Entire home

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

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

Exterior
Private kitchen
Private kitchen
Private kitchen
Living area

Reviews

10 out of 10
Exceptional
9 bedrooms6+ bathroomsSleeps 18631.7 sq m

Popular amenities

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

Explore the area

Map
Tisbury, MA
  • Vineyard Haven Terminal
    ‪4 min walk‬
  • Martha's Vineyard Film Center
    ‪9 min walk‬
  • Martha's Vineyard Museum
    ‪13 min walk‬
  • Vineyard Haven, MA (MVY-Martha's Vineyard)
    ‪12 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 Room

1 Double Futon

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.

One vehicle ferry reservation is INCLUDED with your booking for guests booking weeks of 6/28, 7/5, 7/12, 7/19, 7/26, 8/9, and 8/16. We will modify the ferry reservation when you book the house to match your dates.

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 manager

Alexandra Wild
Premier Host

Languages

English

Add dates for prices

Amenities

Hot tub
Kitchen
Washer
Dryer
Pet-friendly
Free WiFi

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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

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

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. Cape Cod Beaches and Felix Neck Wildlife Sanctuary 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 Chilmark Chocolates. Make sure you get close to the area's animals with activities such as game walks and birdwatching.
Map
Tisbury, MA

What's nearby

  • Vineyard Haven Terminal - 4 min walk - 0.4 km
  • Martha's Vineyard Chamber of Commerce - 4 min walk - 0.4 km
  • Martha's Vineyard Film Center - 9 min walk - 0.8 km
  • Martha's Vineyard Museum - 13 min walk - 1.1 km
  • Inkwell Beach - 16 min drive - 6.8 km

Getting around

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

Restaurants

  • ‪Portuguese American Club - ‬5 min drive
  • ‪The Black Dog Tavern - ‬6 min walk
  • ‪VFW Hall - ‬5 min drive
  • ‪Nancy's Restaurant - ‬6 min drive
  • ‪The Barn Bowl & Bistro - ‬7 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.

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. 59 out of 59 reviews
Rating 8 - Good. 0 out of 59 reviews
Rating 6 - Okay. 0 out of 59 reviews
Rating 4 - Poor. 0 out of 59 reviews
Rating 2 - Terrible. 0 out of 59 reviews

10/10

Cleanliness

10/10

Check-in

10/10

Communication

10/10

Location

10/10

Listing accuracy

Reviews

10/10 Excellent

Terrence C.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Stayed 4 nights in Nov 2024

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

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

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

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

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

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

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

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

Jim H.

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

Wedding Week

House accomidated family & friends quit well. Plenty of places to gather as well as find alone time. Host very responsive. Already planning next years trip.
Stayed 6 nights in Sep 2023

10/10 Excellent

Stephanie A.

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

Bridal House

This house was amazing for all my bridesmaids to get ready in!
Stayed 2 nights in Sep 2023

10/10 Excellent

Bonnita B.

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

Vineyard Haven Family Vacation

Beautifully appointed historical home with all of the modern conveniences! We are a family group ages 72 to 8 months. Everyone loved this beautiful home and the location in downtown Vineyard Haven was perfect! We are already talking about booking for 2024!
Stayed 7 nights in Aug 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

Lori S.

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

AWESOME PROPERTY

Great house in an excellent location. Walkable to many restaurants, coffee, ice cream, shopping and ferry. Kitchen well stocked, lots of board games and a great outdoor area! Great communication with property manager. Highly recommend!
Stayed 7 nights in Jul 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

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

Colin M.

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

60th Birthday March 2023

It was my wife’s 60th, family came in from all over the country, the house was perfect for us, the location was outstanding. I’m a chef so all meals were cooked at the house, the kitchen was well stocked(I did bring my own pots pans and gadgets!!)and large enough for everyone to work together, the fridge held all our supplies, beverages and food. The bedrooms were clean and spacious With bathrooms galore Alex answered any questions timely and with love. We would love to go back
Stayed 5 nights in Mar 2023

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