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Gracious Landmark Home ~ Fabulous Water Views ~ 2 Private Beaches

Gracious Landmark Home ~ Fabulous Water Views ~ 2 Private Beaches

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Gracious and spacious, with 10-mile views to out-islands & beyond...
..the house welcomes  gatherings, inside and out. Here, the view-filled deck.
...and surrounded by  lawns -- great for  a celebration or more informal fun...
Enter through the inviting, central family room
The family room connects to the indoor spaces, kitchen, and outdoor decks

Overview of Gracious Landmark Home ~ Fabulous Water Views ~ 2 Private Beaches

Reviews
10 out of 10 Exceptional
5 bedrooms3+ bathroomsSleeps 103000 sq ft

Popular amenities

  • Pet friendlyPet friendlyPet friendly
  • Outdoor SpaceOutdoor SpaceOutdoor Space
  • Free WiFiFree WiFiFree WiFi
  • Air conditioningAir conditioningAir conditioning
  • KitchenKitchenKitchen
  • Barbecue grillBarbecue grillBarbecue grill

Check out the area

Map
Chilmark, MA
  • Popular LocationAquinnah Cliffs6 min drive
  • Popular LocationMenemsha Beach8 min drive
  • Popular LocationLucy Vincent Beach10 min drive
  • AirportVineyard Haven, MA (MVY-Martha's Vineyard)18 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 Twin 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!

Property manager

Robert Schmidt
Premier Host
Premier Host

Amenities

Kitchen
Washer
Dryer
Pet friendly
Free WiFi
Air conditioning

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

Damage and incidentals

You will be responsible for any damage to the rental property caused by you or your party during your stay.

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
Onsite 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 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 transportation to and from this property

About the neighborhood

Chilmark

Located in Chilmark, this vacation home is in a rural area and near the beach. Waskosim's Rock Reservation and Island Cove Miniature Golf are worth checking out if an activity is on the agenda, while those looking for area attractions can visit Chilmark Chocolates and Menemsha Blues Charters. Fulling Mill Brook Preserve and Island Cove Adventures are also worth visiting. Water skiing and windsurfing offer great chances to get out on the surrounding water, or you can seek out an adventure with horse riding and cycling nearby.
Map
Chilmark, MA

What's nearby

  • Chilmark Chocolates - 4 min drive
  • Gay Head Lighthouse - 6 min drive
  • Aquinnah Cliffs - 6 min drive
  • Menemsha Beach - 8 min drive
  • Lucy Vincent Beach - 10 min drive

Getting around

  • Vineyard Haven, MA (MVY-Martha's Vineyard) - 19 min drive

Restaurants

  • Larsen's Fish Market - 8 min drive
  • Chilmark Tavern - 4 min drive
  • Menemsha Galley - 8 min drive
  • Home Port Restaurant - 8 min drive
  • Outermost Inn - 6 min drive

Frequently asked questions

Is Gracious Landmark Home ~ Fabulous Water Views ~ 2 Private Beaches pet-friendly?

Yes, pets are allowed at this property.

What time is check-in at Gracious Landmark Home ~ Fabulous Water Views ~ 2 Private Beaches?

Check-in begins at 4:00 PM.

What time is check-out at Gracious Landmark Home ~ Fabulous Water Views ~ 2 Private Beaches?

Check-out is at 10:00 AM.

Where is Gracious Landmark Home ~ Fabulous Water Views ~ 2 Private Beaches located?

Situated by the sea, this vacation home is 0.5 mi (0.9 km) from Squibnocket Pond and 2.2 mi (3.6 km) from Chilmark Chocolates. Lucy Vincent Beach and Gay Head Lighthouse are also within 6 mi (10 km).

Reviews

10

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labeled.
Learn moreOpens in a new window
Rating 10 - Excellent. 18 out of 19 reviews" "
Rating 8 - Good. 1 out of 19 reviews" "
Rating 6 - Okay. 0 out of 19 reviews" "
Rating 4 - Poor. 0 out of 19 reviews" "
Rating 2 - Terrible. 0 out of 19 reviews" "

9.6/10

Cleanliness

10/10

Check-in

10/10

Communication

10/10

Location

9.8/10

Listing accuracy

Reviews

10/10 Excellent

Amanda W.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great stay!
We had a wonderful visit! Such a great family house that wonderful memories were made at. We will definitely return!
Stayed 7 nights in Aug 2023

10/10 Excellent

Meghan Z.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Friends and Family
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.
Stayed 7 nights in Jul 2023

10/10 Excellent

Lindsay M., New York, NY

Liked: Cleanliness, check-in, communication, location, listing accuracy
Once again, a great stay!
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.
Stayed 7 nights in Jul 2023

10/10 Excellent

Mercedes K.

Liked: Cleanliness, check-in, communication, location, listing accuracy
What a view!
Our extended family had a great time, thank you
Stayed 7 nights in Jul 2023

10/10 Excellent

Cynthia L., New York, New York

Liked: Cleanliness, check-in, communication, location, listing accuracy
Magical Wedding week
This was our second visit to Lovey's cottage, and our first stay at the Tower House. Robert is a great host and his property is outstanding. We were hosting our daughter and son-in-law's dream wedding. The views, the grounds, the location, the tasteful attention to detail, and the quality of accommodations are all first rate. The house is filled with light, art, and character. Space for large meals around a beautiful table, a porch for morning coffee and afternoon drinks. I was very pleased with the overall condition of this much loved and enjoyed property. All communications were smooth. I cannot imagine a better week, still basking in the glow. We have been renters on the island for 30 years, and this stay exceeded our expectations. Thank you Bob for sharing the Tower House with us all, we have created memories for a lifetime. And we hope to come back for a visit real soon.
Stayed 7 nights in Sep 2022

About the host

Hosted by Robert Schmidt

Host profile image

Premier Host

Premier Host
They consistently provide great experiences for their guests
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