Estate Guesthouse ~ Glorious Water Views ~ 2 Private Beaches!

Chilmark, Massachusetts
$514 avg/night Minimum Stay 4 Nights
Bed 2

Bed

Bath 2

Bath

Home Private Vacation Home

Property Type

Sleep 5

Max Sleeps

Night 4 nights

Min Stay

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!

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  • Feature Features
  • Map Map
  • School District Rates & Availability
  • Review Review

Feature Features

  • PETS

    2 Total Pets Pet Friendly Welcoming Dogs Only
  • BEACH

    Beach Towels Near The Beach
  • DINING

    Dining Table
  • SAFETY

    Carbon Monoxide Detector Not Reported (host Has Not Indicated Whether There Is A Carbon Monoxide Detector On The Property; Consider Bringing A Portable Detector) Fire Extinguisher Smoke Detector Installed (host Has Indicated There Is A Smoke Detector On The Property)
  • BEDROOM

    2 Bedrooms Bed Sheets Provided Sofa Bed
  • GENERAL

    Unit Size: 1400 Sq Ft (130 Sq M)
  • KITCHEN

    Coffee/tea Maker Cookware/dishes/utensils Dishwasher Microwave Oven Paper Towels Refrigerator Stovetop Toaster
  • LAUNDRY

    Laundry Facilities Washing Machine And Dryer
  • PARKING

    Car Required Onsite Parking
  • INTERNET

    Free WiFi
  • OUTDOORS

    Barbecue Grill Garden Porch Or Lanai
  • BATHROOMS

    2 Bathrooms Bathtub Or Shower Soap Toilet Paper Towels Provided
  • LANGS SPOKEN

    English
  • THINGS TO DO

    Birdwatching Nearby Cycling Nearby Fitness Facilities Nearby Golf Nearby Golf Privileges Hiking Nearby Ice Skating Nearby Marina Nearby Mountain Biking Nearby Windsurfing Nearby Winery Tours Nearby
  • ENTERTAINMENT

    Books DVD Player Games Music Library Stereo Video Library TV With Cable/satellite Service
  • LIVING SPACES

    Fireplace Living Room
  • CLIMATE CONTROL

    Heating
  • FAMILY FRIENDLY

    Children's Games
  • LOCATION HIGHLIGHTS

    In A Rural Location In A Village Near A Hospital Near The Bay Near The Sea
  • SERVICES AND CONVENIENCES

    Iron/ironing Board Phone
  • SUITABILITY/ACCESSIBILITY

    If You Have Requests For Specific Accessibility Needs, Please Contact The Property Using The Information On The Reservation Confirmation Received After Booking. Smoke-free Property Wheelchair Accessible

CheckIn Check-in : 04:00 PM CheckOut Check-out : 10:00 AM
No Wheelchair No smoking No pets Children allowed
Occupancy Max occupancy : 5

Map Map

School District Rates & Availability

Review Review

  • Lauren F.

    Submitted Aug 25, 2025

    Stayed Jul 26, 2025

    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!

  • Andrea C.

    Submitted Jun 2, 2025

    Stayed May 29, 2025

    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.

  • Susan S.

    Submitted Sep 21, 2024

    Stayed Sep 11, 2024

    Beautiful & clean property, with very friendly hosts! Gorgeous views! Loved it there!

  • Alison D.

    Submitted Sep 12, 2023

    Stayed Sep 2, 2023

    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.

  • Sara Anne B.

    Submitted Jun 18, 2023

    Stayed May 25, 2023

    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!

  • Mark M.

    Submitted Jun 1, 2023

    Stayed May 20, 2023

    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

  • Jeffrey S.

    Submitted Aug 3, 2022

    Stayed Jul 16, 2022

    Our family enjoyed our time at this wonderful Chilmark cottage! The oceans views, backyard, proximity to amazing beaches, farmstands and hiking trails was amazing!

  • Susan S.

    Submitted Jul 31, 2022

    Stayed Jul 23, 2022

    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.

  • Brian R.

    Submitted Jul 4, 2022

    Stayed Jun 25, 2022

    Property was great. Exactly as advertised. Wonderful views and very easy to deal with the property management. Great private beach which we really enjoyed.

  • Sara Anne B.

    Submitted Jun 12, 2022

    Stayed May 29, 2022

    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!

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Total

Includes taxes and fees
$514+
View details