Chances Are, You'll Love Chatham Rentals

For your upcoming vacation on Cape Cod, head out to Chatham, Massachusetts, an old fishing and whaling community that has retained much of its late colonial flavor. From rustic beach rentals to Chatham cottages, you’ll have a better time in a vacation home than in a single overpriced hotel room. Whether you’re looking to bring the family for a weekend getaway,or just want to get out of town for the summer, this seaside town has much to offer, both indoors and out.

Consider a Chatham beach house near the ocean and spend the afternoons relaxing on the sand with your favorite novel. Don’t worry if sunbathing isn’t your thing. You won’t run out of things to do in Chatham. In fact, you’ll feel as though you’ve stepped back into time when you stroll down Main Street and view its preserved 18th century architecture. Browse through the family-owned shops, including an old fashioned candy store known for its homemade fudge. Buy tickets to a road show at the well- known Monomoy Theatre, or during the summer, catch a free concert at the Gazebo.

If you feel like exploring other parts of Cape Cod, consider taking the ferry to the Monomoy National Wildlife Refuge, home to several species of migratory birds. Or spend a day browsing through the Railroad Museum and learn more than you could from one of those coffee table books that are just for display. Cook meals in the custom kitchen of your home rental and save money to spend on local attractions, like the several art galleries and village shops that populate downtown. No matter what floats your boat, you’ll leave Chatham MA feeling rejuvenated, so begin planning your summer vacation today!
While you're here, check out our guide to Cape Cod vacation rentals on on the ocean.

There are additional vacation properties that the Cape Cod peninsula has to offer. To increase your search selection of Cape Cod vacation rentals consider checking out following rental options: Dennis MA vacation rentals, Bourne area vacation homes, Chatham homes, Eastham beach rentals, lodging in Falmouth MA, Harwich rentals, beach cottages in Orleans MA, Provincetown lodging, vacation lodging in Truro MA, or vacation beach rentals in Yarmouth.

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Chatham: Houses, Cottages & More(603)

5 BR - Beautiful Property-Chatham in-Town & Oyster Beach Inlet
    5 Bedrooms,
  • 2 Bathrooms
  • 1 Half Bath
  • , Sleeps 10
2 - 7 night Minimum Stay
  • 5 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 10
#337824
    (20)
    Chatham - Stage Harbor-Walk to Town
      5 Bedrooms,
    • 4 Bathrooms
    • 1 Half Bath
    • , Sleeps 12
    $4,250 - $8,495
    per week
    7 night Minimum Stay
    • 5 BR,
    • 4 BA,
    • 1 HF BA,
    • Sleeps 12
    #130947
      (8)
      Spectacular Ocean View on Prime Acre: Quintessentially Perfect!
        4 Bedrooms,
      • 3 Bathrooms
      • , Sleeps 8
      3 - 7 night Minimum Stay
      • 4 BR,
      • 3 BA,
      • Sleeps 8
      #106009
        (53)
        Light-Filled Custom Cape on Bay. Water Surrounds! Pets Welcome.
          4 Bedrooms,
        • 4 Bathrooms
        • , Sleeps 10
        7 night Minimum Stay
        • 4 BR,
        • 4 BA,
        • Sleeps 10
        #375389
          (5)
          North Chatham-Water View-Walk to Beach
            3 Bedrooms,
          • 2 Bathrooms
          • , Sleeps 6
          $1,400 - $2,800
          per week
          7 night Minimum Stay
          • 3 BR,
          • 2 BA,
          • Sleeps 6
          #145073
            (10)
            Think Sun, Surf and Sand - $1800 Aug 24 - 31. Walk to Nantucket Sound Beach
              4 Bedrooms,
            • 3 Bathrooms
            • , Sleeps 8
            7 night Minimum Stay
            • 4 BR,
            • 3 BA,
            • Sleeps 8
            #292468
              1 Review
              Walk to Beach- Unsurpassed Amenities- Room to Gather & Scatter
                3 Bedrooms, Sleeps 9
              2 - 7 night Minimum Stay
              • 3 BR,
              • Sleeps 9
              #354414vb
                (23)
                Wildlife Lovers Salt Pond Perch- The Pondhouse- An Authentic Cape Cod Experience
                  3 Bedrooms,
                • 2 Bathrooms
                • , Sleeps 8
                7 night Minimum Stay
                • 3 BR,
                • 2 BA,
                • Sleeps 8
                #225940
                  2 Reviews
                  Chatham Estate Sleeps 20 A/C9 BRS. Overlooking Nantucket Sound and Forrest Beach
                    9 Bedrooms,
                  • 3 Bathrooms
                  • 1 Half Bath
                  • , Sleeps 20
                  2 - 7 night Minimum Stay
                  • 9 BR,
                  • 3 BA,
                  • 1 HF BA,
                  • Sleeps 20
                  #105247
                    (8)
                    4BR-Beautiful Chatham-Year Round-Sleeps up to (8-10) & 1 Mile to Town!
                      4 Bedrooms,
                    • 2 Bathrooms
                    • , Sleeps 10
                    2 - 7 night Minimum Stay
                    • 4 BR,
                    • 2 BA,
                    • Sleeps 10
                    #3540511
                      Chatham -Central Air - Walk to Popular Ridgevale Beach
                        3 Bedrooms,
                      • 2 Bathrooms
                      • , Sleeps 11
                      • 3 BR,
                      • 2 BA,
                      • Sleeps 11
                      #318533
                        (15)
                        4BR-Beautiful Chatham-Year Round-Sleeps up to 8 & 1 Mile to Town!
                          4 Bedrooms,
                        • 2 Bathrooms
                        • 1 Half Bath
                        • , Sleeps 8
                        2 - 7 night Minimum Stay
                        • 4 BR,
                        • 2 BA,
                        • 1 HF BA,
                        • Sleeps 8
                        #376089vb
                          (5)
                          Chatham - Mill Pond - Stage Harbor-Water View
                            5 Bedrooms,
                          • 4 Bathrooms
                          • , Sleeps 16
                          • 5 BR,
                          • 4 BA,
                          • Sleeps 16
                          #105239
                            (40)
                            WOW!! August 25-Sept 1 OPEN! Ridgevale Beach-Spacious Family Paradise!
                              4 Bedrooms,
                            • 3 Bathrooms
                            • 1 Half Bath
                            • , Sleeps 12
                            7 night Minimum Stay
                            • 4 BR,
                            • 3 BA,
                            • 1 HF BA,
                            • Sleeps 12
                            #50380vb
                              (4)
                              Best Of All Worlds! Beach, Bike or Relax - 4BR/2BA
                                4 Bedrooms,
                              • 2 Bathrooms
                              • , Sleeps 12
                              • 4 BR,
                              • 2 BA,
                              • Sleeps 12
                              #422916vb
                                (7)
                                'Right on the Golden Seashore and Water'
                                  2 Bedrooms,
                                • 2 Bathrooms
                                • , Sleeps 7
                                4 - 7 night Minimum Stay
                                • 2 BR,
                                • 2 BA,
                                • Sleeps 7
                                #187500
                                  (8)
                                  Olde Chatham Village, Mill Pond, Custom Beach House
                                    3 Bedrooms, Sleeps 8
                                  • 3 BR,
                                  • Sleeps 8
                                  #117702
                                    7 Reviews
                                    Chatham Waterfront Compound -- 200' of Beach
                                      6 Bedrooms,
                                    • 6 Bathrooms
                                    • , Sleeps 12
                                    • 6 BR,
                                    • 6 BA,
                                    • Sleeps 12
                                    #364760
                                      3 Reviews
                                      $900/week now to June 22!
                                        3 Bedrooms,
                                      • 2 Bathrooms
                                      • , Sleeps 7
                                      • 3 BR,
                                      • 2 BA,
                                      • Sleeps 7
                                      #457397vb
                                        Direct Ocean Front - Private Sandy Beach - 5 Min. Walk to Town
                                          3 Bedrooms,
                                        • 3 Bathrooms
                                        • , Sleeps 7
                                        • 3 BR,
                                        • 3 BA,
                                        • Sleeps 7
                                        #296473vb
                                          3 Bedroom (Sleeps 7), 2 Bath plus outdoor shower near Beaches and Bike Path
                                            3 Bedrooms,
                                          • 2 Bathrooms
                                          • , Sleeps 7
                                          Book it Now!
                                          7 night Minimum Stay
                                          • 3 BR,
                                          • 2 BA,
                                          • Sleeps 7
                                          #986976
                                            2 Reviews
                                            Barcliff Beachhouse - Walk to Town and Beach
                                              4 Bedrooms,
                                            • 3 Bathrooms
                                            • , Sleeps 8
                                            7 night Minimum Stay
                                            • 4 BR,
                                            • 3 BA,
                                            • Sleeps 8
                                            #194312
                                              2 Reviews
                                              8 min. Walk to Ridgevale Beach! Central AC & in great neighborhood on cul de sac
                                                3 Bedrooms,
                                              • 2 Bathrooms
                                              • , Sleeps 6
                                              7 night Minimum Stay
                                              • 3 BR,
                                              • 2 BA,
                                              • Sleeps 6
                                              #269227
                                                10 Reviews
                                                Steps to Ridgevale Beach, Fabulous for families
                                                  3 Bedrooms,
                                                • 3 Bathrooms
                                                • , Sleeps 7
                                                2 - 7 night Minimum Stay
                                                • 3 BR,
                                                • 3 BA,
                                                • Sleeps 7
                                                #130469
                                                  2 Reviews
                                                  Fabulous Chatham home w/in walking distance to Hardings Beach, quiet location
                                                    3 Bedrooms,
                                                  • 2 Bathrooms
                                                  • , Sleeps 8
                                                  2 - 7 night Minimum Stay
                                                  • 3 BR,
                                                  • 2 BA,
                                                  • Sleeps 8
                                                  #190027
                                                    (6)
                                                    Luxury Young Colonial - Great Yard for Kids! Walk to Pleasant St Ocean Beach!
                                                      3 Bedrooms,
                                                    • 2 Bathrooms
                                                    • , Sleeps 8
                                                    1 - 7 night Minimum Stay
                                                    • 3 BR,
                                                    • 2 BA,
                                                    • Sleeps 8
                                                    #293864
                                                      (3)
                                                      Spectacular Neighborhood, Private Beach, Classic Cape Cod
                                                        3 Bedrooms,
                                                      • 2 Bathrooms
                                                      • 1 Half Bath
                                                      • , Sleeps 7
                                                      3 - 7 night Minimum Stay
                                                      • 3 BR,
                                                      • 2 BA,
                                                      • 1 HF BA,
                                                      • Sleeps 7
                                                      #156662
                                                        (4)
                                                        Downtown Chatham 4 Bedroom Home
                                                          4 Bedrooms,
                                                        • 2 Bathrooms
                                                        • , Sleeps 10
                                                        $2,500 - $4,500
                                                        per week
                                                        7 night Minimum Stay
                                                        • 4 BR,
                                                        • 2 BA,
                                                        • Sleeps 10
                                                        #273067
                                                          1 Review
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