INQUIRE ABOUT THIS LISTING

INQUIRE ABOUT THIS LISTING

This question is for testing whether or not you are a human visitor and to prevent automated spam submissions.
Thumbnail
Thumbnail
Thumbnail
Thumbnail
Thumbnail
Thumbnail
Thumbnail
Thumbnail
Thumbnail
Thumbnail
Thumbnail
Thumbnail
Thumbnail
Thumbnail
Thumbnail
Thumbnail
Thumbnail
Thumbnail
Thumbnail
Thumbnail
Thumbnail

Up-Island Chilmark

$4,000 - $6,000/wk

This private Chilmark retreat has a cool vibe with 4 bedrooms and 2 baths plus outdoor shower. The house has an upside-down design, with two bedrooms and a shared full bath on the walk out lower level. The main living space has an open living room, kitchen, dining area with a deck that spans the entire width of the home. The primary bedroom & bathroom is also on this level and has a sliding door to the deck and outdoor shower. The 4th bedroom is accessed through the primary bedroom, but also has its own entrance from the outside.

The house sits on a hill overlooking a large lawn area great for games and outside play.

New AC is provided by mini splits.

When you rent in Chilmark you can get access to beautiful Lucy Vincent ad Squibnocket beaches. The fishing village of Menemsha, Chilmark Store and Community center is a short drive away.

At a glance

Listing # 153540
Town Chilmark
Sq Ft 2000
Bedrooms 4
Sleeps 8
First Floor Bedroom
Yes
Baths 2

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: Sunday
Arrival Date:
Departure Date:
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
6,000
6,000
5,000
4,000

MORE DETAILS

GENERAL INFO

  • Listing # 153540
  • Check in from 4:00 PM
  • Check out by 10:00 AM
  • Town: Chilmark
  • SQ FT: 2000
  • Bedrooms: 4
  • Sleeps: 8
  • Baths: 2
  • Dining Capacity: 10
  • Air Conditioning: AC Split System
  • No Smoking
  • No Pets Accepted

BEDROOM CONFIGURATION

  • 1 Queen Bed(s)
  • 2 Double Bed(s)
  • 2 Single Bed(s)
  • BR 1 - Double, 1st Floor
  • BR 2 - 2 Twins, Lower Level
  • BR 3 - Queen, Lower Level
  • BR 4 - Double, Lower Level

KITCHEN

  • Dishwasher
  • Microwave
  • Coffee Maker
  • Toaster
  • Blender

INTERNET / ELECTRONICS

  • High Speed Internet
  • Wifi
  • 2 TVs
  • DVD
  • 2 DVDs

OUTDOOR

  • Outside Shower
  • Deck
  • Deck Furniture
  • Porch Screened
  • BBQ Gas
  • 10 Dining Capacity (Outside)

HOUSEKEEPING

  • Washer
  • Dryer
  • Vacuum Cleaner
  • Linens Provided

OTHER

  • Ceiling Fans
  • Standard Fans

40 Wintergreen Way, Chilmark

X