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Downtown Captain's Mansion- The Dexter- Family, event, and pet friendly

Photo gallery for Downtown Captain's Mansion- The Dexter- Family, event, and pet friendly

A patio area with outdoor furniture, string lights, and a covered grill.
Property video
A bedroom with a large bed, a nightstand, a chair, and a dresser.
A stone pathway flanked by lush hydrangea bushes and various garden plants.
A two-story white house with a front porch, a stone wall, and a blue truck parked in front.

Reviews

10 out of 10, Loved by Guests
Top 1% of guest reviews in this area

Highlights

  • Family fun awaits
    Top-rated for families.
  • Firepit available
    One of the few properties with a dedicated outdoor firepit.
  • Centrally-located
    You're never far from where you need to be with this convenient location.
  • Discover nearby landmarks
    Walk to Martha's Vineyard Museum
9 bedrooms6+ bathroomsSleeps 18

Popular amenities

  • Onsite parking available
  • Pet-friendly
  • Kitchen
  • Washing machine
  • Air-conditioning
  • Barbecue grill

Explore the area

View in a map
Tisbury, MA
  • Place, Martha's Vineyard Chamber of Commerce
    ‪5 min walk‬
  • Place, Martha's Vineyard Film Center
    ‪9 min walk‬
  • Place, Martha's Vineyard Museum
    ‪13 min walk‬
  • Airport, Vineyard Haven, MA (MVY-Martha's Vineyard)
    ‪18 min drive‬

Rooms & beds

9 bedrooms (sleeps 18)

1st floor bedroom

1 Queen Bed

Captain's Quarters

1 King Bed

Connected to Captain's- Chart Room

1 Double Bed

Crow's Nest

1 Double Bed

Front living Room

1 Queen Sofa Bed

Leeward

1 King Bed

Midship

1 King Bed

Pilot House

1 Queen Bed

Windward

1 Queen Bed

6 bathrooms, 1 half bathroom

Bathroom 1

Toilet · Shower only

Bathroom 2

Toilet · Shower only

Bathroom 3

Toilet

Bathroom 4

Bathtub · Toilet · Shower only

Bathroom 5

Bathtub · Toilet · Shower only

Bathroom 6

Bathtub · Toilet · Shower only

Bathroom 7

Bathtub · Toilet · Shower only

Spaces

Deck or patio
Porch or lanai
Kitchen
Balcony
Outdoor play area
Garden
Dining area

About this property

Downtown Captain's Mansion- The Dexter- Family, event, and pet friendly

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.

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House Rules

Check in after 4:00 PM
Check out before 10:00 AM
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Children

Children allowed: ages 0–17
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Events

Events allowed: family gatherings, birthday parties, weddings
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Pets

Pets allowed: limit 2 total
Dog friendly residence. Yard is partially fenced.
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Smoking

Smoking is not permitted

Check-out instructions

The host requires you to complete the following before checking out:
Load and start the dishwasher
Gather used towels
Remove personal items, remove leftover food and drinks and take out the rubbish
Turn off the lights, lock the doors and return the keys
Failure to complete these may result in a negative review from the host.

Important information

You need to know

Property Registration Number C0363072960
Property # 1940203vb
Extra-person charges may apply and vary depending on property policy
Government-issued photo identification and a credit card, debit card or cash deposit may be required at check-in for incidental charges
Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
Parties and events (including family gatherings, birthday parties and weddings) are allowed on site. Maximum attendees: 30
Long-term renters welcome
Host has indicated that there is a carbon monoxide detector on the property
Host has indicated that there is a smoke detector on the property
Safety features at this property include a fire extinguisher, a first aid kit and a deadlock
This property has outdoor spaces, such as balconies, patios and terraces, which may not be suitable for children; if you have any concerns, we recommend contacting the property prior to your arrival to confirm that they can accommodate you in a suitable room

About the area

Vineyard Haven

Located in Vineyard Haven, this holiday home is in the city centre and near the beach. While the natural beauty of Inkwell Beach and Cape Cod Beaches can be enjoyed by anyone, those looking for an activity can explore Woods Hole Ferry Terminal. Consider Cape Cod Fairgrounds for a night out or Island Cove Miniature Golf if you're travelling with kids. Kayaking, windsurfing and power boating offer great chances to get out on the surrounding water, or you can seek out an adventure with hiking nearby.
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Map
Tisbury, MA

What's nearby

  • Martha's Vineyard Chamber of Commerce - 5 min walk - 0.4 km
  • Vineyard Haven Public Library - 6 min walk - 0.6 km
  • Martha's Vineyard Film Center - 9 min walk - 0.8 km
  • Martha's Vineyard Museum - 13 min walk - 1.1 km
  • Tisbury Town Beach - 17 min walk - 1.5 km

Getting around

  • Vineyard Haven, MA (MVY-Martha's Vineyard) - 12 min drive

Restaurants

  • ‪The Black Dog - Bakery Cafe - ‬3 min drive
  • ‪Nancy's - ‬6 min drive
  • ‪Rocco's Pizzeria - ‬9 min walk
  • ‪Cumberland Farms - ‬5 min walk
  • ‪Mo's Lunch - ‬6 min drive

Frequently asked questions

Is Downtown Captain's Mansion- The Dexter- Family, event, and pet friendly pet-friendly?

Yes, this property allows pets (limit 2 total).

How much does it cost to stay at Downtown Captain's Mansion- The Dexter- Family, event, and pet friendly?

As of 28 Aug, 2026, prices found for a 1-night stay for 2 adults at Downtown Captain's Mansion- The Dexter- Family, event, and pet friendly on 6 Jan, 2027 start from S$3,891, including taxes and fees. This price is based on the lowest nightly price found in the last 24 hours for stays in the next 30 days. Prices are subject to change. Choose your dates for more accurate prices.

How much is parking at Downtown Captain's Mansion- The Dexter- Family, event, and pet friendly?

On-site parking is available at the property.

What time is check-in at Downtown Captain's Mansion- The Dexter- Family, event, and pet friendly?

Check-in begins at 4:00 PM.

What time is check-out at Downtown Captain's Mansion- The Dexter- Family, event, and pet friendly?

Checkout is at 10:00 AM.

Where is Downtown Captain's Mansion- The Dexter- Family, event, and pet friendly located?

This family-friendly Vineyard Haven holiday home is located by the sea, within a 5-minute walk of Vineyard Haven Terminal and Martha's Vineyard Chamber of Commerce. Martha's Vineyard Film Center and Vineyard Haven Public Library are also within 10 minutes.

About the host

Hosted by Alexandra Wild

Host profile image
I grew up on MV, married an islander, and we are raising our family with lots of lucky island time.

Why they chose this property

Our home is on Main Street so it is in the thick of all the Vineyard Haven action. You can sit on our porch to people watch or withdraw to our private patio where you'll feel a world away.

What makes this property unique

Right in town and managed by our family.

Languages:

English

Premier Host

They consistently provide great experiences for their guests
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