Downtown Captain's Mansion- The Dexter- Family, pet, and event friendly | House in Tisbury

10.0 (67 Reviews) |   Pet Friendly   9 Bedrooms  6 Bathrooms  18 Guests
Vineyard Haven House | Downtown Captain's Mansion- The Dexter- Family, pet, and event friendly

9 Bedroom House in Vineyard Haven, Tisbury

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 welcome bachelorette parties, reunions, work retreats, etc, etc, etc.
Accepting books for summer 2026 Saturday-Saturday. One vehicle ferry reservation included with your booking.
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.

Downtown Captain's Mansion- The Dexter- Family, pet, and event friendly is located in Vineyard Haven. Downtown Captain's Mansion- The Dexter- Family, pet, and event friendly provides accommodation, featuring Bedding/Linens, Wellness Facilities, Barbecue/Outdoor Cooking, among other amenities. This House features Bedding/Linens, Wellness Facilities, Barbecue/Outdoor Cooking, to make your stay a comfortable one.

Downtown Captain's Mansion- The Dexter- Family, pet, and event friendly has 9 Bedrooms , 6 Bathrooms, and max occupancy of 18 people. The minimum rental for this property is 1 nights, but this can change depending on the season you plan on staying. Previous guests have given good rated it, and VRBO labeled it a top-rated House because of the excellent services rendered by the owner or manager of this House, and has consistently provided great experiences for their guests. Most families or guests that use it recommend it to their friends and some of them are repeat guests. House has a friendly neighborhood, and the Vineyard Haven has interesting places to visit. If you want to learn more about the House in Vineyard Haven, such as places to visit and things to do nearby, you can check below to learn more.

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Amenities

Air Conditioner
Parking
Pet Friendly
TV
View
Ocean View
Balcony/Terrace
Oceanfront
Accessibility
Security/Safety
Sports/Activities
Bedding/Linens
Wellness Facilities
Fireplace/Heating
Guest Services
Entertainment
Breakfast
Barbecue/Outdoor Cooking
Child Friendly
Internet
Kitchen
Laundry

Facility Overview

Air Conditioner
  • Air conditioning
  • Heating
Bathrooms
  • Shower
  • Toilet paper
  • Towels provided
  • 6+ bathrooms
  • Soap
  • Hair dryer
Bedroom
  • 9 bedrooms
  • Bed sheets provided
  • Sofa bed
  • Breakfast available for a fee
  • Dining table
  • Living room
  • Fireplace
Kitchen
  • Kitchen island
  • Refrigerator
  • Stovetop
  • Dishwasher
  • Coffee/tea maker
  • Oven
  • Toaster
  • Coffee grinder
  • Microwave
Laundry
  • Laundry facilities
  • Washing machine and dryer
Ocean view
  • Beach towels
  • Near the beach
  • Beach sun loungers
Parking
  • Wheelchair-accessible parking available
  • Car not required
  • Onsite parking
Pet Friendly
  • 2 total pets
  • Pet friendly
Accessibility
  • No elevators
  • Upper floors accessible by stairs only
  • Wheelchair accessible
  • If you have requests for specific accessibility needs, please contact the property using the information on the reservation confirmation received after booking.
  • 1 on-site accessible parking spaces
  • Smoke-free property
  • Wheelchair-accessible parking
Activities
  • Fitness facilities nearby
  • Sailing nearby
  • Windsurfing nearby
  • Birdwatching nearby
  • Kayaking nearby
  • Swimming nearby
  • Hiking/biking trails nearby
  • Wildlife and game walks nearby
  • Bicycle on site
  • Marina nearby
  • Hiking nearby
Entertainment
  • DVD player
  • Stereo
  • Games
  • Smart TV with cable/satellite service
  • Books
General
  • Unit size: 6800 sq ft (632 sq m)
  • English
  • Near a hospital
  • Near the bay
  • Near the sea
  • In a village
  • In the city center
  • Near a health or beauty spa
  • Desk
  • Desk chair
Guest Services
  • Playground
  • Children's games
  • Children's toys
  • Highchair
  • Children's books
  • Children's dinnerware
  • Phone
  • Iron/ironing board
Internet
  • Free WiFi
Outdoors
  • Balcony
  • Firepit
  • Barbecue grill
  • Fenced yard
  • Outdoor furniture
  • Garden
Security/Safety
  • First aid kit
  • Smoke detector installed (host has indicated there is a smoke detector on the property)
  • Carbon monoxide detector installed (host has indicated there is a carbon monoxide detector on the property)
  • Deadbolt lock
  • Fire extinguisher

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
Child Policy
Children are welcome.
Event Policy
Events allowed: family gatherings, birthday parties, weddings;maximum event attendees: 30
Pet Policy
2 total pets note from host: dog friendly residence. yard is partially fenced. pets allowed service animals are welcome, and are exempt from fees
Smoking Policy
Smoking is not permitted

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 host has indicated there is a carbon monoxide detector on the property host has indicated there is a smoke detector on the property long-term renters welcome parties and events (including family gatherings, birthday parties and weddings) are allowed on site; maximum attendees: 30 property registration number c0363072960 safety features at this property include a fire extinguisher, a first aid kit, and a deadbolt lock special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed 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

License number: C0363072960

Reviews

Ali M.
Sep 15, 2025 04:08:49 AM
Review Score:   10
Summary: We had a fantastic stay at the Dexter for a wedding weekend. Our group unanimously declared it one of the largest and nicest homes any of us have ever rented. The kitchen is gorgeous- equipped with more than enough dishes, silverware and kitchen gadgets- often a concern in rentals. Every room was clean and coastal chic, the beds were comfy as well. It’s so rare to find a place for such a large group that still allows for privacy, space, and ample bathrooms. The “sofa” bedroom was private and included a half bath- there was so much common living space it didn’t feel like a makeshift accommodation and our friends who stayed in that room were very happy as well. The captains suite was GIGANTIC and our group had a blast getting ready for the wedding together up there. While not well advertised in the listing, the outdoor shower was a favorite feature for many. Others lamented that they wished they had more time to read cozied up on the porch and by the fire pit during down time as it was so peaceful. We honestly didn’t have a single criticism and were just wowed by every aspect of the house- tons of games, fresh flowers on the coffee table, takeout menus, Keurig cups, local tips.With a perfect location, walkable to ferry, beach, cafes and shops, a car is definitely not necessary, but it was a perk to have ample parking. Finally, Alex made all of the logistics a breeze. She was unbelievably quick to reply and generously flexible with timing. We can’t wait to come back!
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