Gracious Landmark Home ~ Fabulous Water Views ~ 2 Private Beaches

Chilmark, Massachusetts
$806 avg/night Minimum Stay 7 Nights
Bed 5

Bed

Bath 3

Bath

Home Private Vacation Home

Property Type

Sleep 10

Max Sleeps

Night 7 nights

Min Stay

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).

Catch frisbee on the expansive lawns, or savor the sunset from deep seating 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. 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 our family's summer home for over 50 years (note: without central heat or AC, fans are provided in summer; space-heaters in shoulder seasons).
Our family's third generation now provides the property's responsive, active care.
Adding to this property's special character: access to two private, unspoiled Chilmark beaches. One of these is below the house (5 minutes by car), the other off South Road (15 minutes by car, key entry).

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!

WEDDINGS.
September is the month of weddings at the property. During this month, weekly rentals of the Tower House run Wed. to Wed., allowing for wedding event set-up/breakdown and a wonderful weekend celebration in-between! The 5-bedroom Tower House allows up to 10 people to easily stay on-site for all or part of the wedding week. This Victorian-era summer house with its ample gathering rooms and decks is without central heat or AC, so fans and space heaters are provided for weather that's extra-hot or -cold.
The expansive and level field adjoining the Tower 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 with ample space for 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!

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

Feature Features

  • PETS

    Pet Friendly
  • 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

    5 Bedrooms Bed Sheets Provided
  • GENERAL

    Unit Size: 3000 Sq Ft (279 Sq M)
  • KITCHEN

    Blender Coffee Grinder Cookware/dishes/utensils Dishwasher Microwave Oven Paper Towels Refrigerator Stovetop
  • LAUNDRY

    Laundry Facilities Near Laundromat Washing Machine And Dryer
  • PARKING

    Car Recommended Onsite Parking
  • INTERNET

    Free WiFi
  • OUTDOORS

    Barbecue Grill Dock Garden Outdoor Furniture Patio
  • BATHROOMS

    3.5 Bathrooms Bathtub Or Shower Hair Dryer Soap Toilet Paper Towels Provided
  • LANGS SPOKEN

    English
  • THINGS TO DO

    Cycling Nearby Fishing Nearby Fitness Facilities Nearby Golf Privileges Hiking/biking Trails Nearby Horse Riding Nearby Sailing Nearby Surfing/body Boarding Nearby Swimming Nearby Water Skiing Nearby Windsurfing Nearby
  • ENTERTAINMENT

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

    Dining Room Living Room
  • CLIMATE CONTROL

    Air Conditioning Heating
  • FAMILY FRIENDLY

    Children's Games
  • LOCATION HIGHLIGHTS

    In A Rural Location 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 : 10

Map Map

School District Rates & Availability

Review Review

  • James S.

    Submitted Aug 31, 2025

    Stayed Aug 27, 2025

    Unbelievable 270 degree view on the back patio was shocking beautiful every morning and evening. With teenagers who can drive at home but not rentals I think being in Edgartown or Oak Bluffs would have been better but for adults and kids chilmark is laid back and gorgeous. Private beach was beautiful, large, and largely empty. House was beautiful in that old vineyard way. Special.

  • Susan K.

    Submitted Aug 26, 2025

    Stayed Aug 16, 2025

    A magical week with three generations, the whole family, ages 1 - 70. The house wraps its arms around you, and there is room in the big kitchen for all the cooks and all the eaters. Fabulous yard for playing games, flying kites, the kiddie pool we brought and a perfect hammock. We hope to go back in a few years when the grandchildren are bigger, it will still be a perfect spot!

  • John W.

    Submitted Jul 9, 2025

    Stayed Jun 28, 2025

    Stayed for a week with my wife, children, cousin and his family. Lovely experience in charming location. Spacious, airy, commanding property with romantic sea views. I highly recommend for large family groups. Like having a B&B to yourselves. Host was highly communicative. Access to private Beach.

  • Naomi H.

    Submitted Aug 18, 2024

    Stayed Aug 10, 2024

    Beautiful house with the BEST view and amazing yard! We had an excellent stay. Absolutely incredible- loved it so much!! One thing to note for others inquiring is that the guest house is very close to main house and was rented by a different group while we were there. If this is a consideration for you, then likely would check in with owners as to whether it will be occupied.

  • nat g.

    Submitted Aug 18, 2024

    Stayed Jul 27, 2024

    This charming Vineyard icon was perfect for a large family gathering. Plenty of room to spread out, sweeping lawns for children to play, and lots of nooks and crannies for a rainy day.

  • Michael M.

    Submitted Aug 4, 2024

    Stayed Jul 20, 2024

    We enjoyed our stay at Tower House, certainly enough room for our family, ages ranging from 10 months to 94. The views from the back patio out to Menemsha Pond and Vineyard Sound beyond were spectacular, just a wonderful spot for a morning coffee or evening cocktail when the weather is right. The house was well stocked with towels, dishes, cookware and glassware and we even made use of the lobster pot. Access to the private ocean beach was great.

  • Amanda W.

    Submitted Aug 23, 2023

    Stayed Aug 5, 2023

    We had a wonderful visit! Such a great family house that wonderful memories were made at. We will definitely return!

  • Meghan Z.

    Submitted Aug 10, 2023

    Stayed Jul 29, 2023

    We had an awesome week at the Tower House in Chilmark. The house itself housed our two families (4 adults and 6 2nd grade to baby boys) with ease. Everyone had space both inside and out. The kids ran through the grass, played in the hammock and ate dinner watching deer and boats in the distance. We enjoyed the porch, kitchen and back deck. Bob was in close contact and Charlie the caretaker was a fast and lovely resource. The gem of this property is the key to Hancock Beach. We’ll never forget our time there and will look to rent again from owners that over the spectacular bonus. Thank you for granting us such beautiful memories.

  • Lindsay M.

    Submitted Jul 24, 2023

    Stayed Jul 8, 2023

    This is our second summer stay at this house, and it was as perfect as it was the last time. The water views from the back of the house, particularly from the fabulous deck, are unmatched on the rest of the island. The house is perched high on land that connects Chilmark to Aquinnah so offers an amazing bucolic vista of pastures and meadows ringed by stone walls, down to Menemsha Pond and Vineyard Sound in the distance. The feeling is very rural and relaxing. There are lots of beaches to explore, many of them noticeably less populated than those on the rest of the island. There is no air conditioning, but you don’t need it because, being at a high point geographically, it has nice breezes all the time.

  • Mercedes K.

    Submitted Jul 11, 2023

    Stayed Jul 1, 2023

    Our extended family had a great time, thank you

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Total

Includes taxes and fees
$806+
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