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.
Property video
A kitchen with wooden cabinets, a large island with stools, a stainless steel refrigerator, and a window with a view of trees.
A bedroom with a large bed, a nightstand, a chair, and a dresser.
A two-story white house with a front porch, a stone wall, and a blue truck parked in front.

Reviews

10 out of 10, Loved by Guests
Top 1% of guest reviews in this area

Highlights

  • Family fun awaits
    Top-rated for families.
  • Firepit available
    One of the few properties with a dedicated outdoor firepit.
  • Centrally-located
    You're never far from where you need to be with this convenient location.
  • Discover nearby landmarks
    Walk to Martha's Vineyard Museum

Popular amenities

  • Balcony
  • Toys
  • Barbecue grill
  • Air-conditioning
  • Pet-friendly
  • Breakfast for a fee

Explore the area

View in a 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

Rooms & beds

9 bedrooms (sleeps 18)

1st floor bedroom

1 Queen Bed

Captain's Quarters

1 King Bed

Connected to Captain's- Chart Room

1 Double Bed

Crow's Nest

1 Double Bed

Front living Room

1 Queen Sofa Bed

Leeward

1 King Bed

Midship

1 King Bed

Pilot House

1 Queen Bed

Windward

1 Queen Bed

6 bathrooms, 1 half bathroom

Bathroom 1

Toilet · Shower only

Bathroom 2

Toilet · Shower only

Bathroom 3

Toilet

Bathroom 4

Bathtub · Toilet · Shower only

Bathroom 5

Bathtub · Toilet · Shower only

Bathroom 6

Bathtub · Toilet · Shower only

Bathroom 7

Bathtub · Toilet · Shower only

Spaces

Deck or patio
Porch or lanai
Kitchen
Balcony
Outdoor play area
Garden
Dining area

Add dates for prices

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About the area

Vineyard Haven

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.
View more Holiday homes in Vineyard HavenOpens in a new window
Map
Tisbury, MA

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

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 does it cost to stay at Downtown Captain's Mansion- The Dexter- Family, event, and pet friendly?

As of 28 Oct 2026, prices found for a 1-night stay for 2 adults at Downtown Captain's Mansion- The Dexter- Family, event, and pet friendly on 1 Jan 2027 start from £2,299, including taxes and fees. This price is based on the lowest nightly price found in the last 24 hours for stays in the next 30 days. Prices are subject to change. Choose your dates for more accurate prices.

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.

Reviews

10

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
Learn moreOpens in a new window
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

10/10

Check-in

10/10

Communication

10/10

Location

10/10

Listing accuracy

Reviews

Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great house, plenty of space. Perfect location. Alex was very accommodating
Stayed 2 nights in Sep 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
The house was accurately described on the website. Beautiful home and the host was very gracious and accommodating.
Stayed 4 nights in Sep 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

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
Response from VrboOwner on 27 Nov 2023
We'd have you back any time! Glad our giant home met your need!
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
Response from VrboOwner on 31 Aug 2023
Thanks!
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
Response from VrboOwner on 24 Jul 2025
Glad you had a great time!
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
Response from VrboOwner on 31 Aug 2023
Thank you! Happy to have you and your friends back any time,
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
Response from VrboOwner on 10 Mar 2025
Thanks! Happy to have you back any time.
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
Response from VrboOwner on 23 Jul 2025
We hope so too!
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
Response from VrboOwner on 31 Aug 2023
Thanks Jack! Glad you all loved the house and the location.
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
Response from VrboOwner on 8 Oct 2024
Happy to have you back any time!
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
Response from VrboOwner on 31 Mar 2025
Happy to host you!
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