Search Guest Houses in Chilmark

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Check prices for these dates

Next weekend
20 Nov - 22 Nov
In two weeks
27 Nov - 29 Nov
In one month
11 Dec - 13 Dec
In two months
8 Jan - 10 Jan

Our top choices for Chilmark guest houses

A cozy living room with a fireplace, bookshelves, a dining area, and a staircase.

1. Madison Inn

Madison Inn
2.5 star property
Oak Bluffs
9.8 out of 10, Exceptional, (84 reviews)
"Good location, friendly staff. More breakfast/drink options would have been good."
United States
Melissa
The price is RM840
RM961 total
includes taxes & fees
22 Nov - 23 Nov
Madison Inn
A residential property with a gravel driveway, a wooden bench, and a house with a shingled exterior.

2. The Lightkeepers Inn

The Lightkeepers Inn
3.0 star property
Edgartown
9.4 out of 10, Exceptional, (221 reviews)
"The lightkeepers in was perfect. Would definitely go back"
United States
Penny
The price is RM924
RM1,033 total
includes taxes & fees
26 Nov - 27 Nov
The Lightkeepers Inn
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Learn more about Chilmark

Menemsha Beach offers spectacular sunsets where locals and visitors gather with picnic dinners to watch the sky change colours. Hike the scenic trails at Waskosim's Rock Reservation or visit nearby Martha's Vineyard for charming shops and restaurants.

See all hotels in Chilmark
A dock with boats, a small wooden structure, and a forested shoreline.