Price Per Week

$ $

Sleeps

Bedrooms

Bathrooms

Booking Options

Property Type

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

Location Type

Even More Filters

Features

Managed By

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

Bailey Island Vacation Rentals with Parking Included(36)

36 Results
3 - 7 night minimum stay
  • 5 BR,
  • 3 BA,
  • Sleeps 10
    (14)
    7 night minimum stay
    • 4 BR,
    • 5 BA,
    • Sleeps 12
      (8)
      $2,300 - $2,600
      per week
      7 night minimum stay
      • 3 BR,
      • 2 BA,
      • Sleeps 6
        (22)
        7 night minimum stay
        • 2 BR,
        • 2 BA,
        • 1 HF BA,
        • Sleeps 6
          2 - 7 night minimum stay
          • 9 BR,
          • 4 BA,
          • Sleeps 24
            (14)
            7 night minimum stay
            • 4 BR,
            • 3 BA,
            • Sleeps 7
              2 - 3 night minimum stay
              • 2 BR,
              • 1 BA,
              • Sleeps 6
                (9)
                7 night minimum stay
                • 5 BR,
                • 2 BA,
                • Sleeps 8
                  (8)
                  $286 - $429
                  per night
                  3 - 7 night minimum stay
                  • 4 BR,
                  • 2 BA,
                  • Sleeps 8
                    7 night minimum stay
                    • 3 BR,
                    • 1 BA,
                    • Sleeps 6
                      (3)
                      3 night minimum stay
                      • 3 BR,
                      • 2 BA,
                      • Sleeps 6
                        (11)
                        3 - 7 night minimum stay
                        • 5 BR,
                        • 2 BA,
                        • Sleeps 6
                          (7)
                          2 - 6 night minimum stay
                          • 4 BR,
                          • 2 BA,
                          • Sleeps 8
                            (15)
                            • 4 BR,
                            • 2 BA,
                            • Sleeps 7
                              (6)
                              7 night minimum stay
                              • 2 BR,
                              • 1 BA,
                              • Sleeps 5
                                (3)
                                3 - 7 night minimum stay
                                • 1 BR,
                                • 1 BA,
                                • Sleeps 2
                                  4 - 31 night minimum stay
                                  • 3 BR,
                                  • 2 BA,
                                  • Sleeps 6
                                    (5)
                                    7 night minimum stay
                                    • 2 BR,
                                    • 1 BA,
                                    • Sleeps 6
                                      (3)
                                      3 - 7 night minimum stay
                                      • 2 BR,
                                      • 1 BA,
                                      • Sleeps 3
                                        (3)
                                        3 - 7 night minimum stay
                                        • 3 BR,
                                        • 1 BA,
                                        • 1 HF BA,
                                        • Sleeps 14
                                          1 Review
                                          • 7 BR,
                                          • 6 BA,
                                          • 1 HF BA,
                                          • Sleeps 17
                                            1 Review
                                            15 more choices from the HomeAway Network
                                            Book it Now!
                                            2 night minimum stay
                                            • 3 BR,
                                            • 2 BA,
                                            • Sleeps 7
                                              3 night minimum stay
                                              • 2 BR,
                                              • 1 BA,
                                              • Sleeps 4
                                                (8)
                                                $171 - $175
                                                per night
                                                2 - 7 night minimum stay
                                                • 1 BR,
                                                • 1 BA,
                                                • Sleeps 7
                                                  3 night minimum stay
                                                  • 3 BR,
                                                  • 1 BA,
                                                  • 1 HF BA,
                                                  • Sleeps 6
                                                    (3)
                                                    6 night minimum stay
                                                    • Studio,
                                                    • 1 BA,
                                                    • Sleeps 4
                                                      $6,000 - $8,000
                                                      per week
                                                      7 - 14 night minimum stay
                                                      • 6 BR,
                                                      • 4 BA,
                                                      • Sleeps 14
                                                        7 night minimum stay
                                                        • 3 BR,
                                                        • 1 BA,
                                                        • 1 HF BA,
                                                        • Sleeps 6
                                                          1 Review
                                                          4 - 7 night minimum stay
                                                          • 2 BR,
                                                          • 1 BA,
                                                          • Sleeps 4
                                                            4 - 7 night minimum stay
                                                            • 3 BR,
                                                            • 1 BA,
                                                            • Sleeps 6
                                                              Advertisement
                                                               

                                                              Recent Bailey Island Reviews

                                                              excellent!

                                                              5 of 5
                                                              We had a fabulous week at the cottage with our two young kids. A great place to rest and enjoy Bailey Island.
                                                              • Submitted: Aug 18, 2014
                                                              • Stayed: Aug 2014

                                                              Wonderful time!!

                                                              5 of 5
                                                              As this was our first trip to Maine, we had a great time at the Friendly Cottage. The owners were very easy to work with. The views from the cottage were spectacular! The kids enjoyed looking for sea glass, and shells each day and climbing the ever changing rock formations. The house was clean, comfortable, and well supplied. During our week there, we enjoyed kayaking, sailing, lobstering, and enjoyed the food at several of the local restaurants. The cottage is conveniently located to Freeport and Portland, about a 30-45 minute drive. We would highly recommend the Friendly Cottage to everyone who is looking for a great home base to relax and recharge. We hope to return again.
                                                              • Submitted: Aug 18, 2014
                                                              • Stayed: Aug 2014

                                                              Charming and relaxing

                                                              5 of 5
                                                              We stayed in Nezinscott for a week with our daughters ages 16 months and 4 years. It was a dream. George and Debbie were very thoughtful and especially accommodating of our children's needs. The girls' favorite toys were the nets to catch insects and crabs in, play law mowers to push around and the slide. My husband and I loved the wraparound porch and the views it provided. We had many excellent meals at Morse's Grille and also enjoyed adventures to Popham beach and the Puffin watch tour. The ice cream at Tiffins was the delicious creamy soft-serve (as well as hard-packed). We enjoyed several treats there. We tend to go to new places for vacations but we could definitely imagine returning here some day.
                                                              • Submitted: Aug 9, 2014
                                                              • Stayed: Jun 2014