Top Vacation Homes in Maryland in 2026

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Top Cities in Maryland

A roller coaster at dusk with illuminated tracks and a Ferris wheel in the background.

Our top choices for Maryland vacation homes

A modern living room with a staircase, a dining area, and a kitchen in the background.

1. Hudson house

Canton

Thelma

A wooden deck with outdoor furniture and a table, overlooking a body of water and surrounded by trees.

2. Chateau Relaxo by Taylor Made Deep Creek

Mountainside

A coastal area with a pier extending into the water, a sandy beach, and a forested hill in the background.

3. CampMd.com

Piney Point

4. Happy Time by Taylor Made Deep Creek

McHenry

A spacious living room with a stone fireplace, a wooden ceiling, and a large sofa.

5. Bear Hollow Lodge by Taylor Made Deep Creek

Oakland

A hot tub with a covered seating area, surrounded by a fenced yard with outdoor furniture.

6. Suite Retreat

Severn

A bed with white and blue pillows, a tufted headboard, and three framed botanical prints on the wall.

7. Bohemia Manor Farm

Chesapeake City

NT$12,229 total

includes taxes & fees

Oct 7 - Oct 8

8. Lucky Penny by Taylor Made Deep Creek

McHenry

Leslie

A log cabin with a covered porch and a fenced area.

9. The Pines by Taylor Made Deep Creek

Swanton

Alexander

10. Picture Perfect by Taylor Made Deep Creek

Mountainside

lakeisha

A hot tub with a wooden deck and a wooden fence in a wooded area.

11. Laurel Brook 39 by Taylor Made Deep Creek

Oakland

Shihab

A floor plan with a family room, two bedrooms, a bathroom, a laundry area, and a walk-in closet.

12. Stone Crest by Taylor Made Deep Creek

Oakland

A living room with a television, sofa, and a teal door.

13. Nanticoke Square 207b 2 Bedroom Townhouse by RedAwning

North Ocean City

"At first it took us a while to find the place since we arrived late and it was dark. We were just tired after a four hour drive. The property was super clean, comfortable and very like home feel. We couldn’t use the pool due to it being emptied. There was some work being done around it for the first days which was a bummer. We were looking forward to it. Everyone around the neighborhood was super friendly. Our walked to the beach was just minutes away. The communication was great, My messages...

Sarahi

A rustic cabin with a metal roof, a stone fire pit, and wooden furniture in a forested area.

14. Bears Lair by Taylor Made Deep Creek

Oakland

Diane

A canal with wooden walkways and boats, surrounded by residential buildings and a water tower.

15. Montego Bay - Peachtree Road 122 3 Bedroom Home by RedAwning

North Ocean City

Linda

A deck with a glass table and chairs, overlooking a lake and hills.

16. Loft of Luxury by Taylor Made Deep Creek

Oakland

"Check-in was easy, and the kitchen was nicely equipped with all the necessary amenities. However, I did have to unload the dishwasher from the previous occupants before I could find the coffee cups. Unfortunately, there were several issues that impacted our stay. The shower curtain had visible mold on it, which seems like a relatively inexpensive and easy issue to address. The dressers were also dusty and gave the impression that the property had not been thoroughly cleaned before our...

Michele

A two-story house with a brown exterior, a front porch, and a snow-covered landscape.

17. Marsh Hill Villa by Taylor Made Deep Creek

McHenry

David

A kitchen with white cabinets, a wooden dining table with chairs, and a wooden floor.

18. Cub House by Taylor Made Deep Creek

McHenry

"NO A/C; NO beach access; NO 2nd full bath; hazardous steps to entrance; ants in fridge; centipedes everywhere inside unit; several miles from anything & no water view or access; found full, moldy dehumidifier in closet then cleaned and set it up - emptied it several times a day despite 50 pint capacity; recent remodel was shoddy; knobs falling off cabinets; bathroom floor stopped short of vanity, causing injuries in the middle of the night; broken blinds for no privacy from road just feet from...

Denise