Vacation Homes in Maryland

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Top Cities in Maryland

Our top choices for Maryland vacation homes

Unit 2 South - New Flooring Stairs & Hallways 2026 4bed/3.5 bath/3 car garage

Unit 2 South - New Flooring Stairs & Hallways 2026 4bed/3.5 bath/3 car garage
Midtown Ocean City
8.6 out of 10, Excellent, (7 reviews)
Unit 2 South - New Flooring Stairs & Hallways 2026 4bed/3.5 bath/3 car garage

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

Sharpsburg Retreat--Civil War Home Near Antietam Battlefield, C&O Canal Towpath
Sharpsburg
9.8 out of 10, Exceptional, (201 reviews)
"We enjoyed our stay and the location was excellent"
United States
Barbara W.
The price is AED 533
AED 646 total
includes taxes & fees
7 Jun - 8 Jun
Sharpsburg Retreat--Civil War Home Near Antietam Battlefield, C&O Canal Towpath

Spacious 4-bedroom house on the water in Caine Keys II, Ocean City, MD.

Spacious 4-bedroom house on the water in Caine Keys II, Ocean City, MD.
North Ocean City
Spacious 4-bedroom house on the water in Caine Keys II, Ocean City, MD.

Rooftop Deck Escape! Free Parking!

Rooftop Deck Escape! Free Parking!
South Baltimore
8.4 out of 10, Very Good, (53 reviews)
"Amazing scenery and relaxing house amazing host would definitely recommend!"
United States
Sean P.
The price is AED 420
AED 1,117 total
includes taxes & fees
10 Jun - 11 Jun
Rooftop Deck Escape! Free Parking!

3 Bedroom Pet Friendly Single Family Home

3 Bedroom Pet Friendly Single Family Home
North Ocean City
9.0 out of 10, Wonderful, (8 reviews)
"Good location, nice area. We’d definitely book again."
United States
Mark C.
3 Bedroom Pet Friendly Single Family Home

Lovely bay views with kayaks, bikes, fire pit, crabbing & more

Lovely bay views with kayaks, bikes, fire pit, crabbing & more
Shady Side
9.8 out of 10, Exceptional, (31 reviews)
"Was a great stay. Was on a work detail and needed something close to elderly parents and work. Coo k ed every night with all needed to achieve dinner. Thx again. JBCAIN"
United States
Barry C.
Lovely bay views with kayaks, bikes, fire pit, crabbing & more

3-B rooms 5 beds & 2 BR Spacious House 1 mile from downtown with 2 free parking.

3-B rooms 5 beds & 2 BR Spacious House 1 mile from downtown with 2 free parking.
Silver Spring
10.0 out of 10, Exceptional, (69 reviews)
"This was a great stay, thank you so much for allowing us to stay at your place."
United States
Rowland
3-B rooms 5 beds & 2 BR Spacious House 1 mile from downtown with 2 free parking.

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

Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!
Historic District
10.0 out of 10, Exceptional, (247 reviews)
"Perfect location and lovely place for a weekend getaway!"
United States
Krista L.
Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!

DE LUXE KING-SIZE BED Master Bedroom + 2 SLEEPING SOFAS in LR - WHOLE SUITE 79

DE LUXE KING-SIZE BED Master Bedroom + 2 SLEEPING SOFAS in LR - WHOLE SUITE 79
Silver Spring
9.2 out of 10, Wonderful, (19 reviews)
"Great place to stay. Very convenient to everything in the city."
United States
Stephen R.
The price is AED 238
AED 792 total
includes taxes & fees
8 Jun - 9 Jun
DE LUXE KING-SIZE BED Master Bedroom + 2 SLEEPING SOFAS in LR - WHOLE SUITE 79

Beautiful Federal Hill home!

Beautiful Federal Hill home!
Federal Hill
9.4 out of 10, Exceptional, (54 reviews)
"Great location and neighborhood, and easy to get to our event at the Convention Center"
United States
Joel S.
Beautiful Federal Hill home!

Charming Annapolis WaterVIEW Home

Charming Annapolis WaterVIEW Home
Arundel on the Bay
9.8 out of 10, Exceptional, (70 reviews)
"The host was very welcoming and responsive before and during the stay for my questions. The house was clean and comfortable. The hot tub was lovely for a soak. We enjoyed the walk to and sitting on the peaceful community beach. Thank you!"
United States
Kathy S.
The price is AED 886
AED 2,044 total
includes taxes & fees
10 Jun - 11 Jun
Charming Annapolis WaterVIEW Home

Charming 4-bedroom Beach House in Ocean Pines

Charming 4-bedroom Beach House in Ocean Pines
Ocean Pines
9.4 out of 10, Exceptional, (3 reviews)
"Our family had a wonderful time! The home was clean and decorated for the holidays. The host was very responsive and kind. We will definitely stay again! "
United States
Alexandra P.
The price is AED 1,355
AED 2,579 total
includes taxes & fees
11 Jun - 12 Jun
Charming 4-bedroom Beach House in Ocean Pines

Cute, Cozy 2-bedroom house in near Annapolis with water access

Cute, Cozy 2-bedroom house in near Annapolis with water access
Herald Harbor
9.6 out of 10, Exceptional, (8 reviews)
"Host was wonderful! Enjoyed our weekend in a very clean, comfortable and peaceful place. Look forward to returning in warmer weather."
United States
Katherine P.
The price is AED 314
AED 848 total
includes taxes & fees
16 Jun - 17 Jun
Cute, Cozy 2-bedroom house in near Annapolis with water access

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

Beautiful family sized townhouse with deck. Close to Washington DC and Baltimore
Crofton
9.8 out of 10, Exceptional, (113 reviews)
"Clean, bright, just as shown, with parking out front and in a convenient location - recommend and would rent again!"
United States
Sue O.
Beautiful family sized townhouse with deck. Close to Washington DC and Baltimore

PERFECT LOCATION in the heart of history

PERFECT LOCATION in the heart of history
Historic District
10.0 out of 10, Exceptional, (223 reviews)
"We had a great time here. It is so close to downtown and USNA. The comfort and convenience is terrific. "
United States
Amy B.
PERFECT LOCATION in the heart of history

3Bd House Walk to DC Metro

3Bd House Walk to DC Metro
Silver Spring
10.0 out of 10, Exceptional, (64 reviews)
"Great place to stay over the holidays while visiting family. "
United States
Katherine F.
3Bd House Walk to DC Metro

Affordable Luxury Town Home in Federal Hill Baltimore.

Affordable Luxury Town Home in Federal Hill Baltimore.
Riverside
9.4 out of 10, Exceptional, (78 reviews)
"Great neighborhood and everything is exactly what you expect from the pictures"
United States
Kelvin S.
Affordable Luxury Town Home in Federal Hill Baltimore.

Renovated Farmhouse located near the C and O Canal

Renovated Farmhouse located near the C and O Canal
Hancock
9.6 out of 10, Exceptional, (24 reviews)
"The house was spacious, clean and well decorated. We enjoyed the older house ambiance with modern amenities at a reasonable price. "
United States
Kevin C.
The price is AED 661
AED 934 total
includes taxes & fees
8 Jun - 9 Jun
Renovated Farmhouse located near the C and O Canal

401 142nd Street

401 142nd Street
North Ocean City
10.0 out of 10, Exceptional, (23 reviews)
"Wonderful stay at a clean cottage"
United States
Jenn C.
The price is AED 551
AED 1,810 total
includes taxes & fees
21 Jun - 22 Jun
401 142nd Street

2 North 4bed/3.5 bath 3 Car Garage New Flooring Stairways&Hallways 2026

2 North 4bed/3.5 bath 3 Car Garage New Flooring Stairways&Hallways 2026
Midtown Ocean City
8.2 out of 10, Very Good, (56 reviews)
"Great location, easy one block walk onto the beach and clean. Our family had a wonderful time and it was spacious 8, could comfortably few more. "
United States
Bhavini D.
2 North 4bed/3.5 bath 3 Car Garage New Flooring Stairways&Hallways 2026
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