The Dexter- Downtown Captain's House

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Entire home

Overview
Amenities
Policies
Location
Host

Exceptional

9 bedrooms6+ bathroomsSleeps 18632 sq m

Popular amenities

Hot tub

Washer

Barbecue grill

Breakfast available

Pet-friendly

Kitchen

Explore the area

Tisbury, MA

Vineyard Haven Terminal4 min walk
Martha's Vineyard Film Center9 min walk
Martha's Vineyard Museum13 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

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.

Sleeps 18 people.

Booking includes vehicle FERRY RESERVATION when you book the following weeks: 7/6-7/13/24, 7/20-7/27/24, 8/17-8/24/24, and 8/24-8/31/24.

AWESOME SPOT FOR YOUR CELEBRATIONS! 5MIN WALK FROM THE FERRY BOAT!

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

Amenities

Hot tub

Kitchen

Washer

Dryer

Pet-friendly

Free WiFi

Pool

Hot tub

Kitchen

Washer

House Rules

Check in after 4:00 PM

Minimum age to rent: 25

Check out before 10:00 AM

Children

Children allowed: ages 0–17

Events

Events allowed: family gatherings, birthday parties, weddings

Pets

Pets allowed: limit 2 total

Dog friendly residence. Yard is partially fenced.

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

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. Woods Hole Ferry Terminal and Island Queen Ferry are worth checking out if an activity is on the agenda, while those wishing to experience the area's natural beauty can explore Inkwell Beach and Cape Cod Beaches. Travelling with kids? Consider Island Cove Adventures and Flying Horses Carousel. With kayaking, power boating and sailing nearby, you'll find plenty of adventures in the water.

Tisbury, MA

What's nearby

Vineyard Haven Terminal - 4 min walk
Martha's Vineyard Chamber of Commerce - 4 min walk
Martha's Vineyard Film Center - 9 min walk
Martha's Vineyard Museum - 13 min walk
Inkwell Beach - 16 min drive

Getting around

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

Restaurants

‪Nancy's Restaurant - ‬6 min drive
‪The Black Dog Tavern - ‬6 min walk
‪Portuguese American Club - ‬5 min drive
‪VFW Hall - ‬5 min drive
‪Black Dog - ‬5 min walk

Frequently asked questions

Is The Dexter- Downtown Captain's House pet-friendly?

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

What time is check-in at The Dexter- Downtown Captain's House?

Check-in begins at 4:00 PM.

What time is check-out at The Dexter- Downtown Captain's House?

Checkout is at 10:00 AM.

Where is The Dexter- Downtown Captain's House located?

This family-friendly Vineyard Haven holiday home is located by the sea, within a 5-minute walk of Vineyard Playhouse, 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.

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.

Learn more

10/10

Cleanliness

10/10

Check-in

10/10

Communication

10/10

Location

10/10

Listing accuracy

10/10 Excellent

Eileen F.

3 June 2024

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.

3 June 2024

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.

24 Mar 2024

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

10 Dec 2023

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.

16 Nov 2023

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.

10 Oct 2023

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.

2 Oct 2023

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.

23 Sept 2023

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.

26 Aug 2023

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.

24 Aug 2023

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.

8 Aug 2023

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.

20 June 2023

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.

29 May 2023

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.

27 Mar 2023

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

10/10 Excellent

Verified traveller

5 Dec 2022

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

Hannah M., Dunbarton, NH

28 Nov 2022

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

The Best Weekend, at the most perfect location!

My husband and I planned our intimate wedding and this house was the perfect place to host it. All of our family and friends were able to stay together in this gorgeous house with ample bedrooms and bathrooms. The kitchen was gorgeous and was the perfect host for our welcome dinner catered by a local restaurant. Our friends and family could not get over the location, just minutes away from the ferry and walking distance from all the shops, and restaurants on Main St in Vineyard Haven. Close to the Stop and Shop as well! Even though you are centrally located the backyard is quiet and the perfect place to hang out. Alex was amazing to work with, very quick to respond and incredibly flexible as we checked in early and stayed a few hours post check out due to flight schedules. She was also incredibly helpful with local recommendations and resources. Our wedding weekend was perfect because of this home! Everyone is still raving about the location! 10/10 would recommend for a family get together or reunion! Hannah

Stayed 2 nights in Sep 2022

10/10 Excellent

Julie B.

6 Nov 2022

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

Cara A.

6 Oct 2022

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

Great for group of friends - September weekend

Group of friends who came to the island for a wedding; host was easy to communicate with and the house was perfect!

Stayed 2 nights in Sep 2022

10/10 Excellent

Patricia W.

30 Sept 2022

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

Beautiful Place to Celebrate Our 50th Anniversary

We spent a week in this beautiful property with our children, their spouses, our "exchange daughter" and her husband and all their children. Due to our advanced age, my husband and I chose the first floor bedroom, which unfortunately did not have an en suite bath. But a perfectly adequate full bath was just a few steps away. The bedrooms and baths on the second and third floors were just plain breathtaking, as was the enormous kitchen. We loved filling the pasta pot directly on the stove. The kitchen and pantry were more than fully stocked, impressing even the son-in-law who works at Chez Panisse. The location was perfect for a big family vacation. We were within walking distance of nightly ice cream cones, lovely shops and the ferry. Our West Coast children and grandchildren were able to fly in to and out of Martha's Vineyard Airport. I was reassured that we were close to a hospital affiliated with Mass General Brigham, since my husband had recently had two cardiac procedures. We specifically did not want a home with a pool, since we had a couple youngsters who couldn't be trusted not to wander. All in all, this was a lovely spot for our long-planned gathering.

Stayed 7 nights in Jul 2022

10/10 Excellent

Chris T., Chicago

12 Sept 2022

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

Captain's House

Beautiful property, within walking distance to everything in Vineyard Haven, plenty of parking if you have a car and want to explore (we had a rental), and tons of space (indoors and out) for a larger group. Alex was extremely responsive and our group was thrilled with the accommodations and our weekend on the island.

Stayed 4 nights in Aug 2022

10/10 Excellent

Todd S.

3 Aug 2022

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

Awesome place

Could not have been better.

Stayed 1 night in Jul 2022

10/10 Excellent

Jon O.

23 July 2022

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

Thanks very much !

Great stay !

Stayed 5 nights in Jul 2022

10/10 Excellent

Verified traveller

7 July 2022

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

Ideal Vineyard Haven Large Home

Highly recommend this home, a beautiful and private place to spend quality time with friends and family right in the heart of downtown Vineyard Haven.

Stayed 4 nights in Jun 2022

10/10 Excellent

Jean K.

4 July 2022

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

family fun

great

Stayed 6 nights in Jun 2022

10/10 Excellent

Janie C.

27 June 2022

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

Fantastic.

We had a fantastic stay at this house. It’s huge, the kids kept getting lost. Even with 14 people in our party you still had no trouble finding private space. We loved being able to walk next door and get sandwiches, there’s a little park/beach only a couple of blocks away. All in all a wonderful house and location. Would return in a heartbeat!

Stayed 5 nights in Jun 2022

About the host

Hosted by Alexandra Wild

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.