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Chilmark vacation rentals

We found 522 vacation rentals — enter your dates for availability

Select from 75 homes, 11 cottages, and other vacation rentals in Chilmark to find one that's perfect for your trip. Vacation homes provide the best amenities for you and your friends, family, or even pets, like air conditioning and cable TV. At the end of the day, you'll find a rental for everyone's needs, including accessible or non-smoking choices.

Vacation rentals with weekly discounts - Chilmark

Showing deals for:Dec 26 - Jan 2

Image gallery for Walk to private beach from beautiful Abels Hill house

Chilmark Pond is a 10 minute walk from the house. The beach is across the pond.
10 out of 10, Exceptional, (32 reviews)
Exceptional
(32 reviews)

Walk to private beach from beautiful Abels Hill house

Chilmark, MA

8% off
Price is $696
$4,871 for 7 nights
All fees included
Walk to private beach from beautiful Abels Hill house

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Find out more about Chilmark

Find out more about Chilmark

Why visit Chilmark

  • Beautiful Beaches: Discover stunning beaches, including a unique nudist beach, perfect for relaxation and sunbathing.
  • Breathtaking Cliffs: Explore scenic cliffs that offer incredible views and a memorable outdoor experience.
  • Charming Neighborhoods: Immerse yourself in the friendly local culture and rich history of Chilmark's picturesque neighborhoods.
  • Outdoor Activities: Engage in various outdoor adventures, from hiking to beachcombing, amidst Chilmark's natural beauty.
  • Cozy Accommodations: Choose from a range of vacation rentals, including charming cottages and modern apartments, for a comfortable stay.

Popular types of accommodation in Chilmark

Planning a getaway to Chilmark? You're in for a treat. Explore our top picks for vacation rentals in Chilmark, featuring charming houses, cozy cottages, and modern apartments. Whether you're seeking a family-friendly house rental or a romantic retreat, we’ve got you covered. Discover the best Chilmark vacation rentals and make your stay on Martha’s Vineyard unforgettable.

  • Houses: The top choice for visitors to Chilmark, offering spacious accommodations ideal for families or groups looking for a home-away-from-home experience.
  • Cottages: A delightful option for those seeking charm and comfort, perfect for a peaceful getaway amidst nature.
  • Apartments: Conveniently located, these rentals provide a practical and cozy base for exploring Chilmark.
  • Condos: A modern choice that combines amenities with beautiful views, great for a relaxing stay.
  • Cabins: Ideal for outdoor enthusiasts, these rustic retreats offer a unique experience close to nature.**

Top attractions in and around Chilmark

Chilmark, Massachusetts, is the perfect destination for outdoor enthusiasts and beach lovers, offering stunning scenery and various attractions. Explore beautiful beaches, including a nudist beach, and enjoy breathtaking cliffs that provide a unique cultural experience. Whether you're looking for relaxation or adventure, Chilmark has something for everyone. Don't miss the opportunity to discover the charm of this picturesque town during your vacation.

  • Menemsha Beach: A charming beach located within Chilmark, Menemsha Beach offers a serene atmosphere with picturesque views, perfect for a relaxing day of sunbathing and swimming. The beach vibes create an inviting space for families and friends alike.
  • Aquinnah Cliffs: About 5 miles from Chilmark, Aquinnah Cliffs is renowned for its stunning views and vibrant sunsets. This outdoor adventure spot features trails and breathtaking scenery, making it a must-visit for nature lovers.
  • Gay Head Lighthouse: Also 5 miles away, this historic lighthouse stands as a cultural icon. Visitors can explore the surrounding area and learn about its rich maritime history while enjoying scenic coastal views.

Things to do recommended for couples

Chilmark offers a charming getaway for couples. Enjoy a fun-filled round at Island Cove Miniature Golf, just 10 miles away, or savor the romance at Coastal Vineyards, located 20 miles from town. Create unforgettable memories in this picturesque setting.

Things to do recommended for families

Families can explore the serene Fulling Mill Brook Preserve for some outdoor relaxation or take a short drive to enjoy the Flying Horses Carousel, a classic outdoor attraction perfect for all ages.

Things to do recommended for groups

Experience the charm of Chilmark with a visit to Chilmark Chocolates for sweet treats, enjoy a captivating performance at The Yard theater, and embark on an adventurous hike at Waskosim's Rock Reservation, where stunning scenery awaits your group.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

What do I need to keep in mind when booking a vacation in Chilmark

If you're traveling with a group, with family, bringing your pets, or seeking extended stays, be sure to use the appropriate filters based on your priorities. Here are some helpful booking tips for Vrbo.

  • Traveling to Chilmark with a group: Think about how many bedrooms you require and any additional features you might want, like a full kitchen or outdoor area for gatherings. Luckily, you can easily filter for all of these options and more on Vrbo.
  • Traveling to Chilmark with young kids: Traveling with young kids can present some challenges. It’s important to prioritize their comfort and safety, along with finding suitable amenities like a private pool. Additionally, keeping close to family-friendly attractions is a wise consideration.
  • Taking your pets with you to Chilmark: For many families, a vacation wouldn't feel complete without their furry companions. If this resonates with you, explore Vrbo listings that welcome pets. Most pet-friendly accommodations offer essentials like feeding bowls and beds, ensuring that everyone feels comfortable and at home.
  • Planning for a long term stay visiting Chilmark: If you’re in search of vacation rentals offering discounts for stays of a month or more, you’ve come to the right spot. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. Don’t forget to include additional features in your search, such as a parking space, a well-equipped kitchen, or a private pool.

Where to stay near Chilmark

Chilmark, Massachusetts, offers a delightful blend of outdoor adventures and stunning scenery, making it a perfect vacation spot. Explore the charming neighborhoods nearby for a taste of friendly locals and rich history. Enjoy the lovely Atlantic views and unwind in a relaxing atmosphere. Whether you're seeking vacation rentals or looking to soak in the area’s natural beauty, Chilmark promises a memorable getaway filled with recreation and breathtaking landscapes.

  • Martha's Vineyard: Located 6 miles from Chilmark, Martha's Vineyard is a picturesque island renowned for its stunning outdoor scenery and beautiful beaches. Visitors can immerse themselves in a variety of activities, including attending lively music concerts, relaxing at upscale resorts, or enjoying a round of golf. The island's coastal charm is further highlighted by its inviting beaches and serene lakes, making it a perfect destination for family outings and nature lovers alike.
  • Falmouth: Situated 16 miles from Chilmark, Falmouth is a vibrant city that offers a delightful blend of outdoor adventures and scenic views. Known for its beautiful beaches and charming family-friendly atmosphere, Falmouth is ideal for those looking to unwind in a coastal setting. The city also features excellent golf courses and private country clubs, alongside educational attractions. Visitors can explore the picturesque cape, making it a great spot for both relaxation and recreation.
  • Edgartown: Just 12 miles from Chilmark, Edgartown is a charming city with an inviting coastal vibe. This picturesque destination is well-loved for its outdoor spaces and stunning beach scenery. Edgartown boasts a plethora of activities, including golfing at its renowned courses and enjoying the amenities of local country clubs. The nearby beaches and tranquil lakes offer serene spots for families and individuals to relax and enjoy the natural beauty of the area.

Best time to go to Chilmark

If you're planning a trip to Chilmark, it's a good idea to check both the weather and property rates. The warmest month is August. Peak season runs from June to August, while off-peak times, like October to December tend to have fewer bookings and better deals.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January35.2°F (1.8°C)Light RainMostly SunnyAverageSlightly Low
February35.2°F (1.8°C)Light RainMostly SunnyAverageSlightly Low
March38.8°F (3.8°C)Light RainMostly SunnyAverageSlightly Low
April46.4°F (8.0°C)Light RainMostly SunnyAverageAverage
May54.5°F (12.5°C)Light RainMostly SunnyAverageAverage
June63.1°F (17.3°C)Light RainMostly SunnyModerately HighSlightly High
July71.1°F (21.7°C)Light RainMostly SunnyModerately HighSlightly High
August71.8°F (22.1°C)Light RainMostly SunnyModerately HighSlightly High
September66.7°F (19.3°C)Light RainMostly SunnyAverageAverage
October58.6°F (14.8°C)Light RainMostly SunnyModerately LowAverage
November49.1°F (9.5°C)Light RainMostly SunnyModerately LowAverage
December41.5°F (5.3°C)Light RainMostly SunnyModerately LowAverage

Booking with Vrbo is simple

Looking to save on your next vacation? Consider being flexible with your travel dates, as prices can fluctuate. Additionally, extending your stay can often result in significant savings. To discover the ideal Vrbo property that fits your budget, utilize our filters to search by price, location, and type of vacation rental. We're here to help you find the perfect getaway.

Save more with One Key

Reserve a qualifying Vrbo for your group getaway and receive OneKeyCash for your booking. Being the planner definitely has its perks. When you enroll in our travel rewards program, One Key, you'll gain immediate access to member discounts and the ability to earn and redeem OneKeyCash on eligible reservations. Sign up today and begin enjoying your savings.

Vrbo Trips: Planning made easy

Vrbo’s Trip Board provides a convenient platform to help you plan new trips, manage your existing arrangements, or revisit and organize your reservations. The properties you’ve saved or booked are neatly categorized into Potential, Upcoming, or Current Trips for easy access. To discover your Trip Boards, simply visit: https://www.vrbo.com/trips.

**Based on Vrbo properties bookings.

Explore the beachside setting in Chilmark

The area's wineries and festivals are just a few of the reasons to vacation in Chilmark. Well-liked for its beaches, hiking and local tours, this city is both relaxing and scenic. If you're looking for accommodations with space to entertain friends and family, Vrbo has plenty of options to choose from. Many rental homes offer full kitchens and laundry facilities, perfect for big groups.

Activities and attractions in and around Chilmark

Are you searching for attractions to see while you're in town? Although it can be tempting to stay in your comfortable vacation rental, you'll want to check out everything that makes Chilmark a one-of-a-kind vacation spot. These are some of the top attractions to see, all within 30 miles (48.2 km) of the city center:

  • Shining Sea Bikeway (17.2 mi / 27.7 km)
  • Farm Neck Golf Club (11.2 mi / 18 km)
  • Oak Bluffs Fishing Pier (12.6 mi / 20.3 km)
  • Cape Cod Winery (18.4 mi / 29.6 km)
  • Chilmark Chocolates (0.1 mi / 0.2 km)
  • Fulling Mill Brook Preserve (2.5 mi / 4 km)

Exploring the natural landscape of Chilmark

Whether you're looking for adventure or just want to take in the scenery, Chilmark is a great spot to appreciate mother nature. These are a few of the area's noteworthy natural features, all within 30 miles (48.2 km) of the city center:

  • Menemsha Beach (1.4 mi / 2.3 km)
  • Aquinnah Cliffs (4.8 mi / 7.8 km)
  • Lambert's Cove Beach (8 mi / 12.9 km)
  • Katama Beach (8.6 mi / 13.9 km)
  • Edgartown Beach (11.4 mi / 18.3 km)
  • South Beach (11.4 mi / 18.3 km)

Transportation options to and around Chilmark

The nearest airport is in Vineyard Haven, MA (MVY-Martha's Vineyard), located 7.6 mi (12.2 km) from the city center. If you're unable to find a flight that fits your schedule, you could book a flight to New Bedford, MA (EWB-New Bedford Regional), which is 25.4 mi (40.8 km) away.

Frequently asked questions

What is the best area to stay in Chilmark when booking a vacation rental?
When considering a vacation rental in Chilmark, Massachusetts, a great area to stay is near the scenic North Road. This charming region offers a mix of tranquility and natural beauty, making it an ideal spot for a relaxing getaway. Properties in this area often provide stunning views of the surrounding landscapes, including lush greenery and picturesque ponds. You'll find a good selection of vacation rentals here, with options ranging from cozy cottages to more spacious homes.

One of the top attractions nearby is the famous Menemsha Beach, known for its breathtaking sunsets and serene atmosphere. It's a superb place for beachcombing, swimming, or simply enjoying a picnic by the water. Additionally, the nearby Chilmark Store is a local gem, offering delicious baked goods and a variety of gourmet products, ideal for stocking up on snacks for your beach day.
How much does it cost to rent a vacation home in Chilmark?
Prices for vacation rentals in Chilmark vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're traveling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in Chilmark to more spacious homes. To get the best value, book early and take advantage of Vrbo's free rewards program.
Are there any discounts for Chilmark vacation house rentals?
You can find great discounts on house rentals in Chilmark on Vrbo, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for Last minute bookings, and Early bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Where are the best areas for renting a beach house in Chilmark?
For renting a beach house in Chilmark, Massachusetts, travelers should focus on the areas along the shores of the Atlantic Ocean, particularly the region around Menemsha Beach. This picturesque fishing village offers charming vacation rentals with easy access to the beach, where visitors can enjoy stunning sunsets and fresh seafood from local shops. Many properties in this area feature amenities such as outdoor decks, spacious living areas, and fully equipped kitchens, ideal for families or groups looking to experience the coastal lifestyle.

Another prime location is near Squibnocket Beach, known for its serene environment and beautiful sandy shores. Beach houses here often come with private access to the water, outdoor showers, and expansive views of the coastline. Some rentals may also include amenities like hot tubs, fire pits, and outdoor grills, superb for enjoying summer evenings under the stars.

Additionally, the area around the Chilmark Community Center is a great option for those looking for a more social atmosphere, where travelers can find rentals that offer proximity to local events and activities. These properties might include features such as game rooms, large yards, and access to communal facilities.
What is the most popular type of vacation rental accomodation in Chilmark?
In Chilmark, vacation houses are the most popular type of rental, with about 57 available throughout the area. These properties are often situated in serene, picturesque settings that provide easy access to the stunning beaches and natural landscapes of Martha's Vineyard. Most vacation houses come equipped with spacious living areas, fully stocked kitchens, and outdoor spaces like decks or patios, superb for soaking in the coastal views.

In addition to vacation houses, there are around 10 cottages that offer a charming, rustic experience, ideal for couples or small families. These cottages typically feature cozy interiors and may include amenities like fireplaces or beach access. While there are several apartments available, they are less common compared to houses and cottages.
Are there any family house rentals in Chilmark?
In Chilmark, Massachusetts, families can choose from a variety of vacation rentals, with around 49 options available. This picturesque area on Martha's Vineyard is known for its stunning landscapes and tranquil beaches, making it an ideal spot for family getaways. Many of these homes feature spacious living areas, full kitchens for preparing meals together, and outdoor spaces great for children to explore.

Visitors will appreciate amenities such as Wi-Fi, air conditioning, and sometimes even private pools or large yards for outdoor activities. The nearby beaches, like Menemsha Beach, offer opportunities for swimming and beachcombing, while the charming local shops and restaurants add to the experience.
Can I rent a vacation home with a pool or hot tub in Chilmark?
In Chilmark, Massachusetts, travelers can find several vacation homes available for rent that feature pools and hot tubs. This quaint town on Martha's Vineyard offers a serene atmosphere, great for relaxation and enjoyment of the natural surroundings. Many of these rentals are situated near scenic coastal areas, providing easy access to beautiful beaches and picturesque landscapes.

Guests can expect a range of amenities, including private pools and inviting hot tubs, ideal for unwinding after a day of exploring the island. Numerous properties also come equipped with spacious outdoor areas, barbecue grills, and fully stocked kitchens, allowing for enjoyable family meals and gatherings.
Can I find long-stay vacation rentals in Chilmark?
A long-stay vacation rental in Chilmark is the best way to experience local living. Plus, you can make the most of long-stay discounts. For month-long stays, save an average of 19%, and for week-long bookings you can save an average of 10%.* Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
Are there pet-friendly house rentals in Chilmark?
In Chilmark, Massachusetts, there are numerous pet-friendly house rentals available, with around 36 options to choose from. This picturesque area on Martha's Vineyard offers a serene coastal environment, making it an ideal spot for travelers with pets. Many of the vacation rentals are equipped with amenities such as spacious yards, outdoor decks, and fully equipped kitchens, ensuring comfort during your stay.

Chilmark is known for its beautiful beaches, such as Lucy Vincent Beach and Squibnocket Beach, both of which are pet-friendly, allowing for fun beach outings with your furry companions. Additionally, the surrounding scenic landscapes provide opportunities for hiking and exploration, with trails that welcome pets. Visitors can enjoy the charming rural atmosphere of the neighborhood while having access to local shops and restaurants that cater to pet owners.
Are there any remote work vacation rentals in Chilmark?
In Chilmark, Massachusetts, there are numerous vacation rentals suitable for remote work, with around 63 options available. This picturesque town on Martha's Vineyard is known for its serene atmosphere, beautiful landscapes, and proximity to the coastline. Many of the properties feature dedicated workspaces equipped with amenities such as Wi-Fi, desks, ergonomic chairs, and even computer monitors to ensure a productive environment.

Travelers can expect to find homes with spacious living areas, fully equipped kitchens, and outdoor spaces superb for enjoying breaks while soaking in the natural beauty. The nearby beaches, hiking trails, and charming local shops provide great opportunities for leisure once the workday is done. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Chilmark vacation rentals with parking?
Vrbo offers a wide selection of vacation rentals in Chilmark with parking available—perfect for families or travelers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details on Vrbo and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
What are popular rental amenities in Chilmark?
In Chilmark, popular vacation rental amenities include WiFi, kitchens equipped with essential appliances such as blenders and coffee/tea makers, and outdoor patios for enjoying the serene surroundings.
When is the best time to visit Chilmark for a vacation rental?
The best time to visit Chilmark for a vacation rental is during the peak season from June to August, with July being particularly popular among travelers. This vibrant time of year draws visitors seeking the quintessential New England summer experience, characterized by warm temperatures averaging in the mid-70s to low 80s Fahrenheit. The stunning coastal views, charming beaches, and inviting community events create an ideal backdrop for outdoor activities and relaxation.

During these summer months, you'll find a variety of activities to enjoy, such as hiking along picturesque trails, exploring the local art scene, and attending summer fairs. The warm weather also provides superb conditions for beach outings, sunbathing, and swimming in the refreshing Atlantic waters, all while soaking in the natural beauty of Martha's Vineyard.

For those looking for a more budget-friendly option, consider planning your visit in October. This month offers a unique charm as the crowds dwindle, providing a quieter experience to explore the area's scenic beauty and autumn foliage.
How early should I book a Chilmark vacation rental?
Book your Chilmark vacation rental at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
What are the top attractions in Chilmark?
In Chilmark, visitors can enjoy a serene coastal atmosphere with top attractions including the stunning beaches of Menemsha and Squibnocket, which are great for sunbathing and sunset watching. The area is renowned for its natural beauty, and vacation rentals often provide easy access to these scenic spots. The Chilmark Community Center hosts various events and activities, making it a great place to experience local culture and community life. For those interested in nature, the nearby state forest offers trails for hiking and exploring the island's diverse flora and fauna.
Can I change or cancel my Chilmark home rental booking on Vrbo?
To find Chilmark vacation rentals with free cancellation, just use Vrbo's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Vrbo rentals give you the privacy of having the entire place to yourself, and for extra flexibility, some travelers can choose to pay over time with Affirm. Whether you're adjusting your plans or looking for flexible payment options, Vrbo makes it easy to book with confidence.
Why should I join Vrbo as a host?
Joining Vrbo as a host opens the door to a global community of travelers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Vrbo makes it easy to list, manage, and succeed. Whether it's a cozy flat or a countryside retreat, you can turn your space into a standout destination—become a host and let Vrbo handle the heavy lifting to help you thrive.
Are all fees included in the Chilmark vacation rental prices shown on Vrbo?
Vrbo provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.

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