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

Vacation home near Inkwell Beach in Oak Bluffs

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

A Victorian-style house with a central entrance, a balcony, and a porch with railings.
A living room with a wooden floor, a blue rug, and two sofas.
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 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 area

Oak Bluffs

In Oak Bluffs .Within a 10-minute walk of this Oak Bluffs vacation home, you'll find Inkwell Beach and Oak Bluffs Harbor. Circuit Avenue and Ocean Park are also within half a mile (1 km).
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What's nearby

  • Circuit Avenue - 3 min walk - 0.3 km
  • Inkwell Beach - 3 min walk - 0.3 km
  • Ocean Park - 5 min walk - 0.4 km
  • Oak Bluffs Harbor - 8 min walk - 0.7 km
  • Oak Bluffs Town Beach - 11 min walk - 1.0 km

Getting around

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

Restaurants

  • ‪Nancy's - ‬9 min walk
  • ‪Rocco's Pizzeria - ‬6 min drive
  • ‪Lookout Tavern - ‬9 min walk
  • ‪Offshore Ale Co. - ‬6 min walk
  • ‪Catboat Coffee Co. - ‬6 min drive

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.

Similar properties

House (6 Bedrooms) | Interior
Steps to Inkwell Beach: Victorian Home!
Oak Bluffs
  • Kitchen
  • Air conditioning
  • Barbecue grill
  • Water view
Steps to Inkwell Beach: Victorian Home!

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
  • Bedsheets 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.
  • 1 accessible parking space
  • 2 steps to reach entrance
  • Area rugs in public areas
  • Handrails in stairways
  • No elevator
  • 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

  • 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

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
Charges for extra guests may apply and vary according to property policy.
A cash deposit, credit card, or debit card for incidental charges and government-issued photo identification may be required upon check-in.
Special requests are subject to availability at the time of check-in. Special requests can't be guaranteed and may incur additional charges.
    This property is managed by a private host, not a professional engaged in trade or business. Onsite parties or group events are strictly prohibited. For guests' safety, the property includes a carbon monoxide detector, a fire extinguisher, and a smoke detector in each accommodation.

Property Registration Number c0288502210

Frequently asked questions

How close is The Legacy House: Walk to Inkwell Beach + Historic Charm, Modern Comfort to the airport?

This vacation home is 7.1 mi (15-min drive) away from the Vineyard Haven, MA (MVY-Martha's Vineyard) airport, the closest popular airport to the property.

Does The Legacy House: Walk to Inkwell Beach + Historic Charm, Modern Comfort have an airport shuttle?

Airport shuttle services are not available at this vacation home.

How close is The Legacy House: Walk to Inkwell Beach + Historic Charm, Modern Comfort to the beach?

This vacation home is a short 5-minute walk from Inkwell Beach and 4-minute walk from Seaview Beach. Don't forget your sunscreen!

Does The Legacy House: Walk to Inkwell Beach + Historic Charm, Modern Comfort offer free breakfast?

This vacation home does not offer free breakfast.

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

No, there is no casino at this vacation home.

What time is check-in at The Legacy House: Walk to Inkwell Beach + Historic Charm, Modern Comfort?

Check-in begins at 3:00 PM.

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

Free parking is not available at this vacation home.

Does The Legacy House: Walk to Inkwell Beach + Historic Charm, Modern Comfort have a pool?

This vacation home does not have a pool.

Does The Legacy House: Walk to Inkwell Beach + Historic Charm, Modern Comfort have a spa?

There are no spa services available at this vacation home.

How close is The Legacy House: Walk to Inkwell Beach + Historic Charm, Modern Comfort to downtown Oak Bluffs?

This vacation home is 0.3 mi away from Oak Bluffs.

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

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 review

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 review

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 review

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 review

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 review

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 review

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 review

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 review

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