Historic cottage with patio, games, walk to beach & dog-friendly fenced yard

Oak Bluffs, Massachusetts
$712 avg/night
Bed 3

Bed

Bath 1

Bath

Home Cottage

Property Type

Sleep 5

Max Sleeps

Pilgrim Cottage

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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.

If you are bringing a dog on your trip, the pet fee is already included in your quote when selecting ‘Yes’ to pets. No more dogs are allowed.
Parking notes: There is free parking available for 1 vehicle.



Damage waiver: The total cost of your reservation for this Property includes a nightly damage waiver fee, plus tax if applicable (the “Damage Waiver”). (A discount may be applied for stays of 28 nights or longer, if permitted.) The Damage Waiver covers you for up to $3,000 of accidental damage to the Property or its contents (such as furniture, fixtures, and appliances) as long as you report the incident to the host prior to checking out. The Damage Waiver fee eliminates the need for a traditional security deposit.
More information can be downloaded from the Rental Agreement on the checkout page.

Due to local laws or HOA requirements, guests must be at least 25 years of age to book. Guests under 25 must be accompanied by a parent or legal guardian for the duration of the reservation.

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  • Feature Features
  • Map Map
  • School District Rates & Availability

Feature Features

  • PETS

    Pet Friendly
  • SAFETY

    Carbon Monoxide Detector Installed (host Has Indicated There Is A Carbon Monoxide Detector On The Property) First Aid Kit Smoke Detector Installed (host Has Indicated There Is A Smoke Detector On The Property)
  • BEDROOM

    3 Bedrooms Bed Sheets Provided
  • GENERAL

    Unit Size: 864 Sq Ft (80 Sq M)
  • KITCHEN

    Coffee/tea Maker Cookware/dishes/utensils Microwave Oven Refrigerator Stovetop Toaster
  • LAUNDRY

    Washing Machine And Dryer
  • PARKING

    Onsite Parking
  • INTERNET

    Internet Access
  • OUTDOORS

    Garden Patio
  • BATHROOMS

    1.5 Bathrooms Hair Dryer Towels Provided
  • LANGS SPOKEN

    English French German Italian Spanish
  • THINGS TO DO

    Birdwatching Nearby Cycling Nearby Ecotours Nearby Kayaking Nearby Marina Nearby Power Boating Nearby Scuba Diving Nearby Snorkeling Nearby Swimming Nearby
  • ENTERTAINMENT

    Books DVD Player Games TV With Cable/satellite Service
  • LIVING SPACES

    Living Room
  • CLIMATE CONTROL

    Air Conditioning Heating
  • LOCATION HIGHLIGHTS

    In A Village Near A Hospital Near The Sea
  • SERVICES AND CONVENIENCES

    Iron/ironing Board
  • SUITABILITY/ACCESSIBILITY

    Note From Host: Smoking Is Not Permitted Anywhere On The Premises. Smoke-free Property

CheckIn Check-in : 04:00 PM CheckOut Check-out : 10:00 AM
No Wheelchair No smoking No pets Children allowed
Occupancy Max occupancy : 5

Map Map

School District Rates & Availability

Your dates are Available!

Total

Includes taxes and fees
$712+
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