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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
Fridge, microwave, oven, stovetop
Aerial view
Smart TV, fireplace, DVD player, books
Outdoor dining

Reviews

10 out of 10

Exceptional

Entire home

9 bedrooms7 bathroomsSleeps 18632 sq m

Popular amenities

  • Hot Tub
  • Washer
  • Breakfast available
  • Pet friendly
  • Parking available
  • Barbecue grill

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 private parking lot.

We book Saturday-Saturday in peak season 6/28/25-8/28/25.

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

Languages

English

Property amenities

Beach

  • Near the beach
  • Beach sun loungers
  • Beach towels

Pool/Spa

  • Spa tub

Internet

  • Free WiFi

Parking and transportation

  • Onsite parking
  • Car not required

Kitchen

  • Refrigerator
  • Stovetop
  • Microwave
  • Oven
  • Dishwasher
  • Spices
  • Paper towels
  • Cookware/dishes/utensils
  • Coffee grinder

Dining

  • Breakfast available for a fee
  • Dining table

Bedrooms

  • 9 bedrooms
  • Bed sheets provided
  • Sofa bed

Bathrooms

  • 6.5 bathrooms
  • Shower
  • Toilet paper
  • Hair dryer
  • Towels provided
  • Soap

Living spaces

  • Fireplace
  • Living room

Entertainment

  • Smart TV with cable/satellite service
  • DVD player
  • Books
  • Games
  • Stereo

Outdoor areas

  • Balcony
  • Fenced yard
  • Barbecue grill
  • Garden
  • Outdoor furniture
  • Firepit

Laundry

  • Washing machine and dryer

Work spaces

  • Desk
  • Desk chair

Comfort

  • Air conditioning
  • Heating

Pets

  • Pet friendly
  • 2 total pets

Suitability/Accessibility

  • Smoke-free property

Services and conveniences

  • Iron/ironing board
  • Phone

Location highlights

  • Near the sea
  • In the city center
  • Near a health or beauty spa
  • Near a hospital
  • Near the bay
  • In a village

Things to do

  • Fitness facilities nearby
  • Bicycle on site
  • Kayaking nearby
  • Hiking nearby
  • Swimming nearby
  • Fishing nearby
  • Wildlife and game walks nearby
  • Power boating nearby
  • Windsurfing nearby
  • Marina nearby
  • Sailing nearby

Safety features

  • Carbon monoxide detector installed (host has indicated there is a carbon monoxide detector on the property)
  • Smoke detector installed (host has indicated there is a smoke detector on the property)
  • Fire extinguisher
  • First aid kit
  • Deadbolt lock

General

  • Unit size: 6800 sq ft (632 sq m)

Similar properties

Exterior

Oak Bluff's Victorian Walk to Town & Beaches

Kitchen
Washer
Dryer
Free WiFi
10.0 out of 10, Exceptional, (1)
Oak Bluff's Victorian Walk to Town & Beaches

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

Pets

Pets allowed
Service animals are welcome, and are exempt from fees
2 total pets
Note from host: Dog friendly residence. Yard is partially fenced.

Children and extra beds

Children are welcome

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
Property Registration Number C0363072960

We should mention

A car is not required for transportation to and from this property

Property is also known as

Vrbo Property

About the neighborhood

Map
Tisbury, MA

What's nearby

  • Martha's Vineyard Film Center - 9 min walk - 0.8 km
  • Martha's Vineyard Museum - 13 min walk - 1.1 km
  • Oak Bluffs Harbor - 6 min drive - 5.2 km
  • Circuit Avenue - 7 min drive - 6.1 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?

Check-out is at 10:00 AM.

Where is Downtown Captain's Mansion- The Dexter- Family, pet, and event friendly located?

This family-friendly Vineyard Haven vacation 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.

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

Reviews

10

Exceptional

Rating 10 - Excellent. 54 out of 54 reviews" "
Rating 8 - Good. 0 out of 54 reviews" "
Rating 6 - Okay. 0 out of 54 reviews" "
Rating 4 - Poor. 0 out of 54 reviews" "
Rating 2 - Terrible. 0 out of 54 reviews" "

10/10

Cleanliness

Reviews

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

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

10/10 Excellent

Jim H.

Liked: Cleanliness
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
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
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
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
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
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
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
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 traveler

Liked: Cleanliness
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

Liked: Cleanliness
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.

Liked: Cleanliness
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.

Liked: Cleanliness
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.

Liked: Cleanliness
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

Liked: Cleanliness
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