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

9 bedrooms, desk, iron/ironing board, travel crib

5.0

Outstanding(55 Reviews)

House in Vineyard Haven, MA

18 guests · 9 bedrooms · 7 baths

Reasons to book

Guests love it hereGuests give this property a top rating

Great for petsBring all your friends and family, even the furry ones

Includes essentialsGarden, Pets allowed, Kitchen or Kitchenette and more

About this house rental

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.

Amenities

Air conditioner

Pets allowed

Kitchen or Kitchenette

Internet / Wifi

Fireplace

Parking

Laundry

Balcony or Patio

Dishwasher

Hot tub or spa

Garden

Family friendly

Map of Vineyard Haven, MA

Nearby attractions

Heritage Museums & Gardens

33.5 mi

Battleship Cove

54 mi

New Bedford Whaling Museum

33.2 mi

New Bedford Whaling National Historical Park

33.3 mi

$$$$

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

$$$$

5.0

Outstanding(55 Reviews)

House in Vineyard Haven, MA

18 guests · 9 bedrooms · 7 baths

Reasons to book

Guests love it hereGuests give this property a top rating

Great for petsBring all your friends and family, even the furry ones

Includes essentialsGarden, Pets allowed, Kitchen or Kitchenette and more

About this house rental

Amenities

Air conditioner

Pets allowed

Kitchen or Kitchenette

Internet / Wifi

Fireplace

Parking

Laundry

Balcony or Patio

Dishwasher

Hot tub or spa

Garden

Family friendly

Map of Vineyard Haven, MA

Nearby attractions

Heritage Museums & Gardens

33.5 mi

Battleship Cove

54 mi

New Bedford Whaling Museum

33.2 mi

New Bedford Whaling National Historical Park

33.3 mi

Reviews

5.0

Outstanding(55 Reviews)

5.0

Aug 2024

The house, amenities, location, and host were all top notch! We had a wonderful experience booking and staying at this home!

5.0

Aug 2024

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.

5.0

Jun 2024

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.

5.0

Jun 2024

Absolutely giant house. Wonderful kitchen. Truly could not beat the location. Would definitely stay again!

5.0

Mar 2024

Hospitable host, perfect location, spacious rooms , beautiful kitchen, all of which made for a wonderful weekend for us!

5.0

Dec 2023

This is such a great house for larger groups.

5.0

Nov 2023

The home was beautiful, convenient and comfortable. We throughly enjoyed our stay.

5.0

Oct 2023

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.

5.0

Oct 2023

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.

5.0

Sep 2023

This house was amazing for all my bridesmaids to get ready in!

5.0

Aug 2023

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!

5.0

Aug 2023

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!!

5.0

Aug 2023

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!

5.0

Jun 2023

The property was as advertised, beautifully appointed with several seating spaces for groups or individuals to gather and commune.

5.0

May 2023

Beautifully restored home perfect for groups. Immediately outside of Vineyard Haven village. Walkable to ferry, dining, shopping

5.0

Mar 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

2.0

Dec 2022

Hi Alex! Everything ran smoothly and the house is gorgeous! We did have an issue with heat. Back of house was about 55. The stovetop didn't have gas so we couldn't do the cooking of food we brought. We were able to use the oven for most things. Someone did come about 10pm Saturday to fill up the empty tank. The house was clean except for shelves in kitchen....dusty and dead bugs. Overall the experience was very good and I thank you. Lori

5.0

Dec 2022

This house was perfect for a relaxing weekend with friends. I would give it 6 stars if VRBO would let me.

5.0

Nov 2022

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

5.0

Nov 2022

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.

5.0

Oct 2022

Group of friends who came to the island for a wedding; host was easy to communicate with and the house was perfect!

5.0

Sep 2022

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.

5.0

Sep 2022

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.

5.0

Aug 2022

Could not have been better.

5.0

Jul 2022

Thanks very much !

Thanks very much !

Great stay !

5.0

Jul 2022

Ideal Vineyard Haven Large Home

Ideal Vineyard Haven Large Home

Highly recommend this home, a beautiful and private place to spend quality time with friends and family right in the heart of downtown Vineyard Haven.

5.0

Jul 2022

family fun

family fun

great

5.0

Jun 2022

Fantastic.

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!

5.0

Jun 2022

Tisbury weekend

Tisbury weekend

The house was excellent and everything we looked for. Would highly recommend this property in the future.

5.0

Jun 2022

Beautiful house

Beautiful house

We were really happy to stay here - the house was beautiful and the location was very nice.

5.0

May 2022

MS charity bike ride weekend

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.

5.0

Oct 2021

Such a GREAT house!

Such a GREAT house!

We were looking for a home on Martha's Vineyard to accommodate extended family for a family wedding on the island. This house was PERFECT. Everyone had a room, the living area was large enough for everyone to be in the same area for multiple conversations, games, meals, etc. Ages ranged from 3 to 77 - the house was perfect for all. Distance to town could not be better! Thank you for sharing your home with us! We could not recommend this house anymore - if we could give 6 stars we would.

5.0

Oct 2021

A must stay!

A must stay!

The Dexter House couldn’t have been more perfect! Alex was very responsive and accommodating and the house itself is within walking distance from the ferry, close to downtown shops, and had every amenity you could think of. Would highly recommend!

5.0

Oct 2021

We celebrated our 40th Wedding Anniversary with our family! It was such a bucolic area!

We celebrated our 40th Wedding Anniversary with our family! It was such a bucolic area!

Alexandra was a wonderful host and everything went smoothly from the booking and any special requests we had! It is a property worthy of a family adventure! You will not be disappointed! We will forever cherish our moments together!! Blessings Miss Karen

5.0

Sep 2021

Excellent stay. Everything as promised.

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!

5.0

Sep 2021

Fabulous place for a family reunion!!

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.

5.0

Aug 2021

Great in-town option for group

Great in-town option for group

The convenient location, walkability, parking, and lovely outdoor spaces made this an ideal spot for our 20-somethings as well as our 65-pluses. Kitchen is very well equipped and made it fun to cook together.

2.5

Jul 2021

This house was spectacular and perfect for family get together.Large porch was heavily used as we had some rainy weather. Kitchen was just amazing and everyone loved the coffee maker. Landscaping was lovely, especially view out of the kitchen window. We catered dinner in one night from Black Sheep. Plenty of room to set up food, etc. Rooms were comfortable and spacious. Alex was quick to respond to any questions prior to visit and during,. I would highly recommend this house and would love to rent again.

5.0

Jul 2021

Perfect for multiple groups/families

Perfect for multiple groups/families

I had my two older kids and the grandkids join us for one week. The house was perfect for the nine of us – – could’ve fit many more. We were able to be together when we wanted to, and we were able to have our private sitting space when we wanted. The house was everything it was described as. The host was very gracious and accommodating.

5.0

Jul 2021

Wonderful place for a multigenerational reunion

Wonderful place for a multigenerational reunion

The house was great. The proximity to town with restaurants and shopping was a huge plus. Alex was incredibly responsive to questions we had leading up to our stay. Overall a wonderful time with lots of memories made.

FAQs

How much does this house cost compared to others in Vineyard Haven?

The average price for a rental in Vineyard Haven is $666 per night. This rental is $1,261 above the average.

Is parking included with this house?

Yes, parking is listed as an amenity at Downtown Captain's Mansion- The Dexter- Family, pet, and event friendly. For more information, we encourage you to contact the property about where to park.

Is there a pool at this house?

We didn’t find pool listed as an amenity for this house. It may be worth double checking if a pool is important for your stay.

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

Yes! This house is pet-friendly. For more information, we recommend contacting the booking provider about animal policies.

What amenities are available at Downtown Captain's Mansion- The Dexter- Family, pet, and event friendly?

We found 13 amenities for this rental. This includes air conditioner, pets allowed, kitchen or kitchenette, internet / wifi, and fireplace.

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Outstanding(98 Reviews)

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Bed and Breakfast

in Vineyard Haven

1 king bed

Pool · Kitchen or Kitchenette · Air conditioner

This Bed and Breakfast in Vineyard Haven, is the right price for your (business stay, family stays, couples stay, getaway vacation, etc.) today!

$$$$

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

House in Vineyard Haven, MA

Reasons to book

About this house rental

Amenities

Map of Vineyard Haven, MA

Nearby attractions

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

House in Vineyard Haven, MA

Reasons to book

About this house rental

Amenities

Map of Vineyard Haven, MA

Nearby attractions

Reviews

FAQs

How much does this house cost compared to others in Vineyard Haven?

Is parking included with this house?

Is there a pool at this house?

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

What amenities are available at Downtown Captain's Mansion- The Dexter- Family, pet, and event friendly?

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