Estate Guesthouse ~ Glorious Water Views ~ 2 Private Beaches! | House in Chilmark

9.6 (32 Reviews) |   Pet Friendly   2 Bedrooms  2 Bathrooms  5 Guests
Chilmark House | Estate Guesthouse ~ Glorious Water Views ~ 2 Private Beaches!

2 Bedroom House in Chilmark

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!

Estate Guesthouse ~ Glorious Water Views ~ 2 Private Beaches! is located in Chilmark. Estate Guesthouse ~ Glorious Water Views ~ 2 Private Beaches! provides accommodation, featuring Wellness Facilities, Fireplace/Heating, Entertainment, among other amenities. This House features Wellness Facilities, Fireplace/Heating, Entertainment, to make your stay a comfortable one.

Estate Guesthouse ~ Glorious Water Views ~ 2 Private Beaches! has 2 Bedrooms , 2 Bathrooms, and max occupancy of 5 people. The minimum rental for this property is 1 nights, but this can change depending on the season you plan on staying. Previous guests have given good rated it, and VRBO labeled it a top-rated House because of the excellent services rendered by the owner or manager of this House, and has consistently provided great experiences for their guests. Most families or guests that use it recommend it to their friends and some of them are repeat guests. House has a friendly neighborhood, and the Chilmark has interesting places to visit. If you want to learn more about the House in Chilmark, such as places to visit and things to do nearby, you can check below to learn more.

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Amenities

Parking
Pet Friendly
TV
View
Ocean View
Balcony/Terrace
Oceanfront
Accessibility
Security/Safety
Sports/Activities
Bedding/Linens
Wellness Facilities
Fireplace/Heating
Entertainment
Barbecue/Outdoor Cooking
Child Friendly
Internet
Kitchen
Laundry

Facility Overview

Air Conditioner
  • Heating
Bathrooms
  • Towels provided
  • Toilet paper
  • 2 bathrooms
  • Bathtub or shower
  • Soap
Bedroom
  • Sofa bed
  • Bed sheets provided
  • 2 bedrooms
  • Dining table
  • Living room
  • Fireplace
Kitchen
  • Microwave
  • Coffee/tea maker
  • Dishwasher
  • Toaster
  • Oven
  • Cookware/dishes/utensils
  • Refrigerator
  • Paper towels
  • Stovetop
Laundry
  • Laundry facilities
  • Washing machine and dryer
Ocean view
  • Beach towels
  • Near the beach
Parking
  • Car required
  • Onsite parking
Pet Friendly
  • Pet friendly
  • Welcoming dogs only
  • 2 total pets
Accessibility
  • Wheelchair accessible
  • 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
Activities
  • Golf privileges
  • Hiking nearby
  • Fitness facilities nearby
  • Birdwatching nearby
  • Horse riding nearby
  • Ice skating nearby
  • Mountain biking nearby
  • Swimming nearby
  • Hiking/biking trails nearby
  • Golf nearby
  • Surfing/body boarding nearby
Entertainment
  • Stereo
  • Books
  • DVD player
  • Music library
  • Games
  • Video library
  • TV with cable/satellite service
General
  • Unit size: 1400 sq ft (130 sq m)
  • English
  • In a rural location
  • In a village
  • Near the sea
  • Near the bay
  • Near a hospital
Guest Services
  • Children's games
  • Iron/ironing board
  • Phone
Internet
  • Free WiFi
Outdoors
  • Garden
  • Barbecue grill
  • Porch or lanai
Security/Safety
  • Fire extinguisher
  • Smoke detector installed (host has indicated there is a smoke detector on the property)
  • Carbon monoxide detector not reported (host has not indicated whether there is a carbon monoxide detector on the property; consider bringing a portable detector)

Policies

Check-in
Check-in time starts at 4:00 pm contactless check-in available minimum check-in age: 21
Check-out
Check-out before 10:00 am contactless check-out available
Child Policy
Children are welcome.
Event Policy
No events allowed
Pet Policy
2 total pets pets allowed service animals are welcome, and are exempt from fees welcoming dogs only
Smoking Policy
Smoking is not permitted

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 host has indicated there is a smoke detector on the property host has not indicated whether there is a carbon monoxide detector on the property; consider bringing a portable detector with you on the trip onsite parties or group events are strictly prohibited property registration number c0019280620 safety features at this property include a fire extinguisher special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed 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 this property is managed through our partner, vrbo. you will receive an email from vrbo with a link to a vrbo account, where you can change or cancel your reservation

License number: C0019280620

Reviews

Lauren F.
Aug 26, 2025 02:48:08 AM
Review Score:   10
Summary: 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!
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