Vacation Rentals & House Rentals in Maryland

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2,110 house rentals

(1) Excellent 

    33

    Luxurious 2 BDR Condo in Bowie Town Center. Close to DC and Annapolis

    Maryland / Bowie

    Bowie condo

    2 6 1 night min

    • 2 bedrooms
    • sleeps 6
    • 1 night min
    • Nearest beach 30 mi
    • Child Friendly
    • Air conditioning

    Price per night from

    $172

    Responds fast!
    avg. 22 minutes

    Price per night from

    $172

    (2) Excellent 

      35

      5 BR - AWESOME lake views, pool, billiards, tennis & hot tub on Wisp Mountain!

      Garrett County / McHenry

      McHenry house

      5 14 min stay varies

      • 5 bedrooms
      • sleeps 14
      • min stay varies
      • Nearest beach 12 mi
      • Swimming pool
      • Ski

      Price per night from

      $252

      Price per night from

      $252

      (4) Excellent 

        20

        Best kept secret by the bay (Entire House)

        Maryland / Fishing Creek

        Fishing Creek house

        3 4 3 nights min

        • 3 bedrooms
        • sleeps 4
        • 3 nights min
        • Air conditioning
        • Private garden

        Price per night from

        $194

        Responds fast!
        avg. 3 hours 10 minutes

        Price per night from

        $194

        (1) Excellent 

          8

          Surfcrest Condo Oceanblock Ocean City MD

          Maryland / Ocean City

          Ocean City condo

          1 6 3 nights min

          • 1 bedroom
          • sleeps 6
          • 3 nights min
          • Child Friendly
          “Great place!” The condo was so cute, and the location was perfect! So close to the beach and the boardwalk but still very quiet other than upstairs neighbors. Very clean! Parking was tough to figure out but was so convienent. Will absolutely keep this
          …see more

          Price per night from

          $155

          Responds fast!
          avg. 1 hour 32 minutes

          Price per night from

          $155

          (1) Excellent 

            32

            Brookie Cottage on the Savage River

            Maryland / Swanton

            Swanton cottage

            2 4 2 nights min

            • 2 bedrooms
            • sleeps 4
            • 2 nights min
            • Beach / lakeside relaxation
            • Child Friendly
            • Car not necessary

            Price per night from

            $224

            Price per night from

            $224

            (5) Very Good 

              56

              *Secluded & Quiet UNIQUE OUTSIDE FIREPLACE *XL HOT TUB*Pool Table-5 Star QUALITY

              Garrett County / Oakland

              Oakland house

              5 13 min stay varies

              • 5 bedrooms
              • sleeps 13
              • min stay varies
              • Nearest beach 8 mi
              • Ski
              • Child Friendly

              Price per night from

              $303

              Responds fast!
              avg. 3 hours 9 minutes

              Price per night from

              $303

                6

                Beautiful Home in Nice Community with up to 7 bedrooms

                Maryland / Severn

                Severn house

                4 10 2 nights min

                • 4 bedrooms
                • sleeps 10
                • 2 nights min
                • Child Friendly
                • Air conditioning
                • Private garden

                Price per night from

                $441

                Responds fast!
                avg. 21 minutes

                Price per night from

                $441

                  26

                  Love Point Luxury Waterfront in Stevensville

                  Kent Island / Stevensville

                  Stevensville house

                  3 10 3 nights min

                  • 3 bedrooms
                  • sleeps 10
                  • 3 nights min
                  • Beach / lakeside relaxation
                  • Child Friendly
                  • Air conditioning

                  Price per night from

                  $1,602

                  Price per night from

                  $1,602

                    10

                    Luxurious Getaway!!

                    Montgomery County / Olney

                    Olney house

                    3 6 5 nights min

                    • 3 bedrooms
                    • sleeps 6
                    • 5 nights min
                    • Swimming pool
                    • Child Friendly
                    • Car not necessary

                    Price per night from

                    $287

                    Price per night from

                    $287

                    (15) Very Good 

                      23

                      Ocean City, Maryland- 2BR on the beach!(2009)

                      Maryland / Ocean City

                      Ocean City apartment

                      2 8 min stay varies

                      • 2 bedrooms
                      • sleeps 8
                      • min stay varies
                      • Beach / lakeside relaxation
                      • Swimming pool
                      • Child Friendly
                      “Beautiful condo and excellent location!” We travelled to Ocean City for a long weekend with our two teenagers. The condo was beautiful and had everything we needed. The view and proximity to the beach was excellent and it was close to everything. G
                      …see more

                      Price per night from

                      $179

                      Price per night from

                      $179

                        32

                        Must See - Beautiful Direct Oceanfront Condo On The Boardwalk - Private Balcony!

                        Maryland / Ocean City

                        Ocean City condo

                        1 6 min stay varies

                        • 1 bedroom
                        • sleeps 6
                        • min stay varies
                        • Swimming pool
                        • Child Friendly
                        • Air conditioning

                        Price per night from

                        $102

                        Responds fast!
                        avg. 1 hour 10 minutes

                        Price per night from

                        $102

                          29

                          NEW! Colonial Home in Cambridge w/Wraparound Porch

                          Maryland / Cambridge

                          Cambridge house

                          3 7 min stay varies

                          • 3 bedrooms
                          • sleeps 7
                          • min stay varies
                          • Child Friendly
                          • Air conditioning

                          Price per night from

                          $264

                          Responds fast!
                          avg. 11 minutes

                          Price per night from

                          $264

                            42

                            Waterfront Room Rentals 2 with Private Beach

                            Talbot County / Trappe

                            Trappe room

                            1 2 min stay varies

                            • 1 bedroom
                            • sleeps 2
                            • min stay varies
                            • Child Friendly
                            • Air conditioning
                            • Pet Friendly

                            Price per night from

                            $115

                            Responds fast!
                            avg. 1 hour 34 minutes

                            Price per night from

                            $115

                            (13) Excellent 

                            Certificate of Excellence

                              17

                              North Ocean City Penthouse Condo

                              Maryland / Ocean City

                              Ocean City condo

                              3 7 7 nights min

                              • 3 bedrooms
                              • sleeps 7
                              • 7 nights min
                              • Beach / lakeside relaxation
                              • Swimming pool
                              • Suitable for children age 5+
                              “Spring Break Family Vacation” I was really glad that I found the room on Flipkey. It was like being at home, but with the view of the ocean. We had all the essentials, and found Ocean City to be the most wonderful vacation spot. I hope more people tak
                              …see more

                              Certificate of Excellence

                              Price per night from

                              $227

                              Price per night from

                              $227

                                11

                                Cosy bedroom with WiFi near metro, UMD NASA USDA Archves

                                Maryland / College Park

                                College Park house

                                1 2 5 nights min

                                • 1 bedroom
                                • sleeps 2
                                • 5 nights min
                                • Nearest beach 65 mi
                                • Car not necessary
                                • Air conditioning

                                Price per night from

                                $57

                                Price per night from

                                $57

                                (5) Average 

                                  55

                                  Waterfront Vacation Home with Private Beach

                                  Talbot County / Trappe

                                  Trappe house

                                  3 6 2 nights min

                                  • 3 bedrooms
                                  • sleeps 6
                                  • 2 nights min
                                  • Beach / lakeside relaxation
                                  • Nearest beach 97 mi
                                  • Child Friendly

                                  Price per night from

                                  $378

                                  Responds fast!
                                  avg. 1 hour 34 minutes

                                  Price per night from

                                  $378

                                  (19) Very Good 

                                  Certificate of Excellence

                                    21

                                    Ocean City, MD Water views and steps to the beach

                                    Maryland / Ocean City

                                    Ocean City condo

                                    3 6 4 nights min

                                    • 3 bedrooms
                                    • sleeps 6
                                    • 4 nights min
                                    • Beach / lakeside relaxation
                                    • Swimming pool
                                    • Child Friendly
                                    “WOW! Wonderful stay with little ones!” Beautiful and well maintained condo. Keyless entry locks were a plus (no keys being lost!). Easy beach and amenity access. We loved the pool! We will definitely be staying again!
                                    …see more

                                    Certificate of Excellence

                                    Price per night from

                                    $315

                                    Responds fast!
                                    avg. 3 hours 52 minutes

                                    Price per night from

                                    $315

                                    (1) Very Good 

                                      34

                                      Waterfront Room Rentals 1 with Private Beach

                                      Talbot County / Trappe

                                      Trappe room

                                      1 2 min stay varies

                                      • 1 bedroom
                                      • sleeps 2
                                      • min stay varies
                                      • Child Friendly
                                      • Air conditioning
                                      • Pet Friendly

                                      Price per night from

                                      $149

                                      Responds fast!
                                      avg. 1 hour 34 minutes

                                      Price per night from

                                      $149

                                        24

                                        Cozy Cumberland Mountain Cabin!

                                        Maryland / Cresaptown

                                        Cresaptown log cabin

                                        1 4 min stay varies

                                        • 1 bedroom
                                        • sleeps 4
                                        • min stay varies
                                        • Child Friendly
                                        • Air conditioning

                                        Price per night from

                                        $81

                                        Responds fast!
                                        avg. 11 minutes

                                        Price per night from

                                        $81

                                        (3) Excellent 

                                          10

                                          Nice Direct Oceanfront Condo

                                          Maryland / Ocean City

                                          Ocean City condo

                                          1 4 7 nights min

                                          • 1 bedroom
                                          • sleeps 4
                                          • 7 nights min
                                          • Beach / lakeside relaxation
                                          • Swimming pool
                                          • Child Friendly

                                          Price per night from

                                          $115

                                          Responds fast!
                                          avg. 2 hours 54 minutes

                                          Price per night from

                                          $115

                                            24

                                            Laurel Home Walk to Main St, MARC Train to DC/BALT

                                            Maryland / Laurel

                                            Laurel house

                                            2 6 min stay varies

                                            • 2 bedrooms
                                            • sleeps 6
                                            • min stay varies
                                            • Child Friendly
                                            • Air conditioning

                                            Price per night from

                                            $147

                                            Responds fast!
                                            avg. 11 minutes

                                            Price per night from

                                            $147

                                            (1) Excellent 

                                              24

                                              New! Beachfront 4BR St. Leonard Cottage w/ Deck!

                                              Calvert County / St. Leonard

                                              Saint Leonard cottage

                                              4 8 2 nights min

                                              • 4 bedrooms
                                              • sleeps 8
                                              • 2 nights min
                                              • Child Friendly
                                              • Air conditioning

                                              Price per night from

                                              $184

                                              Responds fast!
                                              avg. 11 minutes

                                              Price per night from

                                              $184

                                              (3) Very Good 

                                                36

                                                Comfortable, Spacious & Fun! 6+ Acres Pool & Shore. 4 Master Suites Waterview

                                                Talbot County / Wittman

                                                Wittman log cabin

                                                5 10 min stay varies

                                                • 5 bedrooms
                                                • sleeps 10
                                                • min stay varies
                                                • Beach / lakeside relaxation
                                                • Nearest beach 6 mi
                                                • Swimming pool

                                                Price per night from

                                                $716

                                                Price per night from

                                                $716

                                                (1) Excellent 

                                                  25

                                                  Waldins waterfront house with amazing views - Top of the Chesapeake

                                                  Maryland / Charlestown

                                                  Charlestown house

                                                  3 8 3 nights min

                                                  • 3 bedrooms
                                                  • sleeps 8
                                                  • 3 nights min
                                                  • Child Friendly
                                                  • Air conditioning
                                                  • Pet Friendly

                                                  Price per night from

                                                  $315

                                                  Price per night from

                                                  $315

                                                    25

                                                    National Harbor 3BR/2BA ツ Equipped Wyndham Condo!

                                                    Maryland / Oxon Hill

                                                    Oxon Hill condo

                                                    3 8 3 nights min

                                                    • 3 bedrooms
                                                    • sleeps 8
                                                    • 3 nights min
                                                    • Swimming pool
                                                    • Child Friendly
                                                    • Air conditioning

                                                    Price per night from

                                                    $292

                                                    Price per night from

                                                    $292

                                                      13

                                                      Luxury Apartment with Private Entrance

                                                      Maryland / Centreville

                                                      Centreville apartment

                                                      1 3 1 night min

                                                      • 1 bedroom
                                                      • sleeps 3
                                                      • 1 night min
                                                      • Air conditioning
                                                      • Private garden

                                                      Price per night from

                                                      $134

                                                      Price per night from

                                                      $134

                                                      (14) Excellent 

                                                      Certificate of Excellence

                                                        35

                                                        OCEANFRONT w/ Large Pool~Allergy Friendly Enviorment~4 Seasons Furnished Balcony

                                                        Maryland / Ocean City

                                                        Ocean City condo

                                                        2 6 min stay varies

                                                        • 2 bedrooms
                                                        • sleeps 6
                                                        • min stay varies
                                                        • Beach / lakeside relaxation
                                                        • Swimming pool
                                                        • Child Friendly
                                                        “All Superlatives!” Clean. Comfortable. Quiet. Well-supplied. Wonderful ocean view from balcony and bedroom. Easy access to beach. Smooth "registration" system. Convenient to restaurants, shops, entertainment. We loved it!
                                                        …see more

                                                        Certificate of Excellence

                                                        Price per night from

                                                        $126

                                                        Price per night from

                                                        $126

                                                        (5) Excellent 

                                                          14

                                                          Nice! 2 BR, Coastal Cottage Condo, Walk To Beach, Restaurants!

                                                          Maryland / Ocean City

                                                          Ocean City condo

                                                          2 6 7 nights min

                                                          • 2 bedrooms
                                                          • sleeps 6
                                                          • 7 nights min
                                                          • Beach / lakeside relaxation
                                                          • Child Friendly
                                                          “loved it” Very nice place in a great location. Quiet neighborhood, can see people walking their dogs and jogging. Harris Teeter and Food Lion less than 5 minutes away along with a CVS. Beds are very comfy and were able to relax with a family of 8. Par
                                                          …see more

                                                          Price per night from

                                                          $164

                                                          Price per night from

                                                          $164

                                                            44

                                                            Waterfront Room Rentals 3 with Private Beach

                                                            Talbot County / Trappe

                                                            Trappe room

                                                            1 2 min stay varies

                                                            • 1 bedroom
                                                            • sleeps 2
                                                            • min stay varies
                                                            • Child Friendly
                                                            • Air conditioning
                                                            • Pet Friendly

                                                            Price per night from

                                                            $115

                                                            Responds fast!
                                                            avg. 1 hour 34 minutes

                                                            Price per night from

                                                            $115

                                                            (2) Excellent 

                                                              24

                                                              Mayflower's Flat in Historic Downtown Frederick

                                                              Maryland / Frederick

                                                              Frederick apartment

                                                              2 4 1 night min

                                                              • 2 bedrooms
                                                              • sleeps 4
                                                              • 1 night min
                                                              • Child Friendly

                                                              Price per night from

                                                              $156

                                                              Price per night from

                                                              $156

                                                                24

                                                                NEW! Annapolis Home w/ Deck & Whitehall Bay Access

                                                                Maryland / Cape Saint Claire

                                                                Cape Saint Claire house

                                                                4 8 min stay varies

                                                                • 4 bedrooms
                                                                • sleeps 8
                                                                • min stay varies
                                                                • Child Friendly
                                                                • Air conditioning

                                                                Price per night from

                                                                $251

                                                                Responds fast!
                                                                avg. 11 minutes

                                                                Price per night from

                                                                $251

                                                                (5) Excellent 

                                                                Certificate of Excellence

                                                                  28

                                                                  Cozy & Spacious Chestertown Home

                                                                  Maryland / Chestertown

                                                                  Chestertown house

                                                                  4 8 2 nights min

                                                                  • 4 bedrooms
                                                                  • sleeps 8
                                                                  • 2 nights min
                                                                  • Nearest beach 5 mi
                                                                  • Swimming pool
                                                                  • Child Friendly

                                                                  Certificate of Excellence

                                                                  Price per night from

                                                                  $287

                                                                  Responds fast!
                                                                  avg. 2 hours 30 minutes

                                                                  Price per night from

                                                                  $287

                                                                    16

                                                                    Choptank River View House

                                                                    Maryland / Cambridge

                                                                    Cambridge house

                                                                    6 14 3 nights min

                                                                    • 6 bedrooms
                                                                    • sleeps 14
                                                                    • 3 nights min
                                                                    • Beach / lakeside relaxation
                                                                    • Nearest beach 0 mi
                                                                    • Air conditioning

                                                                    Price per night from

                                                                    $1,145

                                                                    Price per night from

                                                                    $1,145

                                                                    (5) Very Good 

                                                                      17

                                                                      Seahorse Guest Cottage near the Bay, dog friendly

                                                                      Calvert County / North Beach

                                                                      North Beach cottage

                                                                      1 5 2 nights min

                                                                      • 1 bedroom
                                                                      • sleeps 5
                                                                      • 2 nights min
                                                                      • Beach / lakeside relaxation
                                                                      • Nearest beach 0.2 mi
                                                                      • Child Friendly

                                                                      Price per night from

                                                                      $184

                                                                      Responds fast!
                                                                      avg. 1 hour 32 minutes

                                                                      Price per night from

                                                                      $184

                                                                        8

                                                                        Sunrise Sea 308

                                                                        Maryland / Ocean City

                                                                        Ocean City apartment

                                                                        2 8 min stay varies

                                                                        • 2 bedrooms
                                                                        • sleeps 8
                                                                        • min stay varies
                                                                        • Swimming pool
                                                                        • Child Friendly
                                                                        • Car not necessary

                                                                        Price per night from

                                                                        $123

                                                                        Price per night from

                                                                        $123

                                                                        (1) Excellent 

                                                                          24

                                                                          Ocean City Condo w/Patio + Indoor & Outdoor Pools!

                                                                          Maryland / Ocean City

                                                                          Ocean City apartment

                                                                          2 8 min stay varies

                                                                          • 2 bedrooms
                                                                          • sleeps 8
                                                                          • min stay varies
                                                                          • Swimming pool
                                                                          • Child Friendly
                                                                          • Air conditioning

                                                                          Price per night from

                                                                          $132

                                                                          Responds fast!
                                                                          avg. 11 minutes

                                                                          Price per night from

                                                                          $132

                                                                            21

                                                                            Luxurious 2 bedrooms 2 baths apartment in a Villa

                                                                            Montgomery County / Derwood

                                                                            Derwood apartment

                                                                            2 6 7 nights min

                                                                            • 2 bedrooms
                                                                            • sleeps 6
                                                                            • 7 nights min
                                                                            • Child Friendly
                                                                            • Air conditioning
                                                                            • Private garden

                                                                            Price per night from

                                                                            $124

                                                                            Price per night from

                                                                            $124

                                                                            (1) Excellent 

                                                                              24

                                                                              NEW! Charming 1BR 18th Century Glenwood Cottage!

                                                                              Maryland / Glenelg

                                                                              Glenelg cottage

                                                                              1 2 2 nights min

                                                                              • 1 bedroom
                                                                              • sleeps 2
                                                                              • 2 nights min
                                                                              • Child Friendly

                                                                              Price per night from

                                                                              $115

                                                                              Responds fast!
                                                                              avg. 13 minutes

                                                                              Price per night from

                                                                              $115

                                                                              About Maryland

                                                                              Maryland's balmy coastal weather, close proximity to the nation's capital and phenomenal beaches make it an excellent place to enjoy a vacation. This small mid-coastal state is home to one of America's most beautiful bays, Chesapeake Bay. Maryland is nicknamed "America in miniature" because it offers a little of everything: urban charm, mountains, rolling plains and grasslands, crystal-clear coastal waters and a rich history. The state is also famous for its food; no vacation to Maryland is complete without sampling the fresh seafood, especially the delectable crab cakes.

                                                                              Some of the many attractions and destinations in the state include:

                                                                              • Baltimore: A vibrant city on the Chesapeake Bay, Baltimore bustles with excitement and glimpses into America's storied history. Scenic Annapolis is also worth checking out if you want to take in a broader sampling of the state's urban style.
                                                                              • Chesapeake Bay: Spanning beyond Baltimore, Maryland's famous bay is a world unto itself, with outstanding fishing, swimming and sightseeing. Spectacular sunsets are a daily occurrence making Chesapeake Bay a perfect romantic getaway for couples.
                                                                              • Antietam Battlefield: The site of the single bloodiest battle in Civil War history, the Antietam Battlefield was the setting for the first Civil War battle fought in the North.
                                                                              • The Appalachian Trail: Even though the Appalachian Trail only meanders through 40 miles of Maryland, it's among the most beautiful and scenic stretches on the entire route.
                                                                              • Assateague Island National Seashore: Perhaps the most unique of the many Maryland National Parks, Assateague Island National Seashore is a barrier island that hosts an astonishing range of flora and fauna, including rare birds and wild ponies.

                                                                              Summer is the perfect time to visit Maryland as Ocean City makes a perfect place for a family vacation. Annapolis' City Dock, which has remained virtually unchanged for a century, has summertime concerts by the shores of the Chesapeake. During the summer, you can also visit Maryland campgrounds and bring the family to one of the many water parks in Maryland.

                                                                              For your accommodations, why not get a beach house if you're staying along the coast or a condo to better enjoy all the sights and sounds of the city? Vacation rentals offer more room and privacy than hotels and come complete with all the comforts of home.

                                                                              Maryland is also close to two of the eastern United States' most storied and popular cities: Philadelphia and Washington, DC. Both are an easy day trip from just about anywhere in the state and offer a more complete glimpse into the vibrant culture of this important corner of the country.

                                                                              If you want to explore more of the area surrounding Delaware, remember that Philadelphia is only about 20 miles from downtown Wilmington. One of America's most historic and popular cities, Philadelphia makes an ideal day trip for those staying in Delaware.