Drayden Vacation Rentals from CA $344: Short-Term Rentals for 2026

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Our top choices for Drayden vacation rentals

A covered patio with a view of a lake, furnished with chairs and a table.

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

Lexington Park

Andrea B.

CA $545 total

includes taxes & fees

Oct 20 - Oct 21

A single-story house with a front porch, a small deck, and a number '4' on the side.

2. Coles Point Marina

Hague

CA $344 total

includes taxes & fees

Oct 5 - Oct 6

A two-story house with a balcony, surrounded by trees and a wooden fence.

3. Charming Waterfront 3-bedroom house in Piney Point

Piney Point

Meira

CA $1,061 total

includes taxes & fees

Oct 20 - Oct 21

A triangular cabin with a wooden staircase leading to a door, surrounded by trees.

4. Soul Oasis - home on the Chesapeake Bay

Lusby

Dusty S.

A coastal area with a sandy beach, a small settlement, and a clear view of the sea.

5. Waterfront, Firepit, Kayak, Game room, Potomac 2hrs from DC, Dogs+EV OK

Montross

Julie P.

CA $673 total

includes taxes & fees

Oct 7 - Oct 8

A spacious room with a high ceiling, large windows, a ceiling fan, a dining area with a table and chairs, and a sofa.

6. Cozy Sunrise Waterfront 2-bedroom Cottage & Dock. Serene Point Lookout/Scotland

Point Lookout

sandi c.

CA $635 total

includes taxes & fees

Oct 26 - Oct 27

7. 2 Bedroom Cottage at Coles Point Marina

Hague

CA $606 total

includes taxes & fees

Oct 5 - Oct 6

A modern kitchen with granite countertops, stainless steel appliances, and large windows offering views of the outdoors.

8. 2 Acre Oasis with Private Beach! Family and dog friendly!

Leonardtown

Jonathan M.

CA $1,183 total

includes taxes & fees

Oct 26 - Oct 27

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Top Drayden Hotel Reviews

Spark by Hilton California Lexington Park

8/10 Good

"Everything was great. Only complaint was in the morning we could hear everything through the walls, from a loud conversation, to a dog barking and someone putting something heavy in the dryer. We were up by then so it was fine but just a heads up for traveling with pets or children."

The Inn at Leonardtown, an Ascend Collection Hotel

8/10 Good

"Welcoming staff, excellently situated in Downtown Leonardtown, decent offering of complimentary breakfast, including pre-made filled croissants. Only issue was my initial room suffered from external noise issues, suspected to be from the hotels air conditioning system (not the room), however the staff were more than happy to move me to another room which was much quieter."

House Right on the Potomac River - Great Sunrises & Sunsets

10/10 Excellent

"My multigenerational family of 9 adults & 2 kids were thoroughly happy in this rental. The outside was surrounded by gorgeous water views and the inside had a large kitchen to cook all the crabs & fish we caught! There are multiple nooks to get comfy in to unwind solo as well as large areas to gather all together. We’ve rented many vacation homes and this was the first that customized the entry combination to the last 4 digits of my cellphone. Nice touch for those renters wondering who else has access. We recommend wholeheartedly!!!"

Relax & Renew in a WATERFRONT Cottage , private pier, kayaks, fishing, wineries.

10/10 Excellent

"Our week stay was so relaxing and fun. We enjoyed the sunrises and sunsets, views from the deck (it's my new 'happy place'!), the wildlife - ospreys, eagles, and the dolphins in the mornings. The games and things to do were also incredibly fun. The place was very clean, as well as beautifully decorated. Loved the towels too! I would highly recommend if you are looking for a relaxing non-hectic vacation on the water!Thank you, Monica, for providing us access to your home-away-from-home! 3"

Quality Inn Solomons - Beacon Marina

8/10 Good

"Everything was good, standard hotel/motel stuff: little coffee pot, mini-fridge, microwave, tv,a/c - everything worked as expected, furniture, carpeting, lights, bathroom all looked newish and everything was very clean. Desk folk were pleasant, didn’t have much interaction. The big plus is the location, right by a huge marina (if you like looking at boats) and the Calvert Marine Museum- combines natural history and the commercial history of the area, has the Drum Point lighthouse (you can tour) and a boat tour of Patuxent Harbor, plus fossils, river otters, fish. Calvert Cliffs / Flag Pond parks are a 10 minute drive if you want to dig for fossils yourself. So: comfortable place, very reasonably priced, close to all sorts of stuff; definitely worth it."

Belle of the Chesapeake Bay

10/10 Excellent

"This house was perfect for a short summer getaway with our family, including our 2 grandkids! The beds were super comfortable and the layout of the house worked perfectly for two couples and a family of 4. The boardwalk in Solomons was lovely with beautiful sunsets. We loved the outdoor sculpture garden, the Calvert State Park cliffs by the beach and the awesome mariners museum. The food at the Pier was outstanding, as was the ice cream shop next to the bait and tackle place down the street. All in all, this was a great visit! Glad we found this house to accommodate us so well!"

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?

3-bedroom house in soothing Saint Leonard with AC for relaxing stays: Visitors like this Drayden vacation home rental. It offers a fireplace, a barbecue grill, and air-conditioning to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a stovetop, and a microwave, 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.

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Check prices for these dates

Our top choices for Drayden vacation rentals

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

2. Coles Point Marina

3. Charming Waterfront 3-bedroom house in Piney Point

4. Soul Oasis - home on the Chesapeake Bay

5. Waterfront, Firepit, Kayak, Game room, Potomac 2hrs from DC, Dogs+EV OK

6. Cozy Sunrise Waterfront 2-bedroom Cottage & Dock. Serene Point Lookout/Scotland

7. 2 Bedroom Cottage at Coles Point Marina

8. 2 Acre Oasis with Private Beach! Family and dog friendly!

9. Waterfront Game-Themed Getaway · Dock & Kayaks

10. 4-BR Waterfront Turret Home

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

12. Waterfront 3BR/3BA Getaway: Beach, Dock, Firepit! AMAZING Sweeping VIEWS!

13. 3-bedroom house in soothing Saint Leonard with AC for relaxing stays

14. Riverside Lodge Bed & Breakfast on the Honga River UNIT C

15. Waterfront home on Mill Creek-5BR-3bath-Hot tub, Kayaks & private dock

16. Riverside Lodge Bed & Breakfast on the Honga River UNIT E

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

18. Lakefront Cabin Near Solomons Island w/ Hot Tub

19. Lakefront Cabin Near Solomons Island w/ Hot Tub

Find vacation rentals that suit your style

Top Drayden Hotel Reviews

Spark by Hilton California Lexington Park

Sleep Inn & Suites California MD

Comfort Inn & Suites Lexington Park near Pax River

The Inn at Leonardtown, an Ascend Collection Hotel

Hilton Garden Inn Solomons

House Right on the Potomac River - Great Sunrises & Sunsets

Relax & Renew in a WATERFRONT Cottage , private pier, kayaks, fishing, wineries.

Quality Inn Solomons - Beacon Marina

Belle of the Chesapeake Bay

Find out more about Drayden

Frequently asked questions

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