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Estate Guesthouse ~ Glorious Water Views ~ 2 Private Beaches!

Estate Guesthouse ~ Glorious Water Views ~ 2 Private Beaches!

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Overlooking a panorama of ponds and sea, with views all the way to Cape Cod....
Enter via an arbor to a walled garden,  a gathering-area deck, and front entry.
The hillcrest-set cottage is part of a landmark, up-island property.
Private from the main house + former barns, its views are spectacular .
And here's your amazing view: over meadows, ponds, ocean and far islands.

Overview of Estate Guesthouse ~ Glorious Water Views ~ 2 Private Beaches!

Reviews
9.6 out of 10 Exceptional
3 bedrooms2 bathroomsSleeps 5130 sq m

Popular amenities

  • Pet-friendlyPet-friendlyPet-friendly
  • FireplaceFireplaceFireplace
  • KitchenKitchenKitchen
  • Barbecue grillBarbecue grillBarbecue grill
  • Free WiFiFree WiFiFree WiFi
  • WasherWasherWasher

Explore the area

Map
Chilmark, MA
  • Popular LocationAquinnah Cliffs6 min drive
  • Popular LocationMenemsha Beach8 min drive
  • Popular LocationLucy Vincent Beach10 min drive
  • AirportVineyard Haven, MA (MVY-Martha's Vineyard)18 min drive

Rooms & beds

3 bedrooms (sleeps 5)

Bedroom 1

1 King Bed

Bedroom 2

2 Single Beds

Bedroom 3

2 Single Beds

2 bathrooms

Bathroom 1

Bathtub or shower · Toilet

Bathroom 2

Toilet · Shower only

Spaces

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!

Property manager

Robert Schmidt
Premier Host
Premier Host

Amenities

Kitchen
Washer
Dryer
Pet-friendly
Free WiFi
Outdoor space

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

Damage and incidentals

You will be responsible for any damage to the rental property caused by you or your party during your stay.

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
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
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. Waskosim's Rock Reservation and Island Cove Miniature Golf are worth checking out if an activity is on the agenda, while those looking for area attractions can visit Chilmark Chocolates and Menemsha Blues Charters. Travelling with kids? Consider Fulling Mill Brook Preserve and Island Cove Adventures. Discover the area's water adventures with snorkelling and waterskiing nearby, or enjoy the great outdoors with horse riding and hiking.
Map
Chilmark, MA

What's nearby

  • Chilmark Chocolates - 4 min drive
  • Gay Head Lighthouse - 6 min drive
  • Aquinnah Cliffs - 6 min drive
  • Menemsha Beach - 8 min drive
  • Lucy Vincent Beach - 10 min drive

Getting around

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

Restaurants

  • Larsen's Fish Market - 8 min drive
  • Chilmark Tavern - 4 min drive
  • Menemsha Galley - 8 min drive
  • Home Port Restaurant - 8 min drive
  • Outermost Inn - 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).

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?

This family-friendly Chilmark holiday home is located by the sea, within 3 mi (5 km) of Squibnocket Pond and Chilmark Chocolates. Menemsha Blues Charters and Fulling Mill Brook Preserve are also within 6 miles (10 km).

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 window
Rating 10 - Excellent. 25 out of 29 reviews" "
Rating 8 - Good. 2 out of 29 reviews" "
Rating 6 - Okay. 1 out of 29 reviews" "
Rating 4 - Poor. 1 out of 29 reviews" "
Rating 2 - Terrible. 0 out of 29 reviews" "

9.2/10

Cleanliness

9.8/10

Check-in

10/10

Communication

10/10

Location

9.6/10

Listing accuracy

Reviews

10/10 Excellent

Alison D.

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

10/10 Excellent

Sara Anne B., Gettysburg

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

10/10 Excellent

Mark M.

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

10/10 Excellent

Jeffrey S.

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

6/10 Okay

Susan S.

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

About the host

Hosted by Robert Schmidt

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Premier Host

Premier Host
They consistently provide great experiences for their guests
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