The Legacy House: Walk to Inkwell Beach + Historic Charm, Modern Comfort

Oak Bluffs, Massachusetts
$884 avg/night Minimum Stay 3 Nights
Bed 6

Bed

Bath 2

Bath

Home Private Vacation Home

Property Type

Sleep 10

Max Sleeps

Night 3 nights

Min Stay

Step into the timeless charm of Oak Bluffs while enjoying the comforts of a thoughtfully renovated home. The Legacy House blends 250 years of history with modern upgrades—creating a one-of-a-kind stay just 2 blocks from Inkwell Beach and a short stroll to everything you love about Oak Bluffs.

Whether you're planning a multi-family summer getaway or a peaceful fall retreat, this home offers the space, location, and character that make Martha’s Vineyard unforgettable.

Why Guests Love The Legacy House
- Unbeatable Location – Walk to Inkwell Beach, Circuit Avenue, Ocean Park, and the ferry
- Historic + Renovated – 250-year-old home with a brand-new kitchen and updated bathrooms
- Perfect for Groups – Comfortably designed for 2 families or group gatherings
- Outdoor Living – Wrap-around porch, large rear deck, and outdoor shower
Peaceful Setting – Quiet, charming neighborhood just steps from the action
No Hidden Fees – Transparent pricing, always

The Space
This spacious home is filled with warmth, personality, and room to gather.

- Large front sitting/family room for relaxing together
- Full dining room for shared meals and memories
- 5 thoughtfully arranged bedrooms across two levels
- 2 full bathrooms (one on each floor)
- Ample off-street private parking

Start your mornings with a sunrise walk to the water—or join the iconic “polar bears” for an early swim. Spend your afternoons biking, shopping, or relaxing on the porch with a drink in hand.

Sleeping Arrangements

Designed for flexibility and comfort:
- Bedroom 1 (Upstairs): King bed, spacious, bright, flat-screen TV
- Bedroom 2 (Upstairs): Queen bed + private balcony
- Bedroom 3 (Upstairs): Double + twin bunk with trundle (ideal for kids)
- Bedroom 4 (Upstairs): Twin with trundle (sleeps 2, great for kids/teens)
- Bedroom 5 (Downstairs): Queen bed, large room, ground-level access, TV

Outdoor + Local Highlights
- 2 blocks to tennis, pickleball, and basketball courts
- Easy walk to beaches, shops, dining, and entertainment
- Classic Oak Bluffs neighborhood full of history and charm

Please Read Before Booking (Important Details)
We want your stay to be seamless, so here are a few important notes:
- 7-night minimum during peak season
- This is a historic 250-year-old home—full of charm, but not a hotel-style property
- Linens & towels are not included by default but we will order them for you
- We arrange rental and delivered prior to arrival based on your guest count
- Accuracy in your reservation is important to ensure proper setup

No pets allowed

A Different Kind of Stay
The Legacy House is for those who appreciate character, history, and togetherness over a cookie-cutter experience. If you're looking for a place where mornings start on the porch, days are spent walking to the beach, and evenings bring everyone back together—you’ll feel right at home here.

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

Feature Features

  • PETS

    No Pets Allowed
  • BEACH

    Beach Sun Loungers
  • DINING

    Dining Table
  • SAFETY

    Carbon Monoxide Detector Installed (host Has Indicated There Is A Carbon Monoxide Detector On The Property) Fire Extinguisher Smoke Detector Installed (host Has Indicated There Is A Smoke Detector On The Property)
  • BEDROOM

    6 Bedrooms Bed Sheets Provided Sofa Bed
  • KITCHEN

    Cookware/dishes/utensils Dishwasher Lobster/crab Pot Microwave Oven Paper Towels Refrigerator Stovetop Toaster
  • LAUNDRY

    Laundry Facilities Washing Machine And Dryer
  • PARKING

    Onsite Parking Onsite Parking Includes Off-street Options Wheelchair-accessible Parking Available
  • INTERNET

    WiFi Available
  • OUTDOORS

    Balcony Barbecue Grill Garden Outdoor Furniture
  • BATHROOMS

    2 Bathrooms Bathtub Toilet Paper Towels Provided
  • ENTERTAINMENT

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

    Living Room
  • CLIMATE CONTROL

    Air Conditioning Ceiling Fan Heating
  • FAMILY FRIENDLY

    Playground
  • SERVICES AND CONVENIENCES

    Iron/ironing Board
  • SUITABILITY/ACCESSIBILITY

    1 On-site Accessible Parking Spaces 2 Stairs To Reach Property Area Rugs In Public Areas Handrails In Stairways If You Have Requests For Specific Accessibility Needs, Please Contact The Property Using The Information On The Reservation Confirmation Received After Booking. No Elevators Smoke-free Property Smooth Flooring In Public Areas Tile Flooring In Public Areas Well-lit Path To Entrance Wheelchair-accessible Parking

CheckIn Check-in : 03:00 PM CheckOut Check-out : 10:00 AM
No Wheelchair No smoking No pets Children allowed
Occupancy Max occupancy : 10

Map Map

School District Rates & Availability

Review Review

  • Anurag

    Submitted May 27, 2024

    Stayed May 25, 2024

    It was charming. The DVD's and board games were a nice touch. Updated kitchen, lots of space and bunk beds. The house is walking distance from the beach, the bustling oak bluffs eating scene and almost everything else. Loved it

  • Madge W.

    Submitted Sep 21, 2025

    Stayed Sep 17, 2025

    Great location in beautiful quirky old house. We could easily walk everywhere and we were comfortable outside, on the porch and in the living room. 2 of the bedrooms best for kids and be prepared for walk-thru bathroom. 6 “Seniors” had fun.

  • Christopher M.

    Submitted Jun 19, 2025

    Stayed Jun 13, 2025

    Absolutely Unforgettable. Love it here!!!From the moment we stepped onto the wraparound porch of this charming Oak Bluffs retreat, we knew our Martha’s Vineyard vacation would be something special. This beautifully maintained Victorian cottage perfectly captures the whimsical spirit that makes Oak Bluffs the crown jewel of the island.The House: Character Meets ComfortThe property seamlessly blends historic charm with modern amenities. Original hardwood floors gleam throughout, while updated fixtures and appliances ensure every convenience. The kitchen is a dream for morning coffee preparation and evening meal planning, with granite countertops and stainless steel appliances that make cooking a pleasure rather than a chore.Each bedroom feels like a private sanctuary, with comfortable beds dressed in crisp linens and charming period details that transport you back to Martha’s Vineyard’s golden age. The master suite’s en-suite bathroom features a clawfoot tub perfect for soaking after long beach days.Can’t wait to come back. Great memories made in Oak Bluffs!

  • Lindsey R.

    Submitted Jun 30, 2024

    Stayed Jun 19, 2024

    Adorable home in a central location of OB. Exceeds the picture, home is comfortable and has everything you need.

  • Hallie L.

    Submitted Jun 29, 2024

    Stayed Jun 5, 2024

    The house was so great and the location was perfect! Enough privacy but walking distance to everything. We loved it!

  • Alyson A.

    Submitted Jun 16, 2024

    Stayed Jun 14, 2024

    Staying at Legacy House will forever be one of the best trips to the vineyard! We travelled for my best friends bachelorette party and it was the perfect house for us 8 girls. The rooms were spacious, the beds were comfy, and the common areas were excellent! The porch was for sure the best spot! The amenities the house has to offer such as a grill to make BBQ-ing easy was amazing! Through out this trip we kept saying we need to come back and make it annual girls trip! Legacy House will for sure see us again!

  • Marya N W.

    Submitted May 19, 2024

    Stayed May 17, 2024

    This place was so great! Perfect location, walking distance from everything (stores, restaurants, bus, ferry). The house is SO cute and was completely what we wanted. The weather was not cooperating when we were there, so it was great to have such a lovely place to hang out. We only wished we could take more advantage of the outdoor spaces! Will definitely come back!

  • Sarah M.

    Submitted May 6, 2024

    Stayed May 3, 2024

    Very nice house, with everything in good working order and clean. Honestly nicer than the photos made it seem, and very spacious. Kitchen was well stocked. I found it confusing that the checkout instructions were only in a binder, and not in the app. There were a ton of requests in terms of work for us in getting out, which with a 10 AM check-out was a little tight. I'm also not sure if it's early in the season, but responsiveness was not great to messages on the VRBO app. Lastly, there was not clear instructions around the linens (we had to make all the beds and unpack the towels, etc.) - would have been nice if the beds were made or at least there was some heads-up on that. Just a couple of little pieces of feedback, otherwise the house was great.

  • Samantha M.

    Submitted Jun 2, 2023

    Stayed May 19, 2023

    We had the BEST time at the Legacy house! The location was perfect and the house/yard was stunning. Everyone had a wonderful time. We will definitely be back!

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Total

Includes taxes and fees
$884+
View details