Gracious Prestige Landmark ~ 2 Private Beaches ~ Fabulous View

Chilmark, Massachusetts
$1710 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

A storied property in Chilmark for almost 150 years, the hilltop Tower House combines current taste, comfort and elegance with its own special provenance -- as an authentic part of the Vineyard's remarkable historic character.*
Today, enjoy this welcoming home's timeless, well-cared-for Summer House vibe: its spacious and well-furnished interior rooms, its many places for family and friends to gather, and its expansive, sunlit lawns. It overlooks a dramatic view -- over bright fields and ponds, a far shoreline, then further islands, and the seas and mainland beyond -- a layered, 30-mile panorama rare for the Vineyard.


FIRST FLOOR
Sunrises, sunsets and day-long sunlight grace this property.
- The large eat-in kitchen with bay windows catches sun all day
- The spacious adjacent deck provides outdoor dining, with separate seating area for enjoying the panoramic view first-hand.
- The formal front hall leads to the well-furnished tower living room with its 6 wrap-around windows
- A traditional dining room is a 3rd place to gather for meals
- The bright and casual 2nd living room opens to a wicker-furnished outdoor porch overlooking the home's wide lawns.
- A Queen bedroom has its own large, wheelchair-accessible bathroom
- A small powder room serves the lower floor rooms
UPPER FLOOR
Each bedroom has ocean views, art, and comfortable beds.
- The large tower Primary bedroom is filled with all-day light.
- A second King bedroom has its own ensuite full bathroom
- A Queen bedroom overlooks Quitsa and Menemsha Ponds
- A 'kids' 2-Twins bedroom is closest to the Primary bedroom
- The upstairs main bathroom (with tub) serves 3 bedrooms
(Note: in summer, all bedrooms are cooled by AC units).

BEACHES
Adding to this property's special character: private access to two closely-held, unspoiled Chilmark beaches, accessible daily and detailed below. (Note: our guests can apply for access, also, to well-known Lucy Vincent Beach or Squibnocket Beach via Chilmark Town Hall).
1) Intimate SHORT BEACH (within 5 minutes by car) on Menemsha Pond is perfect for young and old (no surf), where you can also secure your kayak.
2) Access pristine HANCOCK BEACH (15 minutes by car, key entry) for Atlantic shoreline surf and long beachwalks. Children may enjoy the big adjacent inland pond.

NEARBY...
Plenty of enjoyments lie in close reach of the Tower House.
- Within 3 miles:
Chilmark Tavern
Chilmark General Store
Beetlebung Farm
Chilmark Town Hall, Post Office, Library, & Community Center Martha's Vineyard Bank
Congregational Church
- A bit farther:
Menemsha village's beach, gas station, charming shops, fishing charters, and just-caught seafood from the docks.
A short ride from the house takes you to Aquinnah's magnificent colored cliffs, tiny shops, and working lighthouse.
- Farmer's markets, art galleries, craft and antique fairs start at West Tisbury mid-island with North Tisbury's offerings nearby.
- Just beyond are 3 bustling towns with exceptional shopping boutiques, good live theater, bookstores and ever-changing movies. 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, fast internet, good books, puzzles & games, shady nap-spots!

WEDDINGS.
During September, weekly rentals of the Tower House run Wed. to Wed., allowing for wedding event set-up/breakdown and a wonderful weekend celebration in-between! Up to 10 people may 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 central AC, so bedroom AC units or 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!

*A stand-out home, with an exceptional 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 active kids, active sports, and in September -- weddings' large, tented celebrations.
The Tower House estate property includes a barn, private garage, and a 2 BR guest house (a separate rental). This 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.
Our family's third generation now provides the property's responsive, active care.

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

Feature Features

  • PETS

    Pet Friendly Service Animals Exempt From Fees
  • 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 Dishwasher Lobster/crab Pot 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

    Fishing Nearby Fitness Facilities Nearby Golf Nearby Golf Privileges Hiking Nearby Ice Skating Nearby Surfing/body Boarding Nearby Swimming Nearby Water Skiing Nearby Whale Watching 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 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

Your dates are Available!

Total

Includes taxes and fees
$1,710+
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