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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
Outdoor dining
9 bedrooms, desk, iron/ironing board, travel crib
9 bedrooms, desk, iron/ironing board, travel crib
Fridge, microwave, oven, stovetop

Reviews

10 out of 10
Exceptional

Entire home

9 bedrooms7 bathroomsSleeps 18632 sq m

Popular amenities

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

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 book Saturday-Saturday in peak season 6/28/25-8/28/25. One vehicle ferry reservation is INCLUDED with your booking for guests booking weeks of 6/28, 7/5, 7/12, 7/19, 7/26, 8/9, and 8/16.

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 towels
  • Beach sun loungers

Pool/Spa

  • Hot tub

Internet

  • Free WiFi

Parking and transportation

  • Onsite parking
  • Car not required

Kitchen

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

Dining

  • Breakfast available for a fee
  • Dining table

Bedrooms

  • 9 bedrooms
  • Bed sheets provided
  • Sofa bed

Bathrooms

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

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
  • Hiking nearby
  • Kayaking nearby
  • Wildlife and game walks nearby
  • Fishing nearby
  • Swimming nearby
  • Hiking/biking trails nearby
  • Marina nearby
  • Windsurfing 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)

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Spacious home for entertaining, centrally located to beach, ferry, and airport.

  • Pool
  • Kitchen
  • Washer
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10.0 out of 10, Exceptional, (1)
Spacious home for entertaining, centrally located to beach, ferry, and airport.

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

  • Vineyard Haven Terminal - 4 min walk - 0.4 km
  • Martha's Vineyard Chamber of Commerce - 4 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
  • 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 Haven Terminal and Martha's Vineyard Chamber of Commerce. Martha's Vineyard Film Center and Vineyard Haven Public Library are also within 10 minutes.

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

Reviews

10

Exceptional

Rating 10 - Excellent. 56 out of 56 reviews
Rating 8 - Good. 0 out of 56 reviews
Rating 6 - Okay. 0 out of 56 reviews
Rating 4 - Poor. 0 out of 56 reviews
Rating 2 - Terrible. 0 out of 56 reviews

10/10

Cleanliness

Reviews

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

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

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

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

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

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

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

10/10 Excellent

Verified traveler

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

Verified traveler

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

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

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

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

10/10 Excellent

Stephanie A.

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

Jim H.

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

Bonnita B.

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

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

10/10 Excellent

Lori S.

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

Nancy H.

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

John P., Reading Ma USA

Liked: Cleanliness, check-in, communication, location, listing accuracy
MS charity bike ride weekend
We all had a great weekend in this beautiful house. Alexander was very responsive with questions I had. Can't wait to book again for next year.
Stayed 2 nights in Apr 2022

10/10 Excellent

Christine L.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Exceeded Expectations
Our stay at this lovely home was perfect. Every aspect exceeded our expectations. I wouldn't hesitate to rent this property again. Alex the host was very friendly and accommodating and the condition and location of the property couldn't be better. I highly recommend.
Stayed 2 nights in Jun 2021

10/10 Excellent

Janie C.

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

10/10 Excellent

Julie B.

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

Tom N.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Vinyard Haven VRBO STay
This stay was exceptional in every respect. The house was clean when we entered and the amenties were very nice. I recommend at minimum you installing a hand hold for getting in and out of the tub in the downstairs bathroom. To enter the tub is very high and I'm concerned someone might slip getting in and out of the tub.
Stayed 5 nights in Jun 2021

10/10 Excellent

Steven T.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great stay for Memorial Day weekend
Great property for a getaway with friends. Amazing breakfast and lunch right next door. The BLT is a must. Great food in the area. Something important to note is there are no true bars or nightlife in the immediate area of the house but it was not a problem for us. We had bad weather while there but hanging in the house was just as fun as having the outdoor areas. Just sad we couldn’t take advantage.
Stayed 3 nights in May 2021

10/10 Excellent

Tobey D.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Fabulous place for a family reunion!!
The website does not do the home justice. It is more lovely and spacious in person. Multiple living areas accommodated multiple generations of family. Beautifully appointed kitchen with every possible gadget. The outside areas are also beautifully landscaped and easy to enjoy. The location can't be beat. So close to the businesses on Main Street yet quiet and residential in the evening. We would rent this home again if it is not transitioned back to a B&B.
Stayed 14 nights in Aug 2021