Chilmark vacation rentals

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.

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.

Calendar Month	Temperature	Precipitation	Cloudiness	Occupancy	Pricing
January	35.2°F (1.8°C)	Light Rain	Mostly Sunny	Average	Slightly Low
February	35.2°F (1.8°C)	Light Rain	Mostly Sunny	Average	Slightly Low
March	38.8°F (3.8°C)	Light Rain	Mostly Sunny	Average	Slightly Low
April	46.4°F (8.0°C)	Light Rain	Mostly Sunny	Average	Average
May	54.5°F (12.5°C)	Light Rain	Mostly Sunny	Average	Average
June	63.1°F (17.3°C)	Light Rain	Mostly Sunny	Moderately High	Slightly High
July	71.1°F (21.7°C)	Light Rain	Mostly Sunny	Moderately High	Slightly High
August	71.8°F (22.1°C)	Light Rain	Mostly Sunny	Moderately High	Slightly High
September	66.7°F (19.3°C)	Light Rain	Mostly Sunny	Average	Average
October	58.6°F (14.8°C)	Light Rain	Mostly Sunny	Moderately Low	Average
November	49.1°F (9.5°C)	Light Rain	Mostly Sunny	Moderately Low	Average
December	41.5°F (5.3°C)	Light Rain	Mostly Sunny	Moderately Low	Average

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.