Compare Chilmark Guest House Rentals

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Featured Guest Houses in Chilmark

The Lightkeepers Inn

The Lightkeepers Inn

3 out of 5
25 Simpson's Lane Edgartown MA
Guests staying at The Lightkeepers Inn enjoy free WiFi in public areas, express check-out, and a garden. You can put free parking to good use if you drive. Front-desk staff can help with luggage storage, and provide local restaurant recommendations.
Parking included
Free WiFi
Light-Filled Romantic Cottage Close to Village, Beach, Bike Path, Nature Trails

Light-Filled Romantic Cottage Close to Village, Beach, Bike Path, Nature Trails

Edgartown MA
Guests staying at this guesthouse have access to laundry facilities, a garden, and barbecue grills.
Madison Inn

Madison Inn

2.5 out of 5
18 Kennebeck Avenue Oak Bluffs MA
Guests of Madison Inn enjoy access to free WiFi in public areas, coffee in a common area, and microwave in a common area. You can put free offsite parking to good use if you drive. Front-desk staff can help with luggage storage, and provide local restaurant recommendations. Additional amenities include a refrigerator in a common area, a library, and a terrace.
Spacious Guest House in Falmouth Village

Spacious Guest House in Falmouth Village

Falmouth MA
Guests staying at this guesthouse have access to laundry facilities, barbecue grills, and a garden.
Pet friendly
Free WiFi
Woods Hole Passage Inn

Woods Hole Passage Inn

3 out of 5
186 Woods Hole Road Falmouth MA
Guests staying at Woods Hole Passage Inn enjoy free WiFi in public areas, a terrace, and a garden. If you plan to drive, free parking is available.
The Oak Bluffs Inn

The Oak Bluffs Inn

3 out of 5
64 Circuit Ave Oak Bluffs MA
Guests staying at The Oak Bluffs Inn enjoy free WiFi in public areas, a terrace, and a garden. Airport transportation is made easy with an airport shuttle for a fee. Staff members can answer questions about accommodations, and also provide concierge services. This smoke-free guesthouse also has a picnic area.
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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.

Hotel Options in Chilmark

    Iris Hotel Cape Cod

    Iris Hotel Cape Cod

    291 Jones Rd Falmouth MA
    $121 nightly
    The price is $138 total per night from Jan 7 to Jan 8
    $138 total
    Jan 7 - Jan 8, 2026
    Total with taxes and fees
    8.4/10 Very Good! (158 reviews)
    Faraway Martha's Vineyard

    Faraway Martha's Vineyard

    23 Kelly Street Edgartown MA
    8.8/10 Excellent! (999 reviews)
    Falmouth Inn

    Falmouth Inn

    824 Main Street Falmouth MA
    $113 nightly
    The price is $127 total per night from Jan 6 to Jan 7
    $127 total
    Jan 6 - Jan 7, 2026
    Total with taxes and fees
    7.8/10 Good! (1,000 reviews)

Chilmark Guest Houses essential information

Accommodation
6 Guest Houses
Lowest Price
$127
Highest Price
$138
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