Cancel Clear Filters Apply Filters

Price Per Week

$ $

Sleeps

Bedrooms

Bathrooms

Booking Options

Property Type

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

Location Type

Even More Filters

Features

Managed By

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

Maryland Vacation Rentals with Air Conditioning(2,230)

2,230 Results
Book it Now!
2 night minimum stay
  • 3 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 9
    (64)
    Book it Now!
    3 - 7 night minimum stay
    • 4 BR,
    • 2 BA,
    • Sleeps 9
      (26)
      Book it Now!
      2 - 4 night minimum stay
      • 3 BR,
      • 2 BA,
      • 1 HF BA,
      • Sleeps 9
        (73)
        Book it Now!
        4 night minimum stay
        • 6 BR,
        • 4 BA,
        • 1 HF BA,
        • Sleeps 15
          (53)
          Book it Now!
          2 - 7 night minimum stay
          • 3 BR,
          • 3 BA,
          • Sleeps 9
            (49)
            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)
                3 night minimum stay
                • 5 BR,
                • 4 BA,
                • Sleeps 10
                  (24)
                  Book it Now!
                  2 - 4 night minimum stay
                  • 5 BR,
                  • 2 BA,
                  • 1 HF BA,
                  • Sleeps 15
                    (16)
                    Book it Now!
                    3 - 7 night minimum stay
                    • 2 BR,
                    • 2 BA,
                    • Sleeps 6
                      (37)
                      2 - 3 night minimum stay
                      • 2 BR,
                      • 1 BA,
                      • 1 HF BA,
                      • Sleeps 4
                        (62)
                        Book it Now!
                        2 night minimum stay
                        • 2 BR,
                        • 2 BA,
                        • Sleeps 8
                          (20)
                          Book it Now!
                          3 - 7 night minimum stay
                          • 6 BR,
                          • 5 BA,
                          • 1 HF BA,
                          • Sleeps 16
                            (16)
                            2 - 3 night minimum stay
                            • 4 BR,
                            • 2 BA,
                            • Sleeps 8
                              (42)
                              2 - 3 night minimum stay
                              • 3 BR,
                              • 1 BA,
                              • 1 HF BA,
                              • Sleeps 6
                                (26)
                                2 - 3 night minimum stay
                                • 2 BR,
                                • 1 BA,
                                • Sleeps 4
                                  (75)
                                  Book it Now!
                                  2 night minimum stay
                                  • 3 BR,
                                  • 2 BA,
                                  • 2 HF BA,
                                  • Sleeps 10
                                    (8)
                                    2 - 3 night minimum stay
                                    • 7 BR,
                                    • 5 BA,
                                    • 1 HF BA,
                                    • Sleeps 22
                                      (43)
                                      2 - 7 night minimum stay
                                      • 2 BR,
                                      • 2 BA,
                                      • Sleeps 6
                                        (56)
                                        2 - 3 night minimum stay
                                        • 4 BR,
                                        • 2 BA,
                                        • 1 HF BA,
                                        • Sleeps 8
                                          (33)
                                          Book it Now!
                                          3 - 7 night minimum stay
                                          • 1 BR,
                                          • 1 BA,
                                          • Sleeps 6
                                            (9)
                                            2 - 3 night minimum stay
                                            • 5 BR,
                                            • 4 BA,
                                            • 1 HF BA,
                                            • Sleeps 13
                                              (25)
                                              2 - 3 night minimum stay
                                              • 7 BR,
                                              • 7 BA,
                                              • 1 HF BA,
                                              • Sleeps 22
                                                (16)
                                                2 - 3 night minimum stay
                                                • 3 BR,
                                                • 2 BA,
                                                • Sleeps 8
                                                  (34)
                                                  2 - 3 night minimum stay
                                                  • 3 BR,
                                                  • 2 BA,
                                                  • Sleeps 6
                                                    (32)
                                                    Book it Now!
                                                    3 - 7 night minimum stay
                                                    • 3 BR,
                                                    • 3 BA,
                                                    • 1 HF BA,
                                                    • Sleeps 10
                                                      (30)
                                                      Book it Now!
                                                      3 - 7 night minimum stay
                                                      • 3 BR,
                                                      • 3 BA,
                                                      • Sleeps 9
                                                        (8)
                                                        3 night minimum stay
                                                        • 4 BR,
                                                        • 3 BA,
                                                        • Sleeps 8
                                                          (26)
                                                          4 night minimum stay
                                                          • 5 BR,
                                                          • 5 BA,
                                                          • Sleeps 12
                                                            (13)
                                                            2 night minimum stay
                                                            • 3 BR,
                                                            • 2 BA,
                                                            • Sleeps 8
                                                              (37)
                                                               

                                                              Recent Maryland Reviews

                                                              Awesome Condo!

                                                              5 of 5
                                                              We had a great time at the condo! It was right across the street from the beach and had many places to eat within walking distance. I was impressed as to how clean it was and everything you could ever think of needing was already there for us. Drake provided excellent customer service and answered all questions promptly. Checking in was a breeze with the coded door. We will be booking this again and will most likely be making this a yearly visit!
                                                              • Submitted: Sep 9, 2014
                                                              • Stayed: Sep 2014

                                                              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

                                                              Trust the reviews, this place is spectacular!

                                                              5 of 5
                                                              The massive house was excellent, clean, and all of the amenities were appropriate and well used and exceeded our needs. We had four families, 8 adults, 9 children and plenty of room to spare. Do yourself a favor and read the reviews, they are accurate. The pictures are excellent but they almost don't do it justice, the place is huge and immaculate. The view is probably the best in the area over the cove. I almost don't want this secret slice of paradise to be found. Some of the things to do while there....kayaking, fishing, birdwatching (Bald Eagle seen everyday), small hikes, swimming, sit around fire pit and watch the sunset, view the various wildlife, etc,etc. If you like Alapacas, stop by Painted Sky Alpaca Farm in Earleville, the wonderful owners will give a tour...about a 10 minute ride...or check out Chesapeake City which isn't too far away. Amos was a gracious host and we felt very comfortable knowing we could contact him at any time for any questions or problems we may have had. We were able to create some incredible memories at Eagle's View and will definitely return so please respect and take care of this gem if you decide to book it.
                                                              • Submitted: Jul 3, 2014
                                                              • Stayed: Jun 2014