Vacation Rentals & Apartments in Annapolis

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83 apartments

    26

    Annapolis Crows Nest Cottage: Chesapeake Bay View

    Maryland / Annapolis

    Annapolis villa

    5 20 min stay varies

    • 5 bedrooms
    • sleeps 20
    • min stay varies
    • Beach / lakeside relaxation
    • Nearest beach 0.2 mi
    • Child Friendly

    Price per night from

    $792

    Price per night from

    $792

      55

      Charming Annapolis home with stunning water views

      Maryland / Annapolis

      Annapolis house

      4 11 5 nights min

      • 4 bedrooms
      • sleeps 11
      • 5 nights min
      • Child Friendly
      • Pet Friendly

      Price per night from

      $570

      Price per night from

      $570

      (2) Excellent 

        10

        C/ean & Cozy

        Maryland / Annapolis

        Annapolis room

        1 2 1 night min

        • 1 bedroom
        • sleeps 2
        • 1 night min
        • Child Friendly
        • Air conditioning

        Price per night from

        $68

        Price per night from

        $68

          21

          Annapolis Area Waterfront Home

          Maryland / Annapolis

          Annapolis house

          5 11 min stay varies

          • 5 bedrooms
          • sleeps 11
          • min stay varies
          • Beach / lakeside relaxation
          • Child Friendly
          • Air conditioning

          Price per night from

          $627

          Price per night from

          $627

            7

            2. Private 20 acre waterfront estate - studio apt

            Maryland / Annapolis

            Annapolis apartment

            1 2 1 night min

            • 1 bedroom
            • sleeps 2
            • 1 night min
            • Ask about pets

            Price per night from

            $342

            Price per night from

            $342

            (1) Excellent 

              17

              Excellent Location in Downtown Annapolis- walk to everything !

              Maryland / Annapolis

              Annapolis house

              3 7 2 nights min

              • 3 bedrooms
              • sleeps 7
              • 2 nights min
              • Child Friendly
              • Air conditioning
              • Pet Friendly

              Price per night from

              $325

              Responds fast!
              avg. 1 hour 1 minutes

              Price per night from

              $325

                15

                Location,location,location,walk to city dock,free

                Maryland / Annapolis

                Annapolis apartment

                2 5 min stay varies

                • 2 bedrooms
                • sleeps 5
                • min stay varies
                • Car not necessary
                • Air conditioning
                • Private garden

                Price per night from

                $285

                Price per night from

                $285

                (6) Excellent 

                  19

                  Charming and Spacious Annapolis Victorian

                  Maryland / Annapolis

                  Annapolis house

                  6 12 min stay varies

                  • 6 bedrooms
                  • sleeps 12
                  • min stay varies
                  • Child Friendly
                  • Air conditioning

                  Price per night from

                  $859

                  Responds fast!
                  avg. 1 hour 27 minutes

                  Price per night from

                  $859

                  (2) Excellent 

                    52

                    Walk to Shops/Eateries Charming Cottage. Dogs Wel.

                    Maryland / Annapolis

                    Annapolis house

                    3 6 min stay varies

                    • 3 bedrooms
                    • sleeps 6
                    • min stay varies
                    • Nearest beach 6 mi
                    • Child Friendly
                    • Car not necessary

                    Price per night from

                    $285

                    Responds fast!
                    avg. 27 minutes

                    Price per night from

                    $285

                      25

                      Annapolis Townhome w/Deck by Nature Trails & River

                      Maryland / Annapolis

                      Annapolis house

                      1 4 min stay varies

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

                      Price per night from

                      $102

                      Responds fast!
                      avg. 36 minutes

                      Price per night from

                      $102

                        24

                        Charming Artists Home in Eastport/Annapolis

                        Maryland / Annapolis

                        Annapolis house

                        3 6 3 nights min

                        • 3 bedrooms
                        • sleeps 6
                        • 3 nights min
                        • Ask about children
                        • Air conditioning

                        Price per night from

                        $426

                        Price per night from

                        $426

                          23

                          Charming Eastport Home

                          Maryland / Annapolis

                          Annapolis house

                          3 8 5 nights min

                          • 3 bedrooms
                          • sleeps 8
                          • 5 nights min
                          • Child Friendly
                          • Air conditioning
                          • Private garden

                          Price per night from

                          $285

                          Price per night from

                          $285

                            4

                            Perfect Annapolis with Lots of Parking & Hot Tub

                            Maryland / Annapolis

                            Annapolis townhouse

                            4 10 2 nights min

                            • 4 bedrooms
                            • sleeps 10
                            • 2 nights min
                            • Child Friendly

                            Price per night from

                            $564

                            Price per night from

                            $564

                              31

                              NEW! Annapolis House in Bay Ridge Maryland!

                              Maryland / Annapolis

                              Annapolis house

                              3 6 min stay varies

                              • 3 bedrooms
                              • sleeps 6
                              • min stay varies
                              • Swimming pool
                              • Child Friendly
                              • Air conditioning

                              Price per night from

                              $512

                              Responds fast!
                              avg. 9 minutes

                              Price per night from

                              $512

                              (3) Very Good 

                                30

                                Beautiful Murray Hill Home (Annapolis)

                                Maryland / Annapolis

                                Annapolis house

                                4 9 min stay varies

                                • 4 bedrooms
                                • sleeps 9
                                • min stay varies
                                • Child Friendly
                                • Air conditioning
                                • Ask about pets
                                “Comfortable and secure in a great home - almost as good as at ho” The house is set is a terrific neighborhood of annapolis within easy walking distance to two small parks on the water and to town. We all found the house a delight - the design, decor
                                …see more

                                Price per night from

                                $484

                                Price per night from

                                $484

                                (1) Excellent 

                                  18

                                  Stunning Home in the Heart of Downtown Annapolis

                                  Maryland / Annapolis

                                  Annapolis house

                                  3 11 2 nights min

                                  • 3 bedrooms
                                  • sleeps 11
                                  • 2 nights min
                                  • Ask about children
                                  • Air conditioning
                                  • Private garden

                                  Price per night from

                                  $792

                                  Price per night from

                                  $792

                                    39

                                    Annapolis Home w/ Bay Views - Near Naval Academy!

                                    Maryland / Annapolis

                                    Annapolis house

                                    5 11 min stay varies

                                    • 5 bedrooms
                                    • sleeps 11
                                    • min stay varies
                                    • Swimming pool
                                    • Child Friendly
                                    • Air conditioning

                                    Price per night from

                                    $814

                                    Responds fast!
                                    avg. 9 minutes

                                    Price per night from

                                    $814

                                      24

                                      Charming Annapolis Home w/ Yard - 5 Mins to Dwtn!

                                      Maryland / Annapolis

                                      Annapolis house

                                      4 10 min stay varies

                                      • 4 bedrooms
                                      • sleeps 10
                                      • min stay varies
                                      • Child Friendly
                                      • Air conditioning

                                      Price per night from

                                      $364

                                      Responds fast!
                                      avg. 10 minutes

                                      Price per night from

                                      $364

                                      (1)  

                                        7

                                        Charming Townhouse - Steps to City Dock and USNA

                                        Maryland / Annapolis

                                        Annapolis house

                                        3 8 3 nights min

                                        • 3 bedrooms
                                        • sleeps 8
                                        • 3 nights min
                                        • Child Friendly
                                        • Car not necessary
                                        • Ask about pets

                                        Price per night from

                                        $513

                                        Price per night from

                                        $513

                                        (2)  

                                          26

                                          3BR Annapolis Home on Oyster Creek w/Amazing Views

                                          Maryland / Annapolis

                                          Annapolis house

                                          3 9 2 nights min

                                          • 3 bedrooms
                                          • sleeps 9
                                          • 2 nights min
                                          • Child Friendly
                                          • Air conditioning

                                          Price per night from

                                          $401

                                          Responds fast!
                                          avg. 9 minutes

                                          Price per night from

                                          $401

                                          (4) Excellent 

                                            31

                                            Charming Home close to historic district

                                            Maryland / Annapolis

                                            Annapolis house

                                            2 6 2 nights min

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

                                            Price per night from

                                            $285

                                            Responds fast!
                                            avg. 2 hours 2 minutes

                                            Price per night from

                                            $285

                                            (20) Excellent 

                                              25

                                              *BOOK NOW* Beautiful Cottage in historic Annapolis

                                              Maryland / Annapolis

                                              Annapolis cottage

                                              3 6 2 nights min

                                              • 3 bedrooms
                                              • sleeps 6
                                              • 2 nights min
                                              • Beach / lakeside relaxation
                                              • Nearest beach 1 mi
                                              • Child Friendly

                                              Price per night from

                                              $363

                                              Responds fast!
                                              avg. 2 hours 13 minutes

                                              Price per night from

                                              $363

                                              Great rentals within 20 miles that match your search

                                              Distance approx 10.59 km from Annapolis Show on Map

                                                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

                                                $1,587

                                                Price per night from

                                                $1,587

                                                Distance approx 16.07 km from Annapolis

                                                (3) Very Good 

                                                  15

                                                  Halos'Haven Vacation Rental

                                                  St. Michaels / McDaniel

                                                  McDaniel house

                                                  5 10 2 nights min

                                                  • 5 bedrooms
                                                  • sleeps 10
                                                  • 2 nights min
                                                  • Swimming pool
                                                  • Child Friendly
                                                  • Air conditioning

                                                  Price per night from

                                                  $816

                                                  Price per night from

                                                  $816

                                                  Distance approx 16.06 km from Annapolis

                                                    9

                                                    Holistic Getaway

                                                    Maryland / Bowie

                                                    Bowie house

                                                    2 6 2 nights min

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

                                                    Price per night from

                                                    $165

                                                    Price per night from

                                                    $165

                                                    Distance approx 18.63 km from Annapolis

                                                      9

                                                      Renovated Luxury Waterview House

                                                      Calvert County / North Beach

                                                      North Beach house

                                                      3 6 2 nights min

                                                      • 3 bedrooms
                                                      • sleeps 6
                                                      • 2 nights min
                                                      • Child Friendly

                                                      Price per night from

                                                      $341

                                                      Price per night from

                                                      $341

                                                      Distance approx 17.42 km from Annapolis

                                                      (3) Excellent 

                                                        12

                                                        Sailors Crossing

                                                        Maryland / Rock Hall

                                                        Rock Hall house

                                                        3 10 2 nights min

                                                        • 3 bedrooms
                                                        • sleeps 10
                                                        • 2 nights min
                                                        • Child Friendly
                                                        • Pet Friendly

                                                        Price per night from

                                                        $386

                                                        Responds fast!
                                                        avg. 3 hours 15 minutes

                                                        Price per night from

                                                        $386

                                                        Distance approx 10.54 km from Annapolis Show on Map

                                                        (14) Excellent 

                                                          19

                                                          Love Point Waterfront

                                                          Maryland / Kent Island

                                                          Kent Island house

                                                          3 12 3 nights min

                                                          • 3 bedrooms
                                                          • sleeps 12
                                                          • 3 nights min
                                                          • Beach / lakeside relaxation
                                                          • Nearest beach 5 mi
                                                          • Child Friendly
                                                          “Love Point Retreat” I stayed at Paula's property 3 times so far. We stayed once in October 2014 and twice in April 2015. Here is how I would break it up: Owner: Paula is very nice, accommodating and extremely responsive. She was easy to deal with, ans
                                                          …see more

                                                          Price per night from

                                                          $284

                                                          Price per night from

                                                          $284

                                                          Distance approx 10.1 km from Annapolis Show on Map

                                                          (3) Excellent 

                                                            21

                                                            Peaceful, Waterfront Home on 3 Acres (pier + western view w/gorgeous sunsets)

                                                            Kent Island / Chester

                                                            Chester house

                                                            4 8 min stay varies

                                                            • 4 bedrooms
                                                            • sleeps 8
                                                            • min stay varies
                                                            • Beach / lakeside relaxation
                                                            • Nearest beach 14 mi
                                                            • Child Friendly
                                                            “Unbelievable value” We were a family group of 3 couples plus an infant traveling to a wedding at the Usna chapel. The home was just wonderful, had a great view, was very clean, and was well equipped for the cooking being planned. Stores, restaurants,
                                                            …see more

                                                            Price per night from

                                                            $325

                                                            Responds fast!
                                                            avg. 2 hours 4 minutes

                                                            Price per night from

                                                            $325

                                                            Distance approx 10.42 km from Annapolis Show on Map

                                                              11

                                                              Love Point Bay Vacation Home

                                                              Kent Island / Stevensville

                                                              Stevensville apartment

                                                              2 6 2 nights min

                                                              • 2 bedrooms
                                                              • sleeps 6
                                                              • 2 nights min
                                                              • Child Friendly

                                                              Price per night from

                                                              $375

                                                              Price per night from

                                                              $375

                                                              Distance approx 19.8 km from Annapolis

                                                              (5) Excellent 

                                                                22

                                                                Sandy Pines: Enjoy Harris Creek w/Pool and Boats

                                                                Talbot County / St. Michaels

                                                                St. Michaels house

                                                                4 10 min stay varies

                                                                • 4 bedrooms
                                                                • sleeps 10
                                                                • min stay varies
                                                                • Beach / lakeside relaxation
                                                                • Swimming pool
                                                                • Child Friendly

                                                                Price per night from

                                                                $437

                                                                Price per night from

                                                                $437

                                                                Distance approx 12.44 km from Annapolis Show on Map

                                                                  15

                                                                  BEULAH Residence (Bedroom 2)

                                                                  Maryland / Glen Burnie

                                                                  Glen Burnie guest house

                                                                  1 2 3 nights min

                                                                  • 1 bedroom
                                                                  • sleeps 2
                                                                  • 3 nights min
                                                                  • Child Friendly
                                                                  • Air conditioning
                                                                  • Private garden

                                                                  Price per night from

                                                                  $114

                                                                  Price per night from

                                                                  $114

                                                                  Distance approx 12.44 km from Annapolis Show on Map

                                                                    15

                                                                    BEULAH Residence (Bedroom 1)

                                                                    Maryland / Glen Burnie

                                                                    Glen Burnie guest house

                                                                    1 2 3 nights min

                                                                    • 1 bedroom
                                                                    • sleeps 2
                                                                    • 3 nights min
                                                                    • Child Friendly
                                                                    • Air conditioning
                                                                    • Private garden

                                                                    Price per night from

                                                                    $114

                                                                    Price per night from

                                                                    $114

                                                                    Distance approx 10.8 km from Annapolis Show on Map

                                                                      6

                                                                      Just Like Home (Private Bathrooms & Bedrooms)

                                                                      Maryland / Gambrills

                                                                      Gambrills townhouse

                                                                      3 3 1 night min

                                                                      • 3 bedrooms
                                                                      • sleeps 3
                                                                      • 1 night min
                                                                      • Child Friendly

                                                                      Price per night from

                                                                      $17

                                                                      Price per night from

                                                                      $17

                                                                      Distance approx 3.71 km from Annapolis Show on Map

                                                                      (1) Excellent 

                                                                        18

                                                                        Luxury Boat & Bed 78' Motor Yacht "Laid Off"

                                                                        Maryland / Edgewater

                                                                        Edgewater yacht

                                                                        4 10 1 night min

                                                                        • 4 bedrooms
                                                                        • sleeps 10
                                                                        • 1 night min
                                                                        • Child Friendly
                                                                        • Air conditioning
                                                                        • Pet Friendly

                                                                        Price per night from

                                                                        $1,126

                                                                        Price per night from

                                                                        $1,126

                                                                        Distance approx 18.89 km from Annapolis

                                                                        (1) Average 

                                                                          38

                                                                          St. Michaels award-winning waterfront BayCottage, pool, docks, sundeck, grounds

                                                                          Talbot County / St. Michaels

                                                                          St. Michaels villa

                                                                          6 12 2 nights min

                                                                          • 6 bedrooms
                                                                          • sleeps 12
                                                                          • 2 nights min
                                                                          • Beach / lakeside relaxation
                                                                          • Nearest beach 7 mi
                                                                          • Swimming pool

                                                                          Price per night from

                                                                          $1,139

                                                                          Responds fast!
                                                                          avg. 3 hours 35 minutes

                                                                          Price per night from

                                                                          $1,139

                                                                          Distance approx 17.45 km from Annapolis

                                                                            53

                                                                            2 Twin bed rental located in a 4 bedroom great vacation house in the waterfront

                                                                            Maryland / Rock Hall

                                                                            Rock Hall house

                                                                            1 3 1 night min

                                                                            • 1 bedroom
                                                                            • sleeps 3
                                                                            • 1 night min
                                                                            • Nearest beach 2 mi
                                                                            • Child Friendly
                                                                            • Air conditioning

                                                                            Price per night from

                                                                            $46

                                                                            Responds fast!
                                                                            avg. 2 hours 10 minutes

                                                                            Price per night from

                                                                            $46

                                                                            Distance approx 10.29 km from Annapolis Show on Map

                                                                            (1) Excellent 

                                                                              32

                                                                              KENT ISLAND-OCEAN VIEW Home for rent -4 bedrooms EASTERN SHORE sleeps 10-12

                                                                              Maryland / Kent Island

                                                                              Kent Island house

                                                                              4 10 2 nights min

                                                                              • 4 bedrooms
                                                                              • sleeps 10
                                                                              • 2 nights min
                                                                              • Nearest beach 5 mi
                                                                              • Swimming pool
                                                                              • Air conditioning

                                                                              Price per night from

                                                                              $1,749

                                                                              Price per night from

                                                                              $1,749

                                                                              About Annapolis

                                                                              Come to Annapolis to experience the best of old world style and Chesapeake Bay charm. This distinguished town, located on the salty bay, has provided visitors with the perfect Maryland vacation getaway for centuries. Visit the museums here and learn more about the early settlers of the area, the natural history and the wildlife that populate fragile Maryland ecosystems, and the important events in American history that took place here. Find a vacation rental, summer home, or bayside cottage overlooking the shoreline. Head downtown to experience Maryland's annual festivals celebrating regional music and the famous Maryland blue crab. Go antique and craft shopping in the heart of the city. Explore Annapolis museums and art galleries and spend some time on the emerald green golf courses around the Chesapeake Bay. At night, head downtown for world-class seafood and a live performance at a local theater.

                                                                              Here are a few additional suggestions for your trip:

                                                                              • Visit the Maryland State House: Annapolis was America's first peacetime capitol, and the statehouse is the oldest still in legislative use.
                                                                              • Visit the US Naval Academy: Take a tour of the Naval Academy, one of the proud institutions of Annapolis.
                                                                              • Go on a pirate adventure: Take a real life pirate adventure on a ship in Annapolis Harbor. Pirate Adventures on the Chesapeake offers a full day of true buccaneering on an Annapolis boat, complete with face paint, pirate fashions, and a water cannon battle.
                                                                              • Experience Annapolis sailing: Nothing can compare with a real sailing adventure aboard an authentic Chesapeake Skipjack. Help man the sails, try your hand at Annapolis fishing and crabbing, or just relax on the deck and watch the harbor birds sail overhead.
                                                                              • Visit the William Paca Garden: This colonial garden offers peace, serenity, and history lessons along with guided tours.
                                                                              • Explore Quiet Waters Park: This 340 acre park just outside the city center offers more than six miles of trails perfect for strolling, jogging, or biking.

                                                                              Thousands of visitors come to this area every year to enjoy long weekend getaways, family reunions, and beautiful wedding venues in Annapolis. If you're among them, find the perfect rental apartment in the heart of downtown, or a bayside condo near the harbor. While you're here, consider visiting a few other popular vacation destinations in Maryland like Arnold and Lake Shore.