Downtown Captain's Mansion- The Dexter- Family, pet, and event friendly
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1 room, 2 adults, 0 children
All properties in Vineyard Haven
Downtown Captain's Mansion- The Dexter- Family, pet, and event friendly
Vineyard Haven, Massachusetts 02568, United States
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Amenities
Hiking
Wi-Fi in Public Areas
Kayaking
Sailing
Beach Towel
Fishing
Barbecue
No Smoking in Public Areas
All amenities
Property Description
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. 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 2026 Saturday-Saturday. One vehicle ferry reservation included with your booking.
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.About pets:Pets allowed: limit 2 total.Dog friendly residence. Yard is partially fenced..About checkOut:Check out before 10:00 AM.About children:Children allowed: ages 0-17.About checkIn:Check in after 4:00 PM.About smoking:Smoking is not permitted.About minBookingAge:Minimum age to rent: 25.About events:Events allowed: family gatherings, birthday parties, weddings.Maximum event attendees: 30.
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10.0/10
Cleanliness10.0
Amenities10.0
Location10.0
Service10.0
All 31 reviews
Surroundings
Airport: Martha's Vineyard Airport
(10.3 km)
Airport: Cape Cod Gateway Airport
(60.0 km)
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Overview
Rooms
Guest Reviews
Services & Amenities
Policies
Host
13
9 Bedrooms Private Vacation Home
9 bedrooms: 1 sofa bed 3 queen beds 3 king beds and 2 double beds
Free Wi-Fi
Non-smoking
Air conditioning
Bathtub
Refrigerator
TV
Check Availability
Guest Reviews
10.0/10
Outstanding
31 reviews
Verified Reviews- Cleanliness10.0
- Amenities10.0
- Location10.0
- Service10.0
Average for similar properties in Vineyard Haven
Molly H.
August 1, 2025
Mom’s 80th
Incredible location central to shopping, restaurants, the beach and more! Alex was very responsive to all our questions and the home was perfect for our large family gathering of 15. Many wonderful memories for my mother’s 80th birthday!
Ann V.
May 23, 2025
Great House!
The home was wonderful, such a treasure. Great for family and friends. Large kitchen provides ample room for entertaining, all the supplies you need. Hope to be able to go back.
Rebecca B.
May 28, 2025
House party to celebrate a 70th birthday
The Dexter House is a huge, well-maintained, well-decorated property. It was perfect for our event. At the most, we had 13 people staying in the house. It isn't easy to find a property with so many near-equal bedrooms for adults -- e.g., no bunk-beds. As many of us were between 65 and 75, we had a bit of a challenge matching bedrooms and bathrooms to guests. Note that all the bathrooms with walk-in showers are on the 3rd floor. Alexandra was very patient to answer all my questions about room and bathroom layout so I could figure out in advance whether the property would work for us.There was plenty of room for all our activities: we had a separate "music room" for our instruments and jams; a bright "puzzle room" on the second floor, where we worked a jigsaw puzzle during the week; and the main living/dining area where we did a play-reading with 13 characters, had a wine-tasting with a local sommelier, and had a sit-down birthday dinner for 15 served at the house by The Attic restaurant next door. Wonderful!The kitchen is very well-equipped. It met all our cooking needs. All our guests loved the property and found their beds and their rooms to be comfortable. The Dexter House is a very special property. Thanks for sharing it with us!
ROBYN M.
July 3, 2025
Beautiful House
The house was well stocked and had everything you could need.
Sharon M.
April 1, 2025
Perfect venue for my Mother’s Memorial.
My mom lived on Martha’s Vineyard for over forty years. This was the perfect place to hold a memorial-celebration of life for her. Off island guests could walk from the ferry, no cars needed. Family and friends who traveled from out of state were very comfortable staying here. The beds are luxurious. Bedrooms and bathrooms are nicely furnished and well lit. The kitchen is huge and had everything needed to cater this event ourselves. The large dining table, and kitchen island held an abundance of food. We used the TV for a slideshow. Everyone had room to mingle, or sit as there are plenty of chairs and sofas. I would definitely recommend this house for a family event, or a multi family vacation.
William R.
March 12, 2025
70th birthday gathering
A wonderful base for all my friends and family that traveled to MV for my big birthday party.
Verified traveler
December 9, 2024
Fabulous vacation destination
This house is the perfect destination for a group get together. It is an easy walk to the ferry so cars are not needed on the island. we had a great time and are looking forward to our next stay.
jane d.
November 25, 2024
November family reunion
This place was perfect for us! We had a family reunion of 14 young and old adults and everyone loved the place. The kitchen is fabulous, the bed was super comfortable and we could all gather together or spread out among the many comfy sitting rooms loaded with books. The location couldn’t be more convenient. Our only complaint was a few rainy days.
Julie A.
October 8, 2024
Everything was perfect
Everything was wonderful. The home was clean, beautiful spot. We enjoyed every minute
Services & Amenities
Most popular amenities
Hiking
Off-site
Wi-Fi in Public Areas
More Amenities
Internet
Wi-Fi in Public Areas
Health & wellness
Hiking
Off-site
Kayaking
Off-site
Sailing
Off-site
Activities
Beach Towel
Fishing
Off-site
Public areas
Barbecue
No Smoking in Public Areas
Garden
Facilities for children
Children's Desktop Game/ Jigsaw Puzzle
Children's Toys
Accessibility
Stair-Free Property Entrance
Property Policies
Check-in and Check-out Times
Check-in: after 16:00
Check-out: Before 10:00
Child policies
Children of all ages are welcome at this property.
Additional fees may be charged for children using existing beds. Add the number of children to get a more accurate price.
Cots and Extra Beds
Please contact the hotel for details about cot and extra bed policies.
Age Requirements
The main guest checking in must be at least 25 years old
Property host
Alexandra Wild
Speaks: English
About this property
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. 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 2026 Saturday-Saturday. One vehicle ferry reservation included with your booking.
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.About pets:Pets allowed: limit 2 total.Dog friendly residence. Yard is partially fenced..About checkOut:Check out before 10:00 AM.About children:Children allowed: ages 0-17.About checkIn:Check in after 4:00 PM.About smoking:Smoking is not permitted.About minBookingAge:Minimum age to rent: 25.About events:Events allowed: family gatherings, birthday parties, weddings.Maximum event attendees: 30.
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Frequently Asked Questions
What are the check-in and check-out times at Downtown Captain's Mansion- The Dexter- Family, pet, and event friendly?
Check-in at Downtown Captain's Mansion- The Dexter- Family, pet, and event friendly is from 16:00 and check-out is by 10:00.What are the check-in and check-out times at Downtown Captain's Mansion- The Dexter- Family, pet, and event friendly?
How much does it cost to stay at Downtown Captain's Mansion- The Dexter- Family, pet, and event friendly?
Prices at Downtown Captain's Mansion- The Dexter- Family, pet, and event friendly may change depending on dates, hotel policy, and other factors. Enter your travel dates to see the latest prices.How much does it cost to stay at Downtown Captain's Mansion- The Dexter- Family, pet, and event friendly?
Which airport is closest to Downtown Captain's Mansion- The Dexter- Family, pet, and event friendly?
The nearest airport is Martha's Vineyard Airport, just about 14 mins from hotel by car (10.3 km) away.Which airport is closest to Downtown Captain's Mansion- The Dexter- Family, pet, and event friendly?
What is the cancellation policy for Downtown Captain's Mansion- The Dexter- Family, pet, and event friendly?
The cancellation policy for Downtown Captain's Mansion- The Dexter- Family, pet, and event friendly depends on the room type and booking terms.What is the cancellation policy for Downtown Captain's Mansion- The Dexter- Family, pet, and event friendly?
About This Property
| Nearest Airport | Martha's Vineyard Airport |
|---|---|
| Distance to Airport | 10.31KM |
| Nearest Train Station | Hyannis Transportation Center |
| Distance to Train Station | 40.26KM |
| Hotel Star Rating | 4 |