Chilmark Rentals


Our Chilmark rentals are located in the small, rural community toward the western end of Martha's Vineyard. Most of it's 34 square miles are devoted to residential and agricultural use – you can get fresh flowers from a self-serve stand at Beetlebung Corner, Island-raised lamb and wool items knit from their own sheep at the Allen Farm, eggs from really free range chickens and bacon from local pigs. Enjoy the beautiful rolling land with rambling stone walls as you drive through many parts of Chilmark. Middle road is one of the most beautiful drives on the island.

One of the real perks to choosing from our Chilmark rentals is the access to the two town beaches, Lucy Vincent and Squibnocket, along the South Shore (surf side). This area of the island brings you back in time to enjoy the slow days of summer. Some things you will not want to miss are the many hiking trails with Menemsha Hills being one of the highlights. Chilmark Chocolates is an all time favorite stop for anyone visiting and islanders alike. Chilmark is also fortunate to have the local Film Festival host weekly film festivals each Wednesday evening starting with Cinema Circus for the children and followed by adult films. And, of course, you will not want to miss out on the fabulous sunsets in Menemsha, a traditional fishing village. Menemsha Beach tends to have a full attendance each evening with a wonderful applause for the show as the sun dips down into the horizon.

Not far from our Chilmark vacation rentals is The Chilmark Community Center, which offers a terrific children’s summer program that runs in the mornings from 9-12 each week day along with a great tennis program for the whole family. You can sign up for the season or on a weekly basis. The center also offers many family and adult activities throughout the season. Contact us if you'd like more information about one of the Chilmark rentals below.


Leave this field empty

Map All Results

Available Unavailable Check In Check Out
  • Property Highlights
    Area: Chilmark
    Turnover Day: Saturday
    Pets Allowed: Yes, with approval
    • 3Bedrooms:
    • 1.5Baths:
    • 5Sleeps:
  • Description:
    BR1 King, 2nd floorBR2 (2)Twin beds, 2nd floorBR3 Daybed w/trundle in study, 2nd floorHall bath tub/shower, 2nd floorHal...Read More
October 2020
SuMoTuWeThFrSa
1 2 3
4 5 6 7 8 9 10
11 12 13 14 15 16 17
18 19 20 21 22 23 24
25 26 27 28 29 30 31
November 2020
SuMoTuWeThFrSa
1 2 3 4 5 6 7
8 9 10 11 12 13 14
15 16 17 18 19 20 21
22 23 24 25 26 27 28
29 30
December 2020
SuMoTuWeThFrSa
1 2 3 4 5
6 7 8 9 10 11 12
13 14 15 16 17 18 19
20 21 22 23 24 25 26
27 28 29 30 31
January 2021
SuMoTuWeThFrSa
1 2
3 4 5 6 7 8 9
10 11 12 13 14 15 16
17 18 19 20 21 22 23
24 25 26 27 28 29 30
31
  • Property Highlights
    Area: Chilmark
    Turnover Day: Sunday
    Pets Allowed: No
    • 4Bedrooms:
    • 2.0Baths:
    • 8Sleeps:
  • Description:
    BR1 Queen, 1st floorHall bath tub/shower, 1st floorBR2 Queen, 2nd floorBR3 (2)Twin beds, 2nd floorBR4 Double, 2nd floorH...Read More
October 2020
SuMoTuWeThFrSa
1 2 3
4 5 6 7 8 9 10
11 12 13 14 15 16 17
18 19 20 21 22 23 24
25 26 27 28 29 30 31
November 2020
SuMoTuWeThFrSa
1 2 3 4 5 6 7
8 9 10 11 12 13 14
15 16 17 18 19 20 21
22 23 24 25 26 27 28
29 30
December 2020
SuMoTuWeThFrSa
1 2 3 4 5
6 7 8 9 10 11 12
13 14 15 16 17 18 19
20 21 22 23 24 25 26
27 28 29 30 31
January 2021
SuMoTuWeThFrSa
1 2
3 4 5 6 7 8 9
10 11 12 13 14 15 16
17 18 19 20 21 22 23
24 25 26 27 28 29 30
31
  • Property Highlights
    Area: Chilmark
    Turnover Day: N/A
    Pets Allowed: No
    • 4Bedrooms:
    • 4.0Baths:
    • 8Sleeps:
  • Description:
    Main house:R1 King en suite half bath, 1st floorBR2 (2) Twin beds, 1st floorHall bath tub/shower, 1st floorBR3 Twin bed ...Read More
October 2020
SuMoTuWeThFrSa
1 2 3
4 5 6 7 8 9 10
11 12 13 14 15 16 17
18 19 20 21 22 23 24
25 26 27 28 29 30 31
November 2020
SuMoTuWeThFrSa
1 2 3 4 5 6 7
8 9 10 11 12 13 14
15 16 17 18 19 20 21
22 23 24 25 26 27 28
29 30
December 2020
SuMoTuWeThFrSa
1 2 3 4 5
6 7 8 9 10 11 12
13 14 15 16 17 18 19
20 21 22 23 24 25 26
27 28 29 30 31
January 2021
SuMoTuWeThFrSa
1 2
3 4 5 6 7 8 9
10 11 12 13 14 15 16
17 18 19 20 21 22 23
24 25 26 27 28 29 30
31
  • Property Highlights
    Area: Chilmark
    Turnover Day: Saturday
    Pets Allowed: Yes, with approval
    • 4Bedrooms:
    • 3.5Baths:
    • 10Sleeps:
  • Description:
    BR1 Queen, master en suite tub and shower first floor, BR2 King master en suite of separate shower and soaking tub, 2nd ...Read More
October 2020
SuMoTuWeThFrSa
1 2 3
4 5 6 7 8 9 10
11 12 13 14 15 16 17
18 19 20 21 22 23 24
25 26 27 28 29 30 31
November 2020
SuMoTuWeThFrSa
1 2 3 4 5 6 7
8 9 10 11 12 13 14
15 16 17 18 19 20 21
22 23 24 25 26 27 28
29 30
December 2020
SuMoTuWeThFrSa
1 2 3 4 5
6 7 8 9 10 11 12
13 14 15 16 17 18 19
20 21 22 23 24 25 26
27 28 29 30 31
January 2021
SuMoTuWeThFrSa
1 2
3 4 5 6 7 8 9
10 11 12 13 14 15 16
17 18 19 20 21 22 23
24 25 26 27 28 29 30
31
  • Property Highlights
    Area: Chilmark
    Turnover Day: Saturday
    Pets Allowed: No
    • 4Bedrooms:
    • 1.5Baths:
    • 8Sleeps:
  • Description:
    BR1 King, 2nd floorBR2 King, 2nd floorBR3 (2)Twin beds, 2nd floorBR4 Double, 2nd floorHalf bath, 2nd floorHall bath show...Read More
October 2020
SuMoTuWeThFrSa
1 2 3
4 5 6 7 8 9 10
11 12 13 14 15 16 17
18 19 20 21 22 23 24
25 26 27 28 29 30 31
November 2020
SuMoTuWeThFrSa
1 2 3 4 5 6 7
8 9 10 11 12 13 14
15 16 17 18 19 20 21
22 23 24 25 26 27 28
29 30
December 2020
SuMoTuWeThFrSa
1 2 3 4 5
6 7 8 9 10 11 12
13 14 15 16 17 18 19
20 21 22 23 24 25 26
27 28 29 30 31
January 2021
SuMoTuWeThFrSa
1 2
3 4 5 6 7 8 9
10 11 12 13 14 15 16
17 18 19 20 21 22 23
24 25 26 27 28 29 30
31
  • Property Highlights
    Area: Chilmark
    Turnover Day: N/A
    Pets Allowed: Yes, with approval
    • 4Bedrooms:
    • 2.5Baths:
    • 10Sleeps:
  • Description:
    BR1 King and (Queen in loft) en suite claw foot tub w/shower, 1st floorBR2 Double, 1st floorHalf bath, 1st floorBR3 Quee...Read More
October 2020
SuMoTuWeThFrSa
1 2 3
4 5 6 7 8 9 10
11 12 13 14 15 16 17
18 19 20 21 22 23 24
25 26 27 28 29 30 31
November 2020
SuMoTuWeThFrSa
1 2 3 4 5 6 7
8 9 10 11 12 13 14
15 16 17 18 19 20 21
22 23 24 25 26 27 28
29 30
December 2020
SuMoTuWeThFrSa
1 2 3 4 5
6 7 8 9 10 11 12
13 14 15 16 17 18 19
20 21 22 23 24 25 26
27 28 29 30 31
January 2021
SuMoTuWeThFrSa
1 2
3 4 5 6 7 8 9
10 11 12 13 14 15 16
17 18 19 20 21 22 23
24 25 26 27 28 29 30
31
  • Property Highlights
    Area: Chilmark
    Turnover Day: N/A
    Pets Allowed: Yes, with approval
    • 5Bedrooms:
    • 5.0Baths:
    • 10Sleeps:
  • Description:
    BR1 King en suite separate tub and shower, 1st floorBR2 King en suite with shower, 1st floorBR3 Double en suite tub/show...Read More
October 2020
SuMoTuWeThFrSa
1 2 3
4 5 6 7 8 9 10
11 12 13 14 15 16 17
18 19 20 21 22 23 24
25 26 27 28 29 30 31
November 2020
SuMoTuWeThFrSa
1 2 3 4 5 6 7
8 9 10 11 12 13 14
15 16 17 18 19 20 21
22 23 24 25 26 27 28
29 30
December 2020
SuMoTuWeThFrSa
1 2 3 4 5
6 7 8 9 10 11 12
13 14 15 16 17 18 19
20 21 22 23 24 25 26
27 28 29 30 31
January 2021
SuMoTuWeThFrSa
1 2
3 4 5 6 7 8 9
10 11 12 13 14 15 16
17 18 19 20 21 22 23
24 25 26 27 28 29 30
31
  • Property Highlights
    Area: Chilmark
    Turnover Day: N/A
    Pets Allowed: No
    • 5Bedrooms:
    • 2.5Baths:
    • 10Sleeps:
  • Description:
    BR1 Queen, 1st floorBR2 (2)Twin beds, 1st floorBR3 (2)Twin beds, 1st floorBR4 (2)Twin beds, 1st floorHall bath with tub/...Read More
October 2020
SuMoTuWeThFrSa
1 2 3
4 5 6 7 8 9 10
11 12 13 14 15 16 17
18 19 20 21 22 23 24
25 26 27 28 29 30 31
November 2020
SuMoTuWeThFrSa
1 2 3 4 5 6 7
8 9 10 11 12 13 14
15 16 17 18 19 20 21
22 23 24 25 26 27 28
29 30
December 2020
SuMoTuWeThFrSa
1 2 3 4 5
6 7 8 9 10 11 12
13 14 15 16 17 18 19
20 21 22 23 24 25 26
27 28 29 30 31
January 2021
SuMoTuWeThFrSa
1 2
3 4 5 6 7 8 9
10 11 12 13 14 15 16
17 18 19 20 21 22 23
24 25 26 27 28 29 30
31
  • Property Highlights
    Area: Chilmark
    Turnover Day: N/A
    Pets Allowed: No
    • 8Bedrooms:
    • 4.0Baths:
    • 18Sleeps:
  • Description:
    Main house:BR1 King en suite separate tub and shower, 2nd floorBR2 Queen en suite tub/shower, 1st floorBR3 Queen and Twi...Read More
October 2020
SuMoTuWeThFrSa
1 2 3
4 5 6 7 8 9 10
11 12 13 14 15 16 17
18 19 20 21 22 23 24
25 26 27 28 29 30 31
November 2020
SuMoTuWeThFrSa
1 2 3 4 5 6 7
8 9 10 11 12 13 14
15 16 17 18 19 20 21
22 23 24 25 26 27 28
29 30
December 2020
SuMoTuWeThFrSa
1 2 3 4 5
6 7 8 9 10 11 12
13 14 15 16 17 18 19
20 21 22 23 24 25 26
27 28 29 30 31
January 2021
SuMoTuWeThFrSa
1 2
3 4 5 6 7 8 9
10 11 12 13 14 15 16
17 18 19 20 21 22 23
24 25 26 27 28 29 30
31
  • Property Highlights
    Area: Chilmark
    Turnover Day: Saturday
    Pets Allowed: Yes, with approval
    • 1Bedrooms:
    • 1.0Baths:
    • 2Sleeps:
  • Description:
    BR1 Queen sofabed in living area, 1st floorHall bath with shower stall, 1st floor...Read More
October 2020
SuMoTuWeThFrSa
1 2 3
4 5 6 7 8 9 10
11 12 13 14 15 16 17
18 19 20 21 22 23 24
25 26 27 28 29 30 31
November 2020
SuMoTuWeThFrSa
1 2 3 4 5 6 7
8 9 10 11 12 13 14
15 16 17 18 19 20 21
22 23 24 25 26 27 28
29 30
December 2020
SuMoTuWeThFrSa
1 2 3 4 5
6 7 8 9 10 11 12
13 14 15 16 17 18 19
20 21 22 23 24 25 26
27 28 29 30 31
January 2021
SuMoTuWeThFrSa
1 2
3 4 5 6 7 8 9
10 11 12 13 14 15 16
17 18 19 20 21 22 23
24 25 26 27 28 29 30
31

This website uses cookies to ensure you get the best experience on our website. Learn More

Ok