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

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

Exterior
Smart TV, DVD player, books
Terrace/patio
Dining
6 bedrooms, iron/ironing board, WiFi, bed sheets

Reviews

9.8 out of 10
Exceptional

Entire home

6 bedrooms2 bathroomsSleeps 10

Popular amenities

  • Kitchen
  • Washing machine
  • Dryer
  • Air-conditioning
  • Outdoor space
  • Parking available

Explore the area

View in a map
Oak Bluffs, MA
  • Place, Circuit Avenue
    ‪3 min walk‬
  • Place, Inkwell Beach
    ‪3 min walk‬
  • Place, Oak Bluffs Harbor
    ‪8 min walk‬
  • Airport, Vineyard Haven, MA (MVY-Martha's Vineyard)
    ‪19 min drive‬

Room options

Similar properties

Porch
Summercamp
Oak Bluffs
  • Free Wi-Fi
  • Air-conditioning
  • Parking available
  • Business services
4.7 out of 5, Exceptional, 1,002 reviews
The price is €394
includes taxes & fees
11 Jun - 12 Jun
Summercamp

About this property

Entire place

You'll have the entire home to yourself and will only share it with other guests in your party.

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

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.
During your stay at this vacation home, you're just a quick walk from Inkwell Beach. Features include laundry facilities. The vacation home includes amenities such as a kitchen and 2 bathrooms.
  • Air-conditioned home with kitchen, washing machine, and 2 bathrooms
  • Amenities include laundry facilities
  • Onsite recreation includes a playground
  • Just a 5-minute walk from Inkwell Beach and 3 minutes by foot from Circuit Avenue
As a guest of this vacation home, you'll find barbecue grills, a garden, and laundry facilities. The front desk is open around the clock.

Property amenities

Beach

  • Beach loungers

Internet

  • Available in the house: WiFi

Parking and transport

  • Wheelchair-accessible parking available
  • Onsite parking includes off-street options

Kitchen

  • Coffee/tea maker
  • Cookware, dishware, and utensils
  • Dishwasher
  • Hob
  • Lobster/crab pot
  • Microwave
  • Oven
  • Paper towels
  • Refrigerator
  • Toaster

Dining

  • Dining table

Bedrooms

  • 6 bedrooms
  • Bedsheets provided
  • Sofa bed

Bathroom

  • 2 bathrooms
  • Bathtub
  • Toilet paper
  • Towels provided

Living spaces

  • Dining table
  • Living room

Entertainment

  • Books
  • DVD player
  • Games
  • Smart TV with cable/satellite channels

Outdoor areas

  • Balcony
  • Barbecue grill
  • Garden
  • Outdoor furniture

Laundry

  • Laundry facilities
  • Washing machine

Comfort

  • Air conditioning
  • Ceiling fan
  • Heating

Pets

  • No pets allowed

Suitability/Accessibility

  • If you have requests for specific accessibility needs, please contact the property using the information on the reservation confirmation received after booking.
  • 2 steps to reach entrance
  • Accessible parking space
  • Area rugs in public areas
  • Handrails in stairways
  • No lift
  • Smooth flooring in public areas
  • Tile flooring in public areas
  • Well-lit path to entrance
  • Wheelchair-accessible parking
  • Smoke-free property

Services and conveniences

  • Iron/ironing board

Safety features

  • Carbon monoxide detector (host has indicated there is a carbon monoxide detector on the property)
  • Smoke detector (host has indicated there is a smoke detector on the property)
  • Fire extinguisher

General

  • Garden

Policies

Check-in

Check-in time starts at 3:00 PM
Minimum check-in age: 24

Check-out

Check-out before 10:00 AM

Special check-in instructions

You will receive an email from the host with check-in and check-out instructions
Information provided by the property may be translated using automated translation tools

Pets

  • No pets allowed

Children and extra beds

  • Children are welcome.

Events

No events allowed

Smoking

Smoking is not permitted

Important information

You need to know

This property is managed by a private host (a party not acting within their trade, business or profession). EU consumer law, including the right of withdrawal, will not apply to your booking. The cancellation policy set by the private host will cover your booking.
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 indicated there is a carbon monoxide detector on the property
Host has indicated there is a smoke detector on the property
Safety features at this property include a fire extinguisher
This property is managed through our partner, Vrbo. You will receive an email from Vrbo with a link to a Vrbo account, where you can change or cancel your reservation
You will receive an email from the host with check-in and check-out instructions. You will also receive an email from Vrbo with a link to a Vrbo account which will enable you to manage your booking.
Property Registration Number c0288502210

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

Reviews

9.8

Exceptional

Rating 10 - Excellent. 8 out of 9 reviews
Rating 8 - Good. 1 out of 9 reviews
Rating 6 - Okay. 0 out of 9 reviews
Rating 4 - Poor. 0 out of 9 reviews
Rating 2 - Terrible. 0 out of 9 reviews

9.8/10

Cleanliness

10/10

Amenities

8.0/10

Property conditions & facilities

Reviews

Verified

10/10 Excellent

Hallie L.

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

Great family trip!

The house was so great and the location was perfect! Enough privacy but walking distance to everything. We loved it!
Stayed 2 nights in Jun 2024
Verified

10/10 Excellent

Madge W.

Liked: Cleanliness, check-in, communication, location, listing accuracy
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.
Outside of 32 (not 36)
Lovely porch
Stayed 4 nights in Sep 2025
Verified

10/10 Excellent

Lindsey R.

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

Lovely home is fabulous area

Adorable home in a central location of OB. Exceeds the picture, home is comfortable and has everything you need.
Stayed 4 nights in Jun 2024
Verified

10/10 Excellent

Samantha M.

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

Amazing property & location

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!
Stayed 2 nights in May 2023
Verified

10/10 Excellent

Anurag

Liked: Cleanliness, amenities, property conditions & facilities, communication
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
Stayed 2 nights in May 2024
Verified

10/10 Excellent

Marya N W.

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

Perfect!

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!
Stayed 2 nights in May 2024
Verified

10/10 Excellent

Alyson A.

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

The Best Time

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!
Stayed 2 nights in Jun 2024
Verified

10/10 Excellent

Christopher M.

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

The Legacy

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!
Stayed 6 nights in Jun 2025
Verified

8/10 Good

Sarah M.

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

Oak Bluffs Stay

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.
Stayed 2 nights in May 2024