and St. Mary's College of Maryland.

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.

Recent reviews of Drayden properties
Expedia verified reviews