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Waterfront Retreat w/ Guest Cottage & Sunsets

House in Oak Bluffs, MA

7 guests·4 bedrooms·2 bathrooms
4.8 · 10 reviews

Property details

Escape to the beauty of Martha’s Vineyard at this private waterfront retreat overlooking the Lagoon in Oak Bluffs. Tucked away in a peaceful neighborhood yet conveniently located just minutes from downtown, this one-of-a-kind property offers the perfect blend of coastal tranquility and easy access to the island’s best beaches, restaurants, shops, bike paths, and attractions. This waterfront home provides an unforgettable setting to relax, reconnect, and experience the best of Martha’s Vineyard. Wake up to breathtaking water views, spend your days exploring the island, and return home to enjoy spectacular sunsets from the expansive deck overlooking the Lagoon. With direct shoreline access, a separate guest cottage, and thoughtfully curated amenities, this property was designed to make your Vineyard getaway both comfortable and memorable. What You'll Love: 🌅 Spectacular waterfront sunsets over the Lagoon 🏖️ Private beach and shoreline access via backyard staircase 🏡 Separate guest cottage for added privacy and flexibility 💻 Dedicated workspace and Peloton bike 🚗 Free parking for up to 4 vehicles 🔐 Self check-in with smart lock 📍 Minutes from downtown Oak Bluffs, beaches, dining, and ferries The Space Thoughtfully positioned to maximize its incredible waterfront setting, this property features a bright and welcoming main house alongside a separate guest cottage. Nearly every room enjoys beautiful Lagoon views, creating a relaxing atmosphere throughout your stay. HOME LAYOUT • Open-concept living area • Fully equipped kitchen • Dining area • 4 bedrooms • 2 bathrooms • Waterfront deck • Outdoor dining area • BBQ grill • Private backyard • Direct shoreline access • Separate guest cottage BEDROOMS This waterfront property comfortably accommodates families and groups with sleeping arrangements spread between the main house and detached guest cottage. • Bedroom 1 (Main House): King-size bed with floor-to-ceiling windows and stunning waterfront views • Bedroom 2 (Main House): Two Twin beds with water views and crib available • Bedroom 3 (Guest Cottage): Queen-size bed with air conditioning • Bedroom 4 (Guest Cottage/Office): Twin bed, dedicated workspace, Peloton bike, and air conditioning The separate guest cottage offers additional privacy, making it ideal for grandparents, couples traveling together, remote workers, or guests seeking their own private retreat. BATHROOMS The property includes two full bathrooms. Main House : Full bathroom with bathtub Guest Cottage : Shared Jack-and-Jill bathroom Complimentary shampoo, conditioner, body wash, and essential toiletries are provided. KITCHEN The fully equipped kitchen includes everything needed for preparing meals during your stay: • Refrigerator • Stove & oven • Dishwasher • Microwave • Toaster • Electric kettle • Drip coffee maker • French press • Air fryer • Blender • Magic Bullet • Cookware, dishes, utensils, and glassware DINING The dining area comfortably seats six guests and offers a welcoming space for shared meals while enjoying beautiful waterfront surroundings. LIVING AREA Filled with natural light, the living room features large sliding glass doors that open directly onto the deck, showcasing breathtaking Lagoon views. The comfortable seating arrangement and Smart TV create the perfect space to relax after a day exploring the island. OUTDOOR LIVING One of the home's most memorable features is its exceptional waterfront outdoor space. Enjoy: • Outdoor dining overlooking the Lagoon • Comfortable lounge seating • Stunning sunset views every evening • Private backyard leading directly to the shoreline • Staircase access to the beach • BBQ grill for outdoor cooking Whether you're sipping your morning coffee, enjoying an afternoon read, or gathering with loved ones for dinner by the water, the outdoor spaces offer a quintessential Martha’s Vineyard experience. LOCATION Located in the heart of Oak Bluffs, this property offers the perfect balance of privacy and convenience. Nearby attractions include: • Downtown Oak Bluffs • Local restaurants and seafood spots • Beaches and waterfront activities • Historic Gingerbread Cottages • Island bike paths • Ferry terminals • Shopping and entertainment Explore the island with ease while enjoying a peaceful waterfront setting to return to each day. PARKING Free on-site parking is available for up to four vehicles. • OTHER AMENITIES • ✔ High-speed Wi-Fi ✔ Dedicated workspace ✔ Peloton bike ✔ Smart TV ✔ Washer & dryer ✔ Air conditioning ✔ Central heating ✔ Pack ’n Play and crib ✔ Self check-in with smart lock ✔ Free parking for up to 4 vehicles Guests will enjoy exclusive access to the entire property, including both the main house and guest cottage. One owner's closet remains locked and unavailable for guest use. PLEASE NOTE: Our housekeeping staff is not responsible for setting up or assembling pullout beds, sofa beds, cribs, Pack 'n Plays, or baby beds. Guests are responsible for arranging and preparing these items for use during their stay. IMPORTANT NOTES • Linens & Towels Bed linens, blankets, comforters, bath mats, and kitchen towels are provided. Bath towels and beach towels are not provided. Guests should bring their own or arrange rentals through local linen providers before arrival. • Ferry Reservations Guests bringing vehicles are strongly encouraged to reserve ferry transportation through the Steamship Authority as early as possible, especially during peak season. • Property Maintenance A landscaper may visit periodically during the summer months to maintain the grounds. All work is performed outdoors. • SAFETY & SECURITY • For guest safety, exterior security cameras are installed at entrances and outdoor areas only. There are no cameras inside the home. Noise monitoring devices are present but do not record conversations or audio. Smoke detectors and other standard safety features are provided throughout the property. From sunset views over the Lagoon to private shoreline access and the flexibility of a separate guest cottage, this Oak Bluffs waterfront retreat offers the perfect setting for an unforgettable Martha’s Vineyard getaway. 🌅🏖️🏡 HOUSE RULES • PETS: The unauthorized bringing of pets will have a penalty of $300 which will go towards the deep cleaning of the property. • CHECK-IN: Check-in time is after 4 PM. Early check-in requests are subject to availability and cannot be guaranteed. If we're able to accommodate an early check-in, there's an early check-in fee of $50 starting at 10 AM. Please check the availability of early check-in prior to booking. • CHECK-OUT: Check-out time is before 11 AM. We do not allow late check-out as we schedule cleaning ahead of time. Any unauthorized late check-out will result in a charge of $50 for every 30 minutes. • SMOKING: We do not allow smoking inside the property or in outdoor spaces including the balcony, backyard, and terrace (if applicable). There is a smoking fine of $300. Smoking is only permitted by the fire pit.  • BBQ GRILL: An extra charge of $100 will apply for not cleaning after using the BBQ Grill. • NOISE: Please observe quiet hours after 10 PM. Please be mindful of the neighbors as this property is situated in a quiet neighborhood. If the police are summoned due to noise complaints, this warrants a possible eviction with no refund. • DAMAGES & LOSS: We would truly appreciate it if you could treat our home like yours. You will be responsible for any damages or loss to the property which will be deducted from your security deposit. Excessive damage to the property will have a liability of up to $5000. Guests are responsible for covering the cost to replace lost keys, key cards, fobs, or parking passes. There will be a $200 charge for lost keys. Lock replacement is mandatory for the safety of future guests. • PHOTOSHOOT/MUSIC VIDEOS: This property is for residential use only and not for commercial purposes without the written permission of the owner. Please contact us directly for booking of events.  • LOST AND FOUND: Please note that all shipping is at the traveler's expense. There is a minimum $25 shipping cost plus a $50 service fee. We are not liable for any lost items. Our team will do our best to locate your lost items after check-out. We do not allow any mail deliveries or packages during your stay. PLEASE NOTE: Our housekeeping staff is not responsible for setting up or assembling pullout beds, sofa beds, cribs, Pack 'n Plays, or baby beds. Guests are responsible for arranging and preparing these items for use during their stay.

Sleeping arrangements

Bedroom 1

1 King Bed

Bedroom 2

2 Twin Beds

Bedroom 3

1 Queen Bed

Bedroom 4

1 Twin Bed

What’s included

  • Self check-in

    Self check-in

  • Parking

    Parking

  • Washer

    Washer

  • Dryer

    Dryer

  • Air conditioning

    Air conditioning

  • Heating

    Heating

  • Kitchen

    Kitchen

  • Wi-Fi

    Wi-Fi

Guest reviews

Star icon 4.8 | 10 reviews
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Christopher

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September 2026

Fantastic stay! Gorgeous setting up on a cliff with direct water views and steps down to a little beach area - framed like a post card! Very private with mature trees - felt like we were going into a secret hideaway as we passed the two trees that flanked the entrance. Easy to relax at this property …. Kitchen well stocked, beds are comfortable, and several restaurants are within a 6-10 minute drive in oak bluffs and vineyard Haven - highly recommend!

M

Mary

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August 2026

We had a wonderful stay! Simone was welcoming and very responsive to messages. The house was beautiful, exactly as described, and a lovely place to stay. We would happily return!

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Betsy

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August 2026

Lovely cottage experience with separate cottage for our daughter and her husband with the new baby. Really bright view to the water. Located on a quiet part of Oak Bluffs, great place to bike and walk. The beach is just below the house and just down the stairs. House was very comfortable and great wfi, and nicely remodeled bathrooms. and comfortable beds. We enjoyed our stay in spite of bad weather. Highly recommend.

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Dani

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July 2026

The airbnb was nice, overlooking the water, but was wildly over-priced, especially for the size and layout, not providing towels for guests which was a pain (though mentioned in the listing) and the hiccups along the way. The management company was very responsive but the door code was wrong, the wifi password was wrong, many of the dishes were dirty, and we had to walk through sprinklers to get to our car if we wanted to leave between 7-8am.

Know before you go

Self check-in

House rules

Check-in: 4:00pm

Checkout: 11:00am

No pets allowed

Min. age to rent: 21

No smoking

No parties

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