House in Vineyard Haven, MA
18 guests · 9 bedrooms · 6 baths
Reasons to book
Guests love it hereGuests give this property a top rating
Great for petsBring all your friends and family, even the furry ones
Top-tier experienceA high end property in this area
About this house rental
The Dexter is the perfect place to stay on the Vineyard in ALL seasons. We have 9 bedrooms, 6.5 baths, an outdoor shower, private patio, 2 decks, grill, onsite parking, chef's kitchen, 6 living rooms, and w/d. Vehicle reservation included for guests who book July 5-11th 2026. AWESOME SPOT FOR YOUR CELEBRATIONS! 5min walk from the ferry boat and giant private parking lot. We welcome bachelorette parties, reunions, work retreats, etc, etc, etc.
Accepting books for summer 2027 Saturday-Saturday.
Sleeps 18 people.
The Dexter is a beautiful, historic whaling captain's house in downtown Vineyard Haven. The home was built in 1843 and has undergone creative design and renovations to modernize it into the stunning home it is now. We pair the old with the new and twist the traditional into modern. Each of our nine rooms features unique design and furnishings. Guests enjoy our numerous lounges and common areas, giant kitchen, wrap-around porch, patio, and yard. Several of our bedrooms have views of the harbor. We are located at 92 Main Street, in the heart of the action in Vineyard Haven. Walking distance from the restaurants, the harbor, the beach, and the best ice cream on Martha's Vineyard. We have 4-6 parking spaces in our lot (depending on what you drive).
Bedroom locations:
1st floor: 1 queen bedroom. 1 bedroom with pullout sofa and 1/2 bath. 1 full bathroom with clawfoot tub/shower.
2nd floor: 2 king bedrooms with Jack and Jill bathroom. 1 queen bedroom with an en-suite.
3rd floor: Captain's suite up the back staircase has 1 king bed, sitting room, giant bathroom, and 1 double bedroom attached (double bedroom is also accessible from front staircase). 1 queen bedroom with en-suite. 1 double bedroom with en-suite.
Accepting books for summer 2027 Saturday-Saturday.
Sleeps 18 people.
The Dexter is a beautiful, historic whaling captain's house in downtown Vineyard Haven. The home was built in 1843 and has undergone creative design and renovations to modernize it into the stunning home it is now. We pair the old with the new and twist the traditional into modern. Each of our nine rooms features unique design and furnishings. Guests enjoy our numerous lounges and common areas, giant kitchen, wrap-around porch, patio, and yard. Several of our bedrooms have views of the harbor. We are located at 92 Main Street, in the heart of the action in Vineyard Haven. Walking distance from the restaurants, the harbor, the beach, and the best ice cream on Martha's Vineyard. We have 4-6 parking spaces in our lot (depending on what you drive).
Bedroom locations:
1st floor: 1 queen bedroom. 1 bedroom with pullout sofa and 1/2 bath. 1 full bathroom with clawfoot tub/shower.
2nd floor: 2 king bedrooms with Jack and Jill bathroom. 1 queen bedroom with an en-suite.
3rd floor: Captain's suite up the back staircase has 1 king bed, sitting room, giant bathroom, and 1 double bedroom attached (double bedroom is also accessible from front staircase). 1 queen bedroom with en-suite. 1 double bedroom with en-suite.
Amenities at Downtown Captain's Mansion- The Dexter- Family, event, and pet friendly
Non-smoking
Pets allowed
Family friendly
Map of Vineyard Haven, MA
Ratings and reviews
10 / 10Outstanding·Jul 2026
Super great location for our family. Private gorgeous yard right in the middle of Vineyard Haven and walkable to everything. Host was incredibly responsive addressing questions quickly and thoroughly. A great experience for a three generation family of 14.
10 / 10Outstanding·Jul 2026
Amazing house and location! Really enjoyed our stay here with a large extended family. House is well equipped and walking distance to downtown, the beach, and the ferry.
10 / 10Outstanding·Jun 2026
A beautiful home in the heart of Vineyard Haven. Rooms are comfortable, house is clean, grounds are beautiful, and house is well stocked. I would definitely stay again.
10 / 10Outstanding·May 2026
Beautiful home, beautiful location! Pictures do not do it justice. This home has so much character. Worked excellent for a large family event. Fully equipped kitchen made large meals a breeze. Dog and kid friendly. Layout worked perfect for our group. Large table was perfect for games, separate sitting areas for those needing a little quiet time also worked great. Location to eateries, on site parking, and proximity to ferry and beaches a plus! Beds were so cozy it’s hard to head home! Would stay again!
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Top rated by guests
10Outstanding
(78 Ratings)
"Super great location for our family. Private gorgeous yard right in the middle of Vineyard Haven and walkable to everything. Host was incredibly responsive addressing questions quickly and thoroughly...."
Catherine B.Don't miss out! Price and availability may change
