Escape to The Winthrop, a refined Vineyard retreat set on a serene ⅓ acre just moments from the heart of town. Thoughtfully designed for relaxed luxury, this cottage pairs central air, a chef-grade stove, dishwasher, and in-home laundry with the timeless character of classic island living. Open the doors to a deck overlooking a lush, private lawn, perfect for slow mornings and family gatherings. Stroll 2 minutes to the general store, or enjoy an easy 10 minute walk to town and nearby beaches. The space: Seamless Indoor/Outdoor Living: Access the expansive deck and verdant lawn from 3 different areas of the house. Bask in the sun or find shade under the canopy of trees, creating the ideal spot for lazy afternoons, alfresco dining, or simply sipping the beverage of your choosing. And for those beach days, don't forget to take advantage of the outdoor shower after your short walk home. Thoughtful Renovation: Meticulously restored in 2007, the house retains its original character while offering modern conveniences. From the exposed beams to the cozy fireplace, every detail reflects the care put into preserving its unique personality. Bed/Bath Layout: 1st floor- 1 bedroom (Queen); 1 living room pullout sofa (Queen)/2 full baths 2nd floor- 2 bedrooms (1 Queen; 2 Twins)/no baths Comfortable Living: The cottage offers a retreat for up to 8 guests. Each room is adorned with cozy furnishings, creating an atmosphere of comfort and relaxation. Local Delights: Immerse yourself in the local scene with a short walk to town, where you'll find quaint shops, delightful eateries, and the vibrant energy of the community. The beach beckons for leisurely strolls and breathtaking sunsets, offering the perfect backdrop for unforgettable moments. Additional Amenities: High-speed Wi-Fi Outdoor seating and dining Outdoor shower AC Washer and dryer Parking for 2 cars Unwind in this idyllic Vineyard Cottage, where the fusion of history and modern comfort creates a truly memorable escape. Book your stay now and experience the best of Vineyard living. Other Things to Note: The staircase leading to the second floor—where two bedrooms are located—is original to the home and quite steep. Guests should use extra caution when going up or down the stairs. There are 3 bedrooms that each sleep 2 ppl (Primary/ Bedroom 1- 1 queen bed. Bedroom 2- 1 queen bed. Bedroom 3- 2 twin beds, specifically 1 day bed with additional pop up twin trundle bed). The living room also has a pullout sleeper sofa with a queen mattress that sleeps an additional 2.
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Amenities
Kitchen
Washing machine
Dryer
Air conditioning
Parking available
Fireplace
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Cozy vineyard cottage close to downtown with outdoor living space and amentiies.
Oak Bluffs
Cozy vineyard cottage close to downtown with outdoor living space and amentiies.
The host requires you to complete the following before checking out:
Remove personal items, remove leftover food and drinks and take out the rubbish
Turn off the lights, lock the doors and return the keys
Failure to complete these may result in a negative review from the host.
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 and a first aid kit
Property Registration Number C0464222210
About the area
Oak Bluffs
Oak Bluffs is home to this holiday home. While the natural beauty of Inkwell Beach and Cape Cod Beaches can be enjoyed by anyone, those looking for an activity can explore Woods Hole Ferry Terminal.
Flying Horses Carousel and Island Cove Adventures are also worth visiting.
Vineyard Haven, MA (MVY-Martha's Vineyard) - 15 min drive
Restaurants
Offshore Ale Co. - 14 min walk
The Barn Bowl & Bistro - 8 min walk
Lookout Tavern - 18 min walk
Mo's Lunch - 16 min walk
Portuguese-American Club - 16 min walk
Frequently asked questions
Is Walk to Beach Spacious Retreat pet-friendly?
No, pets are not allowed at this property.
How much does it cost to stay at Walk to Beach Spacious Retreat?
As of 22 Apr 2026, prices found for a 1-night stay for 2 adults at Walk to Beach Spacious Retreat on 29 June 2026 start from AU$692, including taxes and fees. This price is based on the lowest nightly price found in the last 24 hours for stays in the next 30 days. Prices are subject to change. Choose your dates for more accurate prices.
How much is parking at Walk to Beach Spacious Retreat?
On-site parking is available at the property.
What time is check-in at Walk to Beach Spacious Retreat?
Check-in begins at 3:00 PM.
What time is check-out at Walk to Beach Spacious Retreat?
Checkout is at 10:00 AM.
Where is Walk to Beach Spacious Retreat located?
Situated in Oak Bluffs, this holiday home is within a 15-minute walk of Circuit Avenue and Inkwell Beach. Oak Bluffs Public Library and Trinity Park Tabernacle are also within 15 minutes.