Cancel Clear Filters Apply Filters

Price Per Week

$ $

Sleeps

Bedrooms

Bathrooms

Booking Options

Property Type

Apartments
Boats
Condos
Cottages
Homes
Lodges
Townhomes
Villas
Barns
Bungalows
Cabins
Castles
Chalets
Estates
Farmhouses
Hotels
Studios
Yachts

Location Type

Even More Filters

Features

Managed By

Cancel Clear Filters Apply Filters
Use filters to narrow your search results!

Annapolis Vacation Rentals with Online Booking(37)

37 Results
Book it Now!
2 night minimum stay
  • 3 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 9
    (64)
    Book it Now!
    4 night minimum stay
    • 6 BR,
    • 4 BA,
    • 1 HF BA,
    • Sleeps 15
      (52)
      Book it Now!
      2 night minimum stay
      • 3 BR,
      • 2 BA,
      • Sleeps 8
        (42)
        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)
            Book it Now!
            2 night minimum stay
            • 3 BR,
            • 2 BA,
            • 2 HF BA,
            • Sleeps 10
              (8)
              Book it Now!
              2 night minimum stay
              • 4 BR,
              • 4 BA,
              • Sleeps 10
                (4)
                Book it Now!
                2 - 6 night minimum stay
                • 2 BR,
                • 2 BA,
                • Sleeps 6
                  (35)
                  Book it Now!
                  3 - 7 night minimum stay
                  • 3 BR,
                  • 2 BA,
                  • 1 HF BA,
                  • Sleeps 8
                    Book it Now!
                    2 - 7 night minimum stay
                    • 2 BR,
                    • 2 BA,
                    • Sleeps 6
                      Book it Now!
                      2 night minimum stay
                      • 3 BR,
                      • 2 BA,
                      • 1 HF BA,
                      • Sleeps 8
                        (22)
                        $700 - $1,000
                        per night
                        Book it Now!
                        3 - 6 night minimum stay
                        • 6 BR,
                        • 5 BA,
                        • 1 HF BA,
                        • Sleeps 12
                          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
                              $695
                              per night
                              Book it Now!
                              4 night minimum stay
                              • 4 BR,
                              • 4 BA,
                              • Sleeps 7
                                1 Review
                                Book it Now!
                                3 night minimum stay
                                • 5 BR,
                                • 3 BA,
                                • Sleeps 9
                                  Book it Now!
                                  3 night minimum stay
                                  • 3 BR,
                                  • 3 BA,
                                  • 1 HF BA,
                                  • Sleeps 8
                                    Book it Now!
                                    2 night minimum stay
                                    • 2 BR,
                                    • 2 BA,
                                    • 1 HF BA,
                                    • Sleeps 8
                                      (14)
                                      Book it Now!
                                      7 night minimum stay
                                      • 2 BR,
                                      • 2 BA,
                                      • Sleeps 4
                                        Book it Now!
                                        • 4 BR,
                                        • 4 BA,
                                        • Sleeps 12
                                          Book it Now!
                                          3 night minimum stay
                                          • 1 BR,
                                          • 1 BA,
                                          • Sleeps 4
                                            Book it Now!
                                            2 night minimum stay
                                            • 4 BR,
                                            • 3 BA,
                                            • Sleeps 14
                                              Book it Now!
                                              • 2 BR,
                                              • 1 BA,
                                              • Sleeps 3
                                                Book it Now!
                                                2 night minimum stay
                                                • 1 BR,
                                                • 1 BA,
                                                • Sleeps 4
                                                  Book it Now!
                                                  4 night minimum stay
                                                  • 2 BR,
                                                  • 2 BA,
                                                  • Sleeps 5
                                                    12 more choices from the HomeAway Network
                                                    Book it Now!
                                                    2 night minimum stay
                                                    • 2 BR,
                                                    • 1 BA,
                                                    • Sleeps 10
                                                      (14)
                                                      Book it Now!
                                                      2 night minimum stay
                                                      • 2 BR,
                                                      • 1 BA,
                                                      • Sleeps 4
                                                        (4)
                                                        Book it Now!
                                                        2 - 6 night minimum stay
                                                        • 3 BR,
                                                        • 3 BA,
                                                        • 1 HF BA,
                                                        • Sleeps 10
                                                          (4)
                                                          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)
                                                              Advertisement
                                                               

                                                              Recent Annapolis Reviews

                                                              Well-appointed, convenient and comfy getaway

                                                              5 of 5
                                                              We really enjoyed the location and amenities of the house. It was very comfortable and very tastefully decorated. The kitchen was well-supplied for those who wanted to cook. Beds were comfy. The owner was quick to help when we had questions. The amount of stairs might not work for families with very young toddlers or elderly people. We coudln't find many cable channels (possibly user error?) and we couldn't find extra pillow cases. Overall --highly recommended!
                                                              • Submitted: Aug 23, 2014
                                                              • Stayed: Aug 2014