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, comfortable, and spacious home that feels welcoming and well suited for relaxing stays. Guests consistently praised its cleanliness, noting that the cottage was clean, neat, well maintained, and comfortable for families and groups. The property is especially valued for its quiet residential setting while still being within easy walking distance of town, shops, restaurants, the harbor, the beach, and the ferry. Guests also appreciated the convenient layout, the deck and patio spaces, and that the home had what they needed for an enjoyable stay. Overall, Winthrop Cottage is seen as a cozy and convenient home away from home in a highly accessible Oak Bluffs location.
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
We loved how the neighborhood was quiet but was still so close to downtown's shops, restaurants, beach, and the bus.
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Sparkling and spotless stays
Arrive at a completely cleaned and inspected home.
Professionally Managed
Our properties are professionally managed to maintain high standards.
Transparent Pricing
No hidden fees or surprise charges. What you see is what you pay.