Chilmark Resorts
New
House
3 Bedrooms
3 Baths
8 Guests
Oceanfront
Fireplace/Heating
Ocean View
Balcony/Terrace
CA $5,002/Night
7 Nights - CA $35,016
House
10.0(1 Review)
1 Bedroom
4 Baths
8 Guests
3336.81 ft²
- Fireplace/Heating
- Balcony/Terrace
Pet Friendly
Child Friendly
CA $1,251/Night
7 Nights - CA $8,758
House
1 Bedroom
1 Bath
3 Guests
- Fireplace/Heating
Parking
Air Conditioner
Internet
CA $1,920/Night
7 Nights - CA $13,443
New
House
5 Bedrooms
5 Baths
12 Guests
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
CA $3,838/Night
7 Nights - CA $26,867
House
9.0(1 Review)
4 Bedrooms
2 Baths
8 Guests
1679.17 ft²
- Fireplace/Heating
Pool- Balcony/Terrace
View
CA $2,594/Night
7 Nights - CA $18,157
New
House
4 Bedrooms
5 Baths
8 Guests
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
CA $3,319/Night
7 Nights - CA $23,232
House
8.6(6 Reviews)
1 Bedroom
1 Bath
4 Guests
796.53 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Air Conditioner
CA $1,025/Night
7 Nights - CA $7,177
House
10.0(57 Reviews)
2 Bedrooms
1 Bath
3 Guests
480 ft²
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
CA $717/Night
7 Nights - CA $5,019
House
4 Bedrooms
3 Baths
10 Guests
2400.35 ft²
- Oceanfront
Spa- Fireplace/Heating
- Ocean View
CA $661/Night
7 Nights - CA $4,628
House
10.0(29 Reviews)
2 Bedrooms
2 Baths
4 Guests
880 ft²
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
CA $701/Night
7 Nights - CA $4,906
Cottage
10.0(27 Reviews)
1 Bedroom
1 Bath
2 Guests
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
CA $443/Night
7 Nights - CA $3,104
Cottage
10.0(9 Reviews)
2 Bedrooms
1 Bath
5 Guests
1800 ft²
- Oceanfront
- Ocean View
- Balcony/Terrace
- View
CA $566/Night
7 Nights - CA $3,960
Why Choose Rent By Owner for your Chilmark Resorts?
What makes our Resorts special?
Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
Diverse Options
From cozy cabins to luxurious villas, find a rental that suits your style and needs.
Weekly Weather Forecast for Chilmark
How to Book Your Chilmark Resorts
What's our booking process?
Our platform allows you to browse a curated selection of resorts. Once you find the ideal property, you’ll be redirected to a trusted booking partner to complete your reservation securely.
Booking Steps
01
Search Properties
Use our filters to find the right property that fits your needs.
02
Select a Rental
Click on your preferred listing to view details, amenities, and pricing.
03
Book Online
Follow the link to finalize your reservation directly on the partner’s website.
Explore and book the perfect rental in Chilmark
Common Resorts Amenities
What amenities can you expect?
Our Resorts are designed to offer all the comforts of home, often with added perks to make your stay unforgettable. Here’s some common amenities to look forward to:
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
Dukes County
Fulling Mill Brook Preserve
The Yard
Menemsha
Waskosim's Rock Reservation
Menemsha Beach
Menemsha Blues Charters
Chilmark Chocolates
Lucy Vincent Beach
Squibnocket Pond
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:
- Cool, Mid-Century House - Lucy Vincent Beach and Pool!n
- 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
- 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 124 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.
More Rentals You May Like Near Chilmark
House
10.0(8 Reviews)
2 Bedrooms
1 Bath
4 Guests
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
- View
CA $535/Night
7 Nights - CA $3,742
Cottage
10.0(5 Reviews)
2 Bedrooms
1 Bath
5 Guests
1000 ft²
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
CA $828/Night
7 Nights - CA $5,797
Cottage
10.0(1 Review)
2 Bedrooms
1 Bath
4 Guests
- Pet Friendly
Kitchen- Air Conditioner
- Internet
CA $1,354/Night
7 Nights - CA $9,478
House
9.6(32 Reviews)
2 Bedrooms
2 Baths
5 Guests
1400 ft²
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
CA $956/Night
7 Nights - CA $6,689
Apartment
9.6(21 Reviews)
1 Bedroom
1 Bath
2 Guests
- Pool
- Ocean View
- Balcony/Terrace
- View
CA $630/Night
7 Nights - CA $4,409
House
9.2(17 Reviews)
2 Bedrooms
1 Bath
4 Guests
800 ft²
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
CA $508/Night
7 Nights - CA $3,558
Cottage
2 Bedrooms
1 Bath
4 Guests
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
CA $490/Night
7 Nights - CA $3,430
House
10.0(52 Reviews)
4 Bedrooms
2 Baths
8 Guests
1800 ft²
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
- View
CA $1,124/Night
7 Nights - CA $7,867
House
10.0(42 Reviews)
4 Bedrooms
4 Baths
8 Guests
2100 ft²
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
- View
CA $2,861/Night
7 Nights - CA $20,030
House
10.0(35 Reviews)
6 Bedrooms
3 Baths
13 Guests
3000 ft²
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
CA $1,024/Night
7 Nights - CA $7,171
House
10.0(31 Reviews)
3 Bedrooms
2 Baths
10 Guests
2000 ft²
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
CA $1,246/Night
7 Nights - CA $8,723
House
10.0(28 Reviews)
3 Bedrooms
1 Bath
8 Guests
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
- View
CA $689/Night
7 Nights - CA $4,821
