Site logo
Vacation RentalsDestinationsProperty ManagementContact Us
Vacation RentalsDestinationsProperty ManagementContact Us
About Us
About Us

All About Casago

Blog
Blog

Explore Our Blogs

Franchise with Us
Franchise with Us

Become a Franchise

FAQs
FAQs

Most Common Questions

  1. USA >
  2. Massachusetts >
  3. Oak Bluffs

Winthrop Cottage

Cute & cozy cottage with a patio & gas grill in the heart of Martha's Vineyard
Cute & cozy cottage with a patio & gas grill in the heart of Martha's Vineyard
Cute & cozy cottage with a patio & gas grill in the heart of Martha's Vineyard

House in Oak Bluffs, Massachusetts

Guests
6 Guests
Bedrooms
3 Bedrooms
Bathrooms
1 Bathroom

Locally Owned & Operated

Martha's Vineyard

Martha's Vineyard

Casago Franchise Owner

Locally Owned & Operated
Rating4.16

What our guests are saying...

AI-generated from guest reviews for this property

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

Central AC
Central AC
Gas grill
Gas grill
Beach access
Beach access
Board games
Board games
Cable
Cable
Washer/dryer
Washer/dryer
DVD player
DVD player
Space heater
Space heater
Internet
Internet
Microwave
Microwave
Patio
Patio
Stove
Stove
TV
TV

Sleeping Arrangements

Bedroom 1

sleeps 2

Beds
1 queen bed

Bedroom 2

sleeps 2

Beds
2 twin beds

Bedroom 3

sleeps 1

Beds
1 twin bed

Location

Oak Bluffs, Massachusetts, Home

(Exact address will be provided after booking)

Location

Rating

4.16
43 reviews
5 Star
47%
4 Star
35%
3 Star
12%
2 Star
2%
1 Star
5%
search
Rex B2025-09-19

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.

MICHAEL M2025-09-09

Clean quiet

Kevin J2025-07-27

The house was clean. It was within walking distance to downtown.

Rachel G2025-07-20

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.

Collins E2025-07-06

Clean, small, great for a weekend trip

Micah D2025-06-30

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.

$325
avg / night
Rating4.16

You won't be charged yet

Our Destinations
View all
Site logoVeteran Owner

Quick Links

  • Newsroom
  • Videos
  • Executive Team
  • Casago Careers
  • Promotions/Discounts
  • Apps

CONTACT US

  • 850 NW 13th Ave.
  • Suite 400
  • Portland, OR 97209

NEED MORE HELP?

  • Contact us now

©2026 Casago. All rights reserved

Privacy PolicyTerms of Service
FacebookInstagramYouTubeLinkedIn