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

Family-friendly stay near Oak Bluffs Town Beach

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

Outdoor dining
Property video
A bedroom with a large bed, a glass coffee table with a vase of flowers, a wooden desk, and a sliding barn-style door.
Property grounds
A spacious kitchen with wooden cabinets, a central island, and a dining area with wooden chairs.

Reviews

10 out of 10
Exceptional

Entire home

9 bedrooms7 bathroomsSleeps 18632 sq m

Popular amenities

  • Ocean view
  • Kitchen
  • Washer
  • Dryer
  • Pet friendly
  • Free WiFi

Explore the area

View in a map
Tisbury, MA
  • Place, Martha's Vineyard Chamber of Commerce
    ‪5 min walk‬
  • Place, Vineyard Haven Public Library
    ‪6 min walk‬
  • Place, Martha's Vineyard Museum
    ‪13 min walk‬
  • Airport, Vineyard Haven, MA (MVY-Martha's Vineyard)
    ‪18 min drive‬

Room options

About the area

Vineyard Haven

Seaside stay .Within a 5-minute walk of this Vineyard Haven vacation home, you'll find Vineyard Haven Terminal and Martha's Vineyard Chamber of Commerce. Vineyard Haven Public Library and Martha's Vineyard Film Center are also within half a mile (1 km).
View more Vacation homes in Vineyard HavenOpens in a new window

What's nearby

  • Martha's Vineyard Chamber of Commerce - 5 min walk - 0.4 km
  • Vineyard Haven Public Library - 6 min walk - 0.6 km
  • Martha's Vineyard Film Center - 9 min walk - 0.8 km
  • Martha's Vineyard Museum - 13 min walk - 1.1 km
  • Tisbury Town Beach - 17 min walk - 1.5 km

Getting around

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

Restaurants

  • ‪The Black Dog - Bakery Cafe - ‬3 min drive
  • ‪Rocco's Pizzeria - ‬9 min walk
  • ‪Cumberland Farms - ‬5 min walk
  • ‪Catboat Coffee Co. - ‬9 min walk
  • ‪Black Dog - ‬5 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, event, and pet 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. Vehicle reservation included for guests who book July 5-11th 2026. 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 2027 Saturday-Saturday.

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.

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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

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
Information provided by the property may be translated using automated translation tools

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

  • Pets are welcome
  • Maximum 2 pets
  • Service animals are exempt from fees
  • Note from host: Dog friendly residence. Yard is partially fenced.

Children and extra beds

  • Children are welcome.

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 has outdoor spaces, such as balconies, patios, terraces which may not be suitable for children; if you have concerns, we recommend contacting the property prior to your arrival to confirm they can accommodate you in a suitable room
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
Charges for extra guests may apply and vary according to property policy.
A cash deposit, credit card, or debit card for incidental charges and government-issued photo identification may be required upon check-in.
Special requests are subject to availability at the time of check-in. Special requests can't be guaranteed and may incur additional charges.
    This property is managed by a private host, not a professional engaged in trade or business. This property has outdoor spaces, such as balconies, patios, terraces which may not be suitable for children. If you have concerns, we recommend contacting the property prior to your arrival to confirm they can accommodate you in a suitable room. Parties and events (including family gatherings, birthday parties and weddings) are allowed on site. Maximum attendees: 30. Long-term renters welcome. For guests' safety, the property includes a carbon monoxide detector, a fire extinguisher, a smoke detector, a first aid kit, and a deadbolt lock in each accommodation.

Property Registration Number C0363072960

Property is also known as

Vrbo Property

Frequently asked questions

How close is Downtown Captain's Mansion- The Dexter- Family, event, and pet friendly to the airport?

This vacation home is 6.2 mi (12-min drive) away from the Vineyard Haven, MA (MVY-Martha's Vineyard) airport, the closest popular airport to the property.

Does Downtown Captain's Mansion- The Dexter- Family, event, and pet friendly have an airport shuttle?

Airport shuttle services are not available at this vacation home.

How close is Downtown Captain's Mansion- The Dexter- Family, event, and pet friendly to the beach?

This vacation home is a short 14-minute walk from Tisbury Town Beach and 10 mi (55-min drive) from Cape Cod Beaches. Don't forget your sunscreen!

Does Downtown Captain's Mansion- The Dexter- Family, event, and pet friendly offer free breakfast?

This vacation home does not offer free breakfast.

Is there a casino at Downtown Captain's Mansion- The Dexter- Family, event, and pet friendly?

No, there is no casino at this vacation home.

What time is check-in at Downtown Captain's Mansion- The Dexter- Family, event, and pet friendly?

Check-in begins at 4:00 PM.

Is there free parking at Downtown Captain's Mansion- The Dexter- Family, event, and pet friendly?

Free parking is not available at this vacation home.

Does Downtown Captain's Mansion- The Dexter- Family, event, and pet friendly have a pool?

This vacation home does not have a pool.

Does Downtown Captain's Mansion- The Dexter- Family, event, and pet friendly have a spa?

There are no spa services available at this vacation home.

How close is Downtown Captain's Mansion- The Dexter- Family, event, and pet friendly to downtown Vineyard Haven?

This vacation home is 1.1 mi away from Tisbury.

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

Reviews

10

Exceptional

Rating 10 - Excellent. 71 out of 71 reviews
Rating 8 - Good. 0 out of 71 reviews
Rating 6 - Okay. 0 out of 71 reviews
Rating 4 - Poor. 0 out of 71 reviews
Rating 2 - Terrible. 0 out of 71 reviews

10/10

Cleanliness

Reviews

Verified

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
Verified

10/10 Excellent

Loni M.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Alex did a great job communicating and welcoming us to our stay at Dexter house. The house is amazing and perfect for our large group. The kitchen was stocked to perfection with really everything we needed. The location was very convenient just a short walk from the ferry port. We didn’t bring a vehicle over and were easily able to walk to shops/restaurants/grocery store. We had a wonderful stay and we look forward to returning again!
Stayed 2 nights in Jan 2026
Verified

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
Verified

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
Verified

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
Verified

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
Verified

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
Verified

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
Verified

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
Verified

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
Verified

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
Verified

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
Verified

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
Verified

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
Verified

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
Verified

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
Verified

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
Verified

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
Verified

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
Verified

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
Verified

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
Verified

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
Verified

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
Verified

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
Verified

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