Chilmark vacation rentals

We found 475 vacation rentals — enter your dates for availability

Select from 60 homes, 10 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:May 29 - Jun 5

Image gallery for Private cottage nestled in center of the Vineyard

Private yard for meals, games and hanging by the fire pit
10 out of 10, Exceptional, (55 reviews)
Exceptional
(55 reviews)

Private cottage nestled in center of the Vineyard

West Tisbury

5% off
Price is $366
$2,560 for 7 nights
All fees included
Private cottage nestled in center of the Vineyard

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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)
  • 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)
  • Tisbury Town Beach (11.2 mi / 18 km)
  • Edgartown 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

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, consider the picturesque coastline along the north shore of Martha's Vineyard. The area around Menemsha Beach is particularly appealing, offering vacation rentals with stunning views of the water and easy access to sandy shores. Many properties here come with amenities such as outdoor decks, barbecue grills, and spacious living areas, making them ideal for families or groups looking to enjoy a beach getaway.

Additionally, the nearby Lucy Vincent Beach offers a more secluded experience, with rentals often featuring private paths to the beach and scenic surroundings. These homes may include features such as large windows for natural light, outdoor showers, and fully equipped kitchens to cater to your dining needs after a day of sun and surf.

Chilmark's rural charm is enhanced by its proximity to local points of interest, including the Chilmark General Store, which is great for picking up local produce and essentials. The area is also close to hiking trails in the nearby state forest, where some rentals may offer easy access to these natural areas, giving visitors a chance to explore the beautiful landscapes of Martha's Vineyard.
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 55 available throughout the area. These homes typically feature spacious layouts, multiple bedrooms, fully equipped kitchens, and outdoor spaces such as decks or patios—ideal for enjoying the stunning natural surroundings of Martha's Vineyard. Additionally, there are several cottages and apartments available, which provide a more intimate and cozy atmosphere, often located close to local beaches and scenic spots.
Are there any family house rentals in Chilmark?
In Chilmark, Massachusetts, families will find a solid selection of vacation rentals, with around 46 properties available. This picturesque town on Martha's Vineyard offers a charming mix of coastal beauty and rural landscapes, making it an excellent choice for family getaways. Many homes in the area provide ample living space, fully equipped kitchens for preparing meals together, and outdoor areas where children can play safely.

Visitors can also enjoy amenities such as grills for family barbecues, cozy living rooms for movie nights, and sometimes even private beach access for fun-filled days by the water. Additionally, the scenic surroundings are superb for outdoor activities like hiking or exploring the nearby beaches. Chilmark is close to attractions such as the iconic Menemsha Harbor, known for its stunning sunsets and fresh seafood, making it a delightful spot for families looking to create lasting memories.
Can I rent a vacation home with a pool or hot tub in Chilmark?
In Chilmark, Massachusetts, there are several vacation homes available for rent that feature pools and hot tubs. This picturesque town on Martha's Vineyard is known for its stunning landscapes and tranquil atmosphere, making it an ideal getaway. Many of the rental properties come equipped with private pools, hot tubs, and spacious outdoor areas, great for relaxation and enjoying the coastal breeze. Travelers can also expect amenities such as fully equipped kitchens, outdoor dining spaces, and beautiful views of the surrounding nature. The area is great for families or groups seeking a serene retreat while still being close to the island's beaches and local attractions.
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, there are numerous pet-friendly house rentals available, with about 32 options for travelers to choose from. Many of these vacation homes offer amenities such as spacious living areas, fully equipped kitchens, and outdoor spaces that are superb for both pets and their owners. The rentals typically feature comfortable furnishings, private decks, and some even come with beautiful views of the surrounding natural landscape.

Chilmark is known for its serene environment and access to lovely beaches, making it an ideal location for pet owners looking to enjoy the outdoors. Nearby, you can explore dog-friendly beaches and scenic walking trails that allow for enjoyable outings with your furry companions. The area also boasts quaint shops and dining options that welcome pets, ensuring that your stay is both relaxing and accommodating for you and your pet.
Are there any remote work vacation rentals in Chilmark?
In Chilmark, Massachusetts, there are plenty of options for remote work vacation rentals, with around 60 available in the area. This picturesque town on Martha's Vineyard offers a tranquil setting ideal for working remotely while enjoying the natural beauty of the surroundings. Many of these rentals come equipped with high-speed internet and Wi-Fi, ensuring that guests can stay connected during their stay.

Travelers can expect amenities such as dedicated workspaces, comfortable living areas, and fully equipped kitchens, which provide the convenience of preparing meals at home. Some properties also feature outdoor spaces, superb for taking breaks and enjoying the serene landscape.

Chilmark is known for its stunning beaches, like Menemsha Beach, along with scenic hiking trails in the nearby Cedar Tree Neck Sanctuary. 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 fully equipped kitchens, great for preparing meals with local ingredients. Many rentals also feature decks or patios, providing outdoor spaces to relax and enjoy the scenic views of Martha's Vineyard. Travelers can expect additional comforts like blenders for smoothies or frozen drinks, onsite parking for convenience, and cozy fireplaces, ideal for those cooler evenings.
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, particularly in July when the weather is at its finest. This vibrant summer period draws many travelers eager to soak up the sun and enjoy the idyllic coastal charm of Martha's Vineyard. With average temperatures ranging from the mid-60s to mid-80s Fahrenheit, you'll find ideal conditions for outdoor activities, including hiking, biking, and beach outings.

July is particularly popular for families and adventure seekers. The beaches are bustling, and the local community hosts a variety of events and festivals, providing plenty of opportunities for visitors to immerse themselves in the local culture. Whether you're exploring the scenic trails or indulging in fresh seafood at local eateries, the energy of summer in Chilmark is truly captivating.

If you're looking for a more budget-friendly option, consider visiting in October. This month still offers pleasant weather, with cooler temperatures that range from the low 50s to mid-60s Fahrenheit, making it a lovely time for peaceful walks and enjoying the fall foliage without the summer crowds. The tranquility of autumn allows for intimate exploration of Chilmark's stunning landscapes and a chance to experience the local community at a more relaxed pace.
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, Massachusetts, United States of America?
In Chilmark, Massachusetts, visitors can enjoy a range of attractions that showcase the natural beauty and charm of Martha's Vineyard. The picturesque beaches, such as Lucy Vincent Beach and Squibnocket Beach, offer stunning ocean views and serene environments superb for relaxation and swimming. The nearby Menemsha Village provides a quaint fishing village atmosphere, where travelers can enjoy fresh seafood and watch the sunset over the harbor.

Chilmark is also known for its scenic landscapes, with numerous hiking trails available in the surrounding conservation areas, such as the Polly Hill Arboretum, which showcases unique plant collections and beautiful gardens. Additionally, the local art scene is vibrant, with galleries featuring works from local artists, often highlighting the beauty of the island itself.
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 cabin or a beach condo, you can turn your space into a standout destination, become a host and let Vrbo handle the heavy lifting to help you thrive.

Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.
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.
What is VrboCare™ and how does it work?
Vrbo's mission is to help guests relax, reconnect, and enjoy precious time together. With VrboCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable.

If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
What can I expect from Vrbo customer service and VrboCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, VrboCare™ is here to support you every step of the way. For urgent situations like last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to help resolve problems quickly and effectively.

Vrbo also offers support via live chat through our Help Center, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
Can I plan a group trip on Vrbo?
Vrbo's Trip Planner makes organizing group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favorites, and build the perfect itinerary together.

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