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Search Guest Houses in Chilmark

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Compare 7 Guest Houses in Chilmark with updated reviews, rates, and availability.

Spacious Guest House in Falmouth Village
Guest House entrance and comfy Adirondack chairs for your enjoyment

Spacious Guest House in Falmouth Village

9.0 out of 10, Wonderful, (4)
"Great location Nice and clean Great people to work with"
Spacious Guest House in Falmouth Village
Woods Hole Passage Inn
Front of property

Woods Hole Passage Inn

3.0 star property
9.6 out of 10, Exceptional, (59)
"The property was wonderful and the host was excellent. I had lots of questions during our stay as it was our first time in Falmouth, and the host made sure we had answers to everything we needed. They even had a binder full of local recommendations in the room when we checked in! "
Woods Hole Passage Inn
The Lightkeepers Inn
Exterior

The Lightkeepers Inn

3.0 star property
9.6 out of 10, Exceptional, (174)
"A lovely spot near the downtown, shopping, restaurants and the wharf. It had everything we needed."
The Lightkeepers Inn
Charming guest house set on horse farm, walk to downtown Edgartown
Private kitchen

Charming guest house set on horse farm, walk to downtown Edgartown

10.0 out of 10, Exceptional, (16)
"We enjoyed our stay at the guest house. The location is lovely on a quiet horse farm with easy access to the nearby bike path and road into town. The guest house is attached to the main house but with a private and respectful feel. The house is well stocked and the kitchen is top grade. The bedrooms upstairs are small but comfortable. Would return. "
Charming guest house set on horse farm, walk to downtown Edgartown
,Artist Guest House on beautiful estate open concept King Sized Bunk Beds
Exterior

,Artist Guest House on beautiful estate open concept King Sized Bunk Beds

10.0 out of 10, Exceptional, (2)
"Cozy and peaceful place to stay for my sister and me. Had everything we needed. Close to bus routes. Would definitely go back!"
,Artist Guest House on beautiful estate open concept King Sized Bunk Beds
The Oak Bluffs Inn
Front of property

The Oak Bluffs Inn

3.0 star property
9.6 out of 10, Exceptional, (11)
"Such a beautiful, unique spot. Great location, I'll definitely be back."
The Oak Bluffs Inn
Madison Inn
Front of property

Madison Inn

2.5 star property
9.8 out of 10, Exceptional, (76)
"Great location! Very clean rooms and friendly staff."
Madison 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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Other property types in Chilmark

Iconic Mid-Century Home with Gorgeous Ocean Views, Private Pool & Decks

Iconic Mid-Century Home with Gorgeous Ocean Views, Private Pool & Decks

8.6 out of 10, Excellent, (22)
"We didn't realize how beautiful and unique the architecture of this residence was before we arrived. It is a gorgeous place and we were please by the cleanliness and simplicity of it. "
Iconic Mid-Century Home with Gorgeous Ocean Views, Private Pool & Decks
Beautiful dog-friendly home with water view, balcony & washer/dryer

Beautiful dog-friendly home with water view, balcony & washer/dryer

7.8 out of 10, Good, (14)
"A Vacasa managed property that has everything you could want. We stayed 4 nights with our whole family and our small dog. It had everything we could want and we enjoyed ourselves. Recently redone, with good fit and finish and places to hang cook and relax off a dirt road that is well situated. Our only comments would be that there were some things needing fixing like the grill handle, lights not in sockets, and general disarray of bedding and supplies in the closets. While clean and fresh...
Beautiful dog-friendly home with water view, balcony & washer/dryer
Secluded Guest House overlooking Menemsha Pond. Dogs welcome + Lvl 2 EV charger.
Outdoor dining

Secluded Guest House overlooking Menemsha Pond. Dogs welcome + Lvl 2 EV charger.

10.0 out of 10, Exceptional, (45)
"We were in town for a wedding in Chilmark and the property was exactly what we needed!"
Secluded Guest House overlooking Menemsha Pond. Dogs welcome + Lvl 2 EV charger.
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.