The 30 Best Holiday Rentals in Maryland

Ranked 1 out of 1,216 in the Maryland region, as well as being 1 of 214 for holiday rentals in Ocean City.

• “It was a birthday getaway for my son and we didn’t want to leave. Very peaceful and everyone respected others space and”
• “Great place to stay with a dog when visiting Assateague Island.”
• “very pleasant, we recommend”
• See more reviews of Shore Point Cottages

Ranked 2 out of 1,216 in the Maryland region, as well as being 1 of 13 for holiday rentals in Waldorf.

• “Excellent, will be back next year!”
• “The perfect place for our short vacation.”
• “Had so much fun.. loved the place we stayed at and loved the places we visited …”
• See more reviews of Private 2BR Luxe Suite Natl Harbor DC MD VA

Ranked 3 out of 1,216 in the Maryland region, as well as being 1 of 6 for holiday rentals in Grasonville.

• “I highly recommend Jackie’s home. She goes above and beyond to make her feel welcome she has thought of every detail to”
• “This place is so much prettier than the pictures, a definite must return!”
• “My friends a I were there for to short of a time. If we get the chance next year we will definitely add another night.”
• See more reviews of Abay Palace of Kent Narrows in a King Bed!

Ranked 4 out of 1,216 in the Maryland region, as well as being 1 of 7 for holiday rentals in Fort Washington.

• “spacious, very comfortable enough for vacation, nice little...”
• “The unit is in a nice neighborhood and the property is well...”
• “It was a good experience”
• See more reviews of Single family home

Ranked 5 out of 1,216 in the Maryland region, as well as being 2 of 214 for holiday rentals in Ocean City.

• “It’s a great place for the weekend. People are so great. You will be missing out if you dont go check it out.”
• “New updated condo and great places to eat nearby!”
• “Really nice condo apartment💯 I had a great time even though it rained every day for my stay”
• See more reviews of Bahama Princess Condos

Ranked 6 out of 1,216 in the Maryland region, as well as being 3 of 214 for holiday rentals in Ocean City.

• “Our stay was nice but due to the smell I am not sure I would rent the apartment again.”
• “Good value. Great location.”
• “It was quiet, location was great and king bed was comfortable.”
• See more reviews of St. Tropez

Ranked 7 out of 1,216 in the Maryland region, as well as being 2 of 14 for holiday rentals in Silver Spring.

• “Everything”
• “An affordable and beautiful experience”
• “Excellent little stay”
• See more reviews of Elegant 1-BR Apartment

Ranked 8 out of 1,216 in the Maryland region, as well as being 1 of 39 for holiday rentals in Baltimore.

• “The property was charming, and very well put together.”
• “A home away from home 👍🏽”
• “Great adult stay in Fells Point, Baltimore - just what we were looking for!”
• See more reviews of Cozy Modern Apt in the Heart of Fells Point!

Ranked 9 out of 1,216 in the Maryland region, as well as being 4 of 30 for holiday rentals in Annapolis.

• “Great location!”
• “We travel full time and at the moment our trav3l trailer was...”
• “I would recommend this house to anybody who wanted to visit Annapolis!”
• See more reviews of Gaia House

Ranked 10 out of 1,216 in the Maryland region, as well as being 2 of 39 for holiday rentals in Baltimore.

• “I would highly recommend this property. The accommodations an s amenities were very nice.”
• “Spacious”
• “I love staying here”
• See more reviews of Upscale 2BD/1.5BA townhome mins to JHH & downtown

Ranked 11 out of 1,216 in the Maryland region, as well as being 4 of 214 for holiday rentals in Ocean City.

• “Great spot for a group of friends to stay close to the beach!”
• “Friendly staff lots of space”
• “Overall not bad but for close to 1200$ for just two nights there shouldn’t be any issues.”
• See more reviews of Americana Condos 10th street

Ranked 12 out of 1,216 in the Maryland region, as well as being 5 of 214 for holiday rentals in Ocean City.

• “Idk what to say about the breakfast, not provided.”
• “Everything.”
• “Had a wonderful time!”
• See more reviews of Ocean'S Edge 401 Condo

Ranked 13 out of 1,216 in the Maryland region, as well as being 6 of 214 for holiday rentals in Ocean City.

• “Overall, the stay was good.”
• “Weekend at Dhimas”
• “I would visit again”
• See more reviews of Dhimas Bayview Suites

Ranked 14 out of 1,216 in the Maryland region, as well as being 7 of 214 for holiday rentals in Ocean City.

• “Perfect for a weekend getaway”
• “Great Weekend Trip”
• “Great vacation”
• See more reviews of Wilmington Terrace

Ranked 15 out of 1,216 in the Maryland region, as well as being 4 of 14 for holiday rentals in Columbia.

• “Absolutely wonderful”
• “Everything WAS excellent outside of the no tv in the BR”
• “Not worth the price.”
• See more reviews of WhyHotel by Placemakr, Columbia

Ranked 16 out of 1,216 in the Maryland region, as well as being 3 of 39 for holiday rentals in Baltimore.

• “Almost Perfect”
• “This property is excellent for big groups/family trips. The host was very nice and responds quickly,”
• “The house was charming and had the appearance of clean but only surface clean.”
• See more reviews of Reservoir Hill Mansion - 4 bedrooms

Ranked 17 out of 1,216 in the Maryland region, as well as being 1 of 1 for holiday rentals in Sharpsburg.

• “Was therefore family business, but in the future someday would love to take a weeks vacation there!”
• “An absolute gem”
• “Historic house charm with modern amenities”
• See more reviews of Lock Keepers Cottage on C&O Canal/Potomac River

Ranked 18 out of 1,216 in the Maryland region, as well as being 8 of 214 for holiday rentals in Ocean City.

• “I loved the private balcony view of the beach.”
• “not long enough”
• “The location was awesome.”
• See more reviews of Pyramid V

Ranked 19 out of 1,216 in the Maryland region, as well as being 9 of 214 for holiday rentals in Ocean City.

• “Awesome”
• “Loved it”
• “everything”
• See more reviews of Charming Family Home 7 mins to Beach Dog Friendly

Ranked 20 out of 1,216 in the Maryland region, as well as being 10 of 214 for holiday rentals in Ocean City.

• “The property was nice and clean and very comfortable.”
• “Clean nicely decorated condo and loved the proximity to the beach!”
• “Carrying everything up so many steps.”
• See more reviews of Ocean Block Condo 100 Steps From the Beach

Ranked 21 out of 1,216 in the Maryland region, as well as being 7 of 14 for holiday rentals in Silver Spring.

• “Just like being at home”
• “I’m just so glad I found this place, it was our last stop with family and it really allowed us to finish the trip in com”
• “Lovely and spacious family home”
• See more reviews of Upgraded, beautiful 4 BD Colonial in Silver Spring

Ranked 22 out of 1,216 in the Maryland region, as well as being 11 of 214 for holiday rentals in Ocean City.

• “Location ”
• “It was clean, friendly staff.”
• “We had a great time and enjoyed our stay. Aside from a few very minor details it was great.”
• See more reviews of Crystal Sands Apartments

Ranked 23 out of 1,216 in the Maryland region, as well as being 1 of 1 for holiday rentals in Shady Side.

• “Wonderful Waterfront Stay...”
• “Lovely house, fantastic location by the bay.”
• “My husband and I spent 3 nights here and enjoyed it so much...”
• See more reviews of Luxe Chesapeake Bay Getaway Less Than 20 Mi to Annapolis!

Ranked 24 out of 1,216 in the Maryland region, as well as being 12 of 214 for holiday rentals in Ocean City.

• “It was clean and closely located to boardwalk.”
• “Meh.”
• “New, clean and nice! Very convenient location & great hosts. A few more amenities and it's 5 star!!”
• See more reviews of Safari Apartments

Ranked 25 out of 1,216 in the Maryland region, as well as being 13 of 214 for holiday rentals in Ocean City.

• “The property was great, the space worked well for our family...”
• “It was a perfect weekend. The apartment is so cute!”
• “The master shower is amazing!! Master bed is very comfortable. We enjoyed our stay very much!”
• See more reviews of Ocean One

Ranked 26 out of 1,216 in the Maryland region, as well as being 14 of 214 for holiday rentals in Ocean City.

• “staff was very accomadating. Owners work hard every day”
• “Location”
• “All in all, it was a fantastic experience that I would rent again!”
• See more reviews of ELIS APARTMENT

Ranked 27 out of 1,216 in the Maryland region, as well as being 1 of 2 for holiday rentals in Knoxville.

• “lovely spot, has everything you need, quiet and comfortable”
• “Peaceful, secluded, cozy retreat close to hiking trails and historical sites.”
• “If in the area again would definitely stay here again!”
• See more reviews of Peaceful and Secluded Knoxville Retreat with Deck

Ranked 28 out of 1,216 in the Maryland region, as well as being 11 of 30 for holiday rentals in Annapolis.

• “Perfect place for a special family celebration.”
• “Loved the location and the kitchen was excellent.”
• “The bed in the larger room was a bit on the hard side!”
• See more reviews of Spectacular Location Two Bedroom State Circle Apartment

Ranked 29 out of 1,216 in the Maryland region, as well as being 15 of 214 for holiday rentals in Ocean City.

• “the place's wifi never worked and they didn't say...”
• “Excellent Stay”
• “It was a good stay and close to the beach but no real view of the ocean.”
• See more reviews of Marylander Condominiums, 90 steps from the beach

Ranked 30 out of 1,216 in the Maryland region, as well as being 1 of 2 for holiday rentals in McComas Beach.

• “Location was great, house was very clean and maintained.”
• “Looking for a quick and regenerate escape for work pressures and this property delivered. Secluded yet accessible. Comfo”
• “It was a very nice house with a lovely location”
• See more reviews of Private Family Home with Deck, Porch and Forest Views!