Chilmark Rentals by Owner
3336.81 ft²
8 Guests
1 Bedroom
4 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $914/Night
For 7 Nights US $6,398
3 Guests
1 Bedroom
1 Bathroom
Family Friendly
House
- Fireplace/Heating
- Parking
- Air Conditioner
US $1,403/Night
For 7 Nights US $9,821
8 Guests
3 Bedrooms
3 Bathrooms
Ocean View
House
- Oceanfront
- Fireplace/Heating
- Ocean View
US $3,654/Night
For 7 Nights US $25,581
1679.17 ft²
8 Guests
4 Bedrooms
2 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $1,895/Night
For 7 Nights US $13,265
12 Guests
5 Bedrooms
5 Bathrooms
Ocean View
House
- Oceanfront
- Fireplace/Heating
- Ocean View
US $2,666/Night
For 7 Nights US $18,660
796.53 ft²
4 Guests
1 Bedroom
1 Bathroom
Free Cancellation
House
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $749/Night
For 7 Nights US $5,243
8 Guests
4 Bedrooms
5 Bathrooms
Ocean View
House
- Oceanfront
- Fireplace/Heating
- Ocean View
US $2,232/Night
For 7 Nights US $15,621
2400.35 ft²
10 Guests
4 Bedrooms
3 Bathrooms
House
- Oceanfront
- Spa
- Fireplace/Heating
US $483/Night
For 7 Nights US $3,381
480 ft²
3 Guests
2 Bedrooms
1 Bathroom
Ocean View
House
- Oceanfront
- Fireplace/Heating
- Ocean View
US $343/Night
For 7 Nights US $2,398
880 ft²
4 Guests
2 Bedrooms
2 Bathrooms
Ocean View
House
- Oceanfront
- Fireplace/Heating
- Ocean View
US $410/Night
For 7 Nights US $2,867
4 Guests
2 Bedrooms
1 Bathroom
Ocean View
House
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $391/Night
For 7 Nights US $2,734
1400 ft²
5 Guests
2 Bedrooms
2 Bathrooms
Ocean View
House
- Oceanfront
- Fireplace/Heating
- Ocean View
US $698/Night
For 7 Nights US $4,887
Why Choose Rent By Owner for your Chilmark vacation rental?
What makes our Rentals by Owner 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 Rentals by Owner stay?
Choosing the optimal time to vacation here ensures you experience the region's unique charm at its best, making it the perfect setting for your Rent By Owner rental in Chilmark, Massachusetts.
Peak Season Highlights
Summer (June to August)
During the summer months, you will experience warm weather and longer daylight hours, making it ideal for enjoying outdoor activities and relaxing in your rental by owner. This is the most popular time to visit the area, so expect a lively atmosphere and higher demand for accommodations.
Average Temperature Daytime: 75-85°F - Nighttime: 60-70°F
Early Fall (September to October)
The early fall offers pleasant temperatures and fewer crowds, providing a peaceful setting for your stay while still enjoying the region’s natural beauty. The mild weather makes it an excellent season for exploring rentals by owner in this destination.
Average Temperature Daytime: 65-75°F - Nighttime: 50-60°F
Off-Season Highlights
Late Fall to Winter (November to February)
During late fall through winter, the area becomes quieter with cooler temperatures, offering a serene escape for those seeking tranquility away from the peak visitor times. Many rentals by owner are more available and affordable during this period.
Average Temperature Daytime: 45-55°F - Nighttime: 30-40°F
Early Spring (March to May)
As the region transitions into spring, the weather begins to warm gradually, and the landscape starts to bloom. It’s a great time to find deals on vacation rentals by owner before the summer rush begins.
Average Temperature Daytime: 50-65°F - Nighttime: 35-45°F
Weekly Weather Forecast for Chilmark
How to Book Your Chilmark vacation rental
What's our booking process?
Our platform allows you to browse a curated selection of rentals by owner. 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 Rentals by Owner Amenities
What amenities can you expect?
Our Rentals by Owner 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 dining areas perfect for al fresco meals amid the region’s natural beauty.
- Take advantage of spacious patios or decks that offer scenic views of the landscape.
- Relax in private pools or hot tubs available at select vacation rentals nearby.
- Make the most of lush, landscaped gardens that enhance your outdoor experience.
- Utilize barbecue grills for family cookouts under the clear skies of this destination.
- Explore expansive yards or open spaces ideal for outdoor activities and games.
- Benefit from outdoor showers or lounging areas that complement the tranquil environment here.
Top Attractions Around Chilmark
What attractions are nearby?
Here, you can enjoy a variety of outdoor activities and explore the natural beauty that makes this destination a perfect retreat for relaxation and adventure alike.
Family Activities
- Lucy Vincent Beach: Spend a relaxing day with your family on this scenic, family-friendly beach known for its soft sands and calm waters, perfect for kids in the area.
- Island Artisans: Explore local craftsmanship and create memorable souvenirs during craft workshops designed for families looking to experience the region’s artistic heritage.
- Chilmark Community Farm: Discover farm life through hands-on activities such as petting animals and planting, making it an educational outing for children visiting here.
- Menemsha Harbor: Enjoy waterfront picnics and sunset views at this charming harbor, ideal for family outings that capture the essence of this destination’s maritime culture.
Adult Activities
- Chilmark Vineyard Tours: Explore local vineyards to enjoy wine tasting experiences amid scenic views and regional flavors.
- Whale Watching Excursions: Embark on boat trips from nearby marinas to see majestic whales in their natural habitat along the coast.
- Art Galleries and Studios: Discover the area's vibrant arts scene by visiting galleries showcasing regional artists and their work.
- Nature Trails and Birdwatching: Walk through preserved nature trails designed for birdwatching and appreciating the region's diverse flora and fauna.
Other Places to Stay in Chilmark, MA
Dukes County
Fulling Mill Brook Preserve
The Yard
Waskosim's Rock Reservation
Menemsha
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 advantage of the area's fresh produce and dining options to truly experience the regional flavors during your stay.
- Plan outdoor activities early in the morning: Maximize your time by enjoying the region’s scenic landscapes and outdoor pursuits when the weather is at its best.
- Choose a rental with proximity to key attractions: Selecting a property close to the highlights of this destination ensures you spend less time commuting and more time relaxing.
- Engage with the community: Embrace the laid-back vibe by participating in local events or chatting with neighbors, enriching your travel experience here.
Transportation Options
- Car Rentals: You can explore the region at your own pace by renting a car, which offers flexibility to visit local beaches and scenic spots comfortably.
- Public Transit: The local bus services connect you to nearby towns and amenities, making it a convenient option for getting around this area without a vehicle.
- Bicycle Rentals: Biking is an excellent way to enjoy the scenic landscape here, with rental shops offering bikes suitable for all levels of riders.
- Taxi and Rideshare Services: For quick and reliable transportation, taxis and rideshare options are readily available, providing seamless access to your preferred destinations within the region.
Local Customs Options
- Clambake Tradition: Participating in traditional clambakes is a cherished custom here, reflecting the region's rich maritime heritage and local seafood cuisine.
- Harbor Lobstering Etiquette: When engaging with fishermen or observing lobstering activities, it's important to follow local guidelines and show respect for this vital industry.
- Seasonal Farmers' Markets: Visiting seasonal farmers' markets allows you to experience the area's commitment to fresh, locally sourced produce and artisanal goods.
- Respect for Natural Spaces: Preserving the pristine landscapes is a local priority, so mindful behavior in natural areas ensures you blend seamlessly into this environmentally conscious community.
Chilmark Rentals by Owner 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:
- 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
- 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
- Menemsha Pond waterfront Available July 21 till 1 August, Sept ,Oct 2025
- Spectacular Chilmark Sunset Water Views, Walk to Private Beach, Trails, Tennis!
2. How many Vacation Rentals are available in Chilmark?
Currently, the total number of properties listed by RBO in 2026 is over 103 in the Chilmark area, and still counting. By aggregating listings from multiple websites, RBO offers an immense amount of choice of the best Vacation Rentals in Chilmark.
3. How do I find the specific cancellation policy for a rental by owner in Chilmark, Massachusetts?
You can review the cancellation policy listed on the property’s page before booking. For detailed information, it is recommended to contact the property owner directly to clarify any questions about cancellations.
4. What should I know about check-in and check-out times when booking a rental here?
Check-in and check-out times are typically specified in the property listing. To ensure a smooth arrival and departure, confirm these details with the owner prior to your reservation.
5. Are there any additional fees or deposits I should be aware of when reserving a vacation home in this region?
Additional fees such as cleaning fees or security deposits may apply. These details are usually outlined on the listing, but contacting the owner can provide clarification to avoid surprises.
6. What are the policies regarding pets and smoking in rentals by owner here?
Pet and smoking policies vary by property. It is important to review the specific house rules listed on the rental site or speak directly with the owner to confirm their policies.
7. How can I ensure my booking is secure and reliable in this area?
Booking through a reputable platform ensures safety and reliability. Each listing includes reviews and verified owner information that help you make an informed decision, offering peace of mind during your stay.
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2400 ft²
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- Private Pool
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US $1,519/Night
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Ocean View
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US $1,564/Night
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2000 ft²
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- Oceanfront
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