Photo by Wen C.

Search Guest Houses in Chilmark

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Compare 8 Guest Houses in Chilmark with updated reviews, rates, and availability.

The Lightkeepers Inn
Exterior
The Lightkeepers Inn
3.0 star property
9.6 out of 10, Exceptional, (168)
"Perfect location- very walkable to shopping and dining. Staff was always available via text and extremely accommodating. I’ll be back! "
The Lightkeepers Inn
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
Spacious Guest House in Falmouth Village
Guest House entrance and comfy Adirondack chairs for your enjoyment
Spacious Guest House in Falmouth Village
Spacious Guest House in Falmouth Village
Mid Island Family retreat
First floor queen
Mid Island Family retreat
9.4 out of 10, Exceptional, (3)
"This was perfect for our annual trip - different as we usually stay 2 weeks and drive - but only 1 week this year and we flew in. The home was super cute and cozy. My daughter loved the loft! Would definitely recommend. Owners were super nice -allowed early entry for my friend until we arrived from Boston AND especially kind when our Uber Eats was left on their porch in the rain! Only issue were the little bugs/ants from outside coming inside. But hey that’s nature! Thanks for making our...
Mid Island Family retreat
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
9.6 out of 10, Exceptional, (76)
"Great location! Very clean rooms and friendly staff."
Madison Inn
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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.
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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
8.4 out of 10, Very Good, (21)
"Wonderful place for a getaway to MV. Well appointed, comfy home with great pool. Plenty of privacy but easy to get to. Enjoyed our stay"
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
8.0 out of 10, Very Good, (11)
"The house is tucked down a magical driveway with serene surroundings. Unfortunately, there were a few things that left us feeling a bit disappointed. It was clear we were one of the first visitors of the season. The house was quite musty, the washer was filled with water and mold, the showers were not cleaned, showing clear hard water, spider webs, and some build up. The comforter in the master was stained, including some blood. The AC on the top floor was not working. Lastly, the door handle...
Beautiful dog-friendly home with water view, balcony & washer/dryer
Secluded Guest House overlooking Menemsha Pond. Dogs welcome + Lvl 2 EV charger.
Property grounds
Secluded Guest House overlooking Menemsha Pond. Dogs welcome + Lvl 2 EV charger.
10.0 out of 10, Exceptional, (41)
"Beautiful and peaceful "
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.