Estate Guesthouse ~ Glorious Water Views ~ 2 Private Beaches!

Photo gallery for Estate Guesthouse ~ Glorious Water Views ~ 2 Private Beaches!

A dining area with a wooden table, chairs, and a view of the outdoors.
A wooden deck with blue Adirondack chairs and a table, overlooking a grassy landscape and a body of water.
A two-story house with a front deck, a chimney, and a view of a lake.
A bedroom with a large bed, two bedside tables, a mirror, and a view of the outdoors through the windows.
A cozy living room with a fireplace, seating area, and large windows offering a view of the outdoors.

Reviews

9.8 out of 10, Loved by Guests
Top 10% of guest reviews in this area

Popular amenities

  • Dog-friendly
  • Barbecue grill
  • Refrigerator
  • Washing machine
  • Internet
  • Onsite parking available

Explore the area

View in a map
Chilmark, MA
  • Place, Squibnocket Pond
    ‪13 min walk‬
  • Place, Menemsha Beach
    ‪12 min drive‬
  • Place, Inkwell Beach
    ‪41 min drive‬
  • Airport, Vineyard Haven, MA (MVY-Martha's Vineyard)
    ‪27 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

Add dates for prices

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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. The Grey Barn and Farm and Polly Hill Arboretum are also worth visiting. Discover the area's water adventures with snorkelling and waterskiing nearby, or enjoy the great outdoors with hiking/biking trails and cycling.
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Map
Chilmark, MA

What's nearby

  • Squibnocket Pond - 13 min walk - 1.1 km
  • Menemsha Beach - 12 min drive - 8.8 km
  • Oak Bluffs Harbor - 39 min drive - 34.5 km
  • Oak Bluffs Town Beach - 40 min drive - 35.2 km
  • Inkwell Beach - 41 min drive - 35.2 km

Getting around

  • Vineyard Haven, MA (MVY-Martha's Vineyard) - 19 min drive

Restaurants

  • ‪Chilmark Tavern - ‬4 min drive
  • ‪Menemsha Galley - ‬8 min drive
  • ‪Home Port Restaurant - ‬7 min drive
  • ‪The Homeport - ‬7 min drive
  • ‪Aquinnah Shop - ‬6 min drive

Frequently asked questions

Is Estate Guesthouse ~ Glorious Water Views ~ 2 Private Beaches! pet-friendly?

Yes, this property allows dogs (limit 2 total).

How much is parking at Estate Guesthouse ~ Glorious Water Views ~ 2 Private Beaches!?

On-site parking is available at the property.

What time is check-in at Estate Guesthouse ~ Glorious Water Views ~ 2 Private Beaches!?

Check-in begins at 4:00 PM.

What time is check-out at Estate Guesthouse ~ Glorious Water Views ~ 2 Private Beaches!?

Checkout is at 10:00 AM.

Where is Estate Guesthouse ~ Glorious Water Views ~ 2 Private Beaches! located?

Situated by the sea, this holiday home is 0.5 mi (0.9 km) from Squibnocket Pond and within 3 miles (5 km) of Stonewall Beach and Chilmark Chocolates. Chilmark Town Hall and Chilmark Public Library are also within 3 miles (5 km).

Reviews

9.8

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
Learn moreOpens in a new window
Rating 10 - Excellent. 34 out of 38 reviews
Rating 8 - Good. 2 out of 38 reviews
Rating 6 - Okay. 1 out of 38 reviews
Rating 4 - Poor. 1 out of 38 reviews
Rating 2 - Terrible. 0 out of 38 reviews

9.4/10

Cleanliness

9.6/10

Check-in

9.8/10

Communication

9.8/10

Location

9.6/10

Listing accuracy

Reviews

Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Stunning location and a very clean home. The hosts were welcoming and kind. We hope to return!
Stayed 7 nights in Aug 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Beautiful small guest house - super clean - well equipped. We had a great time in this cottage.
Stayed 15 nights in Jun 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
We were charmed by this quaint guest cottage, with its twisted stairs, nooks & crannies, twin closets & built-in bureaus for the two BRs, and a library built into the parlor (expanded by several scattered ‘pocket libraries’ – books on wildflowers, sailing vessels, sailors’ tales). It has all the modern conveniences yet retains its old Vineyard character.The setting never ceased to please us, with the upper lawn giving way to the middle lawn giving way to the lower lawn (passing from one neighbor to the next), each bounded by stone walls and hedge rows, until at last giving way to the wide expanse of Menemsha Pond and a narrow sliver of Menemsha Bight beyond. It's a wonderful location on the quiet side of MV.
Stayed 7 nights in Sep 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
We had a lovely stay. The house was fully stocked with everything we needed. The view is incredible, you can even see the sunset from the lawn. A great place to rest and relax!
Stayed 7 nights in Jul 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Beautiful!

Beautiful & clean property, with very friendly hosts! Gorgeous views! Loved it there!
Stayed 7 nights in Sep 2024
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Gorgeous view!

We love staying at this property! The house is cozy and has everything you need. The view and beaches are amazing. We’ve come for a few years and you can easily see the care and upgrades the owners are putting in regularly. We had a wonderful family vacation!
Stayed 15 nights in May 2023
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Lovely stay at the cottage

The views our breathtaking! Access to the most beautiful beaches. Kitchen has everything you would want to cook in or grill out. We were able to meet the owners who are fabulous. Hidden gem with old Vineyard charm throughout the cottage.
Stayed 4 nights in Sep 2023
Verified review

10/10 Excellent

Liked: Cleanliness
Disliked: Check-in, communication, location

Chilmark Delight

Lovely Chilmark cottage with distant views to sea. Cottage is comfortable with modern conveniences yet captures MV history with a range of collectibles. Outdoor patio has comfy furniture and is a cozy spot to gather for coffee in the morning or a cocktail in the evening. A real get away.
Stayed 4 nights in May 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

The Cottage

Excellent location. Close to several beaches. Prefer that end of the Island . Great views . Book way ahead of time very affordable. Thanks for have us . MM
Stayed 5 nights in May 2023
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great stay, perfect location!

Our family of five had a great stay at this little cottage. During Covid, alot was closed but we were still able to get takeout from the fish markets and grill on the deck overlooking the beautiful views every night. Loved watching the deer in the meadow below. Access to the private beach was great as most days we were the only people there. We have been renting on the island for years and always stay in the Chilmark or Aquinnah neighborhood as we prefer it to the busier side of the island. This little cottage was one of our favorite rentals and we would love to come back again! The only complaint we had was the Wi-Fi was not working at all. Sometimes we could sporadically connect to the house next-door but this was difficult with two adults working remotely and three children doing schoolwork. We had called the real estate office but they were unable to resolve our issue. Also the patio furniture is a bit weathered and broken and needs to be replaced. These things did not stop us from having a most fantastic stay at this lovely little cottage!!
Stayed 7 nights in Jun 2020
Response from VrboOwner on 24 Jun 2020
Hi Gail, We are happy you enjoyed your stay and apologize for the several items that were not up to speed. Normally my wife and I get the houses ready for season but this year with the virus we were unable to travel up to the Vineyard to do the final polish. Verizon was out to the house after you left and got the landline and Internet working. Additionally we are replacing the ageing deck chairs. Best. Bob
Verified review

6/10 Okay

Liked: Check-in, communication, location
Disliked: Cleanliness

Great views, but old, and dirty

This rental actually looks great online and we were very excited to stay at Lovey's. Upon arrival, the place was old and dirty -- crumbs and dirt inside the pullout sofa, ring around the tub, rust around the basin, nasty blankets, towels and rugs oh, and yes, a mouse. The dryer was broken and the rental company said that the owners were aware and had ordered a new one -- when were they going to tell us this? Three of the five beds were lumpy and uncomfortable. There was only one beach towel for 5 people, and no beach amenities except a lame umbrella that constantly blew away. After calling the management company they were great. They came and tried as best they could to provide additional things we needed and we were allowed to use the owners dryer. Oh and one day a handyman just showed up to do some work while we were eating lunch and my daughter was showering. Pros were AMAZING views and close access to a lovely, quiet salt water pond as well as a coveted key to Hancock. Beach.
Stayed 7 nights in Jul 2022
Response from VrboOwner on 2 Aug 2022
It's always our intention that our guests have a great stay at Lovey's, so we're certainly disappointed that Susan did not. Our habit is to address guest issues promptly. Examples: we had the maid service, a handyman, and the exterminating service return to address Susan's housekeeping issues within a day: the house was re-cleaned, exterminated, a second public laundry room 15 feet from Lovey's back door was immediately provided, as were beach towels and extra paper goods. We do not supply beach chairs or umbrellas, as is clearly stated on our website (though our handyman provided her access to our personal supply). Regarding our mattresses, all are new as of 2021 or 2022. A family member was in our main adjacent house to handle any issues without delay.
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Enjoyed our stay very much.
Stayed 5 nights in Sep 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Nice cottage.
Stayed 14 nights in Jul 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
This cottage was so charming and the view was great. The porch was super quiet and relaxing; a great place to read a book or have a glass of wine. The place was very clean which is usually my biggest concern and this place checked all of the boxes for cleanliness. The private beach access was amazing too. The hosts were very helpful and super sweet! We would definitely stay here again!
Stayed 4 nights in Jun 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Amazing stay at Chilmark cottage!

Our family enjoyed our time at this wonderful Chilmark cottage! The oceans views, backyard, proximity to amazing beaches, farmstands and hiking trails was amazing!
Stayed 7 nights in Jul 2022
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Summer Vacation on Martha’s Vineyard

Property was great. Exactly as advertised. Wonderful views and very easy to deal with the property management. Great private beach which we really enjoyed.
Stayed 6 nights in Jun 2022
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

So charming! Wonderful views!

Our vacation couldn’t have been more perfect! The house was cozy and comfortable. The views were amazing as were the hosts/owner. The house has great touches throughout including puzzles, games, beach items - so thought! The area is wonderful. We spent a lovely family vacation at the cottage and will definitely be back!
Stayed 13 nights in May 2022
Verified review

8/10 Good

Liked: Cleanliness, check-in, communication, location, listing accuracy

Relaxing Stay in Chilmark

Had a nice time at Lovey’s Cottage in Chilmark. The property was beautiful with a spectacular view of Menemsha pond. Unique historical home although could use some maintenance/upgrades to make it a 5 star property. Stairs are very steep and take some getting used to. Private beach access was an awesome perk. Hosts provided lots of useful information. Kitchen was well equipped and plenty of linens, towels, and other supplies.
Stayed 6 nights in May 2022
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Relaxing getaway in Chilmark

My family and I spent a fantastic week in this beautiful cottage, and as a result had a much-needed, very relaxing first time on Martha’s Vineyard. We loved the peaceful water views and the cottage’s coziness, especially on those windy, foggy, rainy up-island days, but also spent many wonderful hours on the two(!) gorgeous private beaches getting away from it all. Bob and Kim, thank you so much for your warm hospitality and for making our first visit such a memorable one!
Stayed 5 nights in May 2022
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Perfect location!!

We have been vacationing at MV for a few decades. Lovely’s Cottage is located in one of our favorite spots on the island! The close proximity to Menemsha and the beautiful sunsets coupled with being up island away from the hustle and bustle is our idea of a great vacation! The cottage was absolutely perfect with everything we needed! The owners were very responsive when I found myself accidentally locked out! We highly recommend Lovey’s Cottage and would definitely stay here again!
Stayed 8 nights in Jul 2021
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Vineyard Heaven

This is the perfect Vineyard cottage! It has fabulous views, a well stocked kitchen, comfortable bedrooms and very nicely furnished living spaces. The deck is all you need. The owners were gracious and take very good care of the property. Can’t wait to return!
Stayed 7 nights in Jun 2021
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Martha’s Vineyard sunsets

We stayed in the cottage for 4 nights and had a wonderful time. The sunsets from the property and from the nearby beach in Aquinnah were spectacular! The owner is so very responsive, always answering any questions within a few minutes. Great experience overall.
Stayed 4 nights in May 2021
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Summer’s Twilight

Lovely views, well situated
Stayed 7 nights in Sep 2020
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

LOVELY and relaxing!

Very clean which is extremely important. Description accurate. Lovely home with incredible views! Would rent again!
Stayed 7 nights in Aug 2020
Verified review

8/10 Good

Liked: Communication, location

Charming, rustic Chilmark cottage stay

The location and views cannot be beat and the cottage truly is laid out perfectly for a family of 4. We spent most beach days at Squibnocket given the proximity but loved the private beach access to Hancock. There isn't any A/C which mostly didn't present an issue since there's a really nice cross breeze but we had some hot nights. The owner was super responsive and attentive. Only constructive feedback is for the clean up crew: there was a decent amount of evidence of the prior guests that hadn't been addressed when we arrived.
Stayed 7 nights in Jul 2020
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