Maryland Vacation Homes and Villas with Pools

a living room with a couch and a table at Downtown Silver Spring 2BR Skyline Balcony Suite Walkable to DC Metro LuxePad in Silver Spring

From US $202

Downtown Silver Spring 2BR Skyline Balcony Suite Walkable to DC Metro LuxePad Pool available

8.1 (7 Reviews) Holiday_home

The entire place is yours • 1000 m² size • Free on-site parking

Silver Spring Downtown Silver Spring

Best Price Match

a living room with a couch and a table at Heaven On Baltimore at Harborfront in Baltimore

From US $262

Heaven On Baltimore at Harborfront Pool available

8.8 (4 Reviews) Apartment

Apartments • Private parking • Outdoor swimming pool

Baltimore National Aquarium

Best Price Match

a kitchen and living room with a couch and a chair at 1BR Luxury Apartment With Rooftop Deck & Pool in Baltimore

From US $139

1BR Luxury Apartment With Rooftop Deck & Pool Pool available

9.0 (27 Reviews) Apartment

The entire place is yours • 121 m² size • Kitchen

Best Price Match

a living room with a couch and a table at 2B 2BA Luxury Downtown Suite Rooftop Deck & Gym in Baltimore

From US $157

2B 2BA Luxury Downtown Suite Rooftop Deck & Gym Pool available

7.9 (31 Reviews) Apartment

The entire place is yours • 102 m² size • Kitchen

Best Price Match

a kitchen with a stainless steel refrigerator and white cabinets at Modern Home 2BR 2BA Free Off-Street Parking & Wifi in Baltimore

From US $197

Modern Home 2BR 2BA Free Off-Street Parking & Wifi Pool available

8.5 (15 Reviews) Apartment

The entire place is yours • 137 m² size • Free on-site parking

Baltimore Lexington Market

Best Price Match

a living room with a couch and a table at 2BR Distinguished Apartment Rooftop Deck & Gym in Baltimore

From US $280

2BR Distinguished Apartment Rooftop Deck & Gym Pool available

9.7 (12 Reviews) Apartment

The entire place is yours • 111 m² size • Kitchen

Best Price Match

a living room with a couch and a table at 2B 2BA Distinguished Apartment Rooftop Pool & Gym in Baltimore

From US $169

2B 2BA Distinguished Apartment Rooftop Pool & Gym Pool available

9.6 (20 Reviews) Apartment

The entire place is yours • 102 m² size • Kitchen

Best Price Match

a living room with a couch and a table at Luxury Downtown Crown Apartment in Gaithersburg

From US $229

Luxury Downtown Crown Apartment Pool available

9.5 (6 Reviews) Apartment

The entire place is yours • 116 m² size • Free on-site parking

Gaithersburg Market Square

Best Price Match

a small white house with a porch at Pool, Trail Access! Dog-Friendly Ocean Pines Haven in Ocean Pines

From US $295

Pool, Trail Access! Dog-Friendly Ocean Pines Haven Pool available

9.8 (5 Reviews) Holiday_home

The entire place is yours • 125 m² size • On-site parking

Maryland Ocean Downs Casino

Best Price Match

a living room with a couch and a fireplace at Sunplace 02 in McHenry

From US $286

Sunplace 02 Pool available

9.8 (7 Reviews) Holiday_home

The entire place is yours • 132 m² size • Free on-site parking

Best Price Match

a living room with a pool and a ceiling fan at 3 bedroom w indoor pool hotub in Silver Spring

From US $347

3 bedroom w indoor pool hotub Pool available

8.4 (10 Reviews) Holiday_home

The entire place is yours • Kitchen • Garden

Wheaton Westfield Wheaton

Best Price Match

a wooden deck with a table and an umbrella at Ski Harbor 07 in McHenry

From US $315

Ski Harbor 07 Pool available

9.6 (5 Reviews) Holiday_home

Houses • Kitchen • Lake view

Best Price Match

a brown house with a brown roof at Sunplace 07 in McHenry

From US $298

Sunplace 07 Pool available

9.5 (4 Reviews) Holiday_home

The entire place is yours • 154 m² size • Kitchen

Best Price Match

a log cabin with an american flag in front of it at Cherry Hill Park in College Park

From US $316

Cherry Hill Park Pool available

10.0 (15 Reviews) Camping

Free on-site parking • Outdoor swimming pool • Restaurant

College Park Jack Perry Plaza

Best Price Match

a bar with stools in a room with large windows at 2BR Luxury Apartment Rooftop Pool & Gym in Baltimore

From US $180

2BR Luxury Apartment Rooftop Pool & Gym Pool available

9.8 (4 Reviews) Apartment

The entire place is yours • 111 m² size • Private parking

Best Price Match

a room with a video game console and two chairs at No Black Tie Affair in McHenry

From US $988

No Black Tie Affair Pool available

10.0 (3 Reviews) Holiday_home

The entire place is yours • 377 m² size • Kitchen

Best Price Match

a swimming pool with chairs and a house at Oasis by the Bay - Waterfront Heated Pool Hot Tub in Annapolis

From US $473

Oasis by the Bay - Waterfront Heated Pool Hot Tub Pool available

10.0 (3 Reviews) Holiday_home

The entire place is yours • 520 m² size • Free on-site parking

Annapolis Neck Bay Ridge

Best Price Match

a bedroom with a large bed with orange pillows at Cozy Suite at Towson Center in Towson

From US $245

Cozy Suite at Towson Center Pool available

8.0 (7 Reviews) Apartment

The entire place is yours • 420 m² size • Free on-site parking

Towson Towson Town Center

Best Price Match

a bedroom with two beds and a kitchen at Cove Creek Lodge 209 Standard Double Queen Room in Oakland

From US $268

Cove Creek Lodge 209 Standard Double Queen Room Pool available

9.7 (3 Reviews) Holiday_home

The entire place is yours • Free on-site parking • Outdoor swimming pool

Best Price Match

a hot tub sitting on a deck next to a house at Play-A-Way Chalet in McHenry

From US $432

Play-A-Way Chalet Pool available

8.8 (4 Reviews) Holiday_home

The entire place is yours • 305 m² size • Kitchen

Best Price Match

two beds in a room with wooden walls at Cove Creek Lodge 211 Standard Double Queen Fireplace Room in Oakland

From US $320

Cove Creek Lodge 211 Standard Double Queen Fireplace Room Pool available

9.3 (3 Reviews) Holiday_home

The entire place is yours • Free on-site parking • Outdoor swimming pool

Best Price Match

Maryland Baltimore/Washington International Thurgood Marshall Airport (BWI)

a large blue house with a large yard at Large Home with Private Pool, Gym, Sauna, 7 Bedrooms, Sleeps 21 in Severn

From US $816

Large Home with Private Pool, Gym, Sauna, 7 Bedrooms, Sleeps 21 Pool available

9.3 (3 Reviews) Holiday_home

The entire place is yours • 383 m² size • Kitchen

Best Price Match

a floor plan of a house at Adlerskron in McHenry

From US $498

Adlerskron Pool available

8.7 (4 Reviews) Holiday_home

The entire place is yours • 278 m² size • Kitchen

Best Price Match

a log cabin in the woods with a gravel driveway at Deep Creek Mountain Retreat in McHenry

From US $427

Deep Creek Mountain Retreat Pool available

7.8 (5 Reviews) Holiday_home

The entire place is yours • Swimming pool • Hot tub

Best Price Match

a living room with blue walls and a staircase at 710H Studio Loft One Bath in Oakland

From US $269

710H Studio Loft One Bath Pool available

8.7 (3 Reviews) Holiday_home

The entire place is yours • Free on-site parking • Indoor swimming pool

Best Price Match

a view of a lake from a wooden railing at Highlands Heaven in McHenry

From US $612

Highlands Heaven Pool available

8.0 (3 Reviews) Holiday_home

The entire place is yours • 340 m² size • Kitchen

Best Price Match

a patio with a table and chairs and an umbrella at Newly Remodeled! Luxe Gem - 3 Mi to Johns Hopkins in Baltimore

From US $336

Newly Remodeled! Luxe Gem - 3 Mi to Johns Hopkins Pool available

6.8 (4 Reviews) Holiday_home

The entire place is yours • 166 m² size • Kitchen

Baltimore The Maryland Zoo in Baltimore

Best Price Match

a living room with a couch and a clock on the wall at Sunplace 30 in McHenry

From US $301

Sunplace 30 Pool available

7.3 (3 Reviews) Holiday_home

The entire place is yours • 127 m² size • Free on-site parking

Best Price Match

a living room with a red couch and a glass table at 307C One Bedroom One Bath in Oakland

From US $273

307C One Bedroom One Bath Pool available

7.0 (3 Reviews) Holiday_home

The entire place is yours • Free on-site parking • Indoor swimming pool

Best Price Match

a boat tied to a buoy in the water at Sailboat Experience in Annapolis in Annapolis

From US $191

Sailboat Experience in Annapolis Pool available

8.8 (5 Reviews) Boat

Outdoor swimming pool • Pet friendly • Free WiFi

Annapolis Thurgood Marshall Memorial Plaza

Best Price Match

a living room with a couch and a staircase at 706H Studio Loft One Bath in Oakland

From US $273

706H Studio Loft One Bath Pool available

4.7 (3 Reviews) Holiday_home

The entire place is yours • Free on-site parking • Indoor swimming pool

Best Price Match

a rendering of a tall building in a city at Global Luxury Suites Bethesda Chevy Chase in Bethesda

From US $196

Global Luxury Suites Bethesda Chevy Chase Pool available

7.4 (125 Reviews) Apartment

Apartments • Private parking • Outdoor swimming pool

Washington Friendship Heights

Best Price Match

a kitchen with a counter with a vase of flowers on it at Cozy 2/1.5 Getaway in Lily Ponds in Washington, D.C.

From US $220

Cozy 2/1.5 Getaway in Lily Ponds Pool available

5.7 (39 Reviews) Apartment

The entire place is yours • 74 m² size • Kitchen

Washington Kenilworth

Best Price Match

a bedroom with a bed and two windows at Hidden Gem near Downtown Frederick and shopping in Frederick

From US $220

Hidden Gem near Downtown Frederick and shopping Pool available

8.5 (12 Reviews) Apartment

The entire place is yours • 84 m² size • Kitchen

United States Maryland

Best Price Match

a living room with two red vases with plants in it at Luxury, Chic, Apt with Game Room, Movie Theatre, & 24hr Gym in Rockville

From US $162

Luxury, Chic, Apt with Game Room, Movie Theatre, & 24hr Gym Pool available

10.0 (3 Reviews) Apartment

The entire place is yours • 646 m² size • Private parking

United States Maryland

Best Price Match