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Waterfront Vineyard Haven

$100,000 - $125,000/wk

Step Into the Magic of Chip Chop

Arriving at Chip Chop feels like entering another world. Tucked away down a narrow dirt road, flanked by water on both sides and accessible only through a private gated entrance, the journey itself sets the tone for what’s to come. Surrounded by unspoiled nature, vibrant birdlife, and the gentle rhythms of fishing and swimming, this iconic compound offers sweeping views across to the mainland, where you can watch the ferry come and go—reminding you just how far away from it all you truly are.

Now available to rent, Chip Chop is more than a home—it’s a piece of history. Originally built in the 1940s for celebrated Broadway actress Katharine Cornell, the estate has just completed a meticulous renovation in Summer 2025 that thoughtfully updates the property while honoring its remarkable legacy.

A Storied Retreat, Reimagined

Set between the waters of Lake Tashmoo and Vineyard Sound, the property boasts stunning water views from nearly every room. A private stretch of sandy beachfront along the calm Sound, a tennis court, and a serene swimming pool add to the experience. With two detached guest pavilions, and two additional beach houses, the estate offers privacy, luxury, and space to share.

The Main House

Enter the main house through a welcoming foyer that opens through glass doors to a dune-side outdoor deck—perfect for lounging or entertaining. Inside, the home features two elegant en suite bedrooms, a brand-new kitchen, a custom bar, and a cozy TV den/game room—all completed in 2025 with modern luxury in mind.

At its heart is the wood-paneled great room—where one can easily imagine artists, musicians, and political figures of the mid-20th century gathering in spirited conversation. The room features dramatic, opposing floor-to-ceiling sliding glass doors that capture both sunrise over the pond and sunset over the Sound. This central space invites both quiet retreat and grand entertaining.

Guest Quarters

Just steps from the main house are two detached guest pavilions, each offering private decks and en suite baths—ideal for visiting friends or extended family. Beyond the swimming pool lie two additional guest houses, built in 2007, offering even greater privacy for longer stays or independent guests.

At a glance

Listing # 158798
Town Vineyard Haven
Bedrooms 9
Sleeps 16
First Floor Bedroom
Yes
Baths 9
Half Baths 1
Pool
Yes
Priv|Assoc Beach
Yes

AVAILABILITY & RATES

Once you have selected available Arrival and Departure dates from the calendars below, you can calculate a quote or submit an inquiry.
Turnover day: Saturday
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Clear dates
Owners are currently updating 2026 rates from 2025 and are subject to change. Please call 508.696.9999 or email us to confirm.

RATES

From
To
Weekly
125,000
100,000

MORE DETAILS

GENERAL INFO

  • Listing # 158798
  • Check in from 4:00 PM
  • Check out by 10:00 AM
  • Town: Vineyard Haven
  • Bedrooms: 9
  • Sleeps: 16
  • Baths: 9
  • Pool: Yes
  • Waterfront: Yes
  • Priv|Assoc Beach: Yes
  • Beach Description: Vineyard Sound
  • Air Conditioning: Central AC
  • Air Conditioning: AC Split System
  • No Smoking

BEDROOM CONFIGURATION

  • 5 King Bed(s)
  • 2 Queen Bed(s)
  • 1 Single Bed(s)
  • BR 1 - King with private bath, 2nd Floor
  • BR 2 - King with private bath, 1st Floor ------------------------------------------------------
  • BR 3 - Queen with private bath, 1st Floor "Ocean Pavilion"
  • BR 4 - King with private bath, 1st Floor "Pond Pavilion"
  • BR 5 - King with private bath "East Shack" -----------------------------------------------------
  • BR 6 - King private bath “West Shack”
  • BR 7 - Full (pull out couch) private bath “West Shack” ------------------------------------------------------ COTTAGE
  • BR 8 - Queen bed, shared bath
  • BR 9 - Twin bed, Shared bath

KITCHEN

  • Dishwasher
  • Microwave
  • Coffee Maker
  • Toaster
  • Blender
  • Lobster Pot
  • Food Processor

INTERNET / ELECTRONICS

  • Wifi
  • Cable TV

OUTDOOR

  • Pool
  • Pool is heated
  • Deck
  • Deck Furniture
  • Patio
  • BBQ Gas
  • Hot Tub
  • Tennis Facilities
  • Beach Equipment
  • Balcony

HOUSEKEEPING

  • Washer
  • Dryer
  • Iron
  • Ironing Board
  • Vacuum Cleaner
  • Linens Provided

690 + 794 Chappaquonsett Rd, Vineyard Haven

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