Nestled in a peaceful, historic neighborhood within walking distance of Oak Bluffs' attractions, this charming home offers a tranquil retreat. Enjoy the wrap-around porch and ample off-street private parking or relax on the large rear deck with an outdoor shower.
Reviews
9.89.8 out of 10
Exceptional
Entire home
6 bedrooms2 bathroomsSleeps 10
Popular amenities
Kitchen
Washing machine
Dryer
Air-conditioning
Outdoor space
Parking available
Add dates for prices
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.
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)
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
Pets not 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
On-site parties or group events are strictly prohibited
Host has indicated that there is a carbon monoxide detector on the property
Host has indicated that 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
Property Registration Number c0288502210
We should mention
This property does not have any lifts
About the area
Oak Bluffs is home to this holiday home. Woods Hole Ferry Terminal and Oak Bluffs Ferry Terminal are worth checking out if an activity is on the agenda, while those wishing to experience the area's natural beauty can explore Inkwell Beach and Cape Cod Beaches. Flying Horses Carousel and Island Cove Adventures are also worth visiting. Visit our Oak Bluffs travel guide
Is The Legacy House: Walk to Inkwell Beach + Historic Charm, Modern Comfort pet-friendly?
No, pets are not allowed at this property.
How much is parking at The Legacy House: Walk to Inkwell Beach + Historic Charm, Modern Comfort?
On-site parking is available at the property.
What time is check-in at The Legacy House: Walk to Inkwell Beach + Historic Charm, Modern Comfort?
Check-in begins at 3:00 PM.
What time is check-out at The Legacy House: Walk to Inkwell Beach + Historic Charm, Modern Comfort?
Checkout is at 10:00 AM.
Where is The Legacy House: Walk to Inkwell Beach + Historic Charm, Modern Comfort located?
Situated in Oak Bluffs, this holiday home is within a 5-minute walk of Circuit Avenue and Inkwell Beach. Ocean Park and Seaview Beach are also within 5 minutes.
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The Legacy House: Walk to Inkwell Beach + Historic Charm, Modern Comfort Reviews
Reviews
Exceptional
All reviews shown are from real guest experiences. Only travellers who have booked a stay with us can submit a review. We verify reviews according to our guidelines and publish all reviews, positive or negative.
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.
Adorable home in a central location of OB. Exceeds the picture, home is comfortable and has everything you need.
Lindsey R.
Stayed 4 nights in Jun 2024
Verified
10/10 Excellent
Anurag
27 May 2024
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
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!
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!
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!
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!
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.