Winthrop Cottage



House in Oak Bluffs, Massachusetts
Locally Owned & Operated

Martha's Vineyard
Casago Franchise Owner
What our guests are saying...
Winthrop Cottage is described as a charming, cozy, spacious, and comfortable home that feels welcoming and well suited for family vacations and relaxing stays. The property is repeatedly praised for being very clean, neat, well maintained, and thoughtfully equipped for guests. Its quiet setting adds to the comfort while still offering easy access to Oak Bluffs, downtown shops, restaurants, the harbor, the beach, the ferry, and the bus. Guests also appreciated the deck, patio spaces, and the home's classic charm, along with useful kitchen items and family-friendly touches. Overall, Winthrop Cottage is seen as a convenient, peaceful, and highly enjoyable place to stay.
Overview
If you are planning a family vacation to Martha's Vineyard, consider this affordable and comfortable cottage in Oak Bluffs! With a well-equipped kitchen, furnished patio, and outdoor gas grill, plus two TVs for relaxing after a day in the sun, this property has everything you might need to enjoy a fantastic stay on the Vineyard. Make your vacation a memorable one and book with us today!
What's nearby:
This cottage is just a short drive from the ocean and downtown Oak Bluffs. East Chop Lighthouse is an easy drive north and a fantastic choice for a day trip. Be sure to take a walk through Oak Bluffs as well as Vineyard Haven to experience the great local restaurants and adorable shops.
What's included:
Free WiFi
Full kitchen with a dishwasher
You must be 21 years or older to rent this property.Amenities
Sleeping Arrangements
Bedroom 1
sleeps 2
Bedroom 2
sleeps 2
Bedroom 3
sleeps 1
Rating
The property had good privacy and was clean on arrival, but my stay from September 12–14, 2025, was ruined by pest issues in the master bedroom. On the first night, an insect was found in the bed, and later a spider appeared in the room, making it impossible to rest comfortably. We spent nights uneasy and even slept with the lights on, which is unacceptable for a paid stay. I reported the issue immediately; the response was polite but no real action was taken. No pest control was sent, and management failed to provide any resolution. The lack of follow-through and disregard for guest comfort and safety overshadowed the positive aspects of the property. Until these concerns are addressed, I cannot recommend staying here.
Clean quiet
The house was clean. It was within walking distance to downtown.
The spare bed was bug infested causing us to book a last minute hotel for the remainder of our vacation. We requested a refund immediately and havent heard a word back and it has been 2 weeks. I will update this review if they reach out and resolve this unfortunate issue.
Clean, small, great for a weekend trip
Stayed here for work. Very comfortable cottage. Reasonable(30min) walk, or short bike ride(5-10min) to Oak Harbor. Home was clean and neat. Only reason for 4 not 5 star was that A/C was advertised but they were window units and were not installed. Temps were fine without, it was great to hear the birds sing.
You won't be charged yet