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

Family-friendly vacation home in Vineyard Haven

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Fridge, microwave, oven, stovetop
Fridge, microwave, oven, stovetop
9 bedrooms, desk, iron/ironing board, free WiFi

Reviews

10 out of 10
Exceptional

Entire home

9 bedrooms7 bathroomsSleeps 186800 sq ft

Popular amenities

  • Dryer
  • Breakfast available
  • Washer
  • Fireplace
  • Barbecue grill

Explore the area

View in a map
Tisbury, MA
  • Place, Vineyard Haven Terminal
    ‪5 min walk‬
  • Place, Martha's Vineyard Museum
    ‪13 min walk‬
  • Place, Inkwell Beach
    ‪7 min drive‬
  • Airport, Vineyard Haven, MA (MVY-Martha's Vineyard)
    ‪13 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.
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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
  • Inkwell Beach - 7 min drive - 3.5 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
  • ‪The Attic At Waterside - ‬1 min walk
  • ‪Porto Pizza - ‬3 min walk

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.
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.

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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

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.

Is parking available on site 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.

What do couples enjoy most about Downtown Captain's Mansion- The Dexter- Family, pet, and event friendly?

Amenities that appeal to couples at this historic vacation home include a fireplace and a kitchen in each accommodation with some featuring ocean views.

Are there hot tubs at Downtown Captain's Mansion- The Dexter- Family, pet, and event friendly?

No, there isn't a spa tub at this vacation home.

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.

Are there connecting rooms at this vacation home?

No, there aren't connecting rooms at this vacation home.

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.

Are there rooms with balconies 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.

Reviews

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

10

Exceptional

10/10

Cleanliness
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

Amanda C.

Liked: Cleanliness
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

Susan S.

Liked: Cleanliness
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
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
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

Molly H.

Liked: Cleanliness

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

ROBYN M.

Liked: Cleanliness

Beautiful House

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

10/10 Excellent

Rebecca B., Atlanta, GA

Liked: Cleanliness

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

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

Terrence C.

Liked: Cleanliness
Stayed 4 nights in Nov 2024

10/10 Excellent

Sharon M.

Liked: Cleanliness

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

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 traveler

Liked: Cleanliness

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

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

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

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

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

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

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

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

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

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

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 traveler

Liked: Cleanliness

Wonderful experience

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

10/10 Excellent

Gwen G.

Liked: Cleanliness

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

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