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

10.0 (62 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 TV, Bedding/Linens, Child Friendly, among other amenities. This House features TV, Bedding/Linens, Child Friendly, 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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Tisbury, 02568, USA

Amenities

Air Conditioner
Parking
Pet Friendly
TV
View
Ocean View
Balcony/Terrace
Oceanfront
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
  • Soap
  • Shower
  • 6+ bathrooms
  • Toilet paper
  • Towels provided
  • Hair dryer
Bedroom
  • Sofa bed
  • Bed sheets provided
  • 9 bedrooms
  • Dining table
  • Breakfast available for a fee
  • Living room
  • Fireplace
Kitchen
  • Stovetop
  • Ice maker
  • Refrigerator
  • Microwave
  • Blender
  • Electric kettle
  • Oven
  • Toaster
  • Dishwasher
Laundry
  • Laundry facilities
  • Washing machine and dryer
Ocean view
  • Beach sun loungers
  • Near the beach
  • Beach towels
Parking
  • Car not required
  • Onsite parking
Pet Friendly
  • 2 total pets
  • Pet friendly
Accessibility
  • Smoke-free property
Activities
  • Marina nearby
  • Windsurfing nearby
  • Hiking/biking trails nearby
  • Bicycle on site
  • Swimming nearby
  • Fitness facilities nearby
  • Hiking nearby
  • Power boating nearby
  • Birdwatching nearby
  • Kayaking nearby
  • Sailing nearby
Entertainment
  • Games
  • Books
  • Smart TV with cable/satellite service
  • Stereo
  • DVD player
General
  • Unit size: 6800 sq ft (632 sq m)
  • English
  • Near the bay
  • Near a health or beauty spa
  • Near the sea
  • Near a hospital
  • In a village
  • In the city center
  • Desk
  • Desk chair
Guest Services
  • Children's dinnerware
  • Children's toys
  • Highchair
  • Children's books
  • Playground
  • Children's games
  • Phone
  • Iron/ironing board
Internet
  • Free WiFi
Outdoors
  • Fenced yard
  • Balcony
  • Barbecue grill
  • Outdoor furniture
  • Garden
  • Firepit
Security/Safety
  • Fire extinguisher
  • First aid kit
  • Deadbolt lock
  • 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)

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

Rebecca B.
May 28, 2025 04:32:23 AM
Review Score:   10
Summary: 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!
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FAQ's

Is this Vineyard Haven house pet-friendly for guests?

Yes, pets are allowed at this property. Check the guest reviews to learn what guests had to share.

Does the Vineyard Haven house have a swimming pool?

No, this Vineyard Haven house does not have a swimming pool. Check the Facility Overview section for details about the pool and other available facilities.

How much does it cost per night to stay in Vineyard Haven house?

Best-rates for the Vineyard Haven house starts from $1,273 per night with includes Ocean View, Oceanfront, Guest Services, Barbecue/Outdoor Cooking, Kitchen, Air Conditioner, Sports/Activities, Wellness Facilities, Entertainment, Breakfast, Parking, TV, Bedding/Linens, Child Friendly, Internet, Pet Friendly, View, Balcony/Terrace, Security/Safety, Fireplace/Heating, Laundry With all other amenities included. Treehouse Rentals offers a wide range of treehouses, forest homes, cabins, and off-grid retreats, ensuring each traveler discovers their ideal nature getaway—be it a family adventure, a peaceful retreat, or a pet-friendly retreat with the whole group.

Is Vineyard Haven house a family-friendly place to stay?

Based on the information we have received from the owner or our partner, this is considered to be a family-friendly property. Families have rated this house Good or guests have recommended them suitable for families. As reported by the owner or manager, the house has specified that children are welcome. Please see details about suitability for your family or inquire with the property to learn more.

Is the Vineyard Haven house wheelchair accessible or offer services for disabled guests?

Based on the information received from our partner, the Vineyard Haven house has not specified they are wheelchair accessible. Likewise, there is not an elevator specified as being available at the property. Specific accessibility details may be addressed in the property details section of this page.

What is the minimum night stay policy for the Vineyard Haven house?

Based on the information reported by the owner or manager, the Vineyard Haven house indicates 1 day stay policy at this house. Guests are cautioned that the minimum stay policy may differ based on seasonality or availability and may be at the discretion of the owner or manager.

What cancellation policy is in place for Vineyard Haven house?

Based on the information reported by the owner or manager, details for the cancellation policy for the Vineyard Haven house are as follows: Cancellation policy Guests are cautioned that the cancellation policy may differ based on seasonality, availability, or current travel restrictions. Guests should also be aware that this policy may be subject to change and should be confirmed prior to booking. More details may be available on this page in the property description. However, early check-in or late check-out can sometimes be negotiated between the guest and the owner or the manager of this property.

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