Apartment
Perfect location! By Beach, Harbor & Town! Gorgeous Gingerbread Upstairs Aptmt
Photo gallery for Perfect location! By Beach, Harbor & Town! Gorgeous Gingerbread Upstairs Aptmt





Reviews
9.8 out of 10
Exceptional
1 bedroom 1 bathroom Sleeps 4
Popular amenities
Explore the area

56 Kennebec Ave, Oak Bluffs, MA, 02557
- Oak Bluffs Ferry Terminal5 min walk
- Oak Bluffs Town Beach7 min walk
- Inkwell Beach8 min walk
- Vineyard Haven, MA (MVY-Martha's Vineyard)15 min drive
Rooms & beds
1 bedroom (sleeps 4)
Bedroom
1 Queen Bed
Living Room
1 Double Sofa Bed
1 bathroom
Bathroom
Soap · Toilet · Shower only · Shampoo · Hair dryer
Spaces
Deck or patio
Kitchen
About this property
Perfect location! By Beach, Harbor & Town! Gorgeous Gingerbread Upstairs Aptmt
July and August: Turnover day is generally Friday.
This lovely, in-town, impeccably renovated 1800's historic Oak Bluffs upstairs apartment is adored by all who stay here. With original architectural details and a warmth brought forth by owner Sharon, the apartment is truly an oasis in the heart of Oak Bluffs.
The apartment has a sunlit living room with beautiful breezes through many new windows flanking both sides, a kitchen, full bath with standing shower, and a lovely and spacious sunlit bedroom with meditation nook and skylight.
The house is very special, with beautiful energy from all the wonderful people who have stayed there and graced its walls. Up to four people are welcome in this apartment. The living room has a very comfortable full size sofa bed.
Quiet hours are 9pm to 9am.
Surrounded by all the vibrant and colorful life of Oak Bluffs in every direction, there is never a need to commute into town for the island's most popular events. The August Fireworks, Illumination night, concerts on the park are all around the corner.
The apartment is a very short walk along beautiful Ocean Park from the ferry, a couple of blocks from the islands exceptional transportation system, a couple of blocks to Inkwell Beach, a block from exceptional restaurants and bars, practically next door to performances at the Tabernacle or Union Chapel, a block from the Methodist Campgrounds with their spectacular and colorful historic Gingerbread houses, a few blocks from the Harbor with its magnificent sunsets and waterfront restaurants and nightlife, and the ice cream shops, arcade, movie theatres and live local music of Circuit Ave. The breathtaking bike path from Oak Bluffs to Edgartown, with water on both sides, begins just a few blocks from the house, and running and walking paths through nature trails are a short jog away. Oak Bluffs truly has everything, and in my heart is the jewel of Martha's Vineyard Island.
Most guests find this home to be a generally quiet oasis for being right in the center of town, but just a reminder that the house IS in the center of town, just not on the main shopping drag. ;)
One more IMPORTANT thing for you dog owners:
We LOVE dogs and this property is selectively dog friendly (sorry, no cats)! If you'd like to bring your doggo along, you must ask us first, so we can be sure you agree to our pet guidelines. THANK YOU!
House Story:
I fell in love with this house the minute I saw it. It took me a full winter to be able to be able to call it my own, because when I made the offer the owner was concerned about disappointing someone else, though they had was no contract at all. She was so kind, she spent a few months trying to find this person, who was out of the country and difficult to track down. In the meantime, she knew how much I loved the house, and after several long months she called to say it was mine if I still wanted it, and I could take a few days to let her know. I told her I didn’t even need a few minutes. No other house that I had seen captured my heart as this one had.
It took great amounts of work to prep this house to be my massage center, as it would be for some years before I could make it my home. One day, at my other massage center in Vineyard Haven, I interviewed a lovely massage therapist from Louisiana. I had no idea she had MV ties, but I instantly adored her and her work and hired her on the spot and sent her here to do a massage. Twenty minutes passed, and the phone rang. “You are not going to believe this, Sharon, but this is the house my grandmother grew up in.”
Oma (grandmother in German), came right over the next day from West Tisbury, where she then summered, brought me this photo of her parents and this house as it was in 1908, and gave me a tour of the house, telling me where all the original details used to be. Oma was beautiful, and her granddaughter is beautiful, as was the previous owner. I just kept feeling that it was no wonder that it feels so special in here. Since that time, my friends, family and guests have only added to that feeling. Time and time again, people walk in and comment on the energy of the home. I feel it deeply myself.
To top off all of this wonder, the last bit of amazement for me was the dog in the photo - a dog with a half black and half white face, split down the middle. On the other side of the couch, you can see the photo of my dog, Haffa, at the time. A dog with a half black and half white face, split down the middle, almost 100 years later.
Life is magical, mysterious and beyond imagination.
If these dates are not available, please send us a message. We have other beautiful properties.
(Please note: We do have a guest-centered and considerate cancellation policy. Please see our attached cancellation policy for details.)
This lovely, in-town, impeccably renovated 1800's historic Oak Bluffs upstairs apartment is adored by all who stay here. With original architectural details and a warmth brought forth by owner Sharon, the apartment is truly an oasis in the heart of Oak Bluffs.
The apartment has a sunlit living room with beautiful breezes through many new windows flanking both sides, a kitchen, full bath with standing shower, and a lovely and spacious sunlit bedroom with meditation nook and skylight.
The house is very special, with beautiful energy from all the wonderful people who have stayed there and graced its walls. Up to four people are welcome in this apartment. The living room has a very comfortable full size sofa bed.
Quiet hours are 9pm to 9am.
Surrounded by all the vibrant and colorful life of Oak Bluffs in every direction, there is never a need to commute into town for the island's most popular events. The August Fireworks, Illumination night, concerts on the park are all around the corner.
The apartment is a very short walk along beautiful Ocean Park from the ferry, a couple of blocks from the islands exceptional transportation system, a couple of blocks to Inkwell Beach, a block from exceptional restaurants and bars, practically next door to performances at the Tabernacle or Union Chapel, a block from the Methodist Campgrounds with their spectacular and colorful historic Gingerbread houses, a few blocks from the Harbor with its magnificent sunsets and waterfront restaurants and nightlife, and the ice cream shops, arcade, movie theatres and live local music of Circuit Ave. The breathtaking bike path from Oak Bluffs to Edgartown, with water on both sides, begins just a few blocks from the house, and running and walking paths through nature trails are a short jog away. Oak Bluffs truly has everything, and in my heart is the jewel of Martha's Vineyard Island.
Most guests find this home to be a generally quiet oasis for being right in the center of town, but just a reminder that the house IS in the center of town, just not on the main shopping drag. ;)
One more IMPORTANT thing for you dog owners:
We LOVE dogs and this property is selectively dog friendly (sorry, no cats)! If you'd like to bring your doggo along, you must ask us first, so we can be sure you agree to our pet guidelines. THANK YOU!
House Story:
I fell in love with this house the minute I saw it. It took me a full winter to be able to be able to call it my own, because when I made the offer the owner was concerned about disappointing someone else, though they had was no contract at all. She was so kind, she spent a few months trying to find this person, who was out of the country and difficult to track down. In the meantime, she knew how much I loved the house, and after several long months she called to say it was mine if I still wanted it, and I could take a few days to let her know. I told her I didn’t even need a few minutes. No other house that I had seen captured my heart as this one had.
It took great amounts of work to prep this house to be my massage center, as it would be for some years before I could make it my home. One day, at my other massage center in Vineyard Haven, I interviewed a lovely massage therapist from Louisiana. I had no idea she had MV ties, but I instantly adored her and her work and hired her on the spot and sent her here to do a massage. Twenty minutes passed, and the phone rang. “You are not going to believe this, Sharon, but this is the house my grandmother grew up in.”
Oma (grandmother in German), came right over the next day from West Tisbury, where she then summered, brought me this photo of her parents and this house as it was in 1908, and gave me a tour of the house, telling me where all the original details used to be. Oma was beautiful, and her granddaughter is beautiful, as was the previous owner. I just kept feeling that it was no wonder that it feels so special in here. Since that time, my friends, family and guests have only added to that feeling. Time and time again, people walk in and comment on the energy of the home. I feel it deeply myself.
To top off all of this wonder, the last bit of amazement for me was the dog in the photo - a dog with a half black and half white face, split down the middle. On the other side of the couch, you can see the photo of my dog, Haffa, at the time. A dog with a half black and half white face, split down the middle, almost 100 years later.
Life is magical, mysterious and beyond imagination.
If these dates are not available, please send us a message. We have other beautiful properties.
(Please note: We do have a guest-centered and considerate cancellation policy. Please see our attached cancellation policy for details.)
Property manager
Sharon Strimling
Languages
English
Add dates for prices
Amenities
Kitchen
Pet-friendly
Free WiFi
Air conditioning
Outdoor space
Barbecue grill
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9.8 out of 10, (142 reviews)
House Rules
Check in after 4:00 PM
Check out before 10:00 AM
Children
Children allowed: ages 0–17
Events
No events allowed
Pets
Pets allowed
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
On-site parties or group events are strictly prohibited
Host has not indicated whether there is a carbon monoxide detector on the property; consider bringing a portable detector with you on the trip
Host has indicated that there is a smoke detector on the property
Safety features at this property include a deadlock
Property Registration Number C0132252210
We should mention
This property does not have any lifts
A car is not required for transport to and from this property
About the area
Oak Bluffs
Located in Oak Bluffs, this apartment is in the city centre and by the sea. The area's natural beauty can be seen at Cape Cod Beaches and Felix Neck Wildlife Sanctuary, while Cottage Museum and Martha's Vineyard Film Center are cultural highlights. Flying Horses Carousel and Oak Bluffs Fishing Pier are also worth visiting. Jet skiing and scuba diving offer great chances to get out on the surrounding water, or you can seek out an adventure with hunting and cycling nearby.

Oak Bluffs, MA
What's nearby
- Circuit Avenue - 2 min walk - 0.2 km
- Oak Bluffs Harbor - 5 min walk - 0.4 km
- Oak Bluffs Ferry Terminal - 5 min walk - 0.5 km
- Oak Bluffs Town Beach - 7 min walk - 0.6 km
- Inkwell Beach - 8 min walk - 0.7 km
Getting around
Restaurants
- Lookout Tavern - 6 min walk
- Back Door Donuts - 1 min walk
- Portuguese American Club - 3 min drive
- Offshore Ale Co. - 2 min walk
- VFW Hall - 2 min drive
Frequently asked questions
Reviews
9.8
Exceptional
Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
Learn moreOpens in a new window10/10
Cleanliness
10/10
Check-in
10/10
Communication
10/10
Location
9.8/10
Listing accuracy
Reviews
30 Mar 2025
Liked: Cleanliness, check-in, communication, location, listing accuracy
Stayed 4 nights in Mar 2025
10/10 Excellent
Mike
3 Mar 2025
Liked: Cleanliness, check-in, communication, location, listing accuracy
Awesome locale
Mike
Stayed 3 nights in Feb 2025
10/10 Excellent
Amy M.
28 Dec 2024
Liked: Cleanliness, check-in, communication, location, listing accuracy
Gingerbread apartment
Amy M.
Stayed 3 nights in Dec 2024
10/10 Excellent
Dixie B.
12 Dec 2024
Liked: Cleanliness, check-in, communication, location, listing accuracy
Stormy
Dixie B.
Stayed 2 nights in Dec 2024
10/10 Excellent
Deirdre D.
3 Nov 2024
Liked: Cleanliness, check-in, communication, location, listing accuracy
Halloween in Oak Bluffs
Deirdre D.
Stayed 2 nights in Oct 2024
10/10 Excellent
Summer J.
5 Oct 2024
Summer J.
Stayed 3 nights in Jun 2024
8/10 Good
Rick M.
28 Sept 2024
Liked: Cleanliness, check-in, communication, location, listing accuracy
Great spot to visit MV
Rick M.
Stayed 3 nights in Sep 2024
10/10 Excellent
Michelle Francine P.
31 Aug 2024
Liked: Cleanliness, check-in, communication, location, listing accuracy
Oak Bluffs Apt.
Michelle Francine P.
Stayed 8 nights in Aug 2024
10/10 Excellent
Amy G.
28 June 2024
Liked: Cleanliness, check-in, communication, location, listing accuracy
Lovely and convenient for a long weekend
Amy G.
Stayed 4 nights in Jun 2024
10/10 Excellent
Wendy B.
13 Feb 2024
Liked: Cleanliness, check-in, communication, location, listing accuracy
Great “Work-cation”
Wendy B.
Stayed 2 nights in Feb 2024
10/10 Excellent
Joe T.
7 Nov 2023
Liked: Cleanliness, check-in, communication, location, listing accuracy
Wonderful stay
Joe T.
Stayed 3 nights in Nov 2023
10/10 Excellent
Sandra E.
1 Nov 2019
Liked: Cleanliness, check-in, communication, location, listing accuracy
40th Anniversary Get Away
Sandra E.
Stayed 5 nights in Oct 2019
10/10 Excellent
Stephen F.
15 July 2019
Liked: Cleanliness, check-in, communication, location, listing accuracy
Centrally located for all MV experiences
Stephen F.
Stayed 2 nights in Jun 2019
10/10 Excellent
Mitch R.
3 Aug 2018
Wonderful summer holiday
Mitch R.
Stayed 6 nights in Jul 2018
This review was submitted before 2018 and has not been verified.
8/10 Good
Marie N.
11 Oct 2017
Lovely and just right to walking all around Oaks Bluff
Marie N.
Stayed 5 nights in Sep 2017
This review was submitted before 2018 and has not been verified.
10/10 Excellent
Joanna O.
13 Aug 2017
Lovely, cozy space; excellent location; super charming building
Joanna O.
Stayed 7 nights in Jul 2017
This review was submitted before 2018 and has not been verified.
8/10 Good
Silke S., Madison
13 July 2017
Lovely flat in the heart of Oak Bluffs
Silke S.
Stayed 3 nights in Jun 2017
This review was submitted before 2018 and has not been verified.
8/10 Good
Pia D.
21 May 2017
Fantastic location and great pet friendly rental
Pia D.
Stayed 3 nights in May 2017
This review was submitted before 2018 and has not been verified.
10/10 Excellent
Michael W.
17 Oct 2016
Wonderful location, charming cottage
Michael W.
Stayed 2 nights in Oct 2016
This review was submitted before 2018 and has not been verified.
10/10 Excellent
Nicholas B.
21 Sept 2016
quaint, beachy, comfy,great location
Nicholas B.
Stayed 3 nights in Sep 2016
This review was submitted before 2018 and has not been verified.
10/10 Excellent
Shannon L.
21 July 2016
Can't wait to return...AGAIN
Shannon L.
This review was submitted before 2018 and has not been verified.
10/10 Excellent
Mitch R.
20 July 2016
Great location and wonderful hostess. Right in the middle of everything
Mitch R.
Stayed 7 nights in Jul 2016
This review was submitted before 2018 and has not been verified.
10/10 Excellent
Jack G.
9 June 2016
Cute house with a perfect location all around!
Jack G.
Stayed 4 nights in May 2016
This review was submitted before 2018 and has not been verified.
10/10 Excellent
Misty H.
20 Oct 2015
Amazing!
Misty H.
Stayed 1 night in Oct 2015
This review was submitted before 2018 and has not been verified.
10/10 Excellent
Nadine C.
5 Oct 2015
Great getaway!
Nadine C.
About the host
Hosted by Sharon Strimling

I have lived on Martha's Vineyard full time for 20 years now, but vacationed there as a child. Martha's Vineyard has always been a very special place to me, and I love it dearly. I found this home about 14 years ago and fell in love with it immediately. A massage therapist on Martha's Vineyard, voted 'Best of the Vineyard' in the Vineyard Gazette, I once did massage out of this house, and people adored being there for their massages! You will see - the home is a true, historic beauty, and has a special feeling to it as well.
My favorite morning routine is to go for a run through the beautiful nature trails a short jog away, have a healthy smoothie in the hot tub, and then walk down the street to the local coffee shop for a wonderful cup of tea and to say hi to the locals gathering there.
My nieces and nephews on the other hand, get far more excited about the late afternoon or after dinner walk down to the arcade and ice cream shop to lick their ice cream cones while watching the nightlife walk by on Circuit Ave!
Oh - and of course, the movie theater down the street calls to them from time to time as well!
My favorite morning routine is to go for a run through the beautiful nature trails a short jog away, have a healthy smoothie in the hot tub, and then walk down the street to the local coffee shop for a wonderful cup of tea and to say hi to the locals gathering there.
My nieces and nephews on the other hand, get far more excited about the late afternoon or after dinner walk down to the arcade and ice cream shop to lick their ice cream cones while watching the nightlife walk by on Circuit Ave!
Oh - and of course, the movie theater down the street calls to them from time to time as well!
Why they chose this property
There is no location on Martha's Vineyard like downtown Oak Bluffs, and nowhere in the world I would rather be. With the coffee shops, restaurants and shops in town, the beach just a couple of blocks away, Ocean park separating the house from the ocean, the Tabernacle a block in the other direction, the Flying Horses carousel for children, Union Chapel with its performances and the harbor just down the street, it just doesn't get any better than this. I will never look to be in any other location on Martha's Vineyard than in the charming and lively town of Oak Bluffs!
Languages:
English
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