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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 Single 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!
Superb fields-to-ocean-to-islands views from this charming guesthouse, on a historic Chilmark property. You'll enjoy a wealth of beach options. Squibnocket beach is only 5-minutes away by car. Below the house is our private, child-safe (no surf) beach on lake-like Menemsha Pond (3 minutes by car). Or enjoy key access to our 2nd private beach -- a spectacular site on the South Shore, offering both ocean surf and pond swimming (15 minutes by car).
Large bay windows bring the 10-mile view right into the house.... or you can savor it first-hand from chairs on the quiet, sunny front porch. Upstairs: watch sailboat races on the inland ponds from two bright bedrooms (one king, one double twin/king), and spot rabbits or deer on the estate lawn from the upstairs study (daybed). Downstairs: the sofa pulls out to a bed in the living area (with adjacent handicap-access bathroom/shower room) to accommodate a wheelchair-bound guest. Efficient kitchen, washer/dryer, internet, cable TV, music, games and library promote easy relaxation at home! In fall and winter the house is a snuggery, with warm bedding, central heat.
[Please note: our small, historic but efficient staircase may prove a bit steep for the elderly, those with infirmities, or small pets].
Make your own memories in this historic property!: Lovey's Cottage guesthouse is part of the hilltop Tower House estate, an up-island landmark for its Queen Anne, yellow-painted main house with red roof, and ball-topped tower. The property has changed hands only once since beginning as a multi-acre farm in the early 1800's. It has been in our family for over 50 years now -- and is being cared for by a third generation for whom the estate property was their great summertime home.
Be private -- or part of your own larger group. Lovey's Cottage has its own parking and front entrance through a small walled garden that gives onto the beautiful view. Carefully designed to work as a completely independent and private residence, Lovey's can also be rented together with the Tower House* (which sleeps 10, in 5 bedrooms) -- an arrangement which works very well for weddings, or large groups of friends, or a family with varying needs and ages. Lovey's can be a wonderful solution for grandparents needing separate and quiet time, for in-laws valuing their personal space, or even for a young family with children's nap-time or early-bedtime requirements.
Enjoy the fall, or spring: Lovey's Cottage, with its central heat, is a wonderful spot to spend an off-season week, holiday, or get-away break. The rolling up-island landscape affords splendid open views, town beaches are accessible for long seaside walks, and island staffers at restaurants, attractions, and boutiques can take more time to welcome and converse with you than in their busier months. Many stores and services stay open into late fall, and re-open in early spring, so there's a 'buzz' to savor in these non-summer months!
Large bay windows bring the 10-mile view right into the house.... or you can savor it first-hand from chairs on the quiet, sunny front porch. Upstairs: watch sailboat races on the inland ponds from two bright bedrooms (one king, one double twin/king), and spot rabbits or deer on the estate lawn from the upstairs study (daybed). Downstairs: the sofa pulls out to a bed in the living area (with adjacent handicap-access bathroom/shower room) to accommodate a wheelchair-bound guest. Efficient kitchen, washer/dryer, internet, cable TV, music, games and library promote easy relaxation at home! In fall and winter the house is a snuggery, with warm bedding, central heat.
[Please note: our small, historic but efficient staircase may prove a bit steep for the elderly, those with infirmities, or small pets].
Make your own memories in this historic property!: Lovey's Cottage guesthouse is part of the hilltop Tower House estate, an up-island landmark for its Queen Anne, yellow-painted main house with red roof, and ball-topped tower. The property has changed hands only once since beginning as a multi-acre farm in the early 1800's. It has been in our family for over 50 years now -- and is being cared for by a third generation for whom the estate property was their great summertime home.
Be private -- or part of your own larger group. Lovey's Cottage has its own parking and front entrance through a small walled garden that gives onto the beautiful view. Carefully designed to work as a completely independent and private residence, Lovey's can also be rented together with the Tower House* (which sleeps 10, in 5 bedrooms) -- an arrangement which works very well for weddings, or large groups of friends, or a family with varying needs and ages. Lovey's can be a wonderful solution for grandparents needing separate and quiet time, for in-laws valuing their personal space, or even for a young family with children's nap-time or early-bedtime requirements.
Enjoy the fall, or spring: Lovey's Cottage, with its central heat, is a wonderful spot to spend an off-season week, holiday, or get-away break. The rolling up-island landscape affords splendid open views, town beaches are accessible for long seaside walks, and island staffers at restaurants, attractions, and boutiques can take more time to welcome and converse with you than in their busier months. Many stores and services stay open into late fall, and re-open in early spring, so there's a 'buzz' to savor in these non-summer months!
Our prices include all fees. No hidden fees.
Add dates for prices
Amenities
Kitchen
Washing machine
Dryer
Pet-friendly
Free WiFi
Outdoor space
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Gracious Landmark Home ~ Fabulous Water Views ~ 2 Private Beaches
Gracious Landmark Home ~ Fabulous Water Views ~ 2 Private Beaches
- Ocean view
- Kitchen
- Washing machine
- 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
This property is managed by a private host (a party not acting within their trade, business or profession). EU consumer law, including the right of withdrawal, will not apply to your booking. The cancellation policy set by the private host will cover your booking.
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
On-site 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 that 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 and terraces, which may not be suitable for children; if you have any concerns, we recommend contacting the property prior to your arrival to confirm that they can accommodate you in a suitable room
Property Registration Number C0019280620
We should mention
A car is required for transport to and from this property
About the area
Chilmark
Located in Chilmark, this holiday 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. Travelling with kids? Consider The Grey Barn and Farm and Polly Hill Arboretum. Discover the area's water adventures with snorkelling and waterskiing nearby, or enjoy the great outdoors with cycling and mountain biking.

Chilmark, MA
What's nearby
- Squibnocket Pond - 10 min walk - 0.8 km
- Gay Head Lighthouse - 6 min drive - 7.4 km
- Oak Bluffs Harbor - 29 min drive - 34.2 km
- Oak Bluffs Town Beach - 30 min drive - 35.6 km
- Inkwell Beach - 31 min drive - 35.9 km
Getting around
Restaurants
- Menemsha Galley - 8 min drive
- Chilmark Tavern - 4 min drive
- Home Port Restaurant - 7 min drive
- Beach Plum Inn & Restaurant - 7 min drive
- Cliffhangers - 6 min drive
Frequently asked questions
Reviews
9.6
Exceptional
Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
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
25 Aug 2025
Liked: Cleanliness, check-in, communication, location, listing accuracy
Stayed 7 nights in Jul 2025
Verified
10/10 Excellent
Susan S.
21 Sept 2024
Liked: Cleanliness, check-in, communication, location, listing accuracy
Beautiful!
Susan S.
Stayed 7 nights in Sep 2024
Verified
10/10 Excellent
Andrea C.
2 Jun 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.
18 Jun 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.
12 Sept 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.
1 Jun 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.
24 Jun 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.
31 Jul 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.
9 Jul 2018
Deceiving pictures
Kathy D.
Stayed 7 nights in Jun 2018
Verified
10/10 Excellent
Jeffrey S.
3 Aug 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.
4 Jul 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.
12 Jun 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.
31 May 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.
25 May 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.
13 Jul 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.
16 Jun 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.
5 Jun 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.
23 Sept 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.
3 Sept 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.
5 Aug 2020
Liked: Communication, location
Charming, rustic Chilmark cottage stay
Catherine F.
Stayed 7 nights in Jul 2020
Verified
10/10 Excellent
Betsy O.
2 Aug 2020
Liked: Cleanliness, check-in, communication, location, listing accuracy
Sublime experience all around.
Betsy O.
Verified
10/10 Excellent
Lori M.
11 Jul 2020
Liked: Check-in, communication, location, listing accuracy
The view says it all.
Lori M.
Verified
10/10 Excellent
David G.
27 Sept 2019
Liked: Cleanliness, check-in, communication, location, listing accuracy
Lovey’s ❤️
David G.
Verified
10/10 Excellent
Sarah H.
17 Jun 2019
Liked: Cleanliness, check-in, communication, location, listing accuracy
Serene and charming stay
Sarah H.
Verified
10/10 Excellent
John K.
10 Jun 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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