Title: Downtown Captain's Mansion- The Dexter- Family, pet, and event friendly - Latest Reviews, Deals & Photos 2026 - Expedia.ca [See all properties](http://www.expedia.ca/Hotel-Search?regionId=&selected=49037659&adults=2&children=&sort=RECOMMENDED&useRewards=false&semdtl=&userIntent=&vip=false) Entire home # Downtown Captain's Mansion- The Dexter- Family, pet, and event friendly Family-friendly vacation home in Vineyard Haven ## Photo gallery for Downtown Captain's Mansion- The Dexter- Family, pet, and event friendly ![Outdoor dining - Downtown Captain's Mansion- The Dexter- Family, pet, and event friendly (Tisbury)](https://images.trvl-media.com/lodging/50000000/49040000/49037700/49037659/f65d6d1e.jpg?impolicy=resizecrop&rw=598&ra=fit) ![Property video](https://mediaim.expedia.com/video/9A1CB9973399C0715D59CB4C219CD018/5c23d217-9ac4-4a61-8657-c882f15e35a3-thumbnail.jpg?impolicy=resizecrop&rw=608) ![Fridge, microwave, oven, stovetop - Downtown Captain's Mansion- The Dexter- Family, pet, and event friendly (Tisbury)](https://images.trvl-media.com/lodging/50000000/49040000/49037700/49037659/9c73882b.jpg?impolicy=resizecrop&rw=297&ra=fit) ![Property grounds - Downtown Captain's Mansion- The Dexter- Family, pet, and event friendly (Tisbury)](https://images.trvl-media.com/lodging/50000000/49040000/49037700/49037659/e9981cdb.jpg?impolicy=resizecrop&rw=297&ra=fit) ![Exterior - Downtown Captain's Mansion- The Dexter- Family, pet, and event friendly (Tisbury)](https://images.trvl-media.com/lodging/50000000/49040000/49037700/49037659/6365bc78.jpg?impolicy=resizecrop&rw=297&ra=fit) - Overview - Location - Amenities - Policies In the heart of Vineyard Haven, The Dexter is a historic whaling captain's house offering 9 bedrooms, 6.5 baths and numerous lounges. Take advantage of an outdoor shower, private patio with grill and wrap-around porch overlooking the harbor. ## Reviews 10 Exceptional ### Entire home 9 bedrooms7 bathroomsSleeps 186800 sq ft ## Popular amenities - Ocean view - Kitchen - Washer - Dryer - Pet friendly - Free WiFi ## Add dates for prices Check-in Check-out Travellers ## About this property ### Entire place You'll have the entire home to yourself and will only share it with other guests in your party. ### Downtown Captain's Mansion- The Dexter- Family, pet, and event 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, 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. ## Property amenities ### Beach - Beach nearby - Beach loungers - Beach towels ### Internet - Available in the house: Free WiFi ### Parking and transportation - Car not required - Wheelchair-accessible parking available ### Kitchen - Blender - Coffee grinder - Coffee/tea maker - Cookware, dishware, and utensils - Dishwasher - Electric kettle - Ice maker - Kitchen island - Lobster/crab pot - Microwave - Oven - Paper towels - Refrigerator - Spices - Stovetop - Toaster ### Dining - Breakfast available for a fee - Dining table ### Bedrooms - 9 bedrooms - Bedsheets provided - Sofa bed ### Bathroom - 6.5 bathrooms - Bathtub - Hair dryer - Shower - Soap - Toilet paper - Towels provided ### Living spaces - Dining table - Fireplace - Living room ### Entertainment - Books - DVD player - Games - Smart TV with cable/satellite channels - Stereo ### Outdoor areas - Balcony - Barbecue grill - Fenced yard - Firepit - Garden - Outdoor furniture ### Laundry - Laundry facilities - Washing machine ### Work spaces - Desk - Desk chair ### Comfort - Air conditioning - Heating ### Pets - Pet friendly - 2 pets total ### Suitability/Accessibility - If you have requests for specific accessibility needs, please contact the property using the information on the reservation confirmation received after booking. - 1 accessible parking space - Upper floors accessible by stairs only - Wheelchair accessibility - Wheelchair-accessible parking - Smoking not allowed ### Services and conveniences - Iron/ironing board - Phone ### Location highlights - In a village - In the city center - Near a health/beauty spa - Near a hospital - Near the bay - Near the marina - Near the sea ### Things to do - Bicycles - Birdwatching nearby - Fishing nearby - Hiking/biking trails nearby - Kayaking nearby - Motor boating nearby - Sailing nearby - Swimming nearby - Wildlife walks nearby - Windsurfing nearby ### Safety features - Carbon monoxide detector (host has indicated there is a carbon monoxide detector on the property) - Smoke detector (host has indicated there is a smoke detector on the property) - First aid kit - Fire extinguisher - Deadbolt lock ### General - Bicycles - Garden - Unit size: 6,800 square feet ## Similar properties ![Terrace/patio](https://images.trvl-media.com/lodging/94000000/93450000/93448200/93448195/ef194641.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### PRIVACY & RELAXATION ON MARTHA'S VINEYARD Tisbury - Pool - Kitchen - Washer - Dryer 10 Exceptional 8 reviews [](https://www.expedia.ca/Hotel-Search?startDate=2026-02-05&endDate=2026-02-06&selected=93448195&PinnedHotelID=93448195&HadPinnedHotel=true®ionId=-1&adults=2) ![Exterior](https://images.trvl-media.com/lodging/76000000/75790000/75781300/75781228/a9fca29e.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### Large Falmouth Heights Home Sleeps Up to 17 RPAM030 Falmouth Heights - Ocean view - Kitchen - Washer - Dryer 9.8 Exceptional 57 reviews [](https://www.expedia.ca/Hotel-Search?startDate=2026-02-05&endDate=2026-02-06&selected=75781228&PinnedHotelID=75781228&HadPinnedHotel=true®ionId=-1&adults=2) ![Dining](https://images.trvl-media.com/lodging/113000000/112180000/112175100/112175052/788e32c7.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### Lakefront Stunning Cape Cod Views w Private Lake Beach - Backyard is the Lake ! 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Inner Village, Amazing Pool/ Outdoor Entertaining Areas! Edgartown - Pool - Kitchen - Washer - Dryer 9.8 Exceptional 6 reviews [](https://www.expedia.ca/Hotel-Search?startDate=2026-02-05&endDate=2026-02-06&selected=30522035&PinnedHotelID=30522035&HadPinnedHotel=true®ionId=-1&adults=2) ## 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 ### Special check-in instructions You will receive an email from the host with check-in and check-out instructions Information provided by the property may be translated using automated translation tools ### Check-out instructions The host requires you complete the following before checking out: Load and start the dishwasher Gather used towels Remove personal items, remove leftover food and drinks, and take out the trash Turn off the lights, lock the doors, and return the keys Failure to complete these may result in a negative review from the host. ### Pets Pets allowed Service animals are welcome, and are exempt from fees 2 total pets Note from host: Dog friendly residence. Yard is partially fenced. ### Children and extra beds Children are welcome ### Events Events allowed: family gatherings, birthday parties, weddings ### Smoking Smoking is not permitted ## Important information ### You need to know 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 Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed Parties and events (including family gatherings, birthday parties and weddings) are allowed on site; maximum attendees: 30 Long-term renters welcome Host has indicated there is a carbon monoxide detector on the property Host has indicated there is a smoke detector on the property Safety features at this property include a fire extinguisher, a first aid kit, and a deadbolt lock 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 Property Registration Number C0363072960 ### We should mention This property does not have elevators A car is not required for transportation to and from this property ### Property is also known as Vrbo Property ## About the area Located in Vineyard Haven, this vacation home is in the city center and near the beach. Cape Cod Beaches and Felix Neck Wildlife Sanctuary reflect the area's natural beauty and area attractions include Island Cove Adventures and Flying Horses Carousel. Traveling with kids? Consider Polly Hill Arboretum and Chilmark Chocolates. Be sure to check out the area's animals with activities such as game walks and birdwatching. [Visit our Vineyard Haven travel guide](https://www.expedia.ca/Vineyard-Haven.dx6213) [View more Vacation homes in Vineyard Haven](https://www.expedia.ca/Vineyard-Haven-Private-Vacation-Homes.d6213-aaPrivateVacationHomes.Travel-Guide-Accommodation) ![Map](https://maps.googleapis.com/maps/api/staticmap?&size=660x330&map_id=3b266eb50d2997c6&zoom=13&markers=icon:https%3A%2F%2Fa.travel-assets.com%2Ftravel-assets-manager%2Feg-maps%2Fproperty.png%7C41.45627%2C-70.60332&channel=expedia-HotelInformation&maptype=roadmap&scale=1&key=AIzaSyCYjQus5kCufOpSj932jFoR_AJiL9yiwOw&signature=NBtlF-YZkQ4wCAnBFPERN9AIvmA=) Tisbury, MA ### What's nearby - Martha's Vineyard Chamber of Commerce 5 min walk \- 0.4 km - Vineyard Haven Terminal 5 min walk \- 0.5 km - Martha's Vineyard Film Center 8 min walk \- 0.7 km - Martha's Vineyard Museum 13 min walk \- 1.1 km - Tisbury Town Beach 14 min walk \- 1.2 km ### Getting around - Vineyard Haven, MA (MVY-Martha's Vineyard) 12 min drive ### Restaurants - The Black Dog Tavern 6 min walk - Portuguese-American Club 5 min drive - Porto Pizza 3 min walk - Mo's Lunch 6 min drive - Cumberland Farms 5 min walk ## Frequently asked questions ### Is Downtown Captain's Mansion- The Dexter- Family, pet, and event friendly pet-friendly? ### How much is parking? ### What time is check-in at Downtown Captain's Mansion- The Dexter- Family, pet, and event friendly? ### What time is check-out at Downtown Captain's Mansion- The Dexter- Family, pet, and event friendly? ### Where is Downtown Captain's Mansion- The Dexter- Family, pet, and event friendly located? ## Have a question? Beta Get instant answers with AI powered search of property information and reviews. Ask a question ## Downtown Captain's Mansion- The Dexter- Family, pet, and event friendly Reviews ## Reviews ### Exceptional All reviews shown are from real guest experiences. Only travellers who have booked a stay with us can submit a review. We verify reviews according to our guidelines and publish all reviews, positive or negative. [More information](https://www.expedia.ca/lp/b/content-guidelines) 10 - Excellent 67 8 - Good 0 6 - Okay 0 4 - Poor 0 2 - Terrible 0 ### 10 Cleanliness ### 10 Location ## Reviews ### 10/10 Excellent #### Amanda C. Oct 16, 2025 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! ##### Amanda C. Stayed 4 nights in Oct 2025 ### 10/10 Excellent #### Molly H. Jul 31, 2025 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! ##### Molly H. Stayed 7 nights in Jul 2025 ### 10/10 Excellent #### Christian V. Mar 24, 2024 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! ##### Christian V. Stayed 2 nights in Mar 2024 ### 10/10 Excellent #### Jennifer J. Aug 19, 2024 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! ##### Jennifer J. Stayed 7 nights in Aug 2024 ### 10/10 Excellent #### Gwen G. Nov 16, 2023 Liked: Cleanliness, check-in, communication, location, listing accuracy #### Excellent family vacation The home was beautiful, convenient and comfortable. We throughly enjoyed our stay. ##### Gwen G. Stayed 4 nights in Nov 2023 ### 10/10 Excellent #### Verified traveller Dec 8, 2024 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. ##### Verified traveller Stayed 3 nights in Dec 2024 ### 10/10 Excellent #### Peter S. Jun 3, 2024 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! ##### Peter S. Stayed 2 nights in Apr 2024 ### 10/10 Excellent #### holly g. Sep 30, 2024 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! ##### holly g. Stayed 3 nights in Sep 2024 ### 10/10 Excellent #### Eileen F. Jun 3, 2024 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. ##### Eileen F. Stayed 3 nights in May 2024 ### 10/10 Excellent #### Julie A. Oct 8, 2024 Liked: Cleanliness, check-in, communication, location, listing accuracy #### Everything was perfect Everything was wonderful. The home was clean, beautiful spot. We enjoyed every minute ##### Julie A. Stayed 2 nights in Oct 2024 ### 10/10 Excellent #### jane d. Nov 25, 2024 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. ##### jane d. Stayed 4 nights in Nov 2024 ### 10/10 Excellent #### Nikki J. Aug 24, 2023 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!! ##### Nikki J. Stayed 7 nights in Aug 2023 ### 10/10 Excellent #### Bonnita B. Aug 26, 2023 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! ##### Bonnita B. Stayed 7 nights in Aug 2023 ### 10/10 Excellent #### Lori S. Aug 8, 2023 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! ##### Lori S. Stayed 7 nights in Jul 2023 ### 10/10 Excellent #### Nancy H. Oct 10, 2023 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. ##### Nancy H. Stayed 5 nights in Oct 2023 ### 10/10 Excellent #### Sharon M. Mar 31, 2025 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. ##### Sharon M. Stayed 5 nights in Mar 2025 ### 10/10 Excellent #### Liz G. Aug 5, 2024 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. ##### Liz G. Stayed 7 nights in Jul 2024 ### 10/10 Excellent #### Rebecca B. May 27, 2025 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! ##### Rebecca B. Stayed 7 nights in May 2025 ### 10/10 Excellent #### Susan S. Oct 13, 2025 Liked: Cleanliness, check-in, communication, location, listing accuracy This property is amazing for a large group! Location is incredible too! ##### Susan S. Stayed 3 nights in Oct 2025 ### 10/10 Excellent #### Lesley Z. Sep 28, 2025 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. ![](https://a.travel-assets.com/ugc/hotel-reviews/bae23c6c-8a39-4bdd-86a3-7f360f7e0282-1759099445936.jpg?impolicy=resizecrop&rw=204&ra=fit&q=high) ![](https://a.travel-assets.com/ugc/hotel-reviews/d57dae5e-bbe1-430b-9526-38063217bd8b-1759099443808.jpg?impolicy=resizecrop&rw=204&ra=fit&q=high) ![](https://a.travel-assets.com/ugc/hotel-reviews/4bba84d1-a4ae-43b9-8f59-a2b06ba2ecd2-1759099445730.jpg?impolicy=resizecrop&rw=204&ra=fit&q=high) ![](https://a.travel-assets.com/ugc/hotel-reviews/3f31705b-4714-43a0-8887-45dc2bf81a36-1759099446762.jpg?impolicy=resizecrop&rw=204&ra=fit&q=high) ##### Lesley Z. Stayed 7 nights in Sep 2025 ### 10/10 Excellent #### ROBYN M. Jul 3, 2025 Liked: Cleanliness, check-in, communication, location, listing accuracy #### Beautiful House The house was well stocked and had everything you could need. ##### ROBYN M. Stayed 2 nights in Jun 2025 ### 10/10 Excellent #### Ann V. May 23, 2025 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. ##### Ann V. Stayed 2 nights in May 2025 ### 10/10 Excellent #### William R. Mar 12, 2025 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. ##### William R. Stayed 2 nights in Mar 2025 ### 10/10 Excellent #### George D. Nov 3, 2024 Liked: Cleanliness, check-in, communication, location, listing accuracy #### Wedding weekend We all had the best time and LOVED the house and its location! ##### George D. Stayed 2 nights in Nov 2024 ### 10/10 Excellent #### Megan H. Jun 7, 2022 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. ##### Megan H. 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