Inviting, two-story home with a large yard, sunroom, balcony, & washer/dryer

Oak Bluffs, Massachusetts
$715 avg/night
Bed 3

Bed

Bath 2

Bath

Home Private Vacation Home

Property Type

Sleep 8

Max Sleeps

Gingerbread Dream

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Experience the laidback lifestyle of the Vineyard from this classic, two-story Oak Bluffs vacation rental! Located just a short walk from downtown and the ferry, this home is ideal for those seeking easy access to the coast, local beaches, and an abundance of other family-friendly attractions.

Enjoy a leisurely bike ride, check out the Flying Horses Carousel (the oldest platform carousel in the country!), then spend your afternoon swimming in the warm waters of Nantucket Sound. Or, venture to Joseph Sylvia State Beach, ideal for beachcombing, windsurfing, and fishing for striped bass. Timeless attractions like Martha's Vineyard Performing Arts Center, Flying Horses Carousel, Reliable Market, and Inkwell Beach are all within a three-mile radius. Or check out Obama's favorite Vineyard green, Farm Neck Golf Club.

Brimming with plenty of old-school New England charm, this delightful getaway invites you to enjoy its many comforts and amenities. Brew up your morning coffee or prepare mealtime masterpieces in the bright, full kitchen, then gather in the adjacent dining room or just outside in the furnished and screened sunroom. Stream your favorite channels on the available TVs or bust out a few of the provided board games on rainy days or relaxing nights in.

This home also offers a furnished front porch, an outdoor shower with a convenient changing area, and a private washer/dryer to let you pack light and keep your laundry under control during your stay.

Things to Know
Check-in time: 4:00 PM.
Check-out time: 10:00 AM.
All guests shall abide byour good neighbor policy and shall not engage in illegal activity. Quiet hours are from 10:00 PM to 8:00 AM.
No smoking is permitted anywhere on the premises.

Parking notes: There is free parking available for 2 vehicles.



Damage waiver: The total cost of your reservation for this Property includes a nightly damage waiver fee, plus tax if applicable (the “Damage Waiver”). (A discount may be applied for stays of 28 nights or longer, if permitted.) The Damage Waiver covers you for up to $3,000 of accidental damage to the Property or its contents (such as furniture, fixtures, and appliances) as long as you report the incident to the host prior to checking out. The Damage Waiver fee eliminates the need for a traditional security deposit.
More information can be downloaded from the Rental Agreement on the checkout page.

Due to local laws or HOA requirements, guests must be at least 25 years of age to book. Guests under 25 must be accompanied by a parent or legal guardian for the duration of the reservation.

Read More Expand
  • Feature Features
  • Map Map
  • School District Rates & Availability
  • Review Review

Feature Features

  • PETS

    No Pets Allowed
  • SAFETY

    Carbon Monoxide Detector Installed (host Has Indicated There Is A Carbon Monoxide Detector On The Property) Deadbolt Lock 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 Sofa Bed
  • GENERAL

    Unit Size: 1162 Sq Ft (108 Sq M)
  • KITCHEN

    Coffee/tea Maker Cookware/dishes/utensils Dishwasher Ice Maker Microwave Oven Refrigerator Stovetop Toaster
  • LAUNDRY

    Laundry Facilities Washing Machine And Dryer
  • PARKING

    Onsite Parking
  • INTERNET

    Internet Access
  • OUTDOORS

    Balcony Garden
  • BATHROOMS

    2 Bathrooms Hair Dryer Towels Provided
  • LANGS SPOKEN

    English French German Italian Spanish
  • THINGS TO DO

    Birdwatching Nearby Fishing Nearby Kayaking Nearby Marina Nearby Power Boating Nearby Scuba Diving Nearby Snorkeling Nearby Swimming Nearby Wildlife And Game Walks Nearby
  • ENTERTAINMENT

    Books DVD Player Games Video Library TV With Cable/satellite Service
  • LIVING SPACES

    Dining Room Living Room
  • CLIMATE CONTROL

    Air Conditioning Heating
  • LOCATION HIGHLIGHTS

    In A Village Near A Hospital Near The Sea
  • SERVICES AND CONVENIENCES

    Iron/ironing Board
  • SUITABILITY/ACCESSIBILITY

    Note From Host: Smoking Is Not Permitted Anywhere On The Premises. 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 : 8

Map Map

School District Rates & Availability

Review Review

  • Samantha C.

    Submitted Aug 25, 2025

    Stayed Aug 11, 2025

    We work for a company doing events with the film festival and needed a place for 3 crew to stay multi-day. Was much more affordable than hotel rooms on the island. Convenient location to walk for restaurants and entertainment. Good instructions and easy check in process. Included parking which was great as we had a work vehicle on the island.

  • Sarah C.

    Submitted Aug 21, 2025

    Stayed Jun 28, 2025

    The house is a little older and some of the mattresses and linens could be improved, but

  • Kyle N.

    Submitted Aug 10, 2025

    Stayed Jul 27, 2025

    We loved the location. The outdoor shower was a hit with the kids.

  • Jeanie G.

    Submitted Oct 9, 2024

    Stayed Dec 31, 1969

    The house is in a nice location in Oak Bluffs, and the are a lot of places to sleep. However, there were certain things that were not clean, such as the bedding in the fold out couch. There were also small items that would have been nicer to see replaced like the mirror in the bathroom. Some of the mattresses were also not comfortable. my biggest issue was that the customer service was not good. We almost got locked out two different times because the instructions on where the keys were located were not complete and we did not get any help after we called and texted. Also, we reported several times that the Wi-Fi was broken, but it never got fixed. That was disappointing to us.

  • Julie S.

    Submitted Jul 7, 2024

    Stayed Jul 1, 2024

    We enjoyed how close the cottage was to the center of Oak Bluffs, the ferry and the bus. We were counting on the queen size sleep sofa to accommodate some of us but it was worn-out and very uncomfortable. The property manager couldn't help us with the lock box or the internet.

  • Sarah C.

    Submitted Jun 17, 2024

    Stayed Jun 14, 2024

    We had a wonderful early-June weekend stay at this charming house minutes walk from town. Highlights were reading on the rocking chair on the deck and playing games in the screened-in porch. Everything looks just like in the listing - charming, warm, like staying at your grandpa's beach house. There were a few bumps - the listed dryer was in a locked shed, a faucet wasn't working - but our sense was this is a new listing and details are still being ironed out. None of that interfered with our enjoyment of the house and the weekend.

Your dates are Available!

Total

Includes taxes and fees
$715+
View details