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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
Exceptional
9 bedrooms6+ bathroomsSleeps 18631.7 sq m

Popular amenities

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

Explore the area

View 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)
    ‪13 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. 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. Travelling with kids? Consider Island Cove Adventures and Flying Horses Carousel. 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
  • 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
  • ‪The Attic At Waterside - ‬1 min walk
  • ‪Porto Pizza - ‬3 min walk

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.

Reviews

10

Exceptional

10/10

Cleanliness

10/10

Check-in

10/10

Communication

10/10

Location

10/10

Listing accuracy
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

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

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

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

Christine L.

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

Exceeded Expectations

Our stay at this lovely home was perfect. Every aspect exceeded our expectations. I wouldn't hesitate to rent this property again. Alex the host was very friendly and accommodating and the condition and location of the property couldn't be better. I highly recommend.
Stayed 2 nights in Jun 2021

10/10 Excellent

Nancy H.

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

Highly recommend!!

The house is in a fabulous location - a short walk to shops, restaurants, and food store. Our expectations we exceeded as far as comfort and amenities. You will want for nothing! The owner quickly reply to our message and was very easy to work with. This house is a gem.
Stayed 5 nights in Oct 2023

10/10 Excellent

Julie B.

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

A beautiful home for a Celebration!

My family and I spent two glorious days in this beautiful home, and hosted a Celebration of Life for my sister on the main floor. We could not have asked for a more beautiful home and great location. It is perfect for entertaining, as well as large family gatherings. The owner was very responsive and accommodating. Our only regret is that we only stayed 2 nights! We certainly plan to return.
Stayed 2 nights in Nov 2022

10/10 Excellent

Liz G.

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

Location and charm

After visiting the island for the first time, we are so glad to have chosen Vineyard Haven for our stay. It is quieter than the other towns and had everything we needed. The house is conveniently located near food, bike rentals, and shopping so easy to walk. The Dexter is beautiful - charming, comfortable, well-maintained, and so well appointed with many thoughtful amenities! I rated the online listing a 4, but it's really a 4.5, because i couldn't read some of the room descriptors on the layout. Our family of 14 loved it! The best part was that each of the 5 family groups had their own space to relax.
Stayed 7 nights in Jul 2024

10/10 Excellent

Tom N.

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

Vinyard Haven VRBO STay

This stay was exceptional in every respect. The house was clean when we entered and the amenties were very nice. I recommend at minimum you installing a hand hold for getting in and out of the tub in the downstairs bathroom. To enter the tub is very high and I'm concerned someone might slip getting in and out of the tub.
Stayed 5 nights in Jun 2021

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

Ali M.

Liked: Cleanliness, check-in, communication, location, listing accuracy
We had a fantastic stay at the Dexter for a wedding weekend. Our group unanimously declared it one of the largest and nicest homes any of us have ever rented. The kitchen is gorgeous- equipped with more than enough dishes, silverware and kitchen gadgets- often a concern in rentals. Every room was clean and coastal chic, the beds were comfy as well. It’s so rare to find a place for such a large group that still allows for privacy, space, and ample bathrooms. The “sofa” bedroom was private and included a half bath- there was so much common living space it didn’t feel like a makeshift accommodation and our friends who stayed in that room were very happy as well. The captains suite was GIGANTIC and our group had a blast getting ready for the wedding together up there. While not well advertised in the listing, the outdoor shower was a favorite feature for many. Others lamented that they wished they had more time to read cozied up on the porch and by the fire pit during down time as it was so peaceful. We honestly didn’t have a single criticism and were just wowed by every aspect of the house- tons of games, fresh flowers on the coffee table, takeout menus, Keurig cups, local tips.With a perfect location, walkable to ferry, beach, cafes and shops, a car is definitely not necessary, but it was a perk to have ample parking. Finally, Alex made all of the logistics a breeze. She was unbelievably quick to reply and generously flexible with timing. We can’t wait to come back!
Stayed 2 nights in Sep 2025

10/10 Excellent

Rebecca B.

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

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!
Stayed 7 nights in May 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

Sharon M.

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

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.
Stayed 5 nights in Mar 2025

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

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

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

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

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

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

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

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

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

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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