Estate Guesthouse ~ Glorious Water Views ~ 2 Private Beaches!

Top rated by guests
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 return for long conversations, lighted air and lingering, right at home.
review stars
9.4Outstanding
(33 Ratings)
The property offers breathtaking views, access to beautiful beaches, a well-equipped kitchen, and a hidden gem with old Vineyard charm. Guests enjoyed the proximity to amazing beaches, farmstands, and hiking trails.
From real guest reviews summarized by AI
Don't miss out! Price and availability may change
9.4 / 10
Outstanding(33 Ratings)

House in Menemsha, MA

5 guests · 2 bedrooms · 2 baths

Reasons to book

Guests love it hereGuests give this property a top rating
Great for petsBring all your friends and family, even the furry ones
Top-tier experienceA high end property in this area

About this house rental

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!

Amenities at Estate Guesthouse ~ Glorious Water Views ~ 2 Private Beaches!

Non-smoking
Pets allowed
Family friendly

Map of Menemsha, MA


Ratings and reviews

9.4 / 10
Outstanding(33 Ratings)
review starsSummary of reviews
The property offers breathtaking views, access to beautiful beaches, a well-equipped kitchen, and a hidden gem with old Vineyard charm. Guests enjoyed the proximity to amazing beaches, farmstands, and hiking trails.
From real guest reviews summarized by AI
10 / 10Outstanding·Aug 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!
10 / 10Outstanding·Jun 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.
10 / 10Outstanding·Sep 2024
Beautiful & clean property, with very friendly hosts! Gorgeous views! Loved it there!
6 / 10Average·Jul 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.

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FAQs

Is parking included with this house?

Parking is not specified as an available amenity at Estate Guesthouse ~ Glorious Water Views ~ 2 Private Beaches!. For more information, we encourage you to contact the property about where to park.

Is there a pool at this house?

We didn’t find pool listed as an amenity for this house. It may be worth double checking if a pool is important for your stay.

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

Yes! This house is pet-friendly. For more information, we recommend contacting the booking provider about animal policies.

What amenities are available at Estate Guesthouse ~ Glorious Water Views ~ 2 Private Beaches!?

We found 3 amenities for this rental. This includes non-smoking, pets allowed, and family friendly.