Cancel Clear Filters Apply Filters

Property Type

Booking Options

Location Type

Even More Filters

Features

Managed By

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

Chatham: Vacation Rentals (144)

  • 1 - 30 of 144
    • 4 BR
    • 2 BA
    • Sleeps 10
    16
    Request to Book View Details
    24 hrs Confirmation within 24 hours
      • 1 BR
      • 1 BA
      • Sleeps 2
      9
      Request to Book View Details
      Instant Instant confirmation
        • 4 BR
        • 2 BA
        • 1 HF BA
        • Sleeps 8
        12
        Request to Book View Details
        Instant Instant confirmation
          • 3 BR
          • 3 BA
          • Sleeps 8
          9
          Request to Book View Details
          24 hrs Confirmation within 24 hours
            • 3 BR
            • 2 BA
            • 1 HF BA
            • Sleeps 7
            8
            Request to Book View Details
            24 hrs Confirmation within 24 hours
              • 3 BR
              • 3 BA
              • Sleeps 8
              5
              Request to Book View Details
              24 hrs Confirmation within 24 hours
                • 1 BR
                • 1 BA
                • Sleeps 4
                21
                Request to Book View Details
                24 hrs Confirmation within 24 hours
                  • 5 BR
                  • 2 BA
                  • 1 HF BA
                  • Sleeps 9
                  3
                  Request to Book View Details
                  Instant Instant confirmation
                    $204
                    avg/night
                    • 2 BR
                    • 1 BA
                    • Sleeps 6
                    13
                    Request to Book View Details
                    24 hrs Confirmation within 24 hours
                      • 3 BR
                      • 2 BA
                      • Sleeps 8
                      13
                      Request to Book View Details
                      24 hrs Confirmation within 24 hours
                        • 4 BR
                        • 3 BA
                        • Sleeps 15
                        Request to Book View Details
                        24 hrs Confirmation within 24 hours
                          • 2 BR
                          • 1 BA
                          • 1 HF BA
                          • Sleeps 7
                          1 Review
                          Request to Book View Details
                          Instant Instant confirmation
                            • 3 BR
                            • 2 BA
                            • Sleeps 7
                            1 Review
                            Request to Book View Details
                            Instant Instant confirmation
                              • 2 BR
                              • 1 BA
                              • Sleeps 4
                              16
                              Request to Book View Details
                              24 hrs Confirmation within 24 hours
                                • 4 BR
                                • 2 BA
                                • 1 HF BA
                                • Sleeps 12
                                1 Review
                                Request to Book View Details
                                24 hrs Confirmation within 24 hours
                                  • 4 BR
                                  • 3 BA
                                  • Sleeps 12
                                    • 4 BR
                                    • 3 BA
                                    • Sleeps 12
                                    7
                                    Request to Book View Details
                                    24 hrs Confirmation within 24 hours
                                      • 3 BR
                                      • 3 BA
                                      • Sleeps 9
                                      23
                                      Request to Book View Details
                                      24 hrs Confirmation within 24 hours
                                        • 3 BR
                                        • 2 BA
                                        • 1 HF BA
                                        • Sleeps 8
                                        Special Offer! New Listing for 2016 - Special May / June Promotions April 11 - June 1
                                          • 4 BR
                                          • 3 BA
                                          • Sleeps 8
                                          21
                                            $924
                                            avg/night
                                            • 4 BR
                                            • 3 BA
                                            • Sleeps 10
                                            12
                                              • 4 BR
                                              • 3 BA
                                              • Sleeps 8
                                              4
                                              Request to Book View Details
                                              24 hrs Confirmation within 24 hours
                                                • 4 BR
                                                • 2 BA
                                                • 1 HF BA
                                                • Sleeps 8
                                                17
                                                Request to Book View Details
                                                24 hrs Confirmation within 24 hours
                                                  • 7 BR
                                                  • 4 BA
                                                  • Sleeps 12
                                                  11
                                                  Request to Book View Details
                                                  24 hrs Confirmation within 24 hours
                                                    • 5 BR
                                                    • 4 BA
                                                    • Sleeps 14
                                                    62
                                                    Request to Book View Details
                                                    24 hrs Confirmation within 24 hours
                                                      • 5 BR
                                                      • 2 BA
                                                      • 1 HF BA
                                                      • Sleeps 10
                                                      25
                                                      Request to Book View Details
                                                      24 hrs Confirmation within 24 hours
                                                        • 3 BR
                                                        • 2 BA
                                                        • Sleeps 8
                                                        7
                                                        • 1 - 30 of 144
                                                         

                                                        Recent Chatham Reviews

                                                        Great location.

                                                        5 of 5
                                                        Good for a family get away. Walkable to the beach and center of town. Perfect
                                                        • Submitted: Apr 27, 2016
                                                        • Stayed: Apr 2016

                                                        Outstanding, first class property and amenities

                                                        5 of 5
                                                        Our family of 5 spent Thanksgiving week at this beautiful location. We had dinner for 12 with plenty of elbowroom. Everyone loved the first class furnishings, beautiful antiques, extremely well stocked kitchen supplies and the Bose stereo system. Beds, linens, towels all the quality you'd expect at a 5 star hotel. The owner was friendly and very helpful. Everything you would need to make your vacation perfect. This is a special location that I would highly recommend!
                                                        • Submitted: Dec 12, 2015
                                                        • Stayed: Nov 2015

                                                        Fabulous experience!

                                                        5 of 5
                                                        What can one say about "Mr. Bill" and his wonderful Chatham home except "Fabulous!"?? The house itself is as delightful as it appears in the photos----spotless and beautifully appointed, but homey and very comfortable. Great beds and bedrooms on each end of the house, a big family area with living room, dining room and kitchen inviting lots of together time in the center of the home, the den/poolroom area downstairs as a bonus, and an office upstairs with books and pamphlets that probably provide more information on The Cape (food, shopping, activities, local events) than the local Chamber of Commerce!! (That is in addition to the notebook of house information and concierge notes in the Welcome Folder!!) We had books, DVD's, games, children's toys/books, and everything you could want for cooking/serving meals IF you're inclined to do much "cooking and serving" after all the information Bill provides on where to eat and what to order. When I originally rented this house, I asked Bill in passing if there was a domino set (or I'd have one of the kids bring one)......... He went out and bought one! WHOA!! Since then, in the correspondence back and forth, I have come to understand their much-deserved pride in this home and their desire to go above and beyond to make their tenants feel welcome, comfortable and happy. The check-in/check-out was a breeze; the gals there were most pleasant and obviously are very fond of Bill. (Even the trash guy was great! I had another bag to put out and he waited for me with a smile!........) My adult kids loved the house as well as all the information at our fingertips; within 24 hours THEY were referring to our 'landlord' as "BILL"---like an old family friend! We walked (the beach and the Chatham Bars area), played, dined like kings thanks to Chatham Fish & Lobster, spent time at the beach (NOT in the water, however!!), had great lunches at The Squire in Chatham and The Beacon in Orleans, but most/best of all we relaxed and enjoyed sunsets and our family time. Told Bill I would have to live in that house for at least 4 years to watch all the movies, read all the books that interested me, and take part in the activities that are available in the Chatham area. This was a wonderful experience. Thank you so much, Mr. Bill!!!
                                                        • Submitted: Dec 1, 2015
                                                        • Stayed: Nov 2015