Chilmark Vacation Rentals

Welcome to Chilmark. Scroll down this page to find your favorite travel destination in Chilmark and browse our extensve inventory of accommodations in Chilmark. Leisure travelers planning their family vacations can get offers directly from owners of Chilmark vacation homes or houses in Chilmark. Sometimes these single rental units are referred to as Chilmark cabins or Chilmark villas. Other popular lodging options include vacation rentals in Chilmark, Chilmark apartments and condos in Chilmark. For business travelers we offer several convenient hotels in Chilmark or small boutique hotels in Chilmark area, many with the ability to book online. If you are planning a romantic getaway in Chilmark, we highy recommend our unique inventory of bed and breakfasts in Chilmark. B&Bs can also referred as small country inns in Chilmark.

Finding the perfect vacation rental property can be very time consuming. Unlike many other sites out there that demand travelers (like you) to invest countless hours browsing though each vacation rental listing, at we make it easy for travelers to find best Chilmark vacation rentals using our free inquiry service or Chilmark lodging locator service. Save time searching for Chilmark rental vacations and Chilmark accommodations! Simply click the "Inquire Now" button, complete a short inquiry form, and within minutes you will start receiving multiple offers from Chilmark vacation home rentals owners as well as from Chilmark resorts, Chilmark cabin rentals, and Chilmark vacation homes.

Let Rentalo help you find the perfect place to stay for your next family vacation in Marthas Vineyard area. Our engine will match your specific inquiry criteria with each Chilmark vacation rental listing, Chilmark vacation house or Chilmark villa in our Chilmark rental vacations inventory. Finding Chilmark vacation rentals by owner is easy with our free inquiry service. However, you can also browse our inventory of Chilmark accommodation listings (as listed below) or use the SmartSearch tool to narrow down your search for Chilmark lodging in Marthas Vineyard.

Enter your travel dates and number of people traveling (sleeps) and use one of the following search options:

  1. Inquire on ALL Vacation Rentals in Chilmark. Click "Inquire Now" (Fastest Option - Receive the most Offers)
  2. Inquire on Selected Vacation Rentals in Chilmark. Click "Check to inquire", then click "Inquire Now" (Time-Saving Option - Receive Offers from Selected Properties)
  3. Inquire only on a Specific Chilmark Vacation Rental (Take the time to review each property - Receive an offer on the Property you like)
Inquire on multiple properties - Save time! Inquire, Compare offers, and Book.

ID: 4280
Chilmark Oceanview House - Vacation Rental in Chilmark
5 Bedrooms
Sleeps 12
Located in chilmark featuring beautiful waterviews of both black point pond and the atlantic ocean! the property is situated in a restful private setting on over 4 acres of land and features two, mast ...Read Full Description
ID: 4280
Chilmark Family Compound with Indoor pool - Vacation Rental in Chilmark
5 Bedrooms
Sleeps 9
This private ocean view family compound on five acres, features a huge indoor-pool and five bedroom main house with a separate guest house; ideal for family reunions and weddings. Two private beaches ...Read Full Description
ID: 4280
Chilmark Log Home - Vacation Rental in Chilmark
3 Bedrooms
Sleeps 6
A modern 2 bedroom/loft, 1 bath home which accommodates six (plus) guests. Located 'up island' on four wooded acres the home is accessible to many walking and hiking have access to 2 privat ...Read Full Description
ID: 4280
Family Compound with Pool - Vacation Rental in Chilmark
6 Bedrooms
Sleeps 13
This secluded family compound sleeps thirteen, and is a perfect site for family reunions. It features two houses and a huge 40 by 20 in-ground swimming pool. there is access to two beautiful beaches o ...Read Full Description
ID: 321410
Captain R Flanders House - Bed and Breakfast in Chilmark
6 Bedrooms
Sleeps 12
Situated in the quiet town of chilmark, massachusetts, on the island of martha’s vineyard. This renovated farmhouse, built by whaling captain richard flanders in the late 1700’s is part of an original ...Read Full Description
Inquire on multiple properties - Save time! Inquire, Compare offers, and Book.

Smart Search

*Traveling Dates:

Flexible Dates
1+ (5)
3+ (5)
6+ (5)
11+ (3)

(vacation rentals only)
3 (1)
4+ (4)

Vacation Rental Types:
Apartment (2)
Cottage (1)

Lodging Types:
Bed and Breakfasts (1)
Vacation Rentals (4)

Location Attributes:
Near beach (1)
Near water (1)

Cable/Satellite TV (3)
Utensils (3)
Refrigerator (3)
Microwave (3)
Full Kitchen (3)
Dishwasher (3)

Things To Do:
Boating (4)
Waterskiing (3)
Sailing (4)
Jet Skiing (2)
Theaters / Cinemas (2)
Tennis (2)

Special Features:
Children Welcome (5)
Pet friendly (4)
Handicap accesibility (5)

Add these vicinities to my search:
Note: Use Search Destination box (above) to browse listings in these vicinities.
Menemsha (1)
Vineyard Haven (3)
Aquinnah (1)
West Tisbury (4)
Marthas Vineyard (3)
Oak Bluffs (7)
Edgartown (15)
Woods Hole (1)

Max Budget per Night: