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Entire home

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

Family-friendly holiday home in Vineyard Haven

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

Exterior
Fridge, microwave, oven, stovetop
9 bedrooms, desk, iron/ironing board, free WiFi
Outdoor dining
Fridge, microwave, oven, stovetop
In the heart of Vineyard Haven, The Dexter is a historic whaling captain's house offering 9 bedrooms, 6.5 baths and numerous lounges. Take advantage of an outdoor shower, private patio with grill and wrap-around porch overlooking the harbor.

Reviews

10 out of 10
Exceptional

Entire home

9 bedrooms7 bathroomsSleeps 18632 sq m

Popular amenities

  • Dryer
  • Breakfast available
  • Washer
  • Pet-friendly
  • Fireplace

Add dates for prices

About this property

Entire place

You'll have the entire home to yourself and will only share it with other guests in your party.

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

Property amenities

Beach

  • Beach nearby
  • Beach loungers
  • Beach towels

Internet

  • Available in the house: Free WiFi

Parking and transport

  • Car not required
  • Wheelchair-accessible parking available

Kitchen

  • Blender
  • Coffee grinder
  • Coffee/tea maker
  • Cookware, dishware, and utensils
  • Dishwasher
  • Electric kettle
  • Hob
  • Ice maker
  • Kitchen island
  • Lobster/crab pot
  • Microwave
  • Oven
  • Paper towels
  • Refrigerator
  • Spices
  • Toaster

Dining

  • Breakfast available for a fee
  • Dining table

Bedrooms

  • 9 bedrooms
  • Bedsheets provided
  • Sofa bed

Bathroom

  • 6.5 bathrooms
  • Bathtub
  • Hair dryer
  • Shower
  • Soap
  • Toilet paper
  • Towels provided

Living spaces

  • Dining table
  • Fireplace
  • Living room

Entertainment

  • Books
  • DVD player
  • Games
  • Smart TV with cable/satellite channels
  • Stereo

Outdoor areas

  • Balcony
  • Barbecue grill
  • Fenced yard
  • Firepit
  • Garden
  • Outdoor furniture

Laundry

  • Laundry facilities
  • Washing machine

Work spaces

  • Desk
  • Desk chair

Comfort

  • Air conditioning
  • Heating

Pets

  • Pet friendly
  • 2 pets total

Suitability/Accessibility

  • If you have requests for specific accessibility needs, please contact the property using the information on the reservation confirmation received after booking.
  • Accessible parking space
  • In-room accessibility
  • Upper floors accessible by stairs only
  • Wheelchair-accessible parking
  • Smoke-free property

Services and conveniences

  • Iron/ironing board
  • Phone

Location highlights

  • In a village
  • In the city centre
  • Near a health/beauty spa
  • Near a hospital
  • Near the bay
  • Near the marina
  • Near the sea

Things to do

  • Bicycles
  • Birdwatching nearby
  • Fishing nearby
  • Hiking/biking trails nearby
  • Kayaking nearby
  • Motor boating nearby
  • Sailing nearby
  • Swimming nearby
  • Wildlife walks nearby
  • Windsurfing nearby

Safety features

  • Carbon monoxide detector (host has indicated there is a carbon monoxide detector on the property)
  • Smoke detector (host has indicated there is a smoke detector on the property)
  • First aid kit
  • Fire extinguisher
  • Deadbolt lock

General

  • Bicycles
  • Garden
  • Unit size: 6,800 square feet

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Policies

Check-in

Check-in time starts at 4:00 PM
Minimum check-in age - 25

Check-out

Check-out before 10:00 AM
Contactless check-out

Special check-in instructions

You will receive an email from the host with check-in and check-out instructions

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.

Pets

Pets are allowed
Service animals are welcome, and are exempt from fees
2 total pets
Note from host: Dog friendly residence. Yard is partially fenced.

Children and extra beds

Children are welcome

Events

Events allowed: family gatherings, birthday parties, weddings

Smoking

Smoking is not permitted

Important information

You need to know

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 is managed through our partner, Vrbo. You will receive an email from Vrbo with a link to a Vrbo account, where you can change or cancel your reservation
Property Registration Number C0363072960

We should mention

This property does not have any lifts
A car is not required for transport to and from this property

Property is also known as

Vrbo Property

About the area

Map
Tisbury, MA

What's nearby

  • Martha's Vineyard Chamber of Commerce - 5 min walk - 0.4 km
  • Vineyard Haven Terminal - 5 min walk - 0.5 km
  • Martha's Vineyard Film Center - 8 min walk - 0.7 km
  • Martha's Vineyard Museum - 13 min walk - 1.1 km
  • Inkwell Beach - 6 min drive - 6.4 km

Getting around

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

Restaurants

  • ‪The Black Dog Tavern - ‬6 min walk
  • ‪Catboat Coffee Co. - ‬9 min walk
  • ‪Portuguese-American Club - ‬5 min drive
  • ‪Porto Pizza - ‬3 min walk
  • ‪VFW Hall - ‬5 min drive

Frequently asked questions

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

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

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

Check-in begins at 4:00 PM.

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

Checkout is at 10:00 AM.

Where is Downtown Captain's Mansion- The Dexter- Family, pet, and event 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.

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