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Annapolis Long Term Vacation Rentals(38)

38 Results
Book it Now!
2 night minimum stay
  • 3 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 9
    (64)
    Book it Now!
    2 - 5 night minimum stay
    • 5 BR,
    • 3 BA,
    • Sleeps 21
      (53)
      Book it Now!
      2 - 4 night minimum stay
      • 5 BR,
      • 2 BA,
      • 1 HF BA,
      • Sleeps 15
        (16)
        2 night minimum stay
        • 4 BR,
        • 4 BA,
        • Sleeps 14
          (25)
          2 night minimum stay
          • 3 BR,
          • 2 BA,
          • Sleeps 8
            (37)
            7 night minimum stay
            • 3 BR,
            • 3 BA,
            • Sleeps 10
              (27)
              4 night minimum stay
              • 5 BR,
              • 2 BA,
              • 2 HF BA,
              • Sleeps 11
                (11)
                1 - 3 night minimum stay
                • 2 BR,
                • 2 BA,
                • Sleeps 7
                  (3)
                  Book it Now!
                  2 - 6 night minimum stay
                  • 2 BR,
                  • 2 BA,
                  • Sleeps 6
                    (35)
                    2 - 5 night minimum stay
                    • 3 BR,
                    • 2 BA,
                    • Sleeps 6
                      (17)
                      2 night minimum stay
                      • 4 BR,
                      • 3 BA,
                      • Sleeps 12
                        (29)
                        Book it Now!
                        2 night minimum stay
                        • 2 BR,
                        • 2 BA,
                        • Sleeps 5
                          Book it Now!
                          1 - 2 night minimum stay
                          • 2 BR,
                          • 1 BA,
                          • Sleeps 6
                            2 Reviews
                            31 night minimum stay
                            • 2 BR,
                            • 2 BA,
                            • Sleeps 4
                              (6)
                              • 3 BR,
                              • 2 BA,
                              • 1 HF BA,
                              • Sleeps 10
                                (7)
                                3 night minimum stay
                                • 4 BR,
                                • 2 BA,
                                • Sleeps 8
                                  1 Review
                                  4 night minimum stay
                                  • 3 BR,
                                  • 3 BA,
                                  • Sleeps 10
                                    • 4 BR,
                                    • 2 BA,
                                    • Sleeps 12
                                      (6)
                                      3 night minimum stay
                                      • 4 BR,
                                      • 2 BA,
                                      • 1 HF BA,
                                      • Sleeps 10
                                        (13)
                                        $220 - $350
                                        per night
                                        3 night minimum stay
                                        • 3 BR,
                                        • 2 BA,
                                        • Sleeps 6
                                          2 night minimum stay
                                          • 2 BR,
                                          • 2 BA,
                                          • Sleeps 6
                                            (15)
                                            • 3 BR,
                                            • 2 BA,
                                            • Sleeps 8
                                              16 more choices from the HomeAway Network
                                              2 night minimum stay
                                              • 1 BR,
                                              • 1 BA,
                                              • Sleeps 4
                                                (26)
                                                2 - 7 night minimum stay
                                                • 2 BR,
                                                • 2 BA,
                                                • Sleeps 18
                                                  (8)
                                                  Book it Now!
                                                  2 night minimum stay
                                                  • 4 BR,
                                                  • 1 BA,
                                                  • 1 HF BA,
                                                  • Sleeps 6
                                                    (4)
                                                    Book it Now!
                                                    3 night minimum stay
                                                    • 3 BR,
                                                    • 2 BA,
                                                    • 1 HF BA,
                                                    • Sleeps 10
                                                      (3)
                                                      2 night minimum stay
                                                      • 2 BR,
                                                      • 1 BA,
                                                      • Sleeps 6
                                                        (27)
                                                        3 night minimum stay
                                                        • 1 BR,
                                                        • 1 BA,
                                                        • Sleeps 3
                                                          (19)
                                                          3 night minimum stay
                                                          • 2 BR,
                                                          • 1 BA,
                                                          • Sleeps 4
                                                            1 - 7 night minimum stay
                                                            • 4 BR,
                                                            • 2 BA,
                                                            • 1 HF BA,
                                                            • Sleeps 11
                                                              (4)
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                                                              Recent Annapolis Reviews

                                                              Great Girls Weekend

                                                              4 of 5
                                                              We rented this property for our annual girls weekend and were glad we did. After looking online for a house in or walking distance to Annapolis and being hit by sticker shock for small houses that included no parking, we decided to look further out of town. This house was the perfect get away. The views of the river from just about every room in the house were beautiful, and the large wrap around deck with plenty of seating allowed us to spend just about every waking minute outside. When we wanted to go into town, it was a short cab ride (parking in town is by sheer luck). There is a nice community beach in the development that is walkable, although if you are lugging chairs, coolers, etc I would highly recommend driving the 5 minutes unless you are a mountail climber! There is plenty of parking there. Martin was a real pleasure to work with before, during, and agfter our time at his house. He responded quickly to any questions we had. It was like having two vacations in one. When we wanted the hustle and bustle of town it was a cab ride away, but the relaxing nature of the house and surroundings was the real prize
                                                              • Submitted: Sep 17, 2014
                                                              • Stayed: Sep 2014

                                                              Excellent Location

                                                              5 of 5
                                                              We needed a place to stay in Annapolis at the last minute and were so happy to find this home. It was exactly what we were looking for - a comfortable house in a great location. The house is well-maintained and stocked with everything we needed for our two-week stay. The owner was very accessible and accommodating, even allowing us to store some boxes in the garage. The backyard was a great place to enjoy dinner outside and was large enough to play a game of soccer, which is quite unusual for Annapolis. In addition, the property has four off-street parking spaces, which came in handy on busy summer weekends. The location is excellent - we were able to walk to several Eastport restaurants in 5 minutes and to downtown Annapolis in less than 15 minutes. And nothing beats the view of the sailboats drifting past on Spa Creek as you approach the house from Second Street. We thoroughly enjoyed our stay at this property and highly recommend it.
                                                              • Submitted: Aug 26, 2014
                                                              • Stayed: Jul 2014

                                                              Perfect for Entertaining Family and Friends!

                                                              5 of 5
                                                              This was by far the best house my fiance (now husband) and I stumbled upon while trying to determine the perfect location for our families to meet for the first time. It was probably one of the biggest returns on investment we've found. The house itself provides the perfect amount of privacy away from the hustle and bustle of downtown Annapolis, yet it's still close enough to go out and explore the city if you'd like! The pictures really don't do the house justice. We had about 30 of our immediate family members over for 4th of July and it offered plenty of space for everyone to roam freely or hang out together in about 10 different "hang out" locations. The driveway is huge (probably fits about 15 cars) so we set up a big canopy out front and had the 4th catered by a nearby BBQ place. In itself, the house could probably seat about 40 people at the same time without having to bring in extra chairs/tables, but rented some so that everyone could all sit in the same location out front. There were also plenty of electrical outlets (even on the decks) so we were able to easily hook up a couple different docking stations for our ipods to provide music in different hang-out spots. It also already had string lighting on the deck - which we enhanced with some of our own lighting. The yard is seriously spectacular - it's very unique and charming with the koi pond, cobblestone walkways, bonfires, and the tiered deck levels. As each family member came in, my husband and I were satisfied with their reaction of how amazing the house was. The floating dock in the back yard was a real hit for taking pictures! The backdrop of the river and the woods across the river added even more charm to the location. The front yard provided a beautiful backdrop as well - you don't really even need to do any decorating if you're planning on hosting some sort of event because of the ambiance it provides. The property was well-maintained and super clean. Everything was perfectly in place when we arrived. The owner was very helpful throughout the entire booking process. He went above and beyond to make sure everything went smoothly for us. We were able to coordinate a walk-through to make sure it was exactly what we were looking for and he answered all of our questions. We would recommend this place to anyone, small or large groups. It's the perfect place to host a laid back bbq like we did or for a romantic getaway! We would definitely go back!
                                                              • Submitted: Jul 23, 2014
                                                              • Stayed: Jul 2014