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Captain R. Flanders' House

440 North Rd, Chilmark, Martha's Vineyard, MA 02535-1882
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Room & Suite (2)

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About

#2 of 2 B&Bs in Chilmark
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Situated in the quiet town of Chilmark, Massachusetts on the island of Martha’s Vineyard. This renovated farmhouse, built by whaling Captain Richard Flanders in the late 1700’s is part of an original island homestead. The house has a delightful arrangement of antiques and country primitives that will add charm and uniqueness to your island stay.
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Property amenities
Free parking
Free High Speed Internet (WiFi)
Wifi
Free breakfast
Beach
Room types
Non-smoking rooms
Good to know
HOTEL STYLE
Charming
28Reviews0Q+A5Room tips

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KC wrote a review Oct 2022
1 contribution
This place is nearly impossible to communicate with. I had to book via email back in May because they didn't answer the phone - they said it was off season, OK fine. The day before my reservation I wanted to call and confirm and find out when check-in time was. I called EIGHT times throughout the day, no answer, only response I got was via email. When I arrived, it wasn't clear where to go. I found the innkeeper in the kitchen and she stared at me and I had to ask if she worked there, and asked to check in. She was not super helpful. She charged me for the full stay as soon as I arrived. When she showed me where to access my room, she seemed to be done with her spiel, but I had no room key. I asked for my room key, she said there are no room keys....???? The property is beautiful, the room was just OK. But I ended up not actually staying because I was so uncomfortable with not being able to lock my room. There are locks on the inside, so you can only lock it while you're in it. So your valuables would be unlocked inside with zero supervision or any security measures at all. As a woman traveling alone.... absolutely not. No thank you. When I went back to collect my things and let them know I wouldn't be staying, the entrance to my room had no lights on, so I'm entering a pitch black hallway that has not been locked. The hallway light was also broken and wouldn't turn on. I'm glad I left the light to my room on at least so I could see *something*. I packed up my car and went inside to look for the innkeeper. Nowhere to be found. I called, no answer. So I emailed to let them know I wouldn't be staying and I would need a refund for the full stay. I received an email from who I assume was the owner and they said they never had any issues but agreed to refund me for the full stay thankfully. She said she was surprised I couldn't reach the innkeeper because she lives on the premises -- uh yeah, me too! Innkeeper called to confirm the refund the next day and said she was sorry I felt uncomfortable but that on the island, they don't lock doors. Um, maybe at home but not at a hotel... and also you should disclose that to people up front. Thankfully I had a friend nearby I could stay with. This whole experience was bizarre and they have a lot of nerve charging $275 a night for a room with no locks, barely any amenities, and an incredibly unresponsive innkeeper who appeared to be the only person on staff.
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Date of stay: October 2022
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Cristian A wrote a review Sept 2022
1 contribution
We got the pond room for our one year anniversary and it ended up being like a fishbowl. Even with the blinds down you could see people walking around and listening in on us. Someone tried to open our locked room twice. The door in our room that led to the hallway had a crack under it at least four inches big that anyone leaning down could see our whole bed from. Zero noise cancellation and we could hear everything and everyone could hear us. The bathroom had a door that led outside that could not be locked. None of our windows could lock. No wifi when promised there was as well. We asked if we could cancel, as we booked it yesterday over the phone (you can’t book online) and they never said anything about a canceling policy, and the lady said no. Once we said all the issues with the room she said, “come on it’s just one night”… like what?!? We paid 250 bucks to suffer through a night?!? We left with 0 refund and was told to pay extra if we wanted a safer more private room…
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Date of stay: September 2022Trip type: Travelled as a couple
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.
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Sandra P wrote a review Aug 2022
Norfolk, Massachusetts201 contributions72 helpful votes
We stayed on night this past week, the inn is very quiet and lovely, the breakfast was more than I expected. The only thing that confused me was the brochure said our 2 rooms were $190 a night (shared bathroom) but we were charged $225, we were told the rates went up and the brochures were wrong and they were waiting for new ones from the printer. I would stay there again, the property is exceptional.
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Date of stay: August 2022
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Room Tip: We stayed on the first floor; we had the living room to ourselves and played checkers since there...
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Cruiser57744 wrote a review Sept 2021
1 contribution
+1
Our brief stay (1 night) was nothing short of Wonderful! We felt welcome from the moment we pulled into the driveway! Quiet, peaceful and beautiful are the first words I would use to describe our stay there! The InnKeeper was friendly and accommodating and efficient! We stayed in the stone cottage! Quaint! Wonderful story behind its inception. We hope to return and spend more time there!!
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Date of stay: September 2021Trip type: Travelled on business
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.
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Sidevan wrote a review Aug 2016
Boston, Massachusetts61 contributions9 helpful votes
We were skeptical at first, but were so delighted to be greeted by the staff upon our arrival and showed the house then to our room. The weather was hot and the room has no A/C. We are on an island and even tho, we had a great breeze, a wonderful night's sleep. Breakfast was served promptly at eight am. There was plenty of fresh food to carry anyone through to lunch. The scenery is beautiful, horses roam the property, it sure is steeped in history. We were on the island to attend the MV Agricultural Fair and it was a mere ten minute drive. Menemsha is four minutes away and if you ever want to see a gorgeous sunset, head there. It is a quaint fishing village and has some very nice restaurants. Eat in and take out. We recommend you try the Captain Flanders House. Way more affordable than any hotel on the island.
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Date of stay: August 2016
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Trip type: Travelled on business
Room Tip: Choose the "Wind" Room, beautiful breeze and view.
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This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.
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sac26 wrote a review Aug 2016
CT9 contributions6 helpful votes
I just spent two nights in the Wood Cottage at Captain Flanders House and I'm already plotting my return. The experience up-island is rustic no matter where you stay and CFH is no exception. The grounds are surrounded by stone walls and horses, deer, and geese roam about at their leisure. We arrived very early for our stay and met two of the housekeepers. They were lovely and provided us with our car and walk-on passes for the Chilmark beaches. We were also able to get into the cottage well ahead of our 3PM check-in because it was ready. The cottage is perfect for two people. The great room has big beautiful windows that remain undressed so that you can see the horses, deer, and geese anytime you want. There is a small mini-fridge in the room which was helpful. The bedroom and great room each have a fireplace which is a great touch if you find yourself there in the colder months. There was a wall air conditioner in the great room but temperatures were nice enough to leave the windows open. The bathroom is nice enough - nothing fancy. Cleanliness is most important and the entire place was very clean. We didn't see any bugs but I'm sure they were there - since you're basically sitting in the middle of a huge farm. look on google maps. The only nuisance was that of goose droppings but the maintenance team were cleaning it up shortly after our arrival. Watch where you walk on the entire property! You are free to wander the entire property and watch the horses, deer, geese, and bunnies. Breakfast each morning was continental style and offered scones, fruit, yogurt, cereal, granola, and bagels. Each afternoon they serve lemonade and cookies. I was appreciative that coffee was out and ready ahead of the 8AM breakfast. The property is incredibly low-key. This is the kind of B&B for the traveler that does not want to interact with others while on a getaway. There are two cottages and four rooms inside the Inn. The cottages do no lock and, like I said, the windows are not dressed. As long as you're cool with this then you'll be happy.
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Date of stay: July 2016
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Trip type: Travelled as a couple
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.
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magagoo wrote a review Feb 2016
Atlantic Beach, Florida459 contributions117 helpful votes
Was here for a wedding. It was one of the best weddings I have ever been to. Food was wonderful, service great and the views exceptional. They served lobster rolls as an h'orderve which were to die for.
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Date of stay: October 2015
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.
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Nazareba wrote a review Sept 2015
12 contributions17 helpful votes
This a very good option for those who love nature and quiet places, since this "hotel" that is actually made up of cottages and is located in a ranch/farm with horses and other animals..the Internet in here is really bad but it's definitely a great choice for those in looking for a quiet/relaxing time.
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Date of stay: July 2015
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.
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Lauren T wrote a review Jul 2015
Boston, Massachusetts4 contributions7 helpful votes
Last month, we stayed for almost a week at the Captain Flanders House, and we are still talking about how relaxed, inviting, and comfortable it was! We felt very free to come and go as if it were our own home. Unlike many bed and breakfasts where there is a bit of pressure to socialize with the innkeepers and other guests, the staff members were friendly, but took care of us in a more behind the scenes sort of way. We enjoyed coming downstairs every morning to a lovely breakfast waiting unceremoniously on the porch. Also, the farm setting is absolutely dreamy, so taking in the view was a great way to start the day. The rooms in the main house are cozy and make you feel like a guest in your favorite aunt’s country house, down to the understated furniture and antique-inspired bedding. The two cottages on the property are very private and both adorably appointed, too. Since we were there for a wedding, I can’t end this without mentioning what an unbelievable spot Captain Flanders is for a summer ceremony and reception. And what’s more, it was so great at the end of the party to wander back into the house and fall right asleep after hours of dancing! Could not have asked for a more perfect stay on Martha’s Vineyard!
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Date of stay: June 2015
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Trip type: Travelled with family
Room Tip: go for the cottages if traveling solo/as a couple, but families in need of multiple rooms will...
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This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.
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Becca S wrote a review Jul 2015
Boston, Massachusetts1 contribution
We had an absolutely delightful stay at the Captain Flanders House this summer and hosted our wonderful wedding on its breathtakingly beautiful grounds. The location could not have been more perfect for us. The inn itself is charming, clean, and comfortable, and the staff is very kind and helpful! An unforgettable wedding weekend! Thank you!
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Date of stay: June 2015
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Trip type: Travelled with family
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.
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LOCATION
United StatesMassachusettsMartha's VineyardChilmark
NUMBER OF ROOMS
7
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CAPTAIN R. FLANDERS' HOUSE - Updated 2024 Prices (Chilmark, MA)

Frequently Asked Questions about Captain R. Flanders' House
Which popular attractions are close to Captain R. Flanders' House?
Nearby attractions include Aquinnah Cliffs (0.9 miles), Gay Head Light (Aquinnah Light) (4.3 miles), and Gay Head (4.3 miles).
What are some of the property amenities at Captain R. Flanders' House?
Some of the more popular amenities offered include free wifi, free breakfast, and free parking.
What food & drink options are available at Captain R. Flanders' House?
Guests can enjoy free breakfast during their stay.
Is parking available at Captain R. Flanders' House?
Yes, free parking is available to guests.
What are some restaurants close to Captain R. Flanders' House?
Conveniently located restaurants include Larsen's Fish Market, Menemsha Fish Market, and 7a Foods.
Are there any historical sites close to Captain R. Flanders' House?
Many travellers enjoy visiting Aquinnah Cliffs (0.9 miles).