Entire home
Downtown Captain's Mansion- The Dexter- Family, pet, and event friendly
Family-friendly vacation home in Vineyard Haven
Choose dates to view prices
Photo gallery for Downtown Captain's Mansion- The Dexter- Family, pet, and event friendly
Reviews
1010 out of 10
Exceptional
Entire home
9 bedrooms7 bathroomsSleeps 186800 sq ft
Popular amenities
- Dryer
- Breakfast available
- Washer
- Fireplace
- Barbecue grill
Explore the area
Tisbury, MA
- Martha's Vineyard Chamber of CommercePlace, Martha's Vineyard Chamber of Commerce5 min walk
- Vineyard Haven TerminalPlace, Vineyard Haven Terminal5 min walk
- Martha's Vineyard MuseumPlace, Martha's Vineyard Museum13 min walk
- Vineyard Haven, MA (MVY-Martha's Vineyard)Airport, Vineyard Haven, MA (MVY-Martha's Vineyard)14 min drive
Room options
About the neighborhood
Vineyard Haven
This vacation home places you within a 5-minute walk of Vineyard Haven Terminal and Martha's Vineyard Chamber of Commerce. The vacation home includes a kitchen, a fireplace, and a balcony.
What's nearby
- Martha's Vineyard Chamber of Commerce - 5 min walk - 0.3 miles
- Vineyard Haven Terminal - 5 min walk - 0.3 miles
- Martha's Vineyard Film Center - 8 min walk - 0.5 miles
- Martha's Vineyard Museum - 13 min walk - 0.7 miles
- Tisbury Town Beach - 14 min walk - 0.8 miles
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
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.
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.
The vacation home is air-conditioned and features a kitchen, 6.5 bathrooms, and a balcony, and there's space to spread out with 9 bedrooms. Guests can expect to find free WiFi and a Smart TV with a DVD player. Other standard amenities include a washing machine, a fireplace, and a sofa bed.
Similar properties
Oak Bluff's Victorian Walk to Town & Beaches
Oak Bluff's Victorian Walk to Town & Beaches
Oak Bluffs
- Kitchen
- Washer
- Dryer
- Free WiFi
10.0 out of 10, Exceptional, 7 reviews
10
Exceptional
7 reviews
Gorgeous Spacious Victorian Cape Cod Beach View Retreat
Gorgeous Spacious Victorian Cape Cod Beach View Retreat
Falmouth
- Kitchen
- Washer
- Dryer
- Free WiFi
10.0 out of 10, Exceptional, 16 reviews
10
Exceptional
16 reviews
6bedroom, 4bath, chefs kitchen, central air, ping pong, walking distance to town
6bedroom, 4bath, chefs kitchen, central air, ping pong, walking distance to town
Tisbury
- Kitchen
- Washer
- Dryer
- Air conditioning
10.0 out of 10, Exceptional, 3 reviews
10
Exceptional
3 reviews
Spacious home for entertaining, centrally located to beach, ferry, and airport.
Spacious home for entertaining, centrally located to beach, ferry, and airport.
Edgartown
- Pool
- Kitchen
- Washer
- Dryer
10.0 out of 10, Exceptional, 4 reviews
10
Exceptional
4 reviews
Sleeps 12, amazing view, tennis court, basketball court, beaches
Sleeps 12, amazing view, tennis court, basketball court, beaches
Edgartown
- Kitchen
- Washer
- Dryer
- Pet friendly
9.6 out of 10, Exceptional, 40 reviews
9.6
Exceptional
40 reviews
"The Carousel House" - Ocean Park - Featured in New York Times
"The Carousel House" - Ocean Park - Featured in New York Times
Oak Bluffs
- Ocean view
- Kitchen
- Washer
- Dryer
9.8 out of 10, Exceptional, 59 reviews
9.8
Exceptional
59 reviews
Luxury Loft Historic Center Oak Bluffs
Luxury Loft Historic Center Oak Bluffs
Oak Bluffs
- Kitchen
- Washer
- Dryer
- Air conditioning
9.6 out of 10, Exceptional, 44 reviews
9.6
Exceptional
44 reviews
9-bedroom vacation home near Cape Cod Beaches
9-bedroom vacation home near Cape Cod Beaches
Falmouth
- Kitchen
- Washer
- Dryer
- Pet friendly
9.6 out of 10, Exceptional, 20 reviews
9.6
Exceptional
20 reviews
Coastal chic meets French Provençal in this newly renovated oceanfront home.
Coastal chic meets French Provençal in this newly renovated oceanfront home.
East Falmouth
- Ocean view
- Kitchen
- Washer
- Dryer
10.0 out of 10, Exceptional, 88 reviews
10
Exceptional
88 reviews
$781 nightly
The price is $893
$893 total
Dec 8 - Dec 9
Total with taxes and fees
Fabulous Family Home steps to ocean
Fabulous Family Home steps to ocean
East Falmouth
- Ocean view
- Kitchen
- Washer
- Dryer
10.0 out of 10, Exceptional, 5 reviews
10
Exceptional
5 reviews
Property amenities
Beach
- Beach nearby
- Beach loungers
- Beach towels
Internet
- Available in the house: Free WiFi
Parking and transportation
- Car not required
- Wheelchair-accessible parking available
Kitchen
- Blender
- Coffee grinder
- Coffee/tea maker
- Cookware, dishware, and utensils
- Dishwasher
- Electric kettle
- Ice maker
- Kitchen island
- Lobster/crab pot
- Microwave
- Oven
- Paper towels
- Refrigerator
- Spices
- Stovetop
- 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.
- 1 accessible parking space
- Upper floors accessible by stairs only
- Wheelchair accessibility
- Wheelchair-accessible parking
- Smoking not allowed
Services and conveniences
- Iron/ironing board
- Phone
Location highlights
- In a village
- In the city center
- 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
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 available
Special check-in instructions
You will receive an email from the host with check-in and check-out instructions
Information provided by the property may be translated using automated translation tools
Check-out instructions
The host requires you 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 trash
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
- This property welcomes pets
- 2 total pets
- Service animals exempt from fees
- Note from host: Dog friendly residence. Yard is partially fenced.
Children and extra beds
Children allowed: ages 0-17
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 there is a carbon monoxide detector on the property
Host has indicated there is a smoke detector on the property
Safety features at this property include a fire extinguisher, a first aid kit, and a deadbolt lock
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
- Check-in: 4:00 PM
- Check-out: 10:00 AM
- Minimum check-in age: 25
Property Registration Number C0363072960
We should mention
Details about charges, deposits, or other important information:
- This property is managed by a private host, not a professional engaged in trade or business.
- Charges for extra guests may apply and vary depending on the property's policy.
- A cash deposit, credit card, or debit card for incidental charges, as well as a government-issued photo ID, may be required at check-in.
- Special requests are subject to availability at the time of check-in and can't be guaranteed. Certain requests may come with additional charges.
- Parties and events (including family gatherings, birthday parties and weddings) are allowed on site. Maximum attendees: 30.
- Onsite safety features include a carbon monoxide detector, a fire extinguisher, a smoke detector, a first aid kit, and a deadbolt lock.
Additional information about polices, regulations, and more:
- Long-term renters welcome.
- There are no elevators.
Property is also known as
Vrbo Property
Frequently asked questions
What's there to see close to this vacation home?
This vacation home is located in Vineyard Haven, just steps from Vineyard Haven Terminal and Martha's Vineyard Chamber of Commerce, and within a short walk of Martha's Vineyard Film Center. You'll also find Martha's Vineyard Museum and Tisbury Town Beach less than a mile away.
Will I be able to park at this vacation home?
Yes, there is accessible parking available.
Is this vacation home next to a casino?
No, this vacation home is not connected to a casino.
Is there an indoor pool at this vacation home?
No, there is no indoor pool at this vacation home.
Is Downtown Captain's Mansion- The Dexter- Family, pet, and event friendly good for couples?
Amenities that appeal to couples at this historic vacation home include a fireplace and a kitchen in each accommodation with some featuring ocean views.
Does Downtown Captain's Mansion- The Dexter- Family, pet, and event friendly have a hot tub?
No, this vacation home doesn't have a spa tub.
Does this vacation home provide breakfast?
This vacation home offers breakfast for a surcharge.
Will this vacation home allow pets to stay free of charge?
Although pets can't stay for free, they are welcome at this vacation home.
Does this vacation home have connecting rooms?
No, this vacation home doesn't feature connecting guestrooms.
What is the closest airport to this vacation home?
The closest major airport to this vacation home is Vineyard Haven, MA (MVY-Martha's Vineyard), which is 6.2 mi away (12 minutes by car). Another top airport is Hyannis, MA (HYA-Barnstable Municipal), which is around 21.9 mi away.
Can I book a room with a balcony at Downtown Captain's Mansion- The Dexter- Family, pet, and event friendly?
Yes, every accommodation at Downtown Captain's Mansion- The Dexter- Family, pet, and event friendly comes with a balcony with some featuring ocean views.