Chilmark Villa
House
10.0(57 Reviews)
2 Bedrooms
1 Bath
3 Guests
480 ft²
Oceanfront
Fireplace/Heating
Ocean View
Balcony/Terrace
R8,493/Night
7 Nights - R59,455
House
10.0(1 Review)
1 Bedroom
4 Baths
8 Guests
3336.81 ft²
- Fireplace/Heating
- Balcony/Terrace
Pet Friendly
Child Friendly
R14,819/Night
7 Nights - R103,734
House
1 Bedroom
1 Bath
3 Guests
- Fireplace/Heating
Parking
Air Conditioner
Internet
R22,747/Night
7 Nights - R159,233
House
10.0(29 Reviews)
2 Bedrooms
2 Baths
4 Guests
880 ft²
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
R6,675/Night
7 Nights - R46,727
House
9.0(1 Review)
1 Bedroom
2 Baths
8 Guests
1679.17 ft²
- Fireplace/Heating
Pool- Balcony/Terrace
View
R30,725/Night
7 Nights - R215,072
Cottage
10.0(27 Reviews)
1 Bedroom
1 Bath
2 Guests
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
R5,253/Night
7 Nights - R36,772
House
8.6(6 Reviews)
2 Bedrooms
1 Bath
4 Guests
796.53 ft²
- Fireplace/Heating
- Balcony/Terrace
- View
- Pet Friendly
R12,144/Night
7 Nights - R85,007
Cottage
10.0(9 Reviews)
2 Bedrooms
1 Bath
5 Guests
1800 ft²
- Oceanfront
- Ocean View
- Balcony/Terrace
- View
R6,701/Night
7 Nights - R46,906
House
4 Bedrooms
3 Baths
10 Guests
2400.35 ft²
- Oceanfront
Spa- Fireplace/Heating
- Ocean View
R7,831/Night
7 Nights - R54,818
House
10.0(8 Reviews)
2 Bedrooms
1 Bath
4 Guests
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
- View
R6,333/Night
7 Nights - R44,328
Cottage
10.0(5 Reviews)
2 Bedrooms
1 Bath
5 Guests
1000 ft²
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
R11,063/Night
7 Nights - R77,436
House
9.6(32 Reviews)
2 Bedrooms
2 Baths
5 Guests
1400 ft²
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
R11,319/Night
7 Nights - R79,235
Why Choose Rent By Owner for your Chilmark Villa?
What makes our Villa 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 Villa
What's our booking process?
Our platform allows you to browse a curated selection of villa. 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 Villa Amenities
What amenities can you expect?
Our Villa 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 Rental Villas
1. What are the top Villas 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 Villas in Chilmark:
- Menemsha Home Fully Renovated w/Amazing Waterview's of Vineyard Sound
- Walk to Beach, Kayak from Backyard Dock, Ocean & Squibnocket Pond Views
- Classic Modern House on its Own Point of Land with Astounding Views
- 3 Bedroom House with Guest Cottage on 3 Acres off Middle Road
- Light Open Vacation Home, Sweeping Waterviews, Hill Top, Private
- Post and Beam home with westward views of the ocean and sunsets
- Lovely Chilmark home on Abel's Hill with private beach, pond, tennis, and trails
- Pet-Friendly Historic Chilmark House
- Peaceful Chilmark Farmhouse by Menemsha Beach
- Tucked Away on Tea Lane, Chilmark
2. How many Villas are available in Chilmark?
Currently, the total number of properties listed by RBO in 2026 is over 128 in the Chilmark area, and still counting. By aggregating listings from multiple websites, RBO offers an immense amount of choice of the best Villas in Chilmark.
More Rentals You May Like Near Chilmark
Apartment
9.6(21 Reviews)
1 Bedroom
1 Bath
2 Guests
- Pool
- Ocean View
- Balcony/Terrace
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R7,461/Night
7 Nights - R52,224
New
House
2 Bedrooms
1 Bath
4 Guests
800 ft²
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
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New
Cottage
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1 Bath
6 Guests
- Internet
- Child Friendly
Laundry
Bedding/Linens
R8,041/Night
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New
Cottage
2 Bedrooms
1 Bath
4 Guests
- Fireplace/Heating
- Balcony/Terrace
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R5,804/Night
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House
10.0(52 Reviews)
4 Bedrooms
2 Baths
8 Guests
1800 ft²
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
- View
R13,311/Night
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House
10.0(42 Reviews)
4 Bedrooms
4 Baths
8 Guests
2100 ft²
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
- View
R33,892/Night
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House
10.0(31 Reviews)
3 Bedrooms
2 Baths
10 Guests
2000 ft²
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
R14,760/Night
7 Nights - R103,328
House
10.0(28 Reviews)
3 Bedrooms
1 Bath
8 Guests
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
- View
R8,157/Night
7 Nights - R57,104
House
10.0(26 Reviews)
4 Bedrooms
3 Baths
8 Guests
2400 ft²
Private Pool- Oceanfront
- Fireplace/Heating
- Pool
R25,581/Night
7 Nights - R179,062
House
10.0(25 Reviews)
5 Bedrooms
3 Baths
10 Guests
3000 ft²
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
R24,837/Night
7 Nights - R173,857
House
10.0(24 Reviews)
3 Bedrooms
1 Bath
6 Guests
2000 ft²
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
R9,726/Night
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House
10.0(19 Reviews)
3 Bedrooms
2 Baths
8 Guests
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
R14,359/Night
7 Nights - R100,507
