Entire home

Historic Oak Bluffs home, short walk to town, beach, and harbor.

Photo gallery for Historic Oak Bluffs home, short walk to town, beach, and harbor.

A porch with a rocking chair and a bench, wooden floor, and a view of trees.
A staircase with glass railings, a green upholstered chair, a table with a lamp, a vintage stove, and a painting on the wall.
A living room with a blue sofa, a wooden coffee table, a television on a stand, a piano, and a patterned rug.
A flagpole with an American flag in a wooded area.
A two-story house with a porch, an American flag, and a stone retaining wall.

Reviews

9.6 out of 10
Exceptional

Highlights

  • The great outdoors
    Guests love the outdoor space here.
  • Centrally-located
    You're never far from where you need to be with this convenient location.
  • Discover nearby landmarks
    Near Oak Bluffs Harbor
3 bedrooms0+ bathroomsSleeps 6

Popular amenities

  • Patio
  • Toys
  • Barbecue grill
  • Air conditioning
  • Refrigerator
  • Washer

Explore the area

View in a map
Oak Bluffs, MA
  • Place, Oak Bluffs Harbor
    ‪6 min walk‬
  • Place, Circuit Avenue
    ‪14 min walk‬
  • Place, Oak Bluffs Town Beach
    ‪18 min walk‬
  • Airport, Vineyard Haven, MA (MVY-Martha's Vineyard)
    ‪20 min drive‬

Where you'll sleep

3 bedrooms (sleeps 6)

Back bedroom

1 Queen Bed

Front Bedroom

1 Queen Bed

Middle Bedroom

1 Twin Bed

1 half bathroom

Downstairs bathroom

Towels provided · Toilet

Outdoor shower

Outdoor shower

Upstairs Bath

Towels provided · Toilet · Shower only

Spaces

Deck or patio
Porch or lanai
Outdoor shower
Kitchen
Separate dining area
Outdoor play area
Garden

About this property

Historic Oak Bluffs home, short walk to town, beach, and harbor.

Family owned and kept charming 19th century home in Oak Bluffs highlands near Baptist Temple park. This house is about 1/2 mile walk to ferry terminals for Island Queen, Vineyard Fast Ferry, Seastreak, Hy-Line and Steamship Authority (Oak Bluffs terminal). Three bedrooms total with two queen beds and one twin bed. Full bathroom upstairs with indoor shower, half bathroom downstairs, plus an outdoor shower. Window unit A/C's provided throughout (each bedroom has one A/C). For cooler months, the heating is a working wood stove and electric space heaters which are provided. 10-12 minute walk to downtown Oak Bluffs for all needs. Private parking for up to (4) vehicles. Charming wrap around covered porch in front, small deck in back with very private yard. Wifi internet to work remotely or stream shows/movies. Windows 10 PC available to display Netflix, Hulu, sports, etc. No cable TV.
Our prices include all fees. No hidden fees.

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House Rules

Check in after 4:00 PM
Minimum age to rent: 25
Check out before 10:00 AM
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Children

Children allowed: ages 0-17
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Events

No events allowed
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Pets

No pets allowed
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Smoking

Smoking is not permitted

Check-out instructions

The host requires you complete the following before checking out:
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
Optional- start a wash with all used towels.
Failure to complete these may result in a negative review from the host.

Important information

You need to know

Property Registration Number C0233012960
Property # 1690203
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
Onsite 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 there is a smoke detector on the property
Safety features at this property include a fire extinguisher and a first aid kit
This property has outdoor spaces, such as balconies, patios, terraces which may not be suitable for children; if you have concerns, we recommend contacting the property prior to your arrival to confirm they can accommodate you in a suitable room

About the neighborhood

Oak Bluffs

Located in Oak Bluffs, this vacation home is by the sea. Cottage Museum and Martha's Vineyard Film Center are cultural highlights, and some of the area's landmarks include Trinity Park Tabernacle and East Chop Light. Flying Horses Carousel and Island Cove Adventures are also worth visiting. Discover the area's water adventures with jet skiing, parasailing, and motor boating nearby, or enjoy the great outdoors with cycling.
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Map
Oak Bluffs, MA

What's nearby

  • Oak Bluffs Harbor - 6 min walk - 0.6 km
  • Oak Bluffs Public Library - 11 min walk - 1.0 km
  • Circuit Avenue - 14 min walk - 1.2 km
  • Oak Bluffs Town Beach - 18 min walk - 1.5 km
  • Inkwell Beach - 2 min drive - 1.8 km

Getting around

  • Vineyard Haven, MA (MVY-Martha's Vineyard) - 16 min drive

Restaurants

  • ‪Lookout Tavern - ‬16 min walk
  • ‪Nancy's - ‬13 min walk
  • ‪Nomans - ‬4 min drive
  • ‪Portuguese-American Club - ‬3 min drive
  • ‪Biscuits - ‬13 min walk

Frequently asked questions

Is Historic Oak Bluffs home, short walk to town, beach, and harbor. pet-friendly?

No, pets are not allowed at this property.

How much is parking?

Onsite parking is available at the property.

What time is check-in at Historic Oak Bluffs home, short walk to town, beach, and harbor.?

Check-in begins at 4:00 PM.

What time is check-out at Historic Oak Bluffs home, short walk to town, beach, and harbor.?

Check-out is at 10:00 AM.

Where is Historic Oak Bluffs home, short walk to town, beach, and harbor. located?

Situated by the sea, this vacation home is within 1 mi (2 km) of Martha's Vineyard Hospital Development and Inkwell Beach. Oak Bluffs Harbor and Cottage Museum are also within 15 minutes.

Reviews

9.6

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labeled.
Learn moreOpens in a new window
Rating 10 - Excellent. 33 out of 42 reviews
Rating 8 - Good. 6 out of 42 reviews
Rating 6 - Okay. 3 out of 42 reviews
Rating 4 - Poor. 0 out of 42 reviews
Rating 2 - Terrible. 0 out of 42 reviews

9.2/10

Cleanliness

10/10

Check-in

10/10

Communication

9.8/10

Location

9.8/10

Listing accuracy

Reviews

Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, listing accuracy
Our family of four enjoyed our time at Hillcrest. The home, built in 1877, exudes character despite not being renovated. It was clean and well-equipped with everything we needed and more. The host was incredibly communicative and accommodating, making us feel right at home. We’re already planning our next visit!
Stayed 6 nights in Aug 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great property which was even better than the pictures. Easy walk to Oak Bluffs. Great back yard which was the hangout spot when the kids friends came over.
Stayed 3 nights in Aug 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
A truly wonderful stay in a classic Vineyard property that reminded us of our old familycottage on New York Avenue. Immaculately clean, so much character and history and in a lovely accessible yet secluded area. Great hosts. Would definitely return - magic! Oh and what a porch!
Stayed 7 nights in Jul 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Charming old island home! Great location and fully stocked with everything you could possibly need - felt like home away from home! Would stay here again!
Stayed 4 nights in Sep 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great place!

We enjoy it all.
Stayed 3 nights in Oct 2024
Verified review

8/10 Good

Liked: Check-in, communication, location, listing accuracy

Great location

We had a few bumps the first night but after contacting the host he was quick to respond and very accommodating Really enjoyed our visit to the island.
Stayed 2 nights in Jul 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Excellent Stay

Property was accurately described in the listing. It is clean and we had no issues. We wouldn’t hesitate to stay again.
Stayed 3 nights in Jun 2023
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
What a cool house. A classic. Peter could not have been nicer. I definitely would like to stay here again when I return to the island.
Stayed 2 nights in Sep 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Loved the Vintage Cottage!

We had a wonderful stay at Hillcrest! We enjoyed both the indoor and outdoor spaces! So nice to have the whole house — plenty of room. The weather was hot and the air conditioning was a blessing. Very well appointed! Looking forward to returning.
Stayed 4 nights in Jun 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Charming antique house

Felt right at home! This cute beach house has a lot of charm and was just what we needed for a few days of relaxation and fun. It was well stocked and clean. The wrap around porch and outdoor showers were really nice.
Stayed 3 nights in Aug 2024
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Stay at the Vineyard

House was as advertised. It was clean and at a desirable location for are family . Hosts were professional and had very good communication skills . Friendly to work with . Looking forward to stay at this house again with family if needed and available again .
Stayed 2 nights in May 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great time

The stay was just as described. Old house but it was clean and all amenities available. Close to the Oak Bluffs center and the beach. We enjoyed our stay very much.
Stayed 4 nights in Sep 2023
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Ideal Summer Getaway

A quiet location that is very close to excellent restaurants, bars, shopping, beaches and our ferry with hospitable hosts providing invaluable recommendations for first-time visitors to Martha’s Vineyard. Thanks to this experience, it won’t be out last.
Stayed 2 nights in Jul 2019
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Fun old house full of character. Great place to weather out the Nor’easter! Really appreciated the cable and strong wi-fi! Communication with owner was excellent!One caution, if anyone in your party has mobility issues, be aware that the “short walk” is about a half-mile. Also lots of stairs, including long, steep ones to the second floor.
Stayed 3 nights in Oct 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Amazing Classic Vineyard Home

This home is so lovely and perfectly embodies that classic Vineyard house. While it holds all the charm of an older home, it has some seriously powerful A/C units in every room that kept us extra cool even during the heat wave while we were there. Cannot recommend this home more!
Stayed 2 nights in Jul 2024
Verified review

8/10 Good

Liked: Check-in, communication, location, listing accuracy
Excellent location - quiet, wooded area, and pretty, short walk to downtown Oak Bluffs, harbor, Inkwell Beach, etc. Great value - for the price, well-located and large space. House exactly as pictured - be prepared for true vintage (a bit of dust and misc items sitting around). Beds were new and comfortable and sheets, bathroom, and kitchen were all clean. Also good WiFi. Just be sure to screen shot the check-in instructions before you arrive since cellular at the house is hard to get.
Stayed 3 nights in Aug 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Delightful home tucked away in Oak Bluffs. The house had everything we needed. Peter was extremely communicative and helpful. A/C was a plus.Beach chairs, grill… just lovely. It’s a little bit of a hike with luggage to get up to the house so next year I think I’ll bring a little foldable wagon to pop open for beach trips, luggage hauling and groceries. 10/10. Great stay!!!
Enjoying coffee on the wrap around porch.
Stayed 3 nights in Jul 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
The house was great for myself and my friends to have a beautiful week. There are plenty of bedrooms and we comfortably slept (at one point in the week) six people in the house. John was a pleasure to interact with. Large gathering space indoor and outdoor, brand new appliances, comfortable beds, glorious outdoor shower, lovely grill, unbelievable location. Outdoor rocking chairs. Historic house built in 1877. QUIET! I cannot think of a single complaint. Cannot wait to stay there again. Thanks for everything John.
Stayed 7 nights in Aug 2025
Verified review

8/10 Good

Liked: Check-in, communication, location, listing accuracy
Disliked: Cleanliness

Great!

House was lovely, so charming in a very quiet neighborhood. Quick bike ride to the Oak Bluffs center. Only complaint is the cleanliness. None of the beds were made, there was a load in the dryer, as well as a load in the washer that had been washed but not yet dried, and some more dirty laundry on top of the washer.
Stayed 2 nights in Jul 2024
Verified review

8/10 Good

Liked: Cleanliness, check-in, communication, location, listing accuracy

Step Back in Time

If you like historic homes, this is a hidden gem in a quiet neighborhood. It reminded us of what it would have been like to have a Vineyard "cottage" back in the day. The owners have done a great job maintaining the historic charm. They've updated appliances and the outdoor shower was amazing. Sitting on the porch was equally pleasant. This is a quiet, no frills place, with lots of nooks and crannies to discover. Be sure the read the book about the property. It's not ideal for little, little kids but ours were 6, 8, and 11 and did just fine! Thank you for letting us experience this step back in time.
Stayed 2 nights in Sep 2023
Verified review

8/10 Good

Liked: Cleanliness, check-in, communication, location, listing accuracy

Quaint & Quirky Antique Cottage

Cute rustic cottage built in the 1800’s. It’s a fun little spot filled with nostalgia and antiques. Just lived in enough to compliment the Island lifestyle. Nice yard, porches and back deck. Grill, table and chairs out back as well as rockers on porch are convenient and fun. Small ACs in windows throughout. Steep stairs best for able bodied adults. Some wear and tear, cobwebs, etc… the wardrobe door in back bedroom was off it’s hinges? Someone left clothes from a prior rental in back bedroom bureau. A dust buster would be nice. Tv is good, piano cool, wood stove cool, trap door in living room odd… overall a cool quirky old school summer cottage. We had fun. It served us well. 4 adults over for Tivoli weekend.
Stayed 2 nights in Sep 2024
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Love this house

If you're looking for a sleek, modern property, look elsewhere. But if you like quirky old historic places with a laid-back vibe, this is your place. The house is clean, shady and private. Easy walk to town. Beds are comfy and check in is a breeze. This was our second stay, and I would love to come back again!
Stayed 2 nights in Sep 2022
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Very nice and affordable get away

We had a very nice time. The property is very old 1877 and I know has a lot of wonderful family history!! I definitely recommend this house. The location is perfect too. I love Oak Bluffs area so it is perfect.
Stayed 7 nights in Jul 2022
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Spacious, well-equipped, classic cottage

This house had everything we needed and more. The breezy porch and the window AC units in the bedrooms kept us cool. On the two very hot days, we turned on the downstairs AC units, and they worked great. We loved the roomy outdoor shower, newer washer/dryer, and bright kitchen. Also, the owners provided the things that I always (just in case) pack for rentals, from dish soap to paper towels to a nightlight in the bathroom. It's rustic but clean. The staircase is a little steep and narrow, which is something to consider if bringing small kids or elderly guests. The East Chop location was what we were looking for, and it's an easy walk to town. This historic cottage was a great home base for a wonderful vacation.
Stayed 7 nights in Jul 2022
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Weekend Getaway

Me and my three cousins stayed at this beautiful home for the weekend. The home was well kept and in a great location. I would recommend this property, and I will hopefully be returning soon!
Stayed 2 nights in May 2022

About the host

Hosted by Peter or Jon Chapman

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