Compare Chilmark Guest House Rentals

Earn Orbucks instantly: $1 Orbuck = $1 USD, good toward hotels

Save 10% or more on select hotels with Insider Prices

Book on the app to instantly earn 5% on 350,000+ hotels

Featured Guest Houses in Chilmark

Guests staying at The Lightkeepers Inn enjoy free WiFi in public areas, express check-out, and a garden. Self parking is available for USD 50 per night. Front-desk staff can help with luggage storage, and provide local restaurant recommendations.

Spacious Guest House in Falmouth Village

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

Pet friendly

Free WiFi

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.

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.

Free WiFi

Air conditioning

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.

Free WiFi

Air conditioning

Don't see what you're looking for?

See all available properties in Chilmark

View all properties

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

291 Jones Rd Falmouth MA

$121 nightly

$138 total

Apr 26 - Apr 27

Total with taxes and fees

8.6/10 Excellent! (215 reviews)

Sea Crest Beach Resort

350 Quaker Rd North Falmouth MA

$185 nightly

$212 total

May 3 - May 4

Total with taxes and fees

8/10 Very Good! (264 reviews)

Falmouth Inn

824 Main Street Falmouth MA

$119 nightly

$134 total

Apr 26 - Apr 27

Total with taxes and fees

8/10 Very Good! (1,001 reviews)

Chilmark Guest Houses essential information

Accommodation	5 Guest Houses
Lowest Price	$134
Highest Price	$212
Popular accommodation	The Lightkeepers Inn, Spacious Guest House in Falmouth Village, Woods Hole Passage Inn, Madison Inn, The Oak Bluffs Inn