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Estate Guesthouse ~ Glorious Water Views ~ 2 Private Beaches!
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Reviews
9.6 out of 10
Exceptional
2 bedrooms2 bathroomsSleeps 51400 sq ft
Popular amenities
Explore the area

Chilmark, MA
- Place, Squibnocket Pond10 min walk
- Place, Oak Bluffs Harbor29 min drive
- Place, Inkwell Beach31 min drive
- Airport, Vineyard Haven, MA (MVY-Martha's Vineyard)20 min drive
Rooms & beds
2 bedrooms (sleeps 5)
Bedroom 1
1 King Bed
Bedroom 2
2 Twin Beds
2 bathrooms
Bathroom 1
Bathtub or shower · Toilet
Bathroom 2
Toilet · Shower only
Spaces
Porch or lanai
Kitchen
Garden
Dining area
About this property
Estate Guesthouse ~ Glorious Water Views ~ 2 Private Beaches!
Add dates for prices
Amenities
Kitchen
Washer
Dryer
Pet friendly
Free WiFi
Outdoor Space
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Similar properties

Gracious Landmark Home ~ Fabulous Water Views ~ 2 Private Beaches
Chilmark
Gracious Landmark Home ~ Fabulous Water Views ~ 2 Private Beaches
- Ocean view
- Kitchen
- Washer
- Dryer
10.0 out of 10, Exceptional, (25 reviews)
House Rules
Check in after 4:00 PM
Minimum age to rent: 21
Check out before 10:00 AM
Children
Children allowed: ages 0-17
Events
No events allowed
Pets
Pets allowed: dogs (limit 2 total)
Smoking
Smoking is not permitted
Important information
You need to know
Extra-person charges may apply and vary depending on property policy
Government-issued photo identification and a credit card, debit card, or cash deposit may be required at check-in for incidental charges
Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
Onsite parties or group events are strictly prohibited
Host has not indicated whether there is a carbon monoxide detector on the property; consider bringing a portable detector with you on the trip
Host has indicated there is a smoke detector on the property
Safety features at this property include a fire extinguisher
This property has outdoor spaces, such as balconies, patios, terraces which may not be suitable for children; if you have concerns, we recommend contacting the property prior to your arrival to confirm they can accommodate you in a suitable room
Property Registration Number C0019280620
About the neighborhood
Chilmark
Located in Chilmark, this vacation home is in a rural area and near the beach. Island Cove Miniature Golf and Island Cove Adventures are worth checking out if an activity is on the agenda, while those looking for area attractions can visit Chilmark Chocolates and Fulling Mill Brook Preserve. Traveling with kids? Consider The Grey Barn and Farm and Polly Hill Arboretum. Discover the area's water adventures with snorkeling and water skiing nearby, or enjoy the great outdoors with cycling and hiking/biking trails.

Chilmark, MA
What's nearby
- Squibnocket Pond - 10 min walk - 0.8 km
- Oak Bluffs Harbor - 29 min drive - 34.2 km
- Circuit Avenue - 30 min drive - 34.9 km
- Oak Bluffs Town Beach - 30 min drive - 35.6 km
- Inkwell Beach - 31 min drive - 35.9 km
Getting around
Restaurants
- Home Port Restaurant - 7 min drive
- Chilmark Tavern - 4 min drive
- Menemsha Galley - 8 min drive
- Orange Peel Cafe - 6 min drive
- Beach Plum Inn & Restaurant - 7 min drive
Frequently asked questions
Reviews
9.6
Exceptional
Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labeled.
Learn moreOpens in a new window9.4/10
Cleanliness
9.4/10
Check-in
9.8/10
Communication
9.8/10
Location
9.6/10
Listing accuracy
Reviews
Verified
Aug 25, 2025
Liked: Cleanliness, check-in, communication, location, listing accuracy
Stayed 7 nights in Jul 2025
Verified
10/10 Excellent
Susan S.
Sep 21, 2024
Liked: Cleanliness, check-in, communication, location, listing accuracy
Beautiful!
Susan S.
Stayed 7 nights in Sep 2024
Verified
10/10 Excellent
Andrea C.
Jun 2, 2025
Liked: Cleanliness
Disliked: Check-in, communication, location
Chilmark Delight
Andrea C.
Stayed 4 nights in May 2025
Verified
10/10 Excellent
Sara Anne B.
Jun 18, 2023
Liked: Cleanliness, check-in, communication, location, listing accuracy
Gorgeous view!
Sara Anne B.
Stayed 15 nights in May 2023
Verified
10/10 Excellent
Alison D.
Sep 12, 2023
Liked: Cleanliness, check-in, communication, location, listing accuracy
Lovely stay at the cottage
Alison D.
Stayed 4 nights in Sep 2023
Verified
10/10 Excellent
Mark M.
Jun 1, 2023
Liked: Cleanliness, check-in, communication, location, listing accuracy
The Cottage
Mark M.
Stayed 5 nights in May 2023
Verified
10/10 Excellent
Gail S.
Jun 24, 2020
Liked: Cleanliness, check-in, communication, location, listing accuracy
Great stay, perfect location!
Gail S.
Stayed 7 nights in Jun 2020
Verified
6/10 Okay
Susan S.
Jul 31, 2022
Liked: Check-in, communication, location
Disliked: Cleanliness
Great views, but old, and dirty
Susan S.
Stayed 7 nights in Jul 2022
Verified
4/10 Poor
Kathy D.
Jul 9, 2018
Deceiving pictures
Kathy D.
Stayed 7 nights in Jun 2018
Verified
10/10 Excellent
Jeffrey S.
Aug 3, 2022
Liked: Cleanliness, check-in, communication, location, listing accuracy
Amazing stay at Chilmark cottage!
Jeffrey S.
Stayed 7 nights in Jul 2022
Verified
10/10 Excellent
Brian R.
Jul 4, 2022
Liked: Cleanliness, check-in, communication, location, listing accuracy
Summer Vacation on Martha’s Vineyard
Brian R.
Stayed 6 nights in Jun 2022
Verified
10/10 Excellent
Sara Anne B.
Jun 12, 2022
Liked: Cleanliness, check-in, communication, location, listing accuracy
So charming! Wonderful views!
Sara Anne B.
Stayed 13 nights in May 2022
Verified
8/10 Good
Jon B.
May 31, 2022
Liked: Cleanliness, check-in, communication, location, listing accuracy
Relaxing Stay in Chilmark
Jon B.
Stayed 6 nights in May 2022
Verified
10/10 Excellent
Amanda T.
May 25, 2022
Liked: Cleanliness, check-in, communication, location, listing accuracy
Relaxing getaway in Chilmark
Amanda T.
Stayed 5 nights in May 2022
Verified
10/10 Excellent
Kristen R.
Jul 13, 2021
Liked: Cleanliness, check-in, communication, location, listing accuracy
Perfect location!!
Kristen R.
Stayed 8 nights in Jul 2021
Verified
10/10 Excellent
Michael F.
Jun 16, 2021
Liked: Cleanliness, check-in, communication, location, listing accuracy
Vineyard Heaven
Michael F.
Stayed 7 nights in Jun 2021
Verified
10/10 Excellent
Callie C.
Jun 5, 2021
Liked: Cleanliness, check-in, communication, location, listing accuracy
Martha’s Vineyard sunsets
Callie C.
Stayed 4 nights in May 2021
Verified
10/10 Excellent
Jonathan M.
Sep 23, 2020
Liked: Cleanliness, check-in, communication, location, listing accuracy
Summer’s Twilight
Jonathan M.
Stayed 7 nights in Sep 2020
Verified
10/10 Excellent
Scott T.
Sep 3, 2020
Liked: Cleanliness, check-in, communication, location, listing accuracy
LOVELY and relaxing!
Scott T.
Stayed 7 nights in Aug 2020
Verified
8/10 Good
Catherine F.
Aug 5, 2020
Liked: Communication, location
Charming, rustic Chilmark cottage stay
Catherine F.
Stayed 7 nights in Jul 2020
Verified
10/10 Excellent
Betsy O.
Aug 2, 2020
Liked: Cleanliness, check-in, communication, location, listing accuracy
Sublime experience all around.
Betsy O.
Verified
10/10 Excellent
Lori M.
Jul 11, 2020
Liked: Check-in, communication, location, listing accuracy
The view says it all.
Lori M.
Verified
10/10 Excellent
David G.
Sep 27, 2019
Liked: Cleanliness, check-in, communication, location, listing accuracy
Lovey’s ❤️
David G.
Verified
10/10 Excellent
Sarah H.
Jun 17, 2019
Liked: Cleanliness, check-in, communication, location, listing accuracy
Serene and charming stay
Sarah H.
Verified
10/10 Excellent
John K.
Jun 10, 2019
Liked: Cleanliness, check-in, communication, location, listing accuracy
Wonderful peaceful cottage
John K.
Stayed 14 nights in May 2019
About the host
Hosted by Robert Schmidt
Languages:
English
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