Entire home

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. - Downtown Captain's Mansion- The Dexter- Family, event, and pet friendly (Tisbury)
Property video
A stone pathway flanked by lush hydrangea bushes and various garden plants. - Downtown Captain's Mansion- The Dexter- Family, event, and pet friendly (Tisbury)
A two-story white house with a front porch, a stone wall, and a blue truck parked in front. - Downtown Captain's Mansion- The Dexter- Family, event, and pet friendly (Tisbury)
A kitchen with wooden cabinets, a large island with stools, a stainless steel refrigerator, and a window with a view of trees. - Downtown Captain's Mansion- The Dexter- Family, event, and pet friendly (Tisbury)
You can look forward to a firepit, a garden and a playground at Downtown Captain's Mansion- The Dexter- Family, event, and pet friendly. Stay connected with free in-room WiFi, with a speed of 500+ Mbps (good for 6+ people or 10+ devices), and guests can find other amenities such as laundry facilities.

Reviews

10 out of 10
Exceptional

Popular amenities

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

Add dates for prices

About this property

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, on-site 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 car park. We welcome hen nights, 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 city centre Vineyard Haven. The home was built in 1843 and has undergone creative design and renovations to modernise 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 harbour. We are located at 92 Main Street, in the heart of the action in Vineyard Haven. Walking distance from the restaurants, the harbour, 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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About the area

Located in Vineyard Haven, this holiday home is in the city centre and near the beach. The area's natural beauty can be seen at Inkwell Beach and Cape Cod Beaches. Consider Cape Cod Fairgrounds for a night out or Island Cove Adventures if you're travelling with kids. Kayaking, windsurfing and power boating offer great chances to get out on the surrounding water, or you can seek out an adventure with hiking/biking trails nearby. Visit our Vineyard Haven travel guide
View more Holiday homes in Vineyard Haven
Map
Tisbury, MA

What's nearby

  • Vineyard Playhouse
    1 min walk - 0.0 miles
  • Martha's Vineyard Chamber of Commerce
    5 min walk - 0.3 miles
  • Martha's Vineyard Film Center
    9 min walk - 0.5 miles
  • Martha's Vineyard Museum
    13 min walk - 0.7 miles
  • Tisbury Town Beach
    17 min walk - 1.0 mile

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

Frequently asked questions

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

Yes, this property allows pets (limit 2 total).

How much is parking at Downtown Captain's Mansion- The Dexter- Family, event, and pet friendly?

On-site parking is available at the property.

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

Check-in begins at 4:00 PM.

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

Checkout is at 10:00 AM.

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

This family-friendly Vineyard Haven holiday 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.

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Reviews

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

10

Exceptional

10

Cleanliness

10

Location
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

Reviews

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

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

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

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

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

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

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

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

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 review

10/10 Excellent

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
Verified review

10/10 Excellent

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
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

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
Verified review

10/10 Excellent

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
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

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
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

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
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

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
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Amazing house and location! Really enjoyed our stay here with a large extended family. House is well equipped and walking distance to downtown, the beach, and the ferry.
Stayed 7 nights in Jun 2026
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
The home is an absolutely beautiful historic property that could not be better located for walkability to restaurants and shops. The home was very clean, comfortable beds, and the grounds are just gorgeous. There is so much room and everyone in our party had ample space to spread out. Alex is super responsive and eager to please, in every aspect. I would definitely stay here again and would highly recommend!!
Stayed 7 nights in Jul 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
What a great stay! From the moment we booked Alex was a great communicator. The house really has everything you could need. We do a lot of cooking and found the kitchen well stocked. We had a big crew with varying ages and everyone had plenty of space for group time or reading/working time. Thank you!
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
This could not have been a more perfect location, home and gathering space for our friend reunion.
Stayed 7 nights in Sep 2025