Why Choose Rent By Owner for your Chilmark Resorts?
What makes our Resorts special?
Weekly Weather Forecast for Chilmark
How to Book Your Chilmark Resorts
What's our booking process?
Booking Steps
Search Properties
Select a Rental
Book Online
Explore and book the perfect rental in Chilmark
Common Resorts Amenities
What amenities can you expect?
Indoor Features
- Fully-equipped kitchens with modern appliances
- Comfortable living areas with flat-screen TVs
- Free Wi-Fi for staying connected
- Air conditioning and heating for year-round comfort
- In-unit washers and dryers for convenience
- Luxurious bedrooms with premium bedding
- Spa-like bathrooms with soaking tubs or walk-in showers
Other Places to Stay in Chilmark, MA
Frequently Asked Questions About Chilmark Resorts
1. What are the top Resorts in Chilmark?
There are a lot of options in Chilmark. If you plan on staying in the Chilmark area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Resorts in Chilmark:
- Gracious Landmark Home ~ Fabulous Water Views ~ 2 Private Beaches
- Secluded house in the woods with deck, streamside firepit, Vincent Beach nearby
- House in Chilmark/Menemsha, Martha's Vineyard w/Private Beach, Sunset View.
- Menemsha Home Fully Renovated w/Amazing Waterview's of Vineyard Sound
- Classic Modern House on its Own Point of Land with Astounding Views
- 3 Bedroom House with Guest Cottage on 3 Acres off Middle Road
- Walk to Beach, Kayak from Backyard Dock, Ocean & Squibnocket Pond Views
- Spectacular Oceanfront, 4 BR/4 bath, Hottub, Private Beach, Tennis, AC, WiFi
- Light Open Vacation Home, Sweeping Waterviews, Hill Top, Private
- Post and Beam home with westward views of the ocean and sunsets
2. How many Resorts are available in Chilmark?
Currently, the total number of properties listed by RBO in 2026 is over 118 in the Chilmark area, and still counting. By aggregating listings from multiple websites, RBO offers an immense amount of choice of the best Resorts in Chilmark.

























