Cottage in Oak Bluffs, Massachusetts
New Vacasa Listing
OVERVIEW
Historic cottage with patio, games, walk to beach & dog-friendly fenced yard
Welcome to Pilgrim Cottage, your cozy home base for an authentic Martha’s Vineyard getaway. Set in the very heart of Oak Bluffs, this weathered yet welcoming cottage has been part of the island’s story since 1897, first as a humble “camp” and gradually expanded through the 1940s and 50s. Today, Pilgrim Cottage remains true to its roots: relaxed, comfortable, and filled with character, perfect for guests who appreciate the charm of an unpretentious, truly lived-in home.
The cottage is centrally located, making it easy to stroll to sun-soaked beaches, the vibrant Campground with its famous gingerbread houses, and the shops and restaurants along downtown Circuit Avenue. Inside, you’ll find shelves filled with books and puzzles, classic board games for all ages, and an effortlessly comfortable living area—ideal for quiet evenings or rainy afternoons. The kitchen is well equipped for meals together, and out back you’ll discover a raised herb garden with fresh herbs for guests to pick and enjoy. The backyard patio offers a quiet spot for morning coffee or outdoor dining, surrounded by the serene enclosed yard, which is especially inviting for little ones or furry friends since Pilgrim Cottage is dog-friendly.
Generations of honeymooners and families have found joy here, drawn by the unassuming comfort and timeless spirit of summer. With thoughtful touches like mini-split air conditioning and WiFi, you’ll have the essentials for a carefree island stay while still enjoying the cottage’s historic soul.
Come experience the magic of Oak Bluffs from Pilgrim Cottage, and make your own Martha’s Vineyard memories in this beloved island retreat. Book your stay today—we look forward to welcoming you!
Things to Know
- Check-in time: 4:00 p.m.
- Check-out time: 10:00 a.m.
- All guests shall abide by Vacasa’s good neighbor policy and shall not engage in illegal activity. Quiet hours are from 10:00 p.m. to 8:00 a.m.
- No smoking is permitted anywhere on the premises.
- 1 dog, weighing 40 lbs or less, welcome in this home. No other animals are allowed without specific Vacasa approval.
- Parking notes: There is free parking available for 1 vehicle.
State/province tax number: C0576542210
You must be 25 years or older to rent this property.
AMENITIES
Internet
Washer/dryer (Private)
Cable
Features
Iron
Washer/dryer : Private
Heating & cooling
Partial AC
Space heater
House rules
Dog-friendly
Kitchen & dining
Fridge
Microwave
Stove
Media
Internet
TV
Cable
DVD player
Wireless router
Netflix streaming
Nearby activities & attractions
Golf nearby
On-site activities
Board games
Outdoor
Deck
Patio
Beach chairs
Beach towels
Enclosed yard
Location
(Exact address will be provided after booking)
Rating
Be one of the first to experience this new Vacasa listing. Our local team has the home clean, stocked, and ready for your stay. Even better, we'll be on hand with 24/7 support to make sure your stay is seamless.
What guests say about Vacasa
1 million+
5-stars reviews
9 / 10
Guests would likely recommend Vacasa to a friend
4.5 / 5
Average clean score
