The Winthrop · Summer House, Private Yard, Walk to Town

Top rated by guests
Exterior
Interior
Primary bedroom en suite full bathroom
Bathroom
Spacious primary bedroom is located on the 1st floor and includes en suite full bathroom and dedicated office space
review stars
10Outstanding
(2 Ratings)
"GORGEOUS, clean, spacious, steps away from a cute general store, walking distance to both towns and beaches. Couldn't be nicer! The system didn't send us the check in code for some reason but the host..."
Sarah C.
Don't miss out! Price and availability may change
10 / 10
Outstanding(2 Ratings)

House in Tisbury, MA

8 guests · 3 bedrooms · 2 baths

Reasons to book

Guests love it hereGuests give this property a top rating
Top-tier experienceA high end property in this area
Book with confidenceWe partner with the top travel sites so you know you're getting a great deal on the perfect rental

About this house rental

Escape to The Winthrop, a 1900 Oak Bluffs farmhouse set on a serene ⅓ acre at the quiet edge of town. Thoughtfully restored in 2008, it pairs the timeless character of classic island living, from exposed beams to original pine floors, with central air, a Blue Star gas stove, a dishwasher and in-home laundry. Sleeps 8.

Open the doors to a deck overlooking a lush, private lawn, made for slow mornings, long lunches and family dinners under the trees. Sway in the hammock, settle into an Adirondack chair, and rinse off in the outdoor shower after a day at the beach.

Stroll 2 minutes to the general store, about 12 to the shops and restaurants of Circuit Ave, and about 15 to Inkwell Beach.

Indoor/outdoor living

The deck and lawn open from three doors of the house. Find sun or shade under the canopy of trees for lazy afternoons and dining al fresco.

Sleeping arrangements (up to 8 guests)

1st floor: primary suite with a queen bed and a propane stove for cool evenings; queen sleeper sofa in the living room; 2 full baths

2nd floor: a queen bedroom, and a twin room with a daybed and pop-up trundle

Amenities

High-speed Wi-Fi · central air · washer and dryer · outdoor dining · outdoor shower · parking for 2 cars

Good to know

The staircase to the second floor is original to the home and quite steep. Please take extra care going up and down, especially with small children. Both bathrooms are on the first floor.

Amenities at The Winthrop · Summer House, Private Yard, Walk to Town

Non-smoking
No pets allowed
Family friendly

Map of Tisbury, MA

city location on map

Ratings and reviews

10 / 10
Outstanding(2 Ratings)
10 / 10Outstanding·Jul 2026
GORGEOUS, clean, spacious, steps away from a cute general store, walking distance to both towns and beaches. Couldn't be nicer! The system didn't send us the check in code for some reason but the host replied immediately.

$$$$
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FAQs

Is parking included with this house?

Parking is not specified as an available amenity at The Winthrop · Summer House, Private Yard, Walk to Town. For more information, we encourage you to contact the property about where to park.

Is there a pool at this house?

We didn’t find pool listed as an amenity for this house. It may be worth double checking if a pool is important for your stay.

Is The Winthrop · Summer House, Private Yard, Walk to Town pet friendly?

Unfortunately, this house is not pet-friendly. Try searching again and filter for "Pets Allowed"

What amenities are available at The Winthrop · Summer House, Private Yard, Walk to Town?

We found 3 amenities for this rental. This includes non-smoking, no pets allowed, and family friendly.