Best Vacation Homes in Chilmark
House
10.0(63 Reviews)
2 Bedrooms
1 Bath
3 Guests
480 ft²
Oceanfront
Parking
Ocean View
Balcony/Terrace
US $463/Night
7 Nights - US $3,242
House
10.0(1 Review)
4 Bedrooms
4 Baths
8 Guests
3336.81 ft²
- Balcony/Terrace
View
Air Conditioner
Internet
US $914/Night
7 Nights - US $6,398
House
1 Bedroom
1 Bath
3 Guests
- Parking
- Air Conditioner
- Internet
Child Friendly
US $1,403/Night
7 Nights - US $9,821
House
10.0(30 Reviews)
2 Bedrooms
2 Baths
4 Guests
880 ft²
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
US $542/Night
7 Nights - US $3,795
House
9.0(1 Review)
1 Bedroom
2 Baths
8 Guests
1679.17 ft²
Pool- Balcony/Terrace
- View
- Internet
US $1,895/Night
7 Nights - US $13,265
Cottage
10.0(10 Reviews)
2 Bedrooms
1 Bath
5 Guests
1800 ft²
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
US $470/Night
7 Nights - US $3,288
Cottage
10.0(5 Reviews)
2 Bedrooms
1 Bath
5 Guests
1000 ft²
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
US $406/Night
7 Nights - US $2,841
Apartment
9.6(22 Reviews)
1 Bedroom
1 Bath
2 Guests
- Parking
- Pool
- Ocean View
- Balcony/Terrace
US $444/Night
7 Nights - US $3,108
Chilmark Luxury Rentals
House
2.0(1 Review)
4 Bedrooms
2 Baths
8 Guests
4000 ft²
Hot Tub- Parking
- Ocean View
- Balcony/Terrace
US $7,819/Night
7 Nights - US $54,732
House
4 Bedrooms
4 Baths
6 Guests
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
US $5,672/Night
7 Nights - US $39,705
House
4 Bedrooms
3 Baths
8 Guests
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
US $4,458/Night
7 Nights - US $31,206
New
House
4 Bedrooms
3 Baths
50 Guests
Private Pool- Oceanfront
- Hot Tub
- Parking
US $3,953/Night
7 Nights - US $27,673
House
10.0(1 Review)
4 Bedrooms
3 Baths
8 Guests
2000 ft²
- Private Pool
- Oceanfront
- Hot Tub
- Parking
US $2,975/Night
7 Nights - US $20,824
House
10.0(42 Reviews)
4 Bedrooms
4 Baths
8 Guests
2100 ft²
- Parking
- Ocean View
- Balcony/Terrace
- View
US $2,777/Night
7 Nights - US $19,440
House
3 Bedrooms
3 Baths
8 Guests
- Oceanfront
- Ocean View
- Balcony/Terrace
- View
US $2,733/Night
7 Nights - US $19,129
House
6 Bedrooms
4 Baths
12 Guests
- Parking
- Ocean View
- Balcony/Terrace
- View
US $2,679/Night
7 Nights - US $18,754
Chilmark Pet Friendly Vacation Rentals
House
2 Bedrooms
1 Bath
4 Guests
800 ft²
- Oceanfront
- Ocean View
- Balcony/Terrace
- View
US $502/Night
7 Nights - US $3,517
House
8.6(6 Reviews)
2 Bedrooms
1 Bath
4 Guests
796.53 ft²
- Balcony/Terrace
- View
- Air Conditioner
- Internet
US $502/Night
7 Nights - US $3,515
House
10.0(42 Reviews)
4 Bedrooms
2 Baths
8 Guests
1700 ft²
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
US $893/Night
7 Nights - US $6,251
House
10.0(25 Reviews)
5 Bedrooms
3 Baths
10 Guests
3000 ft²
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
US $913/Night
7 Nights - US $6,393
House
10.0(13 Reviews)
4 Bedrooms
4 Baths
10 Guests
2500 ft²
- Oceanfront
- Hot Tub
- Parking
- Ocean View
US $1,216/Night
7 Nights - US $8,512
House
10.0(9 Reviews)
4 Bedrooms
3 Baths
10 Guests
2800 ft²
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
US $1,086/Night
7 Nights - US $7,599
House
10.0(6 Reviews)
4 Bedrooms
3 Baths
10 Guests
2500 ft²
- Oceanfront
- Hot Tub
- Parking
- Ocean View
US $890/Night
7 Nights - US $6,232
House
10.0(2 Reviews)
4 Bedrooms
2 Baths
8 Guests
- Parking
- Ocean View
- Balcony/Terrace
- View
US $585/Night
7 Nights - US $4,095
Chilmark Large Vacation Homes
House
9.8(38 Reviews)
6 Bedrooms
3 Baths
13 Guests
3000 ft²
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
US $1,206/Night
7 Nights - US $8,445
House
4 Bedrooms
3 Baths
10 Guests
2400.35 ft²
- Oceanfront
- Parking
Spa- Ocean View
US $483/Night
7 Nights - US $3,381
House
9.8(11 Reviews)
5 Bedrooms
2 Baths
10 Guests
3200 ft²
- Oceanfront
- Hot Tub
- Parking
- Ocean View
US $801/Night
7 Nights - US $5,606
House
9.2(42 Reviews)
5 Bedrooms
4 Baths
14 Guests
3500 ft²
- Parking
- Ocean View
- Balcony/Terrace
- View
US $1,174/Night
7 Nights - US $8,216
Cottage
9.2(5 Reviews)
4 Bedrooms
2 Baths
10 Guests
- Parking
- Ocean View
- Balcony/Terrace
- View
US $767/Night
7 Nights - US $5,366
House
5 Bedrooms
4 Baths
10 Guests
4750 ft²
- Hot Tub
- Parking
- Ocean View
- Balcony/Terrace
US $1,754/Night
7 Nights - US $12,278
New
House
5 Bedrooms
3 Baths
10 Guests
- Air Conditioner
- Internet
Pet Friendly- Child Friendly
US $1,186/Night
7 Nights - US $8,302
House
5 Bedrooms
5 Baths
12 Guests
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
US $1,156/Night
7 Nights - US $8,091
Why Choose Rent By Owner for your Chilmark Vacation Rental Homes?
What makes our Vacation Rentals 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.
Best Times to Visit Chilmark
When should you plan your Vacation Rentals stay?
Choosing the right time to visit this charming destination can enhance your experience, allowing you to enjoy its serene landscapes and coastal beauty at their best, whether you're seeking quiet relaxation or vibrant local events throughout the year.
Peak Season Highlights
Summer (June to August)
During the summer months, this destination experiences its peak season with warm weather and lively outdoor activities. It's an ideal time for beach outings and exploring the region's scenic beauty.
Average Temperature Daytime: 75°F to 85°F - Nighttime: 60°F to 70°F
Early Fall (September to October)
The early fall offers pleasant weather and vibrant foliage, making it a popular season for those seeking tranquility and scenic views in the area.
Average Temperature Daytime: 65°F to 75°F - Nighttime: 50°F to 60°F
Off-Season Highlights
Late Fall to Early Winter (November to December)
This period sees fewer visitors as the weather cools, providing a more peaceful experience while still enjoying the region’s natural charm.
Average Temperature Daytime: 50°F to 55°F - Nighttime: 40°F to 45°F
Winter (January to February)
During winter, the quiet atmosphere is perfect for travelers seeking solitude and cozy retreats in the region’s scenic surroundings.
Average Temperature Daytime: 35°F to 45°F - Nighttime: 25°F to 35°F
Weekly Weather Forecast for Chilmark
How to Book Your Chilmark Vacation Rental Home
What's our booking process?
Our platform allows you to browse a curated selection of vacation rentals. 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.
Common Vacation Rentals Amenities
What amenities can you expect?
Our Vacation Rentals 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
Outdoor Amenities
- Enjoy outdoor seating areas perfect for relaxing and dining amid the natural beauty of the region.
- Take advantage of spacious lawns or gardens ideal for outdoor activities and family gatherings.
- Benefit from access to private or community swimming pools, offering a refreshing escape during your stay.
- Explore nearby hiking or walking trails that showcase the scenic landscapes of this coastal destination.
- Make use of outdoor fireplaces or grills to enhance your culinary experience in the fresh air.
- Relax in sheltered patios or verandas designed for enjoying sunrise or sunset views over the area's picturesque surroundings.
- Utilize outdoor showers or hot tubs that provide a luxurious touch to your getaway in this sought-after location.
Top Attractions Around Chilmark
What attractions are nearby?
In this charming destination, you can enjoy a variety of outdoor activities, including pristine beaches, scenic hiking trails, and tranquil nature preserves that showcase the region’s natural beauty.
Family Activities
- Chilmark Vineyard Tours: Discover the region’s renowned vineyards and enjoy family-friendly tastings amidst scenic landscapes.
- Squibnocket Beach: Spend a relaxing day on the sandy shores perfect for swimming, picnicking, and exploring tide pools with your loved ones.
- Alley’s General Store: Experience a charming local shopping spot where you can pick up essentials and regional treats for your family outing.
- Martha’s Vineyard Museum: Engage in educational exhibits that highlight the area's rich history, offering an enriching experience for children and adults alike.
Adult Activities
- Chilmark Vineyard Tours: Explore the region’s renowned vineyards and enjoy tasting sessions amidst scenic farm landscapes.
- Beachcombing at Squibnocket Beach: Spend your days discovering unique shells and enjoying the pristine shoreline of this beloved beach destination.
- Art Gallery Visits: Appreciate local artistry by browsing through galleries featuring works inspired by the area's natural beauty.
- Guided Nature Walks: Discover the region's diverse flora and fauna on expertly guided walks through nearby nature preserves.
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
Chilmark Travel Tips
How Can You Make the Most of Your Stay?
- Explore local markets and eateries: Take the time to discover the region's unique flavors and artisanal products, enriching your stay in Chilmark by supporting local vendors.
- Plan outdoor activities carefully: Make the most of the area's natural beauty by scheduling visits to scenic spots early in the day for optimal weather and fewer crowds.
- Communicate with your hosts: Engage with property owners or managers to gain insider tips and ensure a smooth, enjoyable experience during your visit here.
- Respect the environment: Practice eco-friendly habits to preserve the scenic landscapes that make this destination so special for future travelers.
Transportation Options
- Chilmark Ferry Service: Provides scenic and convenient boat trips connecting this part of the region to nearby islands and coastal destinations.
- Regional Taxi Services: Offers reliable transportation options for exploring the area or traveling to local towns from your vacation rental.
- Rental Car Agencies: Allows you to explore all around here at your own pace with a variety of vehicles available directly in the region.
- Public Bus Transit: Serves as an affordable and eco-friendly way to get around, connecting key points within the area and nearby communities.
Local Customs Options
- Respect for the Land and Nature: Locals hold a deep reverence for the area's natural environment, making sustainable practices and conservation efforts an important part of community life.
- Seafood and Local Cuisine: Sharing freshly caught seafood is a cherished tradition here, often enjoyed during communal gatherings and local festivals.
- Traditional Gatherings and Seasonal Events: Participating in seasonal celebrations and community events helps you connect with regional customs and local residents alike.
- Quiet Respect for Privacy: Maintaining a tranquil ambiance is valued, so visitors are encouraged to keep noise levels considerate, especially in residential areas.
Chilmark Vacation Rental Frequently Asked Questions
1. What are the top vacation rentals 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 Vacation Rentals in Chilmark:
- Unwind in Guest House overlooking Menemsha Pond. Dogs ok+ Lv-2 EV charger.
- Mid-Century Modern - All Glass House - Designed By Frank Lloyd Wright Apprentice
- 10 minutes walk to Lucy Vincent Beach
- Open July 20-27th w/RT Ferry! 4 BR Cape in Chilmark - Pet Friendly
- Menemsha Pond views & access! Mid-century renovated beach house. Dogs welcome.
- Cool, Mid-Century House - Lucy Vincent Beach and Pool!
- Secluded house in the woods with deck, streamside firepit, Vincent Beach nearby
- Gracious Prestige Landmark ~ 2 Private Beaches ~ Fabulous View
- Menemsha Home Fully Renovated w/Amazing Waterview's of Vineyard Sound
- Walk to Beach, Kayak from Backyard Dock, Ocean & Squibnocket Pond Views
2. Which vacation homes in Chilmark are best for families?
If you are looking for a family-friendly vacation home in Chilmark, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Chilmark:
3. How many Rentbyowner vacation rentals are available in Chilmark?
Currently, the total number of properties listed by Rent By Owner in 2026 is over 119 in the Chilmark area, and still counting. By aggregating listings from multiple websites, Rent By Owner offers an immense amount of choice of the best RBO properties in Chilmark.
4. What is the cancellation policy for vacation rentals in Chilmark?
The cancellation policy varies depending on the property owner. You should review the specific listing details or contact the owner directly to understand the refund and cancellation terms before booking.
5. Are there any specific check-in and check-out times I should be aware of when staying in this area?
Check-in and check-out times are set by individual property owners. It's best to confirm these details during your reservation process or by contacting the host directly to ensure a smooth arrival and departure.
6. How do I find the most suitable vacation rental in Chilmark that fits my needs?
You can filter available properties by amenities, price range, and other preferences on the listing platform. For personalized assistance, reaching out to the property owner can also help you select the ideal rental for your stay here.
7. What should I know about the safety and security features of vacation rentals in this region?
Safety features such as locks, security systems, and outdoor lighting are listed on each property’s page. To ensure peace of mind, review these details carefully or contact the owner for additional information.
8. Is there a flexible booking policy for last-minute reservations in the area?
Booking flexibility depends on individual listings and the property owner’s policies. It’s recommended to read the cancellation and modification policies carefully or contact the owner directly for immediate availability and last-minute booking options.
Chilmark Top Rated Vacation Rentals
House
10.0(28 Reviews)
4 Bedrooms
3 Baths
8 Guests
2400 ft²
- Private Pool
- Oceanfront
- Parking
- Pool
US $904/Night
7 Nights - US $6,326
House
10.0(1 Review)
1 Bedroom
2 Baths
8 Guests
1684 ft²
- Private Pool
- Oceanfront
- Pool
- Ocean View
US $996/Night
7 Nights - US $6,974
House
8.6(24 Reviews)
4 Bedrooms
2 Baths
8 Guests
1684 ft²
- Private Pool
- Oceanfront
- Parking
- Pool
US $874/Night
7 Nights - US $6,117
House
5.0(2 Reviews)
4 Bedrooms
4 Baths
8 Guests
2000 ft²
- Private Pool
- Pool
Kitchen- Air Conditioner
US $946/Night
7 Nights - US $6,619
House
7 Bedrooms
5 Baths
12 Guests
- Private Pool
- Oceanfront
Breakfast- Parking
US $8,000/Night
7 Nights - US $56,000
House
4 Bedrooms
3 Baths
8 Guests
- Oceanfront
- Parking
- Pool
- Ocean View
US $6,210/Night
7 Nights - US $43,470
