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

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A Victorian-style house with a central entrance, a balcony, and a porch with railings.
A bedroom with a white canopy bed, wooden flooring, and a chair.
A two-story house with a porch, outdoor seating area, and a visible garage.
A living room with a wooden floor, a blue rug, and two sofas.
A dining area with a table and chairs, a staircase, and a door with frosted glass panels.

Reviews

10 out of 10
Exceptional

Entire home

5 bedrooms2 bathroomsSleeps 10

Popular amenities

  • Kitchen
  • Washer
  • 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

About the neighborhood

Oak Bluffs

This vacation home places you within a 5-minute walk of Inkwell Beach and Circuit Avenue. The vacation home includes a kitchen, a balcony, and a sofa bed.
View more Vacation Homes in Oak BluffsOpens in a new window

What's nearby

  • Circuit Avenue - 3 min walk - 0.2 miles
  • Inkwell Beach - 3 min walk - 0.2 miles
  • Ocean Park - 5 min walk - 0.3 miles
  • Oak Bluffs Harbor - 8 min walk - 0.5 miles
  • Oak Bluffs Town Beach - 11 min walk - 0.6 miles

Getting around

  • Vineyard Haven, MA (MVY-Martha's Vineyard) - 15 min drive

Restaurants

  • ‪Lookout Tavern - ‬9 min walk
  • ‪Nancy's - ‬9 min walk
  • ‪Portuguese-American Club - ‬20 min walk
  • ‪Nomans - ‬2 min drive
  • ‪Biscuits - ‬9 min walk

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.
The vacation home is air-conditioned and features a kitchen, 2 bathrooms, and a balcony, and there's space to spread out with 5 bedrooms. Guests can expect to find a Smart TV with a DVD player. Other standard amenities include a washing machine, a sofa bed, and a coffee maker.

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  • Kitchen
  • Washer
  • Dryer
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Property amenities

Beach

  • Beach loungers

Internet

  • Available in the house: WiFi

Parking and transportation

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

Kitchen

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

Dining

  • Dining table

Bedrooms

  • 5 bedrooms
  • Bed sheets provided
  • Sofa bed

Bathroom

  • 2 bathrooms
  • Bathtub
  • Toilet paper
  • Towels provided

Living spaces

  • Dining table

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
  • Area rugs in public areas
  • Handrails in stairways
  • No elevator
  • Null
  • Smooth flooring in public areas
  • Tile flooring in public areas
  • Well-lit path to entrance
  • Wheelchair-accessible parking
  • Smoking not allowed

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

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

  • This property doesn't allow pets

Children and extra beds

Children allowed: ages 0-17

Events

No events allowed

Smoking

Smoking is not permitted

Important information

You need to know

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
  • Check-in: 3:00 PM
  • Check-out: 10:00 AM
Property Registration Number c0288502210

We should mention

Details about charges, deposits, or other important information:

  • This property is managed by a private host, not a professional engaged in trade or business.
  • Charges for extra guests may apply and vary depending on the property's policy.
  • A cash deposit, credit card, or debit card for incidental charges, as well as a government-issued photo ID, may be required at check-in.
  • Special requests are subject to availability at the time of check-in and can't be guaranteed. Certain requests may come with additional charges.
  • Onsite parties or group events are strictly prohibited.
  • Onsite safety features include a carbon monoxide detector, a fire extinguisher, and a smoke detector.

Additional information about polices, regulations, and more:

  • There are no elevators.

Frequently asked questions

What is there to do around this vacation home?

This vacation home is located in Oak Bluffs, just steps from Inkwell Beach and Circuit Avenue, and within a short walk of Ocean Park. You'll also find Oak Bluffs Harbor and Oak Bluffs Town Beach less than a mile away.

Is there parking available at The Legacy House: Walk to Inkwell Beach + Historic Charm, Modern Comfort?

Yes, there is wheelchair-accessible parking available.

Is this vacation home next to a casino?

No, this vacation home is not connected to a casino.

Is there an indoor pool at this vacation home?

No, there is no indoor pool at this vacation home.

Is The Legacy House: Walk to Inkwell Beach + Historic Charm, Modern Comfort a good place to stay for couples?

Couples staying at this vacation home will appreciate amenities like a kitchen and a smart TV as well as a garden.

Are there hot tubs at The Legacy House: Walk to Inkwell Beach + Historic Charm, Modern Comfort?

No, there isn't a spa tub at this vacation home.

Does this vacation home provide breakfast?

No, this vacation home doesn't offer breakfast.

Does this vacation home allow pets to stay free of charge?

No, pets aren't allowed at this vacation home.

Are there connecting rooms at The Legacy House: Walk to Inkwell Beach + Historic Charm, Modern Comfort?

No, this vacation home doesn't feature connecting guestrooms.

What is the closest airport to this vacation home?

The closest major airport to this vacation home is Vineyard Haven, MA (MVY-Martha's Vineyard), which is 7.1 mi away (15 minutes by car). Another top airport is Hyannis, MA (HYA-Barnstable Municipal), which is around 20.4 mi away.

Are there rooms with balconies at The Legacy House: Walk to Inkwell Beach + Historic Charm, Modern Comfort?

Yes, every house at The Legacy House: Walk to Inkwell Beach + Historic Charm, Modern Comfort comes with a balcony.

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

Reviews

10

Exceptional

Rating 10 - Excellent. 10 out of 11 reviews
Rating 8 - Good. 1 out of 11 reviews
Rating 6 - Okay. 0 out of 11 reviews
Rating 4 - Poor. 0 out of 11 reviews
Rating 2 - Terrible. 0 out of 11 reviews

10/10

Cleanliness

10/10

Amenities

8.0/10

Property conditions & facilities

Reviews

Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
house was great, nice character, clean, and a shaded yard to hang out in. Location was perfect, only a 10 min walk from the ferry, 10 minute walk to the main strip with shops and restaurants, and a 3 min walk to the beach. would definitely recommend the house, just not for the same dates as our future bookings there lol.
Stayed 3 nights in Jun 2026
Verified review

10/10 Excellent

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 review

10/10 Excellent

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 review

10/10 Excellent

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 review

10/10 Excellent

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 review

10/10 Excellent

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 review

10/10 Excellent

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 review

10/10 Excellent

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 review

10/10 Excellent

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 review

8/10 Good

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
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
The host was amazing and lightning fast to communicate with and super helpful and accommodating. Rent in complete confidence and respect the “Legacy” of this amazing home.
Stayed 4 nights in Jun 2026

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