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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
Private kitchen
Private kitchen
Private kitchen
Room

Reviews

10 out of 10, Loved by Guests
9 bedrooms6+ bathroomsSleeps 186800 sq ft

Popular amenities

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

Explore the area

View in a map
Tisbury, MA
  • Place, Martha's Vineyard Chamber of Commerce
    ‪5 min walk‬
  • Place, Vineyard Haven Terminal
    ‪5 min walk‬
  • Place, Martha's Vineyard Museum
    ‪13 min walk‬
  • Airport, Vineyard Haven, MA (MVY-Martha's Vineyard)
    ‪14 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, 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.

Add dates for prices

Amenities

Kitchen
Washing machine
Dryer
Pet-friendly
Free WiFi
Air conditioning

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House Rules

Check in after 4:00 PM
Minimum age to rent: 25
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

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
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

About the area

Vineyard Haven

Located in Vineyard Haven, this holiday home is in the city centre and near the beach. Felix Neck Wildlife Sanctuary and Long Point Wildlife Refuge reflect the area's natural beauty and area attractions include Island Cove Adventures and Flying Horses Carousel. Travelling with kids? Consider Oak Bluffs Fishing Pier and The Grey Barn and Farm. Make sure you get close to the area's animals with activities such as game walks and birdwatching.
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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
  • Tisbury Town Beach - 14 min walk - 1.2 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).

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

On-site parking is available at the property.

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.

Reviews

10

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
Learn moreOpens in a new window
Rating 10 - Excellent. 67 out of 67 reviews
Rating 8 - Good. 0 out of 67 reviews
Rating 6 - Okay. 0 out of 67 reviews
Rating 4 - Poor. 0 out of 67 reviews
Rating 2 - Terrible. 0 out of 67 reviews

10/10

Cleanliness

10/10

Check-in

10/10

Communication

10/10

Location

10/10

Listing accuracy

Reviews

10/10 Excellent

Susan S.

Liked: Cleanliness, check-in, communication, location, listing accuracy
This property is amazing for a large group! Location is incredible too!
Stayed 3 nights in Oct 2025

10/10 Excellent

Lesley Z.

Liked: Cleanliness, check-in, communication, location, listing accuracy
This could not have been a more perfect location, home and gathering space for our friend reunion.
Stayed 7 nights in Sep 2025

10/10 Excellent

Amanda C.

Liked: Cleanliness, check-in, communication, location, listing accuracy
This beautiful historic house was perfectly updated and incredibly spacious - our large group had plenty of room to spread out and feel right at home. Alex was very communicative and flexible, especially when a nor’easter threatened to cancel our ferries. The house had everything we needed and more, and the location couldn’t be better. Highly recommend!
Stayed 4 nights in Oct 2025

10/10 Excellent

ROBYN M.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Beautiful House

The house was well stocked and had everything you could need.
Stayed 2 nights in Jun 2025

10/10 Excellent

Molly H.

Liked: Cleanliness, check-in, communication, location, listing accuracy

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!
Stayed 7 nights in Jul 2025

10/10 Excellent

Ann V.

Liked: Cleanliness, check-in, communication, location, listing accuracy

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.
Stayed 2 nights in May 2025

10/10 Excellent

Christian V.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Excellent Stay!

Hospitable host, perfect location, spacious rooms , beautiful kitchen, all of which made for a wonderful weekend for us!
Stayed 2 nights in Mar 2024

10/10 Excellent

William R.

Liked: Cleanliness, check-in, communication, location, listing accuracy

70th birthday gathering

A wonderful base for all my friends and family that traveled to MV for my big birthday party.
Stayed 2 nights in Mar 2025

10/10 Excellent

Verified traveller

Liked: Cleanliness, check-in, communication, location, listing accuracy

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.
Stayed 3 nights in Dec 2024

10/10 Excellent

Jennifer J.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great experience overall!

The house, amenities, location, and host were all top notch! We had a wonderful experience booking and staying at this home!
Stayed 7 nights in Aug 2024

10/10 Excellent

Gwen G.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Excellent family vacation

The home was beautiful, convenient and comfortable. We throughly enjoyed our stay.
Stayed 4 nights in Nov 2023

10/10 Excellent

George D.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Wedding weekend

We all had the best time and LOVED the house and its location!
Stayed 2 nights in Nov 2024

10/10 Excellent

Peter S.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great place and unbelievable location

Absolutely giant house. Wonderful kitchen. Truly could not beat the location. Would definitely stay again!
Stayed 2 nights in Apr 2024

10/10 Excellent

Megan H.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Beautiful house

We were really happy to stay here - the house was beautiful and the location was very nice.
Stayed 2 nights in May 2022

10/10 Excellent

holly g.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Spotless and spacious historic house

Ideal location to walk through Vineyard Haven. Ample off-street parking. Great kitchen, great bathrooms. Clean and well equipped for large family gatherings. Would come again!
Stayed 3 nights in Sep 2024

10/10 Excellent

Eileen F.

Liked: Cleanliness, check-in, communication, location, listing accuracy

50th bday & anniversary celebration!

Amazing stay, beautiful and charming historical property, very clean and organized, and easy walk to everything including ferry, shopping, food, bus system. Can’t wait to come back to MV and would absolutely stay at this property again.
Stayed 3 nights in May 2024

10/10 Excellent

Julie A.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Everything was perfect

Everything was wonderful. The home was clean, beautiful spot. We enjoyed every minute
Stayed 2 nights in Oct 2024

10/10 Excellent

Janine B.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Amazing Stay

We had an amazing time at the Dexter. W writhing was perfect and Alex was a very accommodating host! She answered all of our questions and was very responsive We hosted an intimate wedding and it was magical. I couldn’t recommend this property more!
Stayed 3 nights in Sep 2024

10/10 Excellent

Verified traveller

Liked: Cleanliness, check-in, communication, location, listing accuracy

Wonderful experience

This is such a great house for larger groups.
Stayed 3 nights in Dec 2023

10/10 Excellent

Verified traveller

Liked: Cleanliness, check-in, communication, location, listing accuracy

wonderful gathering spot

This house was perfect for a relaxing weekend with friends. I would give it 6 stars if VRBO would let me.
Stayed 2 nights in Dec 2022

10/10 Excellent

jane d.

Liked: Cleanliness, check-in, communication, location, listing accuracy

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.
Stayed 4 nights in Nov 2024

10/10 Excellent

Jack A.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Beautiful property

Beautifully restored home perfect for groups. Immediately outside of Vineyard Haven village. Walkable to ferry, dining, shopping
Stayed 4 nights in May 2023

10/10 Excellent

Nikki J.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Amazing Home in MV

We had an amazing stay! The house is just as described and the host is responsive and helpful. The location was perfect and we had more than enough space to spread out. The kitchen, FABULOUS!!
Stayed 7 nights in Aug 2023

10/10 Excellent

Dorothy F.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Celebrating Family & Birthday

The property was as advertised, beautifully appointed with several seating spaces for groups or individuals to gather and commune.
Stayed 5 nights in Jun 2023

10/10 Excellent

Amy S.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Excellent stay. Everything as promised.

Alex and her family were wonderful. Her home is beautiful and well located. We were thrilled to have a large group join us for a summer celebration. They were kind, responsive and anticipated all of our needs. We would definitely stay here again!
Stayed 7 nights in Aug 2021

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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