A historic downtown street at dusk with vintage street lamps, brick buildings, and a sign for 'FELSH POINT'.

Vacation Homes in Maryland

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Top Cities in Maryland

Our top choices for Maryland vacation homes

Rooftop Deck Escape! Free Parking!

Rooftop Deck Escape! Free Parking!
South Baltimore
8.4 out of 10, Very Good, (56 reviews)
"Lots of things to do in walking distance. Very comfortable beds and all necessities provided. Very awesome and would definitely come back. The rooftop fire was amazing too. "
United States
Erika B.
The price is AED 353
AED 1,035 total
includes taxes & fees
29 Jun - 30 Jun
Rooftop Deck Escape! Free Parking!

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, (204 reviews)
"This was an amazing experience to stay in a house that was here during the battle, look forward to may more visits while I see the place I love. "
United States
Dave W.
The price is AED 533
AED 642 total
includes taxes & fees
9 Jul - 10 Jul
Sharpsburg Retreat--Civil War Home Near Antietam Battlefield, C&O Canal Towpath

Grace Cottage, St Michaels Walk to everything!

Grace Cottage, St Michaels Walk to everything!
Downtown St. Michaels
10.0 out of 10, Exceptional, (7 reviews)
"We loved our stay here! The house was adorable, very clean, and perfectly located right in downtown, which made it so easy to walk to everything. It had everything we needed and felt very comfortable. We would absolutely stay here again!"
United States
Tarah B.
Grace Cottage, St Michaels Walk to everything!

“The Train Depot” 2nd oldest in the US

“The Train Depot” 2nd oldest in the US
Downtown Frederick
10.0 out of 10, Exceptional, (101 reviews)
"House was very clean. Close proximity to restaurants and shops."
United States
Mindee S.
“The Train Depot” 2nd oldest in the US

Centrally Located 4 BR 3.5 BA Townhouse with Water Views!

Centrally Located 4 BR 3.5 BA Townhouse with Water Views!
Midtown Ocean City
Centrally Located 4 BR 3.5 BA Townhouse with Water Views!

Cozy Cottage 2 bedroom house one and half bathrooms Cumberland, Md with AC, WiFi

Cozy Cottage 2 bedroom house one and half bathrooms Cumberland, Md with AC, WiFi
Cumberland
9.8 out of 10, Exceptional, (37 reviews)
"House was very clean and comfortable, and very convenient to downtown Cumberland. "
United States
Larry M.
The price is AED 441
AED 709 total
includes taxes & fees
16 Jul - 17 Jul
Cozy Cottage 2 bedroom house one and half bathrooms Cumberland, Md with AC, WiFi

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, (249 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!

Canal-front home with fast WiFi, central ac, and private dock

Canal-front home with fast WiFi, central ac, and private dock
West Ocean City
Canal-front home with fast WiFi, central ac, and private dock

Beautiful Cottage - Sleeps 8 -Bayside

Beautiful Cottage - Sleeps 8 -Bayside
North Ocean City
8.6 out of 10, Excellent, (11 reviews)
"Very clean property and very convenient location, would stay again!"
United States
AJ H.
Beautiful Cottage - Sleeps 8 -Bayside

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
8.8 out of 10, Excellent, (8 reviews)
Unit 2 South - New Flooring Stairs & Hallways 2026 4bed/3.5 bath/3 car garage

Charming Annapolis WaterVIEW Home

Charming Annapolis WaterVIEW Home
Arundel on the Bay
9.8 out of 10, Exceptional, (70 reviews)
"We enjoyed our stay! The property has a beautiful view of the bay. It was a perfect set up for our family of four. "
United States
Jen M.
The price is AED 1,587
AED 2,973 total
includes taxes & fees
30 Jun - 1 Jul
Charming Annapolis WaterVIEW Home

Private Pool & Stunning Bay Views on Kent Island

Private Pool & Stunning Bay Views on Kent Island
Stevensville
9.2 out of 10, Wonderful, (28 reviews)
"Great time at a nice place and location."
United States
Michael S.
Private Pool & Stunning Bay Views on Kent Island

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)
"This was a wonderful experience for our family! The location was super - just off a convenient street with quick access to the freeway and plenty of parking. The kitchen had everything we needed for our week long stay. We highly recommend staying here!"
United States
Tim G.
Beautiful family sized townhouse with deck. Close to Washington DC and Baltimore

Trendy Spot in Downtown Baltimore/Fells Point

Trendy Spot in Downtown Baltimore/Fells Point
Upper Fells Point
9.6 out of 10, Exceptional, (32 reviews)
"Great location. Clean house with plenty of rooms."
United States
Justin P.
Trendy Spot in Downtown Baltimore/Fells Point

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, (29 reviews)
"As riders passing thru the area on the C&O towpath this location was ideal for a single overnight. The farmhouse was very clean and well maintained and had all the amenities that we needed."
United States
Cliff
The price is AED 661
AED 946 total
includes taxes & fees
27 Jun - 28 Jun
Renovated Farmhouse located near the C and O Canal

Waterfront Home with Private Dock, Community Beach

Waterfront Home with Private Dock, Community Beach
Oyster Harbor
10.0 out of 10, Exceptional, (8 reviews)
"Wonderful stay. Delightful property. Great hosts. Scenic, comfortable and near Annapolis!"
United States
Michele R.
Waterfront Home with Private Dock, Community Beach

Ocean Block End Unit Townhome 300ft Feet From Beach W/ Ocean View

Ocean Block End Unit Townhome 300ft Feet From Beach W/ Ocean View
Midtown Ocean City
8.2 out of 10, Very Good, (55 reviews)
"Lots of stairs but loved the location "
United States
Jill L.
Ocean Block End Unit Townhome 300ft Feet From Beach W/ Ocean View

VellaVue Luxury Estate: Private Indoor Pool, Sauna, Gym & Theater – Sleeps 20

VellaVue Luxury Estate: Private Indoor Pool, Sauna, Gym & Theater – Sleeps 20
Friendsville
10.0 out of 10, Exceptional, (23 reviews)
"Super responsive host and amazing property with ALL the amenities! The pool is incredible! We had a blast!"
United States
Todd C.
VellaVue Luxury Estate: Private Indoor Pool, Sauna, Gym & Theater – Sleeps 20

Adorable, waterfront beach cottage w/ bay view, full kitchen, & free WiFi

Adorable, waterfront beach cottage w/ bay view, full kitchen, & free WiFi
North Ocean City
Adorable, waterfront beach cottage w/ bay view, full kitchen, & free WiFi

4 BR 3.5 BA Waterfront Townhouse with Great Midtown Location

4 BR 3.5 BA Waterfront Townhouse with Great Midtown Location
North Ocean City
4 BR 3.5 BA Waterfront Townhouse with Great Midtown Location
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