Holiday Homes in Maryland

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1 Aug - 3 Aug
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22 Aug - 24 Aug
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19 Sept - 21 Sept

Top Cities in Maryland

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Featured Holiday Homes in Maryland

Charming Historic Townhouse Steps From USNA
Fridge, microwave, oven, stovetop

Charming Historic Townhouse Steps From USNA

10.0 out of 10, Exceptional, (27)
"It was great!"
Charming Historic Townhouse Steps From USNA
Sunset Island is Loved for it's Amazing Amenities
Relax by the pool surrounded by lounge chairs and umbrellas, with a gazebo and ocean views.

Sunset Island is Loved for it's Amazing Amenities

Sunset Island is Loved for it's Amazing Amenities
9 Mi to National Mall: Spacious Bethesda Retreat!
Relax in comfort with a large flat-screen TV, plush sofas, and a glass coffee table.

9 Mi to National Mall: Spacious Bethesda Retreat!

8.6 out of 10, Excellent, (8)
"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!
Beautiful Cottage - Sleeps 8 -Bayside
2 bedrooms, free WiFi, bed sheets

Beautiful Cottage - Sleeps 8 -Bayside

9.0 out of 10, Wonderful, (4)
"Everything was very nice, host was amazing."
Beautiful Cottage - Sleeps 8 -Bayside
The Pea Pod - Deep Creek Lake
Relax on the covered porch with comfortable seating and ambient lighting.

The Pea Pod - Deep Creek Lake

10.0 out of 10, Exceptional, (34)
"Property is just as listed. Have atayed here multiple times and as always its a great place to stay. "
The Pea Pod - Deep Creek Lake
Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!
Enjoy serene waterfront views and easy access to moorings and facilities.

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

10.0 out of 10, Exceptional, (227)
"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!
Canton’s Finest Luxury Stay: Walk to Park, Bars!
Timekeeping and dining in a serene, stylish space with a dining area for two and a touch of greenery.

Canton’s Finest Luxury Stay: Walk to Park, Bars!

9.8 out of 10, Exceptional, (16)
"The host was great, the place was adorable and perfect for our stay. Very clean, had everything we needed and was close to everything. I highly recommend!"
Canton’s Finest Luxury Stay: Walk to Park, Bars!
Beautiful 3 BR 2 BA Home in Montego Bay - Community Pool
Enjoy cooking in this well-equipped kitchen with a refrigerator, microwave, oven, and sink.

Beautiful 3 BR 2 BA Home in Montego Bay - Community Pool

9.8 out of 10, Exceptional, (42)
"This is a nice property located a short drive or "
Beautiful 3 BR 2 BA Home in Montego Bay - Community Pool
The Cozy Crab- Your Charming Haven in Lovely North Beach!
Outdoor dining

The Cozy Crab- Your Charming Haven in Lovely North Beach!

9.4 out of 10, Exceptional, (3)
"The place was inviting and beautiful. Will definitely stay there again."
The Cozy Crab- Your Charming Haven in Lovely North Beach!
Downtown Perch W/ Free WiFi, Private Balcony/Patio, Easy Beach Access & More
Overlooking a wide sandy beach, this property offers stunning views of the calm sea.

Downtown Perch W/ Free WiFi, Private Balcony/Patio, Easy Beach Access & More

9.4 out of 10, Exceptional, (19)
"Well cared for"
Downtown Perch W/ Free WiFi, Private Balcony/Patio, Easy Beach Access & More
Beautiful 3 BR 2.5 BA New Home in West Ocean City's Bayside Community
Enjoy meals in the kitchen with a stove, oven, and dining area.

Beautiful 3 BR 2.5 BA New Home in West Ocean City's Bayside Community

10.0 out of 10, Exceptional, (7)
Beautiful 3 BR 2.5 BA New Home in West Ocean City's Bayside Community
Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina
Boats docked at the marina, offering scenic views of the calm water.

Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina

9.8 out of 10, Exceptional, (11)
"Vacationed here with our family of 5. Very cute and nice layout. Perfect walk to downtown and the docks. "
The price is €454
includes taxes & fees
26 Aug - 27 Aug
Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina
Charming Historic Victorian 4 bedroom guesthouse in Rohrersville with WiFi, AC
Microwave, oven, stovetop, dishwasher

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 €424
includes taxes & fees
3 Aug - 4 Aug
Charming Historic Victorian 4 bedroom guesthouse in Rohrersville with WiFi, AC
Wave Watcher's Condo - Steps to the beach!
Relax in a spacious living area with a sofa and dining table, featuring a washer and dryer.

Wave Watcher's Condo - Steps to the beach!

9.8 out of 10, Exceptional, (6)
"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!
Cozy Guesthouse w/ free parking, 15 minutes to D.C., Pet Friendly
Enjoy a compact apartment with a kitchenette, dining area, and flat-screen TV.

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

9.4 out of 10, Exceptional, (31)
"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
Spacious Waterfront Home secluded on 60 ac with Beach and Boat Ramp
Relax on the spacious deck with a wicker sofa, cushioned chairs, and a hammock, perfect for unwinding in a serene atmosphere.

Spacious Waterfront Home secluded on 60 ac with Beach and Boat Ramp

9.8 out of 10, Exceptional, (69)
"Property was exactly as advertised. Charming Farmhouse with plenty of space situated on a large property with a private beach. We even enjoyed some of the local restaurants, Captain Pat's Seafood and Tacos Haciendas."
Spacious Waterfront Home secluded on 60 ac with Beach and Boat Ramp
Affordable Luxury Town Home in Federal Hill Baltimore.
Enjoy cooking in this well-equipped kitchen with a granite countertop, wooden cabinets, and modern appliances.

Affordable Luxury Town Home in Federal Hill Baltimore.

9.4 out of 10, Exceptional, (51)
"Home was in a great location convenient to many restaurants and bars. Listing stated they had a grill but unfortunately did not. There was a fire pit in the back yard but no propane tank so we couldn’t use it. Parking was a challenge every night we came back from the family we were there visiting. House is decorated nicely but living room furniture was super uncomfortable but beds were very comfortable."
Affordable Luxury Town Home in Federal Hill Baltimore.
Quiet Relaxing Waterfront Suisse Chalet
Guests gather at the ceremony site, surrounded by lush greenery and a serene water view.

Quiet Relaxing Waterfront Suisse Chalet

9.6 out of 10, Exceptional, (76)
"Overall this was the most amazing experience from the location and the house itself to the property manager. The property manager was so amazing and made sure that if you needed anything in your stay they would make it happen. They were also very good about communication and responding quickly. On top of all of this the house itself is amazing and in the perfect location. Whether you want to have a chill getaway or explore Annapolis and the other amazing locations around it is the perfect house."
Quiet Relaxing Waterfront Suisse Chalet
Sharpsburg Retreat--Civil War Home Near Antietam Battlefield, C&O Canal Towpath
Relax on the covered porch with a bench and two chairs, surrounded by the serene beauty of the autumn trees.

Sharpsburg Retreat--Civil War Home Near Antietam Battlefield, C&O Canal Towpath

9.8 out of 10, Exceptional, (181)
"It was such a treat to stay in this unique old house. The basement is built right into the rock hill! The house is comfortable and convenient even though it has seen so many years. The hosts did a great job decorating and taking care of it. We would love to come back on a warmer weekend and enjoy the yard. "
Sharpsburg Retreat--Civil War Home Near Antietam Battlefield, C&O Canal Towpath
421 Irie: Simply Charming 2 Story COTTAGE!! Private Pool!! 1 Off Street Parking!
Enjoy cooking in this well-lit kitchen with a central island, wooden cabinetry, and stainless steel appliances.

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

10.0 out of 10, Exceptional, (112)
"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!
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.
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Top Maryland Hotel Reviews

Princess Royale Oceanfront Resort

Princess Royale Oceanfront Resort

10/10 Excellent
"One of the best places in OC! "
Scottie 2-night trip
Posted 1 day ago
Princess Royale Oceanfront Resort