Holiday Homes in Maryland

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
In two weeks
In one month
In two months

Top Cities in Maryland

Featured Holiday Homes in Maryland

Deep Creek Lake and Wisp just minutes away, includes pass to CARC (pool/gym)

10.0 out of 10, Exceptional, (292)
"We enjoyed our stay so much we hope to come again soon! Communication was awesome with the owners! The kitchen had every thing we could have needed! So much space and enjoyable for all ages! Out of the way from the hustle bustle but close enough to enjoy all the near by attractions . Everything was super clean and check in and out was so easy! Highly recommend this home to everyone!!"
Deep Creek Lake and Wisp just minutes away, includes pass to CARC (pool/gym)

9 Mi to National Mall: Spacious Bethesda Retreat!

8.6 out of 10, Excellent, (9)
"Well. The owner was very nice but property was being worked on. They had walls unpainted basement floor was not done so no one wanted to stay downstairs plumbing had to be readjusted two of the 5 beds upstairs caved in the middle. Also the heating only worked well in one room you had to put it at 75 so that it could be felt elsewhere but the one room would then be too hot. Should not rent out again until he fixes floors walls mirrors and beds "
9 Mi to National Mall: Spacious Bethesda Retreat!

Ocean City Bayside Retreat Unit B - Cozy Family Getaway Near Beach & Dining!

9.6 out of 10, Exceptional, (109)
"Had a great time house was very clean!"
Ocean City Bayside Retreat Unit B - Cozy Family Getaway Near Beach & Dining!

Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably

10.0 out of 10, Exceptional, (31)
"Great place for gathering. Plenty of space to hang out. Kitchen is big, well stocked and great for a large crowd. "
Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably

Bay view from Calvert Cliffs, Solomons Island & State Park nearby

10.0 out of 10, Exceptional, (49)
"Awesome home wnd location! Would stay again!"
Bay view from Calvert Cliffs, Solomons Island & State Park nearby

Charming Historic Townhouse Steps From USNA

10.0 out of 10, Exceptional, (27)
"It was great!"
Charming Historic Townhouse Steps From USNA

⭐️Stunning Renovated Large Balcony 20 Steps to Beach⭐️

9.2 out of 10, Wonderful, (7)
"The location was amazing! Just steps from the beach! The condo was a perfect size for our family which was 5 adults and 2 young kids. It had everything we needed."
The price is €581
includes taxes & fees
1 Sept - 2 Sept
⭐️Stunning Renovated Large Balcony 20 Steps to Beach⭐️

Chesapeake Bay House with Dock & Private Beach

10.0 out of 10, Exceptional, (166)
"Great place for a long weekend. Easy travel to surrounding areas to explore."
Chesapeake Bay House with Dock & Private Beach

Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!

10.0 out of 10, Exceptional, (228)
"Loved everything! Parking garage included, close to everything, very comfortable. Would stay there again!"
Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!

In the Heart of Deep Creek, Wood Fire, steps Lake, Coffee, Pizza, minutes Whisp,

8.4 out of 10, Very good, (52)
"We had a great time, the location was great and the place was clean"
In the Heart of Deep Creek, Wood Fire, steps Lake, Coffee, Pizza, minutes Whisp,

Cozy Guesthouse w/ free parking, 15 minutes to D.C., Pet Friendly

9.2 out of 10, Wonderful, (33)
"The property was convenient to public transit, a nice park, and Dunkin Donuts. It has two televisions, so no need to compromise on the channel to watch "
Cozy Guesthouse w/ free parking, 15 minutes to D.C., Pet Friendly

FletchersCove-DeepCreekLake-PrivateDock-HotTub

9.8 out of 10, Exceptional, (44)
"We had a great time with her family. Everything was meticulous neat and clean, and the Property is right on the lakefront which made it beautiful would definitely consider coming back."
FletchersCove-DeepCreekLake-PrivateDock-HotTub

Cozy home with fenced in yard-Dog Friendly . 2 block walk to historic downtown!

9.6 out of 10, Exceptional, (59)
"Lovely location"
Cozy home with fenced in yard-Dog Friendly . 2 block walk to historic downtown!

3-bedroom townhome in tranquil Delmar with WiFi, AC. Relax and unwind

10.0 out of 10, Exceptional, (1)
"The property was lovely. The host so very accommodating, The neighborhood close to restaurants and stores. The flowers, beverages and goodie basket was really a nice touch and very much appreciated. The beds were very comfortable as well. There is access to the community Pool too. The weather did not permit us to use it. Thank You."
The price is €608
includes taxes & fees
16 Aug - 17 Aug
3-bedroom townhome in tranquil Delmar with WiFi, AC. Relax and unwind

Cottage near the Bay

9.0 out of 10, Wonderful, (41)
"great, peaceful "
The price is €165
includes taxes & fees
13 Aug - 14 Aug
Cottage near the Bay

Wave Watcher's Condo - Steps to the beach!

9.8 out of 10, Exceptional, (7)
"The place was very clean and very cool, which was nice on the hot days. Some of my party slept on the floor so I'd say it sleeps 10 but overall, wonderful place would recommend to anyone!"
Wave Watcher's Condo - Steps to the beach!

1 Mi to Dtwn: Townhome w/ Patio in Baltimore!

8.6 out of 10, Excellent, (8)
"This place was very beautiful and I really enjoyed my stay. When they said first come, first serve for parking it was definitely true. For anyone who doesn’t know the area (like my family) there’s barely parking available as none of the cars moved the entire weekend. Once we found parking we spent a lot using the Lyft app to move around, if not we would not have found parking for blocks upon returning from some of the planned destinations of our trip. Other than that the stay really was...
1 Mi to Dtwn: Townhome w/ Patio in Baltimore!

Beautiful family sized townhouse with deck. Close to Washington DC and Baltimore

9.6 out of 10, Exceptional, (87)
"Great location in quiet neighborhood."
Beautiful family sized townhouse with deck. Close to Washington DC and Baltimore

421 Irie: Simply Charming 2 Story COTTAGE!! Private Pool!! 1 Off Street Parking!

10.0 out of 10, Exceptional, (114)
"My friends and I were looking for a relaxing place to have a long weekend - this place was great! The location was wonderful and the house had everything we needed. The host was a fabulous communicator and helped us with everything we needed! Can’t wait to stay here again! "
421 Irie: Simply Charming 2 Story COTTAGE!! Private Pool!! 1 Off Street Parking!

Charming Historic Victorian 4 bedroom guesthouse in Rohrersville with WiFi, AC

10.0 out of 10, Exceptional, (1)
"Beautiful setting with wonderful indoor and outdoor spaces. The house is charming, renovated, updated, clean, and comfortable. Great location for a family gathering to bike, visit the battlefield or visit Shepherdstown. Hosts went above and beyond to be sure we had all we needed. Would definitely stay again if in the area. "
The price is €373
includes taxes & fees
18 Aug - 19 Aug
Charming Historic Victorian 4 bedroom guesthouse in Rohrersville with WiFi, AC
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Maryland Hotel Reviews