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Iconic Mid-Century Home with Gorgeous Ocean Views, Private Pool & Decks
Iconic Mid-Century Home with Gorgeous Ocean Views, Private Pool & Decks
Chilmark
Iconic Mid-Century Home with Gorgeous Ocean Views, Private Pool & Decks
Beautiful dog-friendly home with water view, balcony & washer/dryer
Beautiful dog-friendly home with water view, balcony & washer/dryer
Chilmark
Beautiful dog-friendly home with water view, balcony & washer/dryer
Secluded mid-century home with wraparound deck, yard, grill, partial AC, & W/D
Secluded mid-century home with wraparound deck, yard, grill, partial AC, & W/D
Chilmark
Secluded mid-century home with wraparound deck, yard, grill, partial AC, & W/D
Private cottage nestled in center of island, access to Lambert's Cove beach
Private cottage nestled in center of island, access to Lambert's Cove beach
West Tisbury
Private cottage nestled in center of island, access to Lambert's Cove beach
Unique Up-Island Home
Unique Up-Island Home
West Tisbury
Unique Up-Island Home
Water-view home with large deck, balcony, enclosed sunroom & peaceful location
Water-view home with large deck, balcony, enclosed sunroom & peaceful location
Aquinnah
Water-view home with large deck, balcony, enclosed sunroom & peaceful location
Fernbank Hideaway | House in West Tisbury near up-island beaches
Fernbank Hideaway | House in West Tisbury near up-island beaches
West Tisbury
Fernbank Hideaway | House in West Tisbury near up-island beaches
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Beautiful view of the beach with palm trees

Black Friday: Members save 30%+

Members save 30%+ on selected hotels until December 4 with our Black Friday deals. Stay by December 15, 2025.