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Book Online or call HomeAway Booking Assistance 888-640-7927
Book Online or call HomeAway Booking Assistance 888-640-7927

Elegant; endless water views. Labor Day week wedding venue. 2 private beaches.

Bedrooms 5
Half Baths1
Space 3,000 sq. ft.
Property type house
Minimum Stay 1 - 7 nights


About the property

5 bedrooms, 3 full bathrooms, 1 half bath. Sleeps 10.

Sunrises, sunsets and all-day sunlight grace this welcoming, elegant and beautifully-kept hilltop home. Its glorious wrap-around views extend over fields, meadows, ponds, far-islands and many miles of ocean -- rare indeed for the Vineyard.

Linger over breakfast in the bright, eat-in kitchen, or savor the panorama first-hand from the large dining table on the spacious, sunny deck, where lounge chairs also encourage lingering. Relax in 2 well-furnished and comfortable living rooms (one casual). Watch frisbee on the lawn, or savor the sunset from deep chairs on the front porch. Seafood meals get merry around the gracious dining table, followed by drinks or cards in the tower living room. Your master bedroom is upstairs in the same lovely tower, or choose the 1st floor master with joining handicap-accessible bathroom. Each bedroom has ocean views, art, and comfortable beds.

Accessible daily: just down the hill is our intimate, private Beach #1, perfect for young and old (no surf), where you can also secure your kayak or small sailboat. Visit 2 local town beaches, or access our pristine, key-member Beach #2 for surf -- or quieter pursuits in the big adjacent pond.

A stand-out home, with an outstanding history, the house is an up-island landmark for its yellow-painted Queen Anne main house with red roof, and ball-topped tower. The grounds include a meadow-sized lawn beyond the main house, perfect for weddings and large, tented parties or celebrations (see Weddings heading, below). The grounds also include the property's large, original barn, and a charming guest house (see Lovey's Cottage heading, below). The Tower House estate 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 now actively cared for by a third generation.

Access to two private beaches has also been part of this property's special character, for a half-century or more.

Enjoy the use of one house -- or two!: The Tower House can be rented two ways: as a gracious single residence, or together with its fully-equipped guest house, which is located close by on the estate grounds.

LOVEY'S COTTAGE --a 2-story guest house -- sleeps 5 people in 3 bedrooms, and has its own entrance, private deck and walled garden. Like the Tower House, Lovey's Cottage provides an outstanding fields-to-ocean view, and is also handicap-accessible with 1st floor sleeping capacity and handicap bathroom with shower. See more about the cottage at HomeAway #293733.

Combined, the Tower House and Lovey's Cottage sleep 15 guests -- an arrangement which works very well for weddings... for large groups of friends... or for large families with varying needs and ages (ie. grandparents favoring quiet time, in-laws valuing their personal space, or a young family with children's separate nap or early-bedtime requirements). Note: Lovey's is designed to be its own private, independent rental residence on the estate grounds, when not rented in unison with the Tower House.

A wealth of activities nearby...: Countless memorable enjoyments are within close reach of the Tower House -- besides our lovely beaches! Sample wonderful restaurants, good casual eateries, an active community center, public library, and lively grocery store within 3 miles. Menemsha village is just across the pond, with charming shops, fishing charters, and just-caught seafood arriving off traditional trawlers as they dock. A brisk bike-ride from the house takes you to Lobsterville for 'insider' shoreline fishing, or to Aquinnah's beaches and magnificently colored cliffs. Farmer's markets, art galleries, craft and antique fairs start at West Tisbury mid-island, with exceptional shopping boutiques, good live theater, bookstores and ever-changing movies just beyond in 3 bustling towns. Nature walks and bike trails criss-cross the island, 3 golf courses offer tee-times, and history comes alive in charming byways and museums. Or simply relax at home, with ball games on the lawn, internet, good books, puzzles & games, shady nap-spots!


September is the month of weddings at the property. During this month, weekly rentals run Wed. to Wed., allowing for wedding event set-up/breakdown and a wonderful weekend celebration in-between!

Both the Tower House and guest house (Lovey's Cottage) are rented as a combined unit for weddings, to allow up to 15 guests to stay on-property, and to assure privacy for your event. The expansive, level field adjoining the main house accommodates large dining, dancing and kitchen tents as well as additional bar stations, lounge areas, etc. The marriage ceremony most often takes place overlooking the water-and-islands view, on a side lawn complete with guest seating. The property's vine-trimmed stone walls, planting beds, arched garden arbor and gingerbread-trimmed porches add further areas for exceptional family and wedding party photography.

Our guest book attests to our many wedding families' joyful memories made here!

More Details


Chilmark House Accommodation and Amenities

Property Type:
  • house
Floor Area:
  • 3000 sq. ft.
House Rules:
  • Max. occupancy: 10
  • pets considered
  • children welcome
  • non smoking only
Location Type:
  • Beach
  • Rural
  • Away From It All
  • Family
  • Activities Guide
  • Alarm Clock
  • Basic Soaps
  • Clothes Dryer
  • Internet
  • Iron & Board
  • Laundry Soap
  • Linens Provided
  • Local Activities Guide
  • Local Maps
  • Paper Towels
  • Parking Off Street
  • Telephone
  • Toilet Paper
  • Towels Provided
  • Washing Machine
  • Wireless Internet
  • 4 Ring Stove
  • Blender
  • Coffee Grinder
  • Coffee Maker
  • Cooking Utensils
  • Dishwasher
  • Freezer
  • Grill
  • Ice Maker
  • Lobster Pot
  • Microwave
  • Oven
  • Refrigerator
  • Toaster
  • Dining Room
  • seating for 10 people
  • 3 Bathrooms
  • 1 Half Bath
  • Bathroom 1 - toilet , combination tub/shower
    Bathroom 2 - toilet , shower
    Bathroom 3 - toilet , shower , Handicap, first floor
    Bathroom 4 - toilet
  • Bathroom #3 is on the main floor level and has full wheelchair access.
  • 5 Bedrooms, Sleeps 10
  • Bedroom 1 - 1 king , 270 degree views from tower
    Bedroom 2 - 1 king , sunrise and sunset views
    Bedroom 3 - 1 queen , handicap bath, water views
    Bedroom 4 - 1 double , water views
    Bedroom 5 - 2 twin/ single , sunset view
  • Books
  • Books for Adults
  • Books for Kids
  • CD Player
  • DVD Player
  • Games
  • Games for Kids
  • Music Library
  • Radio
  • Satellite / Cable
  • Stereo
  • Television
  • Video Library
  • Barbecue
  • Beach Towels
  • Binoculars
  • Lawn / Garden
  • Outdoor Grill Gas
  • Small Cooler
  • Wood Deck
  • suitable for elderly or infirm
  • wheelchair accessible
  • arboretum
  • autumn foliage
  • bay/sound
  • botanical garden
  • churches
  • cinemas
  • forests
  • library
  • live theater
  • marina
  • museums
  • nude beach
  • playground
  • pond
  • recreation center
  • restaurants
Leisure Activities:
  • antiquing
  • beachcombing
  • bird watching
  • horseback riding
  • paddle boating
  • scenic drives
  • sight seeing
  • walking
  • whale watching
Local Services & Businesses:
  • ATM/bank
  • Babysitter
  • fitness center
  • groceries
  • hospital
  • laundromat
  • massage therapist
  • medical services
Sports & Adventure Activities:
  • cycling
  • deepsea fishing
  • fishing
  • fly fishing
  • golf
  • golf privileges optional
  • hiking
  • ice skating
  • pier fishing
  • roller blading
  • sailing
  • sound/bay fishing
  • surf fishing
  • surfing
  • swimming
  • tennis
  • water skiing
  • wind-surfing
The house is wheelchair accessible, with ramp entry to deck, and first-floor bedroom and joining wheelchair-friendly bathroom with roll-up sink and roll-in shower. Security deposit. A $500.00 fully refundable security deposit is required.


5/5 -
(5 traveler reviews)

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Elegant; endless water views. Labor Day week wedding venue. 2 private beaches.
average rating of 5.0 based on 13 reviews

Take me away to my Happy Place

  • 5 of 5

Exceptional Property.

We’ve long been enjoying our time at this property as repeat summer guests. A much-loved family tradition!

We take the big main house as well as the smaller guest house (Lovey’s Cottage), which allows our 3-generation family a lot of flexibility.

Here’s what we enjoy about the Tower House, specifically:

- The house is beautifully kept – well-furnished and maintained. And we love being part of its special history!

- Such a spacious feel – and lots of light -- in all the rooms (comfortable beds in the bedrooms!)

- The kitchen’s big and sunny, very inviting. And the huge back hang-out deck…sublime.

- Fabulous view: all the way to Menemsha fishing village, and past the islands beyond.

- The property’s big, private grounds. Great for kids running around, exploring, and just having fun.

- Having Lovey’s Cottage guest house on the property, which we also really enjoy renting, for smaller family groups, and our guests.

- The 2 private beaches are a big deal for us… Lovey’s beach (fantastic for small kids), and Hancock beach (wow, no crowds!).

- 3 other public beaches only minutes from the house: Squibnocket, Lucy Vincent, and Aquinnah.

- Wonderful restaurants within a 5-10 minute drive: Outermost, Chilmark Tavern, HomePort, Beach Plum.

- A lot of nice island walking trails in close range of the house.

- Grocery stores, gas, library, community center (with kids’ programs), farm stands and fish markets all in Chilmark and nearby Menemsha..

These are some of the best weeks of every summer for us.

  • Submitted: Aug 22, 2016
  • Stayed: June 2016
  • Source: HomeAway
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McLean, VA

It was wonderful as always

  • 5 of 5

The house has great views and delightful sea breezes. It is always relaxing to enjoy the slower pace of life, the farmers market twice a week in West Tisbury, the wonderful fresh fish from the fish market in Menemsha, a trip into Vineyard Haven or Edgartown to walk along the main street and enjoy the shops, and to wander down along the harbor and watch the boats. There is always something going on around the Island, or you can just sit on the back porch and enjoy the view of Menemsha Pond and Vineyard Sound. There are good restaurants in all the towns to discover, sample, and enjoy. We always look forward to our time every summer at the house!

  • Submitted: Aug 18, 2016
  • Stayed: July 2016
  • Source: HomeAway
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Dream Come True

  • 5 of 5

What a gem! The solemn stateliness of this historic home's exterior is matched by tasteful and modern comforts inside-- wifi, well-equipped kitchen, bathrooms, bedrooms and tons of spacious, yet cozy common areas. The entire house is styled w/ great original paintings and an artist's eye for color and style. As for the hilltop grounds, and the NONSTOP VIEWS --simply as good as it gets. For us, Chilmark is the perfect location; we revel in its tranquility and natural beauty, and we can always hop in the car for a short drive when we're jones-ing for some (commercial) Vineyard action. Manager was helpful and attentive.

  • Submitted: Jul 5, 2015
  • Stayed: June 2015
  • Source: HomeAway
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perfect for a wedding

  • 5 of 5

We rented the house the Wednesday before our wedding through the Wednesday after. Our wedding party used the house and the cottage next door leading up to our Saturday wedding and our parents and families used the houses after the big day to wind down. Everybody only had wonderful things to say about these beautiful beach cottages. We had our wedding reception in a tent on the lawn and our cocktail hour near the deck overlooking Mememsha pond. Not a lot of people who come to the Vineyard for a weekend get to see the beauty of up island and it was amazing to have our own little piece of this paradise for the week to show our guests. I look forward to hopefully renting again with our family someday!

  • Submitted: Jan 31, 2014
  • Stayed: September 2013
  • Source: HomeAway
Owner's Response: Our warm Congratulations on your wedding! We're delighted you so enjoyed our property, its widespread lawns, extensive views and its ability to accommodate you, your parents and many of your close family members for the week -- as your party combined the use of the big main house and the on-site guest cottage also! Quick question though -- we weren't sure about the 'beach cottages' you mentioned, as our property with its two houses crowns a hill (though it overlooks several beaches -- and offers private access to 2 others!). Regardless, we're certainly appreciative that you chose to celebrate your wedding surrounded by the real beauty of up-island, and in "our own little piece of paradise" -- which you made your own, and were able to show and share with guests in your wonderful wedding week! We welcome you back with your family, in years to come!
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A perfect place to stay, year after year ...

  • 5 of 5

Time spent at The Tower House is like taking a step back in time where I feel transported to a more leisurely gracious pace of life. I instantly feel at ease in the spacious rambling Victorian house surrounded by a big expanse of lawn (ideal for croquet or just about any sport). I love the feel of the airy, cheery rooms (lovingly decorated with artwork and beautiful bedding). The light is spectacular in and out. The front porch is perfect for afternoon tea bathed in sunset light. The back deck is perfect for just about anything … outdoor meals, reading, napping, bird watching … but one of my favorite pastimes is simply soaking up the breathtaking unobstructed vista and expansive view of Menemsha Pond. The updated kitchen is cook and company friendly and a great place to gather a large group in the morning and end of day. I’ve slept in almost all of the bedrooms and each one is welcoming.

If we can tear ourselves away from the house … the choice of private beaches is an especially cherished perk of the house. Lovey’s Beach is walking distance from the house, and a favorite place for an early morning or sunset walk. The access to Hancock Beach is one of the most anticipated repeat experiences. It rates as one of the top beaches I’ve ever visited – as good for walking along the water’s edge as swimming. A majestic setting that leaves an indelible imprint.

It’s been fun to see the local food movement develop over recent years … and there are any number of small farms where you can pick up fresh vegetables, cheeses, and meats either directly at the farms or at the farmers markets.

This is a place that I look forward to visiting again and again – both for the familiar pleasures as well as exploring and discovering new ones. It’s a little piece of heaven. And it seems to get better each time I visit.

  • Submitted: Jul 12, 2011
  • Stayed: June 2011
  • Source: HomeAway
Owner's Response: We're delighted that you and your family enjoy so many of the welcoming elements that make the Tower House and its hilltop location a place where guests feel simultaneously special and at home!
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Robert Schmidt
Member since: 2010
Speaks: english
Response time:
Within a few hours
Response rate:
Calendar last updated:
February 24, 2018

Guestbook comments from the owner

This place (your beautiful home) is the most spectacular place I've ever been to. My family and I come and stay here every summer for a week. We all love it!!!
Jun 2014
  • 1 of 8


Car: recommended

USA Massachusetts Martha's Vineyard Chilmark




Additional information about rental rates

Cleaning $400
Wedding event $2,500

Owner's Cancellation Policy

100% refund if canceled at least 30 days before arrival date.

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