Cancel Clear Filters Apply Filters

Price Per Week

$ $

Sleeps

Bedrooms

Bathrooms

Booking Options

Property Type

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

Location Type

Even More Filters

Features

Managed By

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

Oak Bluffs Vacation Rentals with Online Booking(52)

52 Results
Book it Now!
1 - 7 night minimum stay
  • 4 BR,
  • 3 BA,
  • Sleeps 15
    (7)
    Book it Now!
    4 - 5 night minimum stay
    • 3 BR,
    • 2 BA,
    • 1 HF BA,
    • Sleeps 6
      (3)
      Book it Now!
      7 night minimum stay
      • 5 BR,
      • 1 BA,
      • 1 HF BA,
      • Sleeps 9
        (5)
        Book it Now!
        3 - 7 night minimum stay
        • Studio,
        • 1 BA,
        • Sleeps 2
          Book it Now!
          2 - 7 night minimum stay
          • 5 BR,
          • 2 BA,
          • Sleeps 13
            (14)
            Book it Now!
            2 - 7 night minimum stay
            • 5 BR,
            • 1 BA,
            • 1 HF BA,
            • Sleeps 9
              (5)
              Book it Now!
              7 night minimum stay
              • 3 BR,
              • 3 BA,
              • Sleeps 8
                1 Review
                $275 - $425
                per night
                Book it Now!
                4 - 7 night minimum stay
                • 4 BR,
                • 3 BA,
                • Sleeps 9
                  1 Review
                  Book it Now!
                  • 4 BR,
                  • 4 BA,
                  • Sleeps 8
                    Book it Now!
                    7 night minimum stay
                    • 2 BR,
                    • 1 BA,
                    • Sleeps 5
                      (5)
                      Book it Now!
                      2 - 7 night minimum stay
                      • 2 BR,
                      • 2 BA,
                      • Sleeps 6
                        1 Review
                        $37 - $340
                        per night
                        Book it Now!
                        2 - 28 night minimum stay
                        • 2 BR,
                        • 1 BA,
                        • Sleeps 4
                          Book it Now!
                          2 night minimum stay
                          • 2 BR,
                          • 1 BA,
                          • 1 HF BA,
                          • Sleeps 7
                            Book it Now!
                            2 - 7 night minimum stay
                            • 4 BR,
                            • 4 BA,
                            • 1 HF BA,
                            • Sleeps 9
                              (6)
                              Book it Now!
                              2 night minimum stay
                              • 1 BR,
                              • 1 BA,
                              • Sleeps 2
                                1 Review
                                Book it Now!
                                3 - 7 night minimum stay
                                • 3 BR,
                                • 3 BA,
                                • Sleeps 12
                                  Book it Now!
                                  4 - 5 night minimum stay
                                  • 4 BR,
                                  • 2 BA,
                                  • 1 HF BA,
                                  • Sleeps 9
                                    1 Review
                                    Book it Now!
                                    2 - 7 night minimum stay
                                    • 3 BR,
                                    • 2 BA,
                                    • 1 HF BA,
                                    • Sleeps 8
                                      Book it Now!
                                      7 night minimum stay
                                      • 2 BR,
                                      • 1 BA,
                                      • 1 HF BA,
                                      • Sleeps 4
                                        Book it Now!
                                        2 - 7 night minimum stay
                                        • 3 BR,
                                        • 1 BA,
                                        • Sleeps 6
                                          (9)
                                          Book it Now!
                                          2 - 7 night minimum stay
                                          • 2 BR,
                                          • 1 BA,
                                          • Sleeps 4
                                            (7)
                                            Book it Now!
                                            1 - 7 night minimum stay
                                            • 1 BR,
                                            • 1 BA,
                                            • Sleeps 4
                                              (8)
                                              Book it Now!
                                              2 - 7 night minimum stay
                                              • Studio,
                                              • 1 BA,
                                              • Sleeps 4
                                                (7)
                                                Book it Now!
                                                7 - 30 night minimum stay
                                                • 5 BR,
                                                • 2 BA,
                                                • Sleeps 9
                                                  (5)
                                                  Book it Now!
                                                  3 - 7 night minimum stay
                                                  • 3 BR,
                                                  • 2 BA,
                                                  • Sleeps 6
                                                    (4)
                                                    Book it Now!
                                                    3 - 7 night minimum stay
                                                    • 4 BR,
                                                    • 1 BA,
                                                    • 1 HF BA,
                                                    • Sleeps 8
                                                      2 Reviews
                                                      Book it Now!
                                                      7 night minimum stay
                                                      • 2 BR,
                                                      • 2 BA,
                                                      • Sleeps 5
                                                        (4)
                                                        Book it Now!
                                                        3 - 7 night minimum stay
                                                        • 3 BR,
                                                        • 1 BA,
                                                        • 1 HF BA,
                                                        • Sleeps 6
                                                          (4)
                                                          Book it Now!
                                                          7 night minimum stay
                                                          • 3 BR,
                                                          • 1 BA,
                                                          • 1 HF BA,
                                                          • Sleeps 8
                                                            (4)
                                                            Book it Now!
                                                            5 - 7 night minimum stay
                                                            • 3 BR,
                                                            • 3 BA,
                                                            • Sleeps 6
                                                              Advertisement
                                                               

                                                              Recent Oak Bluffs Reviews

                                                              Great property and stay

                                                              5 of 5
                                                              We stayed here this past weekend and it was great. It is a beautiful house in a very quiet and peaceful part of the vineyard. John and Lauren were very accommodating and helpful, it was a breeze renting from them. Highly recommended!
                                                              • Submitted: Aug 28, 2014
                                                              • Stayed: Aug 2014

                                                              It's all about the front porch!

                                                              5 of 5
                                                              My wife and I have a close group of friends that we have been traveling with for the past 12 years. We have rented private homes from coast to coast in places like Tahoe, Jackson Hole, Telluride, and Whistler. We unanimously decided that this house was one of our favorites. A summer vacation in Oak Bluffs is all about the front porch and this home has a great one. It has plenty of space to line up the chairs along the front rail so everyone can kick back and relax during the hottest times of the day. But, it also has a large open area to the side with a comfortable outdoor dining table that is perfect for building a puzzle with your morning coffee or playing cards if it decides to rain. The beds are comfortable and the rooms are spacious with new and easy-opening windows to allow the breeze to flow through on a warm day (last season the windows of our rental were all painted shut). The kitchen is nicely laid out with a second full size refrigerator in an adjoining pantry space (a very welcome addition for large groups) and the indoor dining room comfortably seats 10 people. As much as we loved the house we were even happier with the location. You can see the beach from the front porch which is only a 2 minute walk away. You are also an easy 5 minute walk to either the ferry or downtown Oak Bluffs where you have many options for dining, shopping, supplies, or just a morning latte and bagel. The only downside is that our group is now second guessing our plans to go to Italy next summer instead of the Vineyard because we had such a great time. But that is a good thing isn't it?
                                                              • Submitted: Aug 11, 2014
                                                              • Stayed: Jul 2014

                                                              Perfect Vineyard Charm, Beautiful Lagoon View!!!

                                                              5 of 5
                                                              We just got back from two weeks at this lovely home. This was our second year at the home, and we hope to return again next year. Views are stunning, especially around dinner. We did not want to leave the house. We would recommend this home very highly. The owners are great...very responsive and easy to deal with.
                                                              • Submitted: Aug 10, 2014
                                                              • Stayed: Jul 2014