Chilmark Resorts
Cottage
10.0(27 Reviews)
1 Bedroom
1 Bath
2 Guests
Oceanfront
Fireplace/Heating
Ocean View
Balcony/Terrace
US $402/Night
7 Nights - US $2,811
House
10.0(1 Review)
4 Bedrooms
4 Baths
8 Guests
3336.81 ft²
- Fireplace/Heating
- Balcony/Terrace
View
Pet Friendly
US $914/Night
7 Nights - US $6,398
House
1 Bedroom
1 Bath
3 Guests
- Fireplace/Heating
Parking
Air Conditioner
Internet
US $1,403/Night
7 Nights - US $9,821
Cottage
10.0(9 Reviews)
2 Bedrooms
1 Bath
5 Guests
1800 ft²
- Oceanfront
- Ocean View
- Balcony/Terrace
- View
US $478/Night
7 Nights - US $3,343
House
9.0(1 Review)
1 Bedroom
2 Baths
8 Guests
1679.17 ft²
- Fireplace/Heating
Pool- Balcony/Terrace
- View
US $1,895/Night
7 Nights - US $13,265
House
10.0(8 Reviews)
2 Bedrooms
1 Bath
4 Guests
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
- View
US $420/Night
7 Nights - US $2,938
House
8.6(6 Reviews)
2 Bedrooms
1 Bath
4 Guests
796.53 ft²
- Fireplace/Heating
- Balcony/Terrace
- View
- Pet Friendly
US $749/Night
7 Nights - US $5,243
Cottage
10.0(5 Reviews)
2 Bedrooms
1 Bath
5 Guests
1000 ft²
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $683/Night
7 Nights - US $4,784
House
4 Bedrooms
3 Baths
10 Guests
2400.35 ft²
- Oceanfront
Spa- Fireplace/Heating
- Ocean View
US $483/Night
7 Nights - US $3,381
House
9.6(32 Reviews)
2 Bedrooms
2 Baths
5 Guests
1400 ft²
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $555/Night
7 Nights - US $3,886
Apartment
9.6(21 Reviews)
1 Bedroom
1 Bath
2 Guests
- Pool
- Ocean View
- Balcony/Terrace
- View
US $414/Night
7 Nights - US $2,901
New
Cottage
2 Bedrooms
1 Bath
6 Guests
- Internet
Child Friendly
Laundry
Bedding/Linens
US $503/Night
7 Nights - US $3,519
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:
- Menemsha Pond waterfront Available July 18-25, 2026 BOOK NOW!
- Beautiful Chilmark beach house. Great screen porch. Fun house. Pet friendly.
- Secluded Chilmark Estate: Pool & Pvt Quansoo Beach
- NEW Construction on Old Farmland, a Love Letter to The Vineyard
- Peaceful Scenic Up-Island Retreat With Private Martha's Vineyard Beach
- Walk to private beach from beautiful Abels Hill house
- Peaceful Wooded Retreat, Short Car Ride to Everything. Week is Friday to Friday
- Quintessential Chilmark Retreat - Marthas Vineyard
- Charming Chilmark beach house with private Abel's Hill beach access
- Private Hillside Home, Fully Equipped Kitchen, Dog-Friendly, A/C, W/D
2. How many Resorts 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 Resorts in Chilmark.
More Rentals You May Like Near Chilmark
Cottage
2 Bedrooms
1 Bath
4 Guests
- Fireplace/Heating
- Balcony/Terrace
Kitchen- Parking
US $358/Night
7 Nights - US $2,506
House
10.0(42 Reviews)
4 Bedrooms
4 Baths
8 Guests
2100 ft²
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
- View
US $1,420/Night
7 Nights - US $9,941
House
10.0(41 Reviews)
4 Bedrooms
2 Baths
8 Guests
1700 ft²
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $893/Night
7 Nights - US $6,251
House
10.0(26 Reviews)
4 Bedrooms
3 Baths
8 Guests
2400 ft²
Private Pool- Oceanfront
- Fireplace/Heating
- Pool
US $909/Night
7 Nights - US $6,363
House
10.0(25 Reviews)
5 Bedrooms
3 Baths
10 Guests
3000 ft²
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $917/Night
7 Nights - US $6,422
House
10.0(17 Reviews)
3 Bedrooms
3 Baths
6 Guests
2000 ft²
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $1,047/Night
7 Nights - US $7,330
House
10.0(13 Reviews)
4 Bedrooms
4 Baths
10 Guests
2500 ft²
- Oceanfront
Hot Tub- Fireplace/Heating
- Ocean View
US $1,208/Night
7 Nights - US $8,458
House
10.0(13 Reviews)
4 Bedrooms
3 Baths
8 Guests
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $1,110/Night
7 Nights - US $7,772
House
10.0(7 Reviews)
4 Bedrooms
2 Baths
8 Guests
2400 ft²
- Oceanfront
- Hot Tub
- Fireplace/Heating
- Ocean View
US $1,515/Night
7 Nights - US $10,603
House
10.0(6 Reviews)
4 Bedrooms
3 Baths
10 Guests
2500 ft²
- Oceanfront
- Hot Tub
- Fireplace/Heating
- Ocean View
US $782/Night
7 Nights - US $5,473
Cottage
10.0(5 Reviews)
3 Bedrooms
1 Bath
7 Guests
1 ft²
- Oceanfront
- Ocean View
- Balcony/Terrace
- View
US $746/Night
7 Nights - US $5,219
House
10.0(4 Reviews)
4 Bedrooms
2 Baths
8 Guests
1397 ft²
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $1,098/Night
7 Nights - US $7,686
