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Pilgrim Cottage

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

House in Oak Bluffs, Massachusetts

Guests
5 Guests
Bedrooms
3 Bedrooms
Bathrooms
1 Bathroom
Half baths
1 Half bath
Pets allowed
Pets allowed

Locally Owned & Operated

Martha's Vineyard

Martha's Vineyard

Casago Franchise Owner

Locally Owned & Operated

Overview

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 our 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.

You must be 25 years or older to rent this property.

Amenities

Central AC
Central AC
Beach access
Beach access
Board games
Board games
Cable
Cable
Washer/dryer
Washer/dryer
DVD player
DVD player
Space heater
Space heater
Internet
Internet
Iron
Iron
Microwave
Microwave
Patio
Patio
Dog-friendly
Dog-friendly
Stove
Stove
TV
TV

Sleeping Arrangements

Bedroom 1

sleeps 2

Beds
1 double bed

Bedroom 2

sleeps 2

Beds
1 double bed

Bedroom 3

sleeps 1

Beds
1 twin bed

Location

Oak Bluffs, Massachusetts, Home

(Exact address will be provided after booking)

Location

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$366
avg / night

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