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

Oak Bluffs, Massachusetts
$370 avg/night
Bed 3

Bed

Home Private Vacation Home

Property Type

Sleep 6

Max Sleeps

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.

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  • Feature Features
  • Map Map
  • School District Rates & Availability
  • Review Review

Feature Features

  • PETS

    No Pets Allowed
  • BEACH

    Beach Sun Loungers Beach Towels
  • DINING

    Dining Table
  • SAFETY

    Carbon Monoxide Detector Not Reported (host Has Not Indicated Whether There Is A Carbon Monoxide Detector On The Property; Consider Bringing A Portable Detector) Fire Extinguisher First Aid Kit Smoke Detector Installed (host Has Indicated There Is A Smoke Detector On The Property)
  • BEDROOM

    3 Bedrooms Bed Sheets Provided
  • KITCHEN

    Blender Coffee/tea Maker Lobster/crab Pot Microwave Oven Refrigerator Spices Stovetop Toaster
  • LAUNDRY

    Laundry Facilities Near Laundromat Washing Machine And Dryer
  • PARKING

    Onsite Parking
  • INTERNET

    Free WiFi
  • OUTDOORS

    Barbecue Grill Garden Outdoor Furniture Patio
  • BATHROOMS

    Hair Dryer Outdoor Shower Shampoo Shower Soap Toilet Paper Towels Provided
  • WORKSPACES

    Computer Monitor
  • LANGS SPOKEN

    English
  • THINGS TO DO

    Basketball Nearby Cycling Nearby Fishing Nearby Fitness Facilities Nearby Golf Nearby Jet Skiing Nearby Marina Nearby Parasailing Nearby Power Boating Nearby Swimming Nearby
  • ENTERTAINMENT

    Smart TV With Cable/satellite Service
  • LIVING SPACES

    Dining Room Living Room Wood Stove
  • CLIMATE CONTROL

    Air Conditioning Heating
  • FAMILY FRIENDLY

    Children's Games Children's Toys Playground
  • LOCATION HIGHLIGHTS

    Near A Hospital Near The Sea
  • SUITABILITY/ACCESSIBILITY

    Smoke-free Property

CheckIn Check-in : 04:00 PM CheckOut Check-out : 10:00 AM
No Wheelchair No smoking No pets Children allowed
Occupancy Max occupancy : 6

Map Map

School District Rates & Availability

Review Review

  • Mary P.

    Submitted Oct 14, 2025

    Stayed Oct 11, 2025

    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.

  • Tim M.

    Submitted Oct 12, 2025

    Stayed Sep 26, 2025

    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.

  • Walter S.

    Submitted Sep 12, 2025

    Stayed Sep 7, 2025

    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!

  • Jen K.

    Submitted Aug 17, 2025

    Stayed Aug 10, 2025

    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.

  • Rebecca K.

    Submitted Aug 7, 2025

    Stayed Aug 3, 2025

    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.

  • Maria P.

    Submitted Aug 5, 2025

    Stayed Jul 23, 2025

    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.

  • Kimberly H.

    Submitted Jul 23, 2025

    Stayed Jul 20, 2025

    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!!!

  • Elizabeth M.

    Submitted Jun 27, 2025

    Stayed Jun 19, 2025

    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.

  • James W.

    Submitted May 17, 2025

    Stayed May 14, 2025

    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 .

  • Laura S.

    Submitted Oct 14, 2024

    Stayed Oct 11, 2024

    We enjoy it all.

  • Craig C.

    Submitted Sep 22, 2024

    Stayed Sep 20, 2024

    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.

  • suzanne h.

    Submitted Aug 28, 2024

    Stayed Aug 25, 2024

    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.

  • Maddie T.

    Submitted Aug 7, 2024

    Stayed Jul 26, 2024

    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!

  • Ava W.

    Submitted Aug 2, 2024

    Stayed Jul 14, 2024

    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.

Your dates are Available!

Total

Includes taxes and fees
$370+
View details