Seaside Homes in Westport

This historic destination is home to the first colonial villages. The beautiful backdrop of Buzzard Bay and the Rhode Island Sound can be enjoyed from well-maintained seaside masterpieces. Sweeping views from expansive decks have gourmet grills and hot tubs. Washers and dryers, Wi-Fi, cable with large screen televisions, and chef’s kitchens are more pampering amenities guests enjoy.

Cruise Buzzard Bay

Seal or whale watching cruises are activities to add to the itinerary. Vessels sail from Mattapoisett Harbor with refreshments such as baked pastries, cappuccino, and soft drinks for tourists. Groups can make reservations for a lunch or intimate dinner cruise while sightseeing the islands. A sunset cruise is a romantic option for honeymoons and anniversaries. Before setting sail tour the town wharf and Tinkham Hill section of the city.

Tour the Cape Cod Islands

Westport has a strategic location that makes it easy to reach historic and sought-after destinations. Gooseberry and Cuttyhunk Islands are colonial treasures that showcase the first English settlements. Lighthouse tours or grabbing some sun on the beaches is a favorite tourist pastime. Renowned Martha’s Vineyard is close enough to savor with a coastal drive before taking a ferry.

  • Gooseberry Island: This southern lookout island has two beaches with Horseneck in the north and East Beach to the south. Bring plenty of suntan lotion and sunglasses during the summer. Bird watching enthusiasts will be able to add numerous entries to their journal with the migration of Warblers, Snowy Owl, Egrets, Swallows, and others. Mole crabs also add an interesting twist to the hub of activity.
  • Cuttyhunk Island: Plan on spending the day in this island wonderland that is part of the Elizabeth Islands. There are beaches for sunbathing or bird watching the famed Massachusetts American oystercatchers and others. Indigenous wildflowers, sweet peas, and bayberry dart the landscape. Bring or rent fishing gear to try your hand at catching the next world-record striped bass off Sow and Pigs Reef. Hike to Lookout Hill with views of the entire island.
  • Martha’s Vineyard: The name of this special place says it all. It is located an hour away after a scenic ride along the coast of Massachusetts. The final leg includes a ferry ride that offers the chance for a bit of whale watching. Once there, take a deep sea charter out for exceptional bluefish or striped bass fishing. Beaches such as Chappaquiddick line a vast swath of the island with a bevy of water sports to engage in. Sailboats can be chartered for a waterside tour. Downtown Edgartown offers shopping and dining opportunities after a tour of the harbor and five lighthouses in the area.

Visit Nearby Newport, Rhode Island

The imaginary line that divides the states of Massachusetts and Rhode Island is no deterrent for a quick 24-mile breathtaking drive to Newport. The sailboats that are moored with others on the ocean are an inspiring backdrop. Depending on the time of year, take part in the plethora of festivals including the annual flower show. Stroll through the cobble stone streets eating homemade ice cream or enjoying a meal at an outdoor café.

The Climate in Westport

Summers are generally mild due to the ocean breezes, although the occasional heat wave is possible. Winters are snowy with temperatures dipping below freezing. This is considered a spring, summer, and fall getaway destination.

Ways to Reach Westport

Travel options are plentiful when it comes to reaching this picturesque destination. Rental cars from nearby New Bedford Regional Airport or Boston Logan will get you here. A personal car from home is always a good option. There is a plethora of parks with modern amenities that accommodate RVs. Depending on the time of year, motorcycles offer the chance for enjoying the fresh air and open spaces.

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!
  • 1 - 30 of 62
    • 4 BR
    • 2 BA
    • Sleeps 12
    1 Review
    Request to Book View Details
    24 hrs Confirmation within 24 hours
      • 1 BR
      • 1 BA
      • Sleeps 3
      3
        • 5 BR
        • 4 BA
        • 1 HF BA
        • Sleeps 12
          • 3 BR
          • 2 BA
          • Sleeps 6
            • 3 BR
            • 2 BA
            • Sleeps 7
            6
            Request to Book View Details
            24 hrs Confirmation within 24 hours
              • 2 BR
              • 2 BA
              • Sleeps 4
              16
              Request to Book View Details
              24 hrs Confirmation within 24 hours
                • 4 BR
                • 2 BA
                • 1 HF BA
                • Sleeps 10
                1 Review
                Request to Book View Details
                24 hrs Confirmation within 24 hours
                  • 2 BR
                  • 1 BA
                  • Sleeps 5
                  Request to Book View Details
                  24 hrs Confirmation within 24 hours
                    $457
                    avg/night
                    • 2 BR
                    • 1 BA
                    • Sleeps 7
                    Request to Book View Details
                    24 hrs Confirmation within 24 hours
                      • 2 BR
                      • 2 BA
                      • Sleeps 4
                      Request to Book View Details
                      24 hrs Confirmation within 24 hours
                        • 2 BR
                        • 1 BA
                        • Sleeps 6
                        5
                        Request to Book View Details
                        24 hrs Confirmation within 24 hours
                          • 2 BR
                          • 1 BA
                          • Sleeps 4
                          Request to Book View Details
                          24 hrs Confirmation within 24 hours
                            • 3 BR
                            • 1 BA
                            • Sleeps 7
                            4
                              • 2 BR
                              • 1 BA
                              • 1 HF BA
                              • Sleeps 4
                                • 2 BR
                                • 1 BA
                                • 1 HF BA
                                • Sleeps 4
                                5
                                  • 2 BR
                                  • 2 BA
                                  • Sleeps 4
                                  5
                                    • 4 BR
                                    • 2 BA
                                    • Sleeps 7
                                      • 4 BR
                                      • 2 BA
                                      • Sleeps 7
                                      1 Review
                                        • 1 BR
                                        • 1 BA
                                        • Sleeps 2
                                        1 Review
                                          • 3 BR
                                          • 1 BA
                                          • Sleeps 6
                                          2 Reviews
                                            • 4 BR
                                            • 2 BA
                                            • Sleeps 8
                                            2 Reviews
                                              • 4 BR
                                              • 2 BA
                                              • Sleeps 8
                                              6
                                                • 4 BR
                                                • 1 BA
                                                • Sleeps 8
                                                1 Review
                                                  • 3 BR
                                                  • 2 BA
                                                  • Sleeps 8
                                                  Request to Book View Details
                                                  24 hrs Confirmation within 24 hours
                                                    • 3 BR
                                                    • 3 BA
                                                    • Sleeps 6
                                                    Request to Book View Details
                                                    24 hrs Confirmation within 24 hours
                                                      • 1 BR
                                                      • 1 BA
                                                      • Sleeps 2
                                                      Request to Book View Details
                                                      24 hrs Confirmation within 24 hours
                                                        • 3 BR
                                                        • 1 BA
                                                        • Sleeps 8
                                                        3
                                                        Request to Book View Details
                                                        24 hrs Confirmation within 24 hours
                                                          • 5 BR
                                                          • 3 BA
                                                          • Sleeps 15
                                                          2 Reviews
                                                          Request to Book View Details
                                                          24 hrs Confirmation within 24 hours
                                                            • 4 BR
                                                            • 3 BA
                                                            • 1 HF BA
                                                            • Sleeps 9
                                                            Request to Book View Details
                                                            24 hrs Confirmation within 24 hours
                                                              • 3 BR
                                                              • 2 BA
                                                              • 2 HF BA
                                                              • Sleeps 6
                                                              Request to Book View Details
                                                              24 hrs Confirmation within 24 hours
                                                              • 1 - 30 of 62
                                                               

                                                              Recent Westport Reviews

                                                              Whimsical and relaxing

                                                              5 of 5
                                                              My now husband and I rented this property for our wedding weekend. Ciara and Lucas let us bring stuff over the day before we had the place rented, which was a huge help and stress reliever. The house and yard are absolutely stunning. We had several friends come from out of town and it was so nice to be able to provide them with a place to stay and get to spend extra time with them. We had a small reception while at the house- we chose this house over others we saw in Westport because not only is the yard huge, with a nice deck, and fire pit, but the interior is open which made it great for entertaining-serving food off of the kitchen island, having drinks set up on the deck, and everyone gathering in the yard for music and games. This house definitely made our wedding weekend. ?
                                                              • Submitted: May 25, 2016
                                                              • Stayed: May 2016

                                                              Lovely week at Chaffee Cottage

                                                              5 of 5
                                                              We (my husband, self, and pup) spent a wonderful week here, enjoying the sunny and comfortable cottage and beautifully maintained lawn and patio. The cottage is well-situated, very quiet and spotless. A short drive to Elephant Rock beach, great farm stand goods at Orr's, and an easy drive to Goosewing Beach. We have vacationed in the area for many years, and Chaffee Cottage is a real highlight of our experience in this special part of New England. Highly recommended!
                                                              • Submitted: Sep 27, 2015
                                                              • Stayed: Sep 2015

                                                              Lovely house on the river

                                                              5 of 5
                                                              We had a marvelous stay at this property. Simple, quiet, well maintained property in the town of Westport. Well stocked kitchen, and a nice breeze and sunlight throughout the house. We enjoyed sitting out on the porch all times of day, biking around the area was a treat and we found a really nice beach not too far away. The town has some nice features, strawberry picking, a local vineyard, a brewery (right down the road) and some nice places to eat. Breakfast at Marguerite's was a highlight. We took a nice drive over to Newport, RI one day. Great place to kick back and relax!!
                                                              • Submitted: Aug 25, 2015
                                                              • Stayed: Jul 2015