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

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

A patio area with outdoor furniture, string lights, and a covered grill.
Property video
A two-story white house with a front porch, a stone wall, and a blue truck parked in front.
A stone pathway flanked by lush hydrangea bushes and various garden plants.
A kitchen with wooden cabinets, a large island with stools, a stainless steel refrigerator, and a window with a view of trees.

Reviews

10 out of 10
Exceptional

Entire home

9 bedrooms7 bathroomsSleeps 18632 sq m

Popular amenities

  • Ocean view
  • Kitchen
  • Washing machine
  • Dryer
  • Pet-friendly
  • Free Wi-Fi

Explore the area

View map
Tisbury, MA
  • Place, Vineyard Playhouse
    ‪1 min walk‬
  • Place, Martha's Vineyard Chamber of Commerce
    ‪5 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

A family-friendly stay in the heart of Vineyard Haven awaits you at this holiday home. Within steps you'll find Vineyard Playhouse and Vineyard Haven Terminal within a short 5-minute stroll. Highlights at this holiday home include a kitchen, a washing machine and free WiFi. .You can enjoy Smart televisions with a DVD player, and home features 6.5 bathrooms, a fireplace and a balcony. In-room dining is easy with a kitchen that comes equipped with a fridge, a microwave and a stovetop. A sofa bed, a fenced private garden and a TV are also available. .This pet-friendly holiday home offers a garden and barbecues. Additionally, you'll find laundry facilities. .Near this Vineyard Haven holiday home, you'll find Inkwell Beach.
View more Holiday homes in Vineyard HavenOpens in a new window

What's nearby

  • Vineyard Playhouse - 1 min walk - 0.0 km
  • Martha's Vineyard Chamber of Commerce - 5 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
  • 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
  • ‪Cumberland Farms - ‬5 min walk
  • ‪Portuguese-American Club - ‬5 min drive
  • ‪Rocco's Pizzeria - ‬9 min walk
  • ‪The Black Dog Tavern - ‬6 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 transport

  • Car not required
  • Wheelchair-accessible parking available

Kitchen

  • Blender
  • Coffee grinder
  • Coffee/tea maker
  • Cookware, dishware, and utensils
  • Dishwasher
  • Electric kettle
  • Hob
  • Ice maker
  • Kitchen island
  • Lobster/crab pot
  • Microwave
  • Oven
  • Paper towels
  • Refrigerator
  • Spices
  • 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

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.
  • Accessible parking space
  • In-room accessibility
  • Upper floors accessible by stairs only
  • Wheelchair-accessible parking
  • Smoke-free property

Services and conveniences

  • Iron/ironing board
  • Phone

Location highlights

  • In a village
  • In the city centre
  • 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

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 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.

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 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
This property has outdoor spaces, such as balconies, patios and terraces, which may not be suitable for children; if you have any concerns, we recommend contacting the property prior to your arrival to confirm that 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 and terraces, which may not be suitable for children. If you have any concerns, we recommend contacting the property prior to your arrival to confirm that 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 all accommodation.

Property Registration Number C0363072960

Property is also known as

Vrbo Property

Frequently asked questions

Are there any beaches close to Downtown Captain's Mansion- The Dexter- Family, event, and pet friendly?

Yep, Downtown Captain's Mansion- The Dexter- Family, event, and pet friendly is a short 14-minute walk from Tisbury Town Beach. Fun beach activities include windsurfing, kayaking and sailing. You can also find motor boats.

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

No, this holiday home doesn't have a pool.

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

You bet! With amenities such as a playground and laundry facilities, as well as highchairs and children's dinnerware, it's no surprise that Downtown Captain's Mansion- The Dexter- Family, event, and pet friendly is a winner with our family travellers.

Is there a free airport shuttle available at Downtown Captain's Mansion- The Dexter- Family, event, and pet friendly?

No, Downtown Captain's Mansion- The Dexter- Family, event, and pet friendly does not offer an airport shuttle service.

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

Check-in begins at 4:00 PM. Check-out time is 10:00 AM.

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

Reviews

10

Exceptional

Rating 10 - Excellent. 77 out of 78 reviews
Rating 8 - Good. 1 out of 78 reviews
Rating 6 - Okay. 0 out of 78 reviews
Rating 4 - Poor. 0 out of 78 reviews
Rating 2 - Terrible. 0 out of 78 reviews

10/10

Cleanliness

Reviews

Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Super great location for our family. Private gorgeous yard right in the middle of Vineyard Haven and walkable to everything. Host was incredibly responsive addressing questions quickly and thoroughly. A great experience for a three generation family of 14.
Stayed 7 nights in Jul 2026
Verified review

10/10 Excellent

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 review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Beautiful home, beautiful location! Pictures do not do it justice. This home has so much character. Worked excellent for a large family event. Fully equipped kitchen made large meals a breeze. Dog and kid friendly. Layout worked perfect for our group. Large table was perfect for games, separate sitting areas for those needing a little quiet time also worked great. Location to eateries, on site parking, and proximity to ferry and beaches a plus! Beds were so cozy it’s hard to head home! Would stay again!
Stayed 6 nights in May 2026
Verified review

10/10 Excellent

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 review

10/10 Excellent

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 review

10/10 Excellent

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 review

10/10 Excellent

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 review

10/10 Excellent

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 review

10/10 Excellent

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 review

10/10 Excellent

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 review

10/10 Excellent

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 review

10/10 Excellent

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 review

10/10 Excellent

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 review

10/10 Excellent

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 review

10/10 Excellent

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 review

10/10 Excellent

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 review

10/10 Excellent

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 review

10/10 Excellent

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 review

10/10 Excellent

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 review

10/10 Excellent

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 review

10/10 Excellent

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 review

10/10 Excellent

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 review

10/10 Excellent

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 review

10/10 Excellent

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 review

10/10 Excellent

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