Photo by Wen C.
Search Guest Houses in Chilmark
- Plan, book, stay with confidence
Be picky
Search almost a million properties worldwide
Change your mind
Book hotels with free cancellation
Check prices for these dates
Next weekend
In two weeks
In one month
In two months
Compare 7 Guest Houses in Chilmark with updated reviews, rates, and availability.

The Lightkeepers Inn
The Lightkeepers Inn
9.6 out of 10, Exceptional, (174)

Charming guest house set on horse farm, walk to downtown Edgartown
Charming guest house set on horse farm, walk to downtown Edgartown
10.0 out of 10, Exceptional, (16)

Woods Hole Passage Inn
Woods Hole Passage Inn
9.6 out of 10, Exceptional, (59)

,Artist Guest House on beautiful estate open concept King Sized Bunk Beds
,Artist Guest House on beautiful estate open concept King Sized Bunk Beds
10.0 out of 10, Exceptional, (2)

Spacious Guest House in Falmouth Village
Spacious Guest House in Falmouth Village
9.0 out of 10, Wonderful, (4)

The Oak Bluffs Inn
The Oak Bluffs Inn
9.6 out of 10, Exceptional, (11)

Madison Inn
Madison Inn
9.8 out of 10, Exceptional, (76)
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.
Save an average of 15% on thousands of hotels when you're signed in
Other property types in Chilmark

Peaceful, dog-friendly home on 3 acres with lovely yard, near beaches
Peaceful, dog-friendly home on 3 acres with lovely yard, near beaches
8.8 out of 10, Excellent, (9)

InnSeason Resorts Captain's Quarters
InnSeason Resorts Captain's Quarters
9.8 out of 10, Exceptional, (162)
The price is SAR 441
SAR 504 total
includes taxes & fees
1 Apr - 2 Apr

The Club at New Seabury
The Club at New Seabury
9.0 out of 10, Wonderful, (314)
The price is SAR 840
SAR 962 total
includes taxes & fees
1 Apr - 2 Apr
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.
Recent reviews of Chilmark hotels
Recent reviews of Chilmark hotels

Inn on the Square
5/5 Excellent
"Rooms were comfy and the location was great. Easy to walk to shops and restaurants "
A verified traveler stayed at Inn on the Square
Posted 5 days ago