Book Guest Houses in Chilmark, MA
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Top Guest Houses in Chilmark
The Lightkeepers Inn
25 Simpson's Lane Edgartown MA
This guesthouse doesn't skimp on freebies - guests receive free WiFi and free self parking. A garden, express check-out, and luggage storage are also on offer.
Parking included
Free WiFi
Light-Filled Romantic Cottage Close to Village, Beach, Bike Path, Nature Trails
Edgartown MA
This guesthouse features a garden, laundry facilities, and barbecue grills.
Free WiFi
Air conditioning
Madison Inn
18 Kennebeck Avenue Oak Bluffs MA
Free WiFi in public areas, a terrace, and a snack bar/deli are available at this guesthouse. A lobby fireplace, a library, and luggage storage are also on offer.
Free WiFi
Air conditioning
Spacious Guest House in Falmouth Village
Falmouth MA
This guesthouse features a garden, laundry facilities, and barbecue grills.
Pet friendly
Free WiFi
Woods Hole Passage Inn
186 Woods Hole Road Falmouth MA
This guesthouse doesn't skimp on freebies - guests receive free WiFi and free self parking. A terrace and a garden are also provided.
Parking included
Free WiFi
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.
Top hotels in Chilmark
Mansion House Inn And Spa
9 Main Street Vineyard Haven MA
$189 nightly
The price is $209 total per night from Jan 4 to Jan 5
$209 total
Jan 4 - Jan 5, 2026
Total with taxes and fees
9.2/10 Wonderful! (1,001 reviews)
Chilmark Guest Houses essential information
Accommodation | 6 Guest Houses |
|---|---|
Lowest Price | $125 |
Highest Price | $356 |
Popular accommodation | The Lightkeepers Inn, Light-Filled Romantic Cottage Close to Village, Beach, Bike Path, Nature Trails, Madison Inn, Spacious Guest House in Falmouth Village, Woods Hole Passage Inn, The Oak Bluffs Inn |
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