Book a Chilmark Rental for a Perfect Massachusetts Getaway

When you think of a Massachusetts vacation, Martha’s Vineyard probably comes to mind. Chilmark is on the western coast of the island and is often referred to as “up-island” by the locals. It is known for its stone walls, rolling meadows, and one of the best beaches on the island, Lucy Vincent Beach. Chilmark also has the highest property values in the state, which makes a Chilmark rental quite prestigious.

Chilmark Vacation Rentals in a Fishing Village


With Chilmark rentals, it is possible to take in the rustic charm of Menemsha, a small fishing village opening up to the Vineyard Sound. It was in this village that much of the film “Jaws” was shot. Local fishermen and visitors from Chilmark vacation rentals alike take advantage of the well-populated waters. Visitors to a Chilmark rental may charter a fishing boat or visit Dutcher’s Dock for a plethora of fresh fish markets.

Best Beach Offered to Chilmark Rentals


Lucy Vincent Beach is one of the best beaches available to those who stay in Chilmark rentals. It is a private beach, intended for island residents only, but if you have a Chilmark rental, this won’t be a problem as you can get the proper identification issued at the city hall. The popular beach may shock some people who stay in Chilmark vacation rentals as nudity is allowed, so just be advised when you arrive!

With a Chilmark Rental, There’s Plenty to Do


With a Chilmark rental, you don’t have to stay right in town. Martha’s Vineyard is small enough that you can visit each small town on a different day and still enjoy your time at your Chilmark rentals in the evening. There are plenty of antique shops and specialty stores to fill your days after beach bumming and eating! Chilmark vacation rentals allow for a true Massachusetts getaway and are perfect for three-day weekends or a week in the summer.

Increase your search options for Martha's Vineyard lodging in the following areas: vacation rentals in Chappaquiddick, lodging in Edgartown MA, Katama beach homes, Vineyard Haven home rental, or vacation accommodation West Tisbury MA.



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Chilmark: Houses, Cottages & More(228)

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Bright and Whimsical 4 Bedroom House Ocean View
    4 Bedrooms,
  • 2 Bathrooms
    • , Sleeps 10

Bright and Whimsical 4 Bedroom House Ocean View

  • 4 BR,
  • 2 BA,
  • Sleeps 10
  1. Martha's Vineyard >
  2. Chilmark House
#467844vb
    Spacious, Sunny, Private Chilmark Home
      4 Bedrooms,
    • 3 Bathrooms
      • , Sleeps 12
    $3,500 - $5,000
    per week

    Spacious, Sunny, Private Chilmark Home

    7 night Minimum Stay
    • 4 BR,
    • 3 BA,
    • Sleeps 12
    1. Martha's Vineyard >
    2. Chilmark House
    #136112
      (4)
      22 High Mark Road, Sweeping Ocean Views
        3 Bedrooms,
      • 2 Bathrooms
        • , Sleeps 6
      $450
      per night

      22 High Mark Road, Sweeping Ocean Views

      6 night Minimum Stay
      • 3 BR,
      • 2 BA,
      • Sleeps 6
      1. Martha's Vineyard >
      2. Chilmark House
      #975601
        Chilmark Home w/Roof Deck Water View; Sleeps 8+; Fits 2 Groups
          3 Bedrooms,
        • 3 Bathrooms
          • , Sleeps 8
        $330
        per night

        Chilmark Home w/Roof Deck Water View; Sleeps 8+; Fits 2 Groups

        3 - 7 night Minimum Stay
        • 3 BR,
        • 3 BA,
        • Sleeps 8
        1. Martha's Vineyard >
        2. Chilmark House
        #231734
          2 Reviews
          Landmark house. Exceptional hilltop and ocean views, 2 private beaches.
            5 Bedrooms,
          • 3 Bathrooms, 
          • 1 Half Bath
            • , Sleeps 10
          $2,500 - $7,500
          per week

          Landmark house. Exceptional hilltop and ocean views, 2 private beaches.

          7 night Minimum Stay
          • 5 BR,
          • 3 BA,
          • 1 HF BA,
          • Sleeps 10
          1. Martha's Vineyard >
          2. Chilmark House
          #293730
            1 Review
            Landmark-estate guesthouse. Pond & ocean views, 2 private beaches.
              3 Bedrooms,
            • 2 Bathrooms
              • , Sleeps 6
            $1,200 - $3,500
            per week

            Landmark-estate guesthouse. Pond & ocean views, 2 private beaches.

            7 night Minimum Stay
            • 3 BR,
            • 2 BA,
            • Sleeps 6
            1. Martha's Vineyard >
            2. Chilmark House
            #293733
              1 Review
              Menemsha Pond 4 bedroom private home with two master suites
                6 Bedrooms,
              • 3 Bathrooms, 
              • 1 Half Bath
                • , Sleeps 9
              $1,075 - $1,215
              per night

              Menemsha Pond 4 bedroom private home with two master suites

              14 night Minimum Stay
              • 6 BR,
              • 3 BA,
              • 1 HF BA,
              • Sleeps 9
              1. Martha's Vineyard >
              2. Chilmark House
              #3003027
                CHILMARK. Comfy 6BR, 2 BA, sleeps 12, deck, WiFi. July, Lbr Day open!
                  6 Bedrooms,
                • 2 Bathrooms
                  • , Sleeps 12
                $3,325 - $3,675
                per week

                CHILMARK. Comfy 6BR, 2 BA, sleeps 12, deck, WiFi. July, Lbr Day open!

                7 night Minimum Stay
                • 6 BR,
                • 2 BA,
                • Sleeps 12
                1. Martha's Vineyard >
                2. Chilmark House
                #362288
                  (4)
                  49 Post Oak Road
                    4 Bedrooms,
                  • 3 Bathrooms, 
                  • 1 Half Bath
                    • , Sleeps 8
                  $4,000 - $7,000
                  per week

                  49 Post Oak Road

                  7 night Minimum Stay
                  • 4 BR,
                  • 3 BA,
                  • 1 HF BA,
                  • Sleeps 8
                  1. Martha's Vineyard >
                  2. Chilmark House
                  #3024982
                    CHILMARK, PET FRIENDLY, Martha's Vineyard
                      2 Bedrooms,
                    • 1 Bathroom
                      • , Sleeps 5
                    $300
                    per night

                    CHILMARK, PET FRIENDLY, Martha's Vineyard

                    4 - 6 night Minimum Stay
                    • 2 BR,
                    • 1 BA,
                    • Sleeps 5
                    1. Martha's Vineyard >
                    2. Chilmark Cottage
                    #240371
                      BLACK POINT BEACH KEY! 5-acre privacy, in Quansoo, 2013 WiFi!
                        4 Bedrooms, Sleeps 8
                      $2,500 - $4,200
                      per week

                      BLACK POINT BEACH KEY! 5-acre privacy, in Quansoo, 2013 WiFi!

                      7 night Minimum Stay
                      • 4 BR,
                      • Sleeps 8
                      1. Martha's Vineyard >
                      2. Chilmark House
                      #120243
                        FERRY TIX! Waterview, A/C, wifi, totally private 3-acre setting w/ a large yard
                          4 Bedrooms,
                        • 2 Bathrooms
                          • , Sleeps 8
                        $2,500 - $3,900
                        per week

                        FERRY TIX! Waterview, A/C, wifi, totally private 3-acre setting w/ a large yard

                        7 night Minimum Stay
                        • 4 BR,
                        • 2 BA,
                        • Sleeps 8
                        1. Martha's Vineyard >
                        2. Chilmark House
                        #133117
                          Chilmark Cottage and Studio, 5 acre privacy, WiFi, Lucy Vincent access
                            3 Bedrooms,
                          • 1 Bathroom, 
                          • 1 Half Bath
                            • , Sleeps 6
                          $1,600 - $2,450
                          per week

                          Chilmark Cottage and Studio, 5 acre privacy, WiFi, Lucy Vincent access

                          7 night Minimum Stay
                          • 3 BR,
                          • 1 BA,
                          • 1 HF BA,
                          • Sleeps 6
                          1. Martha's Vineyard >
                          2. Chilmark Cottage
                          #120447
                            2 Reviews
                            AUGUST FERRY TIX! sweeping sunset waterviews, 4-5 BR, A/C, beach, tennis
                              4 Bedrooms,
                            • 2 Bathrooms, 
                            • 1 Half Bath
                              • , Sleeps 10
                            $2,000 - $4,000
                            per week

                            AUGUST FERRY TIX! sweeping sunset waterviews, 4-5 BR, A/C, beach, tennis

                            7 night Minimum Stay
                            • 4 BR,
                            • 2 BA,
                            • 1 HF BA,
                            • Sleeps 10
                            1. Martha's Vineyard >
                            2. Chilmark House
                            #291917
                              2 Reviews
                              Newly renovated spacious Chilmark contemporary with two ocean views
                                5 Bedrooms,
                              • 3 Bathrooms
                                • , Sleeps 10
                              $1,995 - $7,525
                              per week

                              Newly renovated spacious Chilmark contemporary with two ocean views

                              7 night Minimum Stay
                              • 5 BR,
                              • 3 BA,
                              • Sleeps 10
                              1. Martha's Vineyard >
                              2. Chilmark House
                              #244367
                                Chilmark Getaway! Avail July 6-13 wk $2000. Boat ticket available.
                                  3 Bedrooms,
                                • 2 Bathrooms
                                  • , Sleeps 6
                                $1,800 - $2,700
                                per week

                                Chilmark Getaway! Avail July 6-13 wk $2000. Boat ticket available.

                                7 night Minimum Stay
                                • 3 BR,
                                • 2 BA,
                                • Sleeps 6
                                1. Martha's Vineyard >
                                2. Chilmark House
                                #372010
                                  Charming Country Home in pristine area of Chilmark
                                    4 Bedrooms,
                                  • 2 Bathrooms, 
                                  • 1 Half Bath
                                    • , Sleeps 8

                                  Charming Country Home in pristine area of Chilmark

                                  • 4 BR,
                                  • 2 BA,
                                  • 1 HF BA,
                                  • Sleeps 8
                                  1. Martha's Vineyard >
                                  2. Chilmark House
                                  #116157
                                    3 Reviews
                                    Quintessential Chilmark Retreat With Water Views In Martha's Vineyard
                                      3 Bedrooms,
                                    • 2 Bathrooms
                                      • , Sleeps 7

                                    Quintessential Chilmark Retreat With Water Views In Martha's Vineyard

                                    • 3 BR,
                                    • 2 BA,
                                    • Sleeps 7
                                    1. Martha's Vineyard >
                                    2. Chilmark House
                                    #454191vb
                                      Spacious, High Ceilings, On Acre of Woods
                                        1 Bedrooms,
                                      • 1 Bathroom
                                        • , Sleeps 2
                                      $1,450 - $1,650
                                      per week

                                      Spacious, High Ceilings, On Acre of Woods

                                      7 night Minimum Stay
                                      • 1 BR,
                                      • 1 BA,
                                      • Sleeps 2
                                      1. Martha's Vineyard >
                                      2. Chilmark House
                                      #106058
                                        'SEABREEZE' Private beach on the Atlantic , tennis courts, kayaks
                                          1 Bedrooms, Sleeps 2
                                        $749 - $1,400
                                        per week

                                        'SEABREEZE' Private beach on the Atlantic , tennis courts, kayaks

                                        7 night Minimum Stay
                                        • 1 BR,
                                        • Sleeps 2
                                        1. Martha's Vineyard >
                                        2. Chilmark Studio
                                        #165500
                                          (8)
                                          French Country Style Farmhouse, New Hot Tub and close to beaches!
                                            3 Bedrooms,
                                          • 2 Bathrooms
                                            • , Sleeps 7
                                          $3,225 - $3,700
                                          per week

                                          French Country Style Farmhouse, New Hot Tub and close to beaches!

                                          4 - 7 night Minimum Stay
                                          • 3 BR,
                                          • 2 BA,
                                          • Sleeps 7
                                          1. Martha's Vineyard >
                                          2. Chilmark Farmhouse
                                          #994085
                                            1 Review
                                            Luminous rural retreat with spectacular ocean views.
                                              5 Bedrooms,
                                            • 3 Bathrooms
                                              • , Sleeps 9
                                            $3,500 - $5,000
                                            per week

                                            Luminous rural retreat with spectacular ocean views.

                                            7 night Minimum Stay
                                            • 5 BR,
                                            • 3 BA,
                                            • Sleeps 9
                                            1. Martha's Vineyard >
                                            2. Chilmark House
                                            #980094
                                              1 Review
                                              Waterfront Chilmark Home w/ fabulous view and private mooring
                                                4 Bedrooms,
                                              • 4 Bathrooms
                                                • , Sleeps 10
                                              $3,500 - $5,950
                                              per week

                                              Waterfront Chilmark Home w/ fabulous view and private mooring

                                              7 night Minimum Stay
                                              • 4 BR,
                                              • 4 BA,
                                              • Sleeps 10
                                              1. Martha's Vineyard >
                                              2. Chilmark House
                                              #137445
                                                3BR home on Menemsha Pond with beach & dock
                                                  3 Bedrooms,
                                                • 2 Bathrooms
                                                  • , Sleeps 8
                                                $2,450 - $5,005
                                                per week

                                                3BR home on Menemsha Pond with beach & dock

                                                7 night Minimum Stay
                                                • 3 BR,
                                                • 2 BA,
                                                • Sleeps 8
                                                1. Martha's Vineyard >
                                                2. Chilmark House
                                                #960269
                                                  Wide Angle Sunset Waterview with Pool
                                                    6 Bedrooms,
                                                  • 5 Bathrooms
                                                    • , Sleeps 11
                                                  $875 - $1,150
                                                  per night

                                                  Wide Angle Sunset Waterview with Pool

                                                  4 - 6 night Minimum Stay
                                                  • 6 BR,
                                                  • 5 BA,
                                                  • Sleeps 11
                                                  1. Martha's Vineyard >
                                                  2. Chilmark House
                                                  #115208
                                                    Luxury Home, Quansoo, Association Beach Rights, Central Air, 4500 sq. ...
                                                      5 Bedrooms,
                                                    • 3 Bathrooms, 
                                                    • 1 Half Bath
                                                      • , Sleeps 8
                                                    $7,200 - $9,200
                                                    per week

                                                    Luxury Home, Quansoo, Association Beach Rights, Central Air, 4500 sq. ...

                                                    7 night Minimum Stay
                                                    • 5 BR,
                                                    • 3 BA,
                                                    • 1 HF BA,
                                                    • Sleeps 8
                                                    1. Martha's Vineyard >
                                                    2. Chilmark House
                                                    #942172
                                                      Oceanfront, Waterview, Private Beach and Tennis
                                                        4 Bedrooms,
                                                      • 4 Bathrooms, 
                                                      • 1 Half Bath
                                                        • , Sleeps 8
                                                      $5,000 - $25,000
                                                      per week

                                                      Oceanfront, Waterview, Private Beach and Tennis

                                                      7 night Minimum Stay
                                                      • 4 BR,
                                                      • 4 BA,
                                                      • 1 HF BA,
                                                      • Sleeps 8
                                                      1. Martha's Vineyard >
                                                      2. Chilmark House
                                                      #942261
                                                        Squibnocket Farm Waterfront, Private Beach,
                                                          4 Bedrooms,
                                                        • 2 Bathrooms
                                                          • , Sleeps 9
                                                        $10,000 - $20,000
                                                        per week

                                                        Squibnocket Farm Waterfront, Private Beach,

                                                        7 night Minimum Stay
                                                        • 4 BR,
                                                        • 2 BA,
                                                        • Sleeps 9
                                                        1. Martha's Vineyard >
                                                        2. Chilmark House
                                                        #942263
                                                          Waterview, Association Beach
                                                            6 Bedrooms,
                                                          • 4 Bathrooms, 
                                                          • 1 Half Bath
                                                            • , Sleeps 10
                                                          $7,900 - $10,400
                                                          per week

                                                          Waterview, Association Beach

                                                          7 night Minimum Stay
                                                          • 6 BR,
                                                          • 4 BA,
                                                          • 1 HF BA,
                                                          • Sleeps 10
                                                          1. Martha's Vineyard >
                                                          2. Chilmark House
                                                          #942316
                                                            House in Chilmark, Martha's Vineyard
                                                              5 Bedrooms,
                                                            • 4 Bathrooms
                                                              • , Sleeps 12
                                                            $2,750 - $5,750
                                                            per week

                                                            House in Chilmark, Martha's Vineyard

                                                            7 night Minimum Stay
                                                            • 5 BR,
                                                            • 4 BA,
                                                            • Sleeps 12
                                                            1. Martha's Vineyard >
                                                            2. Chilmark House
                                                            #942193
                                                              • 1 - 30 of 228
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