Best Deal in Chilmark Spring Fling: Book May or June for 10% off. 4-day minimum.

Chilmark, Massachusetts
$574 avg/night Minimum Stay 4 Nights
Bed 5

Bed

Bath 2

Bath

Home Private Vacation Home

Property Type

Sleep 8

Max Sleeps

Night 4 nights

Min Stay

Chilmark is quiet, laid back and much less congested than down-island counterparts. If you want to spread out and relax, this is an excellent part of the Island to visit. Alley's General Store and the Chilmark Tavern are nearby if you need provisions or a nice dinner. The rental itself is set back, very private, and has a massive grass yard for kids to play in. A great stay!
-Alison, guest, May 2018
Thanks Alison. Here's more:
Bright and open Chilmark split-level home perfect for your next family vacation. FULLY AIR CONDITIONED. New refrigerator and commercial washing machine perfect for long stays. Fresh exterior paint and newly rebuilt wrap-around deck. Some interior upgrades expected by spring 2025. Wrap-around deck perfect for early morning reading, evening cocktails or star-gazing. Close to Alley's General Store, West Tisbury Farmer's Market, hiking trails and bike paths. Guests may purchase guest passes to Lucy Vincent Beach through Town of Chilmark. Walking access to nearby private Chilmark beach. Ten minute drive to Menemsha sunsets and lobsters or juicy whole belly fried clams at the Fish House in Edgartown-best take-out option for quick up-island dinners.

Read More Expand
  • Feature Features
  • Map Map
  • School District Rates & Availability
  • Review Review

Feature Features

  • PETS

    No Pets Allowed
  • 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) Deadbolt Lock Fire Extinguisher First Aid Kit Smoke Detector Installed (host Has Indicated There Is A Smoke Detector On The Property)
  • BEDROOM

    5 Bedrooms Bed Sheets Provided
  • GENERAL

    Unit Size: 1300 Sq Ft (121 Sq M)
  • KITCHEN

    Coffee Grinder Cookware/dishes/utensils Dishwasher Lobster/crab Pot Microwave Oven Refrigerator Stovetop Toaster
  • LAUNDRY

    Laundry Facilities Near Laundromat Washing Machine And Dryer
  • PARKING

    Car Required
  • INTERNET

    WiFi Available
  • OUTDOORS

    Barbecue Grill Garden Patio Yard
  • POOL/SPA

    Hot Tub
  • BATHROOMS

    2 Bathrooms Bathtub Or Shower Hair Dryer Outdoor Shower Soap Toilet Paper Towels Provided
  • LANGS SPOKEN

    English
  • THINGS TO DO

    Cycling Nearby Fishing Nearby Fitness Facilities Nearby Golf Privileges Hiking Nearby Hiking/biking Trails Nearby Horse Riding Nearby Ice Skating Nearby Parasailing Nearby Rafting Nearby Whale Watching Nearby
  • ENTERTAINMENT

    Books DVD Player Games Smart TV With Cable/satellite Service
  • LIVING SPACES

    Living Room
  • CLIMATE CONTROL

    Air Conditioning Heating
  • LOCATION HIGHLIGHTS

    In A Rural Location Near A Health Or Beauty Spa Near A Hospital Near The Sea
  • SERVICES AND CONVENIENCES

    Iron/ironing Board Limited Housekeeping
  • SUITABILITY/ACCESSIBILITY

    Note From Host: Absolutely No Smoking. Smoke-free Property

CheckIn Check-in : 04:00 PM CheckOut Check-out : 11:00 AM
No Wheelchair No smoking No pets Children allowed
Occupancy Max occupancy : 8

Map Map

School District Rates & Availability

Review Review

  • Ted S.

    Submitted Sep 1, 2025

    Stayed Aug 23, 2025

    Excellent stay. Great host.

  • Gianfranco C.

    Submitted Jun 25, 2025

    Stayed Jun 7, 2025

    Great stay in a beutifull island

  • Renee D.

    Submitted Jun 23, 2024

    Stayed Jun 17, 2024

    I have to admit this was a good deal for the Vineyard, but overall it wasn't a good experience. When we showed up everything was off or unplugged including the refrigerator. The basement was extremely musty, so we turned the dehumidifier on, which made it very hot. Then, we tried the brand new AC system and it wouldn't cool. I let the host know and she gave me instructions. It still wasn't working so she said she would contact a HVAC company, but I never heard back. It was very hot while there, and very uncomfortable. The house itself is very private and a good size, but it definitely needs more TLC. There were updates made over the years, but it needs more love. Pros: Private location, good size home. Access to private beach. Cons: AC not working. Needs TLC. There were ants everywhere (which has been a universal problem this year due to rain).

  • Dumi Aisha L.

    Submitted Dec 26, 2023

    Stayed Jul 29, 2023

    My family and I absolutely loved our stay in this beautiful home in quiet Chilmark. The bucolic grounds were lush, green, and peaceful with cute natural neighbors (rabbits, which delighted my young children). We rode our bikes to the beach which was a highlight of our stay. The wrap-around deck with lounge chairs on one side and a large table with patio chairs and an umbrella on the other. There was also a grill that we didn't end up using but was great to have as an option. The open kitchen had plenty of utensils and a dishwasher. The dining room table was large with drawers that held lobster forks. I cannot stop raving about this amazing home, location and wonderful host. Thank you for an amazing 3 weeks!

  • Nancy S.

    Submitted Sep 30, 2023

    Stayed Sep 10, 2023

    Unfortunately, Hurricane Lee shortened our stay at this location.The grounds are beautiful, the beach is breathtaking and we love Chilmark. The house itself needs some attention. We were disappointed as the pictures looked as if everything was in good shape. The outside deck is where we spent most of our time, at least when it wasn't raining.

  • Judith C.

    Submitted Sep 8, 2022

    Stayed Aug 14, 2022

    Book ferry in Jan. 1/3 mile walk to road, not lighted at night. Deer along the way. Bus will stop to pick you up if you flag it down and will drop you off at end of street. Limited supplies at general stores in area

  • Jill S.

    Submitted Sep 3, 2022

    Stayed Aug 27, 2022

    We loved this stay so much. The pictures do not do it any justice. The property itself is stunning. Huge lawn and beautiful tree to hang out on. We spent every afternoon playing ladder ball after the beach. Then we would either cook or drive to Menemsha for dinner. The fact that there is a fantastic market and wine market just 15 minutes down the road make it SO much easier than it used to be. Especially if you are used to staying far up island. The keyed beaches are so lovely. I can’t believe that there were so few of us on it, especially considering that there was a giant music festival while we were there. Communication with Carolyn was swift and kind and helpful. We are already planning on coming back.

  • Lucy C.

    Submitted Oct 21, 2021

    Stayed Oct 6, 2021

    Beautiful well kept house and really nice host. Location was perfect!

  • Ryan H.

    Submitted Sep 19, 2021

    Stayed Sep 14, 2021

    Second time staying in this comfortable and well-located home. Perfect for days at the nearby private Quansoo beach. Cooked at home most evenings with ample pots, pans, etc, large oven, and gas grill. Thank you, Carolyn!

  • Jill S.

    Submitted Jul 25, 2021

    Stayed Jul 17, 2021

    Another great week on Wososket Lane. Smooth check in, perfect location to Menemsha, and access to beautiful cycling routes. No words to describe beach days and moon rises on Quansoo beach. Carolyn is an excellent host.

Your dates are Available!

Total

Includes taxes and fees
$574+
View details