Entire home
Gracious Landmark Home ~ Fabulous Water Views ~ 2 Private Beaches
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Reviews
10 out of 10
Exceptional
5 bedrooms 3+ bathrooms Sleeps 10 278.7 sq m
Popular amenities
Explore the area

Chilmark, MA
- Place, Lucy Vincent Beach8 min drive
- Place, Gay Head Lighthouse8 min drive
- Place, Menemsha Beach10 min drive
- Airport, Vineyard Haven, MA (MVY-Martha's Vineyard)25 min drive
Rooms & beds
5 bedrooms (sleeps 10)
Bedroom 1
1 King Bed
Bedroom 2
1 King Bed
Bedroom 3
1 Queen Bed
Bedroom 4
1 Double Bed
Bedroom 5
2 Single Beds
3 bathrooms, 1 half bathroom
Bathroom 1
Bathtub or shower · Toilet
Bathroom 2
Toilet · Shower only
Bathroom 3
Toilet · Shower only
Bathroom 4
Toilet
Spaces
Deck or patio
Porch or lanai
Kitchen
Separate dining area
Garden
About this property
Gracious Landmark Home ~ Fabulous Water Views ~ 2 Private Beaches
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!
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!
Add dates for prices
Amenities
Kitchen
Washing machine
Dryer
Pet-friendly
Free WiFi
Air conditioning
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House Rules
Check in after 4:00 PM
Check out before 10:00 AM
Children
Children allowed: ages 0–17
Events
No events allowed
Pets
Pets allowed
Smoking
Smoking is not permitted
Important information
You need to know
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
Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
On-site parties or group events are strictly prohibited
Host has not indicated whether there is a carbon monoxide detector on the property; consider bringing a portable detector with you on the trip
Host has indicated that there is a smoke detector on the property
Safety features at this property include a fire extinguisher
Property Registration Number C0019280620
We should mention
A car is recommended for transport to and from this property
About the area
Chilmark
Located in Chilmark, this holiday home is in a rural area and near the beach. Island Cove Miniature Golf and Island Cove Adventures are worth checking out if an activity is on the agenda, while those looking for area attractions can visit Chilmark Chocolates and Fulling Mill Brook Preserve. The Grey Barn and Farm and Polly Hill Arboretum are also worth visiting. Waterskiing and windsurfing offer great chances to get out on the surrounding water, or you can seek out an adventure with hiking and horse riding nearby.

Chilmark, MA
What's nearby
- Squibnocket Pond - 5 min drive - 0.8 km
- Lucy Vincent Beach - 8 min drive - 6.8 km
- Gay Head Lighthouse - 8 min drive - 7.4 km
- Aquinnah Cliffs - 8 min drive - 7.4 km
- Menemsha Beach - 10 min drive - 7.0 km
Getting around
Restaurants
- Menemsha Galley - 8 min drive
- Chilmark Tavern - 4 min drive
- Home Port Restaurant - 7 min drive
- Aquinnah Shop - 6 min drive
- Aquinnah Restaurant - 6 min drive
Frequently asked questions
About the host
Hosted by Robert Schmidt

Languages:
English
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