50 Best Maryland Apartments on Holiday Lettings - Vacation rentals

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Vacation rentals Ocean City
561 properties
Garrett County
531 properties
Swanton
133 properties
Montgomery County
36 properties
Apartments Baltimore
31 properties
Talbot County
21 properties
Apartments Annapolis
19 properties
Oxon Hill
17 properties
National Harbor
10 properties
Apartments Fort Washington
10 properties
Calvert County
8 properties
Chestertown
7 properties
Bowie
6 properties
Sabillasville
6 properties
Kent Island
6 properties
Cambridge
5 properties

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1,482 Vacation rentals

11

Vacation home in Maryland

Maryland / Parkville

1 1 1 night min

  • 1 bedroom
  • Sleeps 1
  • 1 night min
  • Child friendly
  • Air conditioning
Close to Towson University, University of Maryland Baltimore County, and Morgan State University. The airport is 45 minutes (car, shuttle, Uber ) away. You’ll love the house because the location is perfect for those who don't want heavy traffic, and it's a very quite ne …see more

from $30 / night

$210 / week

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from $30 / night

(15) Excellent 

25

Cottage rental in Maryland

Maryland / Annapolis

3 6 2 nights min

  • 3 bedrooms
  • Sleeps 6
  • 2 nights min
  • Beach/lakeside relaxation
  • Nearest beach 1 mi
  • Child friendly
Half a block to walk to the Naval Academy Stadium and minutes away from stunning Annapolis town center. This adorable little cottage has lots of sleeping and great outdoor space. Sun Porch & Plenty of parking. A perfect place to relax and enjoy Annapolis, the pro …see more

from $350 / night

$2100 / week

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from $350 / night

(8) Excellent 

56

Vacation home in Baltimore

Maryland / Baltimore

3 6 2 nights min

  • 3 bedrooms
  • Sleeps 6
  • 2 nights min
  • Child friendly
  • Air conditioning
Built in the 1920s, this Tudor style house retains its original charm, it is spacious and creatively painted, with hardwood floors throughout. Fully furnished and decorated with artwork, rugs and antiques from our travels around the world. Two bedrooms with comfortable …see more

from $130 / night

$750 - $960 / week

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from $130 / night

23

Vacation home with shared pool in Preston

Maryland / Preston

1 2 1 night min

  • 1 bedroom
  • Sleeps 2
  • 1 night min
  • Swimming pool
  • Child friendly
  • Air conditioning
Beautiful 18 acres large deck over looks historical woods. Nature at its best... Hawks, rabbits, deer, all kinds of birds.... Our hummin birds are fabulous... WE have a complimentary canoe, bikes, we can set up a water slide for a fee also manicures and pedicures plus …see more

from $75 / night

$350 - $420 / week

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from $75 / night

20

Preston Vacation home rental

Maryland / Preston

1 2 1 night min

  • 1 bedroom
  • Sleeps 2
  • 1 night min
  • Swimming pool
  • Child friendly
  • Air conditioning
Our home has a beautiful fire fly show in our historical wooded back yard. Always enjoy our wildlife our humming birds are the best. Go four leaf clover hunting. The deck is comfortable with lounge chairs for basting in the summer sun. We have goats that get loose... …see more

from $87 / night

$250 / week

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from $87 / night

16

Vacation home in Maryland

Maryland / Capitol Heights

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Child friendly
  • Air conditioning
  • Pet friendly
This is a nice, clean 2-bedroom detached home with great amenities located in close-in suburban Washington DC metro area. The home has a large fenced back yard suitable for kids to play or for your bring-along pets. There is off-street parking, including a driveway wi …see more

from $122 / night

$850 / week

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from $122 / night

11

Maryland Vacation townhouse rental

Maryland / Parkville

1 2 1 night min

  • 1 bedroom
  • Sleeps 2
  • 1 night min
  • Child friendly
  • Air conditioning
Near Towson University, Morgan State University, Goucher College, and University of Maryland Baltimore County. Also close to Samaritan Hospital, Towson Mall, and easy access to I-695 bound for Washington D.C., New York City, etc. Plaza in walking distance (6 blocks) (Wa …see more

from $55 / night

$385 / week

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from $55 / night

39

Vacation guest house in Maryland

Kent Island / Stevensville

2 6 2 nights min

  • 2 bedrooms
  • Sleeps 6
  • 2 nights min
  • Child friendly
Come to our beautiful vacation home and enjoy the scenic view while having fun on the water. Love Point Bay Vacation Home is at the mouth of the Chester River, where it connects to the Chesapeake Bay on Maryland's Eastern Shore. You will feel right at home, yet free of …see more

from $299 / night

$2093 / week

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from $299 / night

12

Vacation home in Maryland

Kent Island / Stevensville

3 10 3 nights min

  • 3 bedrooms
  • Sleeps 10
  • 3 nights min
  • Child friendly
Come to our private luxury waterfront property that sits on 17 acres located on the Chester River where it meets the mouth of the Chesapeake Bay on Maryland's Eastern Shore. Get away from the city and enjoy the scenic view while having fun on the water. Love Point Bay L …see more

from $900 / night

$6300 / week

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from $900 / night

11

Vacation home in Maryland

Maryland / Oxon Hill

4 12 2 nights min

  • 4 bedrooms
  • Sleeps 12
  • 2 nights min
  • Child friendly
  • Air conditioning
  • Pet friendly
Barbie's palace very large home sits on a corner lot lots of privacy wraparound porch patio and deck four bedrooms four bathrooms formal living room and dining room large family large basement that goes throughout the whole house must-see very nicely decoratedHouse is …see more

from $399 / night

$2500 - $3725 / week

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from $399 / night

14

Home rental in Frederick

Maryland / Frederick

2 6 2 nights min

  • 2 bedrooms
  • Sleeps 6
  • 2 nights min
  • Child friendly
If you like the show Fixer-Upper, you'll love the Uptown Cottage! Near Downtown Frederick, great restaurants, beautiful parks, historic sites and shopping. Less than an hour from Baltimore and Washington DC. Fully renovated, a great space for relaxing when you are not o …see more

from $135 / night

$945 / week

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from $135 / night

(11) Excellent 

9

Apartment accommodation in Maryland

Maryland / Ocean City

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Beach/lakeside relaxation
  • Child friendly
  • Car not necessary
Oceanfront on 51st street, #306, Ocean City, MD. One bedroom, Queen size with pull-out couch. 1.5 bath. Recently renovated building. Freshly painted & carpeted. End unit - third floor - elevator. Washer & dryer. Furnished kitchen. High-Def TVs. Reserved …see more

from $200 / night

$1000 - $1300 / week

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from $200 / night

40

Vacation home in Oakland

Garrett County / Oakland

5 14 Min stay varies

  • 5 bedrooms
  • Sleeps 14
  • Min stay varies
  • Ask about children
  • Air conditioning
  • Pet friendly
When you step through the doors of Boxer Overlook, you will immediately be taken in by the unparalleled elegance this home showcases. Ideally located in a quiet community, this 5 bedroom chalet is perfect for large or multi-family gatherings. Offering an open concept fl …see more

from $390 / night

$1715 - $2472 / week

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from $390 / night

20

Vacation apartment with shared pool in Maryland

Maryland / Ocean City

1 6 Min stay varies

  • 1 bedroom
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0.2 mi
  • Swimming pool
Come try this excellent located condo. It is close to all the amenities of downtown OC including the famous OC boardwalk, ball fields, large recreational park for children to play, and bay board walk for fishing. The unit has 2 flat screen TVs as well as a fully furnish …see more

from $60 / night

$400 - $999 / week

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from $60 / night

(1) Excellent 

12

Vacation apartment in Maryland

Maryland / Rock Hall

1 4 2 nights min

  • 1 bedroom
  • Sleeps 4
  • 2 nights min
  • Ask about children
  • Ask about pets
Enjoy the gentle tidal waters of the Chesapeake Bay and its tributaries from your private overlook. The Captain’s Quarters at Spring Cove is a crisp and contemporary second floor living space with great water views. An exterior stairway leads to an ample deck where you …see more

from $180 / night

$1200 / week

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from $180 / night

(1) Good 

21

Vacation apartment in Maryland

Maryland / National Harbor

2 8 2 nights min

  • 2 bedrooms
  • Sleeps 8
  • 2 nights min
  • Child friendly
Stay just walking distance from the Gaylord Convention Center! Enjoy the beautiful Wyndham National Harbor Resort, where all the comforts of home await you after a day of exploration. Each unit contains a full kitchen. The resort has all the amenities, such as an indoor …see more

from $249 / night

$1750 / week

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from $249 / night

(3) Excellent 

14

Vacation home in Maryland

Maryland / Sabillasville

7 16 1 night min

  • 7 bedrooms
  • Sleeps 16
  • 1 night min
  • Child friendly
  • Car not necessary
  • Pet friendly
Do you have a large family that wants to vacation together in a beautiful location in the mountains? Or do you need a scenic location for a wedding or corporate retreat? Then this is your solution! Caboose Farm is a compound made up of three fully furnished homes …see more

from $600 / night

$4200 / week

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from $600 / night

6

Vacation apartment in Ocean City

Maryland / Ocean City

2 5 3 nights min

  • 2 bedrooms
  • Sleeps 5
  • 3 nights min
  • Child friendly
  • Air conditioning
  • Pet friendly
Please note : This property has a 3PM checkin and 10AM checkout time. Please note: Linens are not included with this property. Linens are available upon request. This small masonry building is conveniently located on the bayside and within one block is miniature gol …see more

from $80 / night

$560 - $1645 / week

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from $80 / night

13

Cottage rental in Saint Leonard

Calvert County / Saint Leonard

1 2 2 nights min

  • 1 bedroom
  • Sleeps 2
  • 2 nights min
  • Beach/lakeside relaxation
  • Ask about children
  • Air conditioning
Come relax at this charming updated one bedroom bungalow. It overlooks the waters of Wells Cove, a tributary to the Patuxent River which is itself, a tributary to the Chesapeake Bay. This cottage is secluded from the main house, surrounded by water and a wild flower mea …see more

from $85 / night

$595 - $630 / week

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from $85 / night

(1) Very Good 

26

Apartment rental in Maryland

Maryland / National Harbor

3 10 2 nights min

  • 3 bedrooms
  • Sleeps 10
  • 2 nights min
  • Child friendly
Stay just walking distance from the Gaylord Convention Center! Enjoy the beautiful Wyndham National Harbor Resort, where all the comforts of home await you after a day of exploration. Each unit contains a full kitchen. The resort has all the amenities, such as an indoor …see more

from $329 / night

$2200 / week

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from $329 / night

36

Vacation home in Maryland

Garrett County / McHenry

5 12 Min stay varies

  • 5 bedrooms
  • Sleeps 12
  • Min stay varies
  • Ask about children
  • Air conditioning
Nestled on the shores of Deep Creek Lake, Wispering Waters is an ideal choice for your next getaway with family and friends. Ideal for gathering with your favorite people, the main level has an open floor plan with scenic lake views and plenty of space for everyone to …see more

from $422 / night

$1993 - $3184 / week

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from $422 / night

7

Vacation home in Annapolis

Maryland / Annapolis

3 8 3 nights min

  • 3 bedrooms
  • Sleeps 8
  • 3 nights min
  • Child friendly
  • Car not necessary
  • Ask about pets
Shellback house is a three bedroom, one and 1/2 bath historic townhouse in the heart of Downtown Annapolis with a private garden. The house has views of Ego Alley (Annapolis Waterfront) from the front stoop and the master bedroom. BOOK NOW FOR 2015 LEGISLATIVE SESSION …see more

from $450 / night

$3900 / week

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from $450 / night

(2) Very Good 

15

Rock Hall Vacation cottage rental

Maryland / Rock Hall

3 6 3 nights min

  • 3 bedrooms
  • Sleeps 6
  • 3 nights min
  • Child friendly
  • Ask about pets
The Cottage takes advantage of its unique environment with a large deck overlooking the extensive lawn and the tranquil waters of Spring Cove. The deck includes a dining set and barbeque grill.The first level includes a screened porch accessed through a first floor bedr …see more

from $250 / night

$1500 / week

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from $250 / night

(5) Good 

55

Vacation home in Maryland

Talbot County / Trappe

3 6 2 nights min

  • 3 bedrooms
  • Sleeps 6
  • 2 nights min
  • Beach/lakeside relaxation
  • Nearest beach 97 mi
  • Child friendly
Beautiful, serene waterfront home on the Chesapeake Bay. One hour from the Atlantic Ocean (Ocean City, Assateague Island) and Annapolis, One and a half hours from Washington DC and Baltimore. Many nearby places worth visiting, including picturesque St. Michaels and th …see more

from $330 / night

$1980 / week

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from $330 / night

(5) Very Good 

15

Vacation home in Highland

Maryland / Highland

1 5 1 night min

  • 1 bedroom
  • Sleeps 5
  • 1 night min
  • Nearest beach 300 mi
  • Child friendly
  • Air conditioning
Welcome to the American Dream! Our home is set in a picturesque suburban neighborhood of the nation's capital. We have spacious rooms with private access, restrooms, and a full complement of amenities. Our 1.6 acre yard is perfect for anything from a peaceful lounge to …see more

from $90 / night

$450 - $1080 / week

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from $90 / night

(4) Excellent 

17

Vacation condo with shared pool in Maryland

Maryland / Ocean City

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Suitable for children age 5+
Great deal for OC!. The building's exteior, and pool had been recently remodeled with upgrades. This spacious yet simply decorated three bedroom penthouse condo has a full kitchen, 3 bedrooms and 2 baths; amenities include elevator, AC, cable TV, WI-FI internet access, …see more

from $90 / night

$625 - $1225 / week

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from $90 / night

14

Apartment rental in Ocean City

Maryland / Ocean City

2 8 3 nights min

  • 2 bedrooms
  • Sleeps 8
  • 3 nights min
  • Suitable for children age 5+
  • Air conditioning
Please note : This property has a 3PM checkin and 10AM checkout time. Please note: Linens are not included with this property. Linens are available upon request. This well designed building includes central courtyard, six elevators, indoor and outdoor pools, game ro …see more

from $200 / night

$1400 - $3115 / week

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from $200 / night

10

Vacation home in Maryland

Maryland / Laurel

1 2 1 night min

  • 1 bedroom
  • Sleeps 2
  • 1 night min
  • Child friendly
  • Air conditioning
  • Private garden
Our home is located in a very safe and quiet neighborhood. The bedroom and bathroom are 100% clean. The bedroom have enough space for two people. You will have access to a beautiful and green backyard. Close to a variety of shopping centers and restaurants. Few minutes …see more

from $50 / night

$350 / week

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from $50 / night

(4) Excellent 

46

Vacation villa in Ocean City

Maryland / Ocean City

3 10 Min stay varies

  • 3 bedrooms
  • Sleeps 10
  • Min stay varies
  • Child friendly
  • Air conditioning
  • Private garden
At A Glance (two kayaks included for use in rental price) For summer 2017- Gas Grill (maybe please check with me) For summer 2016 purchased paddle board and bikes (we have two helmets and four PFDs) Please note: If you require linens there is standard price of 125USD …see more

from $199 / night

$899 - $2125 / week

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from $199 / night

(1) Excellent 

23

Vacation home with swimming pool, golf nearby in National Harbor

Maryland / National Harbor

5 17 Min stay varies

  • 5 bedrooms
  • Sleeps 17
  • Min stay varies
  • Nearest beach 20 mi
  • Swimming pool
  • Child friendly
Beautiful Rustic Italian Villa- suburban oasis...set among mature treed private lot. Large open concept living areas, great for family entertainment. Chefs kitchen with island and stainless high end appliances. Glass doors surrrond for optimal light...Waterviews of the …see more

from $425 / night

$2700 - $6973 / week

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from $425 / night

14

Vacation home in Ocean Pines

Maryland / Ocean Pines

3 10 4 nights min

  • 3 bedrooms
  • Sleeps 10
  • 4 nights min
  • Beach/lakeside relaxation
  • Nearest beach 7 mi
  • Child friendly
Two story home in a beach community, Ocean Pines, Berlin Md, just outside Ocean City Md. 4 miles to restaurants, outlet stores, beaches and lakes. King, Queen, double/twin bunk, twin, 2 sleepers. Open floor plan, deck, with BBQ, WI-FI and flat screens. Parking off …see more

from $155 / night

$1100 / week

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from $155 / night

24

Ocean City Vacation apartment rental

Maryland / Ocean City

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Escape to beautiful Ocean City for a rejuvenating getaway when you stay at this 2-bedroom, 1-bathroom condo that comfortably sleeps 6. With a community pool and prime location, only 5 blocks from the beach, this comfortable vacation rental condo is the ideal getaway for …see more

from $95 / night

$665 - $1365 / week

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from $95 / night

(2) Excellent 

10

Vacation apartment rental

Maryland / Ocean City

1 6 Min stay varies

  • 1 bedroom
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
Our lovely Condo is located on the ocean side of Coastal Highway at 127th Street and is only 90 steps to the beach and a five minute walk to Northside Park. The park is a fifty-eight acre complex that has walking and jogging paths, baseball and soccer fields, a fishing …see more

from $79 / night

$475 - $1755 / week

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from $79 / night

13

Vacation apartment in Ocean City

Maryland / Ocean City

2 8 Min stay varies

  • 2 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach/lakeside relaxation
  • Suitable for children age 5+
  • Air conditioning
Please note : This property has a 3PM checkin and 10AM checkout time. Please notes :Linens are not included with this property. Linens are available upon request.This property offers a Fee Based service for WiFi usage. Attractive mid-rise condominium located in midtow …see more

from $180 / night

$1260 - $2695 / week

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from $180 / night

11

Maryland Vacation home rental

Maryland / Ocean City

3 10 3 nights min

  • 3 bedrooms
  • Sleeps 10
  • 3 nights min
  • Suitable for children age 5+
  • Air conditioning
  • Pet friendly
Please note : This property has a 3PM checkin and 10AM checkout time. Please note: Linens are not included with this property. Linens are available upon request. Enjoy a relaxing time in this quaint beach cottage. The 3 bedroom, 2 bath single family home is well equ …see more

from $140 / night

$980 - $2205 / week

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from $140 / night

10

Vacation condo rental

Maryland / National Harbor

2 8 2 nights min

  • 2 bedrooms
  • Sleeps 8
  • 2 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
This two bedroom condo is newly built and decorated. There is a full kitchen, and Wireless Internet for your convenience. This is a awesome place to stay with all the comfort you need. Treasured Past, Trendsetting Present - Just minutes from Washington, D.C., along t …see more

from $279 / night

$1953 / week

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from $279 / night

7

Home rental in Maryland

Maryland / Port Tobacco

4 8 1 night min

  • 4 bedrooms
  • Sleeps 8
  • 1 night min
Elegant French Style Bed and Breakfast, located in the historic area of Port Tobacco, Md. Large spacious rooms all with private bath and skylight, sofa, wing chair, writing desks, ceiling, wall mouldings and chandeliers. Some with balcony and Fireplace. All with large …see more

from $269 / night

$1788 - $3468 / week

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from $269 / night

7

Vacation condo with shared pool in Oxon Hill

Maryland / Oxon Hill

1 4 4 nights min

  • 1 bedroom
  • Sleeps 4
  • 4 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
This new city complex called National Harbor is just minutes from Washington, DC.It is an exciting, self-contained area with everything you could ask for in a vacation destination. With Wyndham Vacation Resorts at National Harbor, you can settle in and enjoy the neighb …see more

from $225 / night

$1750 - $2100 / week

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from $225 / night

(9) Excellent 

12

Vacation apartment in Maryland

Maryland / Ocean City

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Beach/lakeside relaxation
  • Child friendly
  • Car not necessary
It's All in the Details.... Located on the top floor of an 8 unit building with parking underneath, this newly remodeled condo offers 2 brand new beds (Queen and Full - pillowtop mattresses) in the bedroom with a Queen sleeper fold out in the living room (sleeps 4 comfo …see more

from $175 / night

$1200 - $1500 / week

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from $175 / night

(12) Very Good 

Certificate of Excellence

23

Vacation condo with shared pool in Ocean City

Maryland / Ocean City

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
Relax and unwind at the beach, shop, or enjoy a night out! Located on Jamestown Rd. (116th St.), this condo is a first-floor unit, centrally located and beautifully decorated. Enjoy bay views and the convenience of having the ocean steps away from your front doo …see more

Certificate of Excellence

from $220 / night

$1540 / week

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from $220 / night

1