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Chilmark vacation rentals

We found 527 vacation rentals — enter your dates for availability

Select from 74 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:Nov 7 - Nov 14

Image gallery for Relaxing Island Retreat, Cozy Cottage, Lamberts Cove Beach Access!

Living area
9.6 out of 10 rating
Exceptional
(20 reviews)

Relaxing Island Retreat, Cozy Cottage, Lamberts Cove Beach Access!

Vineyard Haven, MA

8% off
Price is $400
$2,797 for 7 nights
All fees included
Relaxing Island Retreat, Cozy Cottage, Lamberts Cove Beach Access!

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Find out more about Chilmark

Find out more about Chilmark

Why visit Chilmark

  1. Stunning Coastal Scenery: Enjoy breathtaking views of Vineyard Sound and dramatic cliffs while exploring the area.
  2. Beaches and Nudist Beaches: Relax on pristine sandy shores, including unique nudist beaches for a liberating experience.
  3. Cultural Experiences: Immerse yourself in local culture through art, events, and vineyard tours that enhance your visit.
  4. Charming Accommodations: Choose from cozy cottages, stylish apartments, and private vacation homes for a perfect stay.
  5. Outdoor Recreation: Engage in various outdoor activities, from hiking to beachcombing, in this picturesque setting.

Popular types of accommodation in Chilmark

If you’re planning a getaway to Chilmark, you’ll find a variety of charming accommodations to suit your needs. The most popular options include houses, cozy cottages, and stylish apartments. Whether you're searching for a Chilmark vacation rental home or exploring other Chilmark properties, our platform offers transparency and reassurance to help you find the perfect vacation rental in Chilmark. Enjoy your stay in this beautiful destination!

  • Houses: These spacious residences are the top choice for travelers seeking comfort and privacy during their stay in Chilmark.
  • Cottages: Quaint and cozy, cottages offer a charming atmosphere perfect for a relaxing getaway.
  • Apartments: Ideal for those who prefer a home-like setting, apartments provide all the essential amenities.
  • Condos: A great blend of comfort and convenience, condos often feature shared amenities like pools and fitness centers.
  • Cabins: For a rustic experience, cabins immerse you in nature while offering a unique retreat.**

Top attractions in and around Chilmark

Chilmark, Massachusetts, is a perfect destination for outdoor enthusiasts and beach lovers, offering stunning coastal scenery and attractions like beaches, nudist beaches, and cliffs. Visitors can immerse themselves in cultural experiences while enjoying the natural beauty of the area. For those looking to enhance their vacation, consider exploring local vineyards for a unique experience that complements your beach getaway.

  1. Menemsha Beach: Experience the quintessential beach vibes at Menemsha Beach, where you can relax on sandy shores, enjoy stunning sunsets, and savor fresh seafood from local vendors. It's a perfect spot for sunbathing and swimming.
  2. Aquinnah Cliffs: Venture to the breathtaking Aquinnah Cliffs, known for their striking natural beauty and outdoor adventures. Hike along scenic trails that offer panoramic views of the ocean and vibrant landscapes.
  3. Gay Head Lighthouse: Discover the rich history and culture at Gay Head Lighthouse, a charming historic site. Climb to the top for stunning views of the coastline and learn about its significance in maritime navigation.

Things to do recommended for couples

In Chilmark, enjoy a playful round at Island Cove Adventures or Island Cove Miniature Golf, both offering family fun and adventure vibes. For a romantic evening, savor fine wines at Coastal Vineyards, where the ambiance is perfect for couples seeking entertainment and romance.

Things to do recommended for families

Families visiting Chilmark can explore the serene Fulling Mill Brook Preserve for relaxation and outdoor fun. A short drive away, the Flying Horses Carousel offers delightful rides and a charming family atmosphere, making it a perfect stop for creating lasting memories together.

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

When traveling with a group, family, pets, or planning an extended stay, be sure to use filters that align with your priorities. Here are some helpful Vrbo booking tips to assist you.

  • Traveling to Chilmark with a group: Think about how many bedrooms you'll require, along with features like a complete kitchen or outdoor areas for group activities. Thankfully, you can easily refine your search for these options and more on Vrbo.
  • Traveling to Chilmark with young kids: Traveling with young kids can be tough. It's important to prioritize their comfort and safety, along with suitable amenities like a private pool. Additionally, it's wise to think about how close you are to family-friendly attractions.
  • Taking your pets with you to Chilmark: For many families, a trip wouldn't feel complete without their furry companion by their side. If that resonates with you, explore Vrbo listings that welcome pets. Many of these pet-friendly properties offer amenities like food bowls and beds, ensuring that all members of the family feel comfortable and at home.
  • Planning for a long term stay visiting Chilmark: If you're searching for vacation rentals with great offers 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 features like a parking space, a spacious kitchen, or a private pool in your search as well.

Where to stay near Chilmark

Chilmark, Massachusetts, offers a perfect blend of relaxation and stunning scenery for your vacation. Explore the breathtaking sunsets over Vineyard Sound and enjoy easy beach access for a refreshing day by the sea. This charming area is known for its friendly atmosphere and opportunities for recreation. Don't miss the chance to unwind in the picturesque landscapes and experience the unique vibe of Chilmark during your stay!

  • Martha's Vineyard: This picturesque island, located 6 miles from Chilmark, is renowned for its breathtaking outdoor scenery and beautiful beaches. Visitors flock to Martha's Vineyard for its diverse experiences, from enjoying music concerts to trying their luck at local casinos. The island is dotted with lovely family beaches and serene lakes, making it an ideal spot for relaxation and recreation. Whether you’re taking a leisurely stroll along the shore or exploring charming towns, Martha's Vineyard promises a delightful escape into nature and culture.
  • Edgartown: Situated 12 miles from Chilmark, Edgartown is a charming city that invites travelers to immerse themselves in its rich history and stunning coastal views. Known for its outdoor activities, this town features beautiful beaches and scenic landscapes. Golf enthusiasts will appreciate the local golf courses and private country clubs that offer a perfect blend of leisure and sport. The family-friendly beaches and tranquil lakes nearby provide ample opportunities for swimming, picnicking, and relaxation, making Edgartown a must-visit destination for travelers seeking both adventure and tranquility.
  • Oak Bluffs: Located 12 miles away from Chilmark, Oak Bluffs is a vibrant city known for its lively beach atmosphere and scenic beauty. Visitors enjoy a variety of outdoor activities, from beach lounging to exploring the local shopping scene. The area is also home to golf courses that cater to enthusiasts of all skill levels. With its family-friendly beaches and picturesque marina, Oak Bluffs offers a perfect mix of relaxation and recreation, making it an ideal spot for tourists looking to soak in the sun and enjoy the coastal charm of Martha's Vineyard.

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.

calendar iconCalendar Monthtemperature iconTemperaturerain iconPrecipitationmostly cloudy iconCloudinessoccupation rate iconOccupancyprice iconPricing
January35.2°F (1.8°C)Light RainMostly SunnyAverageModerately Low
February35.2°F (1.8°C)Light RainMostly SunnyAverageModerately Low
March38.8°F (3.8°C)Light RainMostly SunnyAverageModerately 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 HighModerately High
July71.1°F (21.7°C)Light RainMostly SunnyModerately HighModerately High
August71.8°F (22.1°C)Light RainMostly SunnyModerately HighModerately 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 a breeze

Looking to save on your next trip? Consider being flexible with your travel dates, as prices can fluctuate. Plus, extending your stay can often result in significant savings. To discover the ideal Vrbo property that fits your budget, take advantage of our filters to narrow your search by price, location, and type of vacation rental.

Unlock savings with One Key

Reserve a qualifying Vrbo for your group getaway and earn OneKeyCash™ on your booking. It's rewarding to take on the planning role! When you join 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 as easy as it gets

Vrbo's Trip Board is a great tool that allows you to plan new trips, pick up right where you left off, and keep your travel plans organized. You can easily find the properties you've saved or booked in the sections for Potential, Upcoming, or Current Trips. To start using Trip Boards, simply visit: https://www.vrbo.com/en-ca/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.