Photo by Wen C.

Chilmark holiday lettings

We found 538 holiday rentals — enter your dates for availability

Select from 70 homes, 11 cottages and other holiday rentals in Chilmark to find one that's perfect for your trip. Holiday homes offer the amenities that you expect for your stay with friends, family or just your pet, such as cable TV and a washer and dryer. At the end of the day, you're sure to find a property to rent to meet everyone's needs, including accessible or non-smoking choices.

Holiday rentals with weekly discounts - Chilmark

Showing deals for:10 Oct - 17 Oct
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Why visit Chilmark

  • Stunning beaches: Chilmark boasts beautiful beaches, including a renowned nudist beach, perfect for sunbathing and relaxation.
  • Scenic cliffs: The dramatic cliffs provide breathtaking views and excellent opportunities for photography and exploration.
  • Charming community: The welcoming local community offers a delightful atmosphere for visitors, enhancing the holiday experience.
  • Outdoor adventures: Enjoy various outdoor activities, from hiking to swimming, amidst picturesque surroundings.
  • Quaint accommodations: Choose from a range of charming cottages and vacation rentals tailored to every traveller's needs.

Popular types of accommodation in Chilmark

Vrbo offers a delightful selection of vacation rentals in Chilmark, catering to various preferences and group sizes. Whether you're seeking a charming cottage, a spacious private vacation home, or a cosy apartment, we have something to suit every traveller’s needs. Discover the perfect base for your holiday in Chilmark and enjoy the stunning surroundings with the reassurance of transparent pricing and top-notch service.

  • Houses: The foremost choice for visitors to Chilmark, these homes offer tailored comfort for families, couples, or groups of friends.
  • Cottages: A delightful option for a quaint and snug experience, perfect for those seeking a charming getaway.
  • Apartments: Ideal for independent travellers, these rentals provide flexibility and convenience in the heart of Chilmark.
  • Condos: A popular choice for those desiring modern amenities alongside scenic views and shared facilities.
  • Cabins: For a rustic escape, cabins offer a serene retreat surrounded by nature.**

Top attractions in and around Chilmark

Chilmark, Massachusetts, is an idyllic destination for those seeking outdoor adventures and stunning scenery, particularly along its beautiful beaches. Notable attractions include the picturesque nudist beach and dramatic cliffs, perfect for a cultural experience. Whether you're travelling solo, as a couple, or with family, be sure to explore the local Chilmark beaches for a truly delightful vacation.

  • Menemsha Beach: A serene stretch of sand offering quintessential beach vibes, perfect for sunbathing and swimming. Enjoy stunning sunsets while soaking in the relaxed atmosphere.
  • Aquinnah Cliffs: A breathtaking natural wonder located 3.1km from Chilmark, these cliffs provide thrilling outdoor adventures and awe-inspiring scenery, ideal for hiking and photography.
  • Gay Head Lighthouse: This historic lighthouse, also 3.1km away, embodies local culture and history, offering fascinating insights and picturesque views of the surrounding coastline.

Things to do recommended for couples

For a romantic getaway in Chilmark, indulge in a round of mini golf at Island Cove Adventures, just 6.2km away. Alternatively, explore the enchanting atmosphere of Coastal Vineyards, 12.4km distant, where you can savour fine wines amidst a charming setting.

Things to do recommended for families

Families can unwind at Fulling Mill Brook Preserve, a serene recreational area in Chilmark, perfect for wellness and relaxation. For a touch of nostalgia, visit the Flying Horses Carousel, located 8.1km away, offering delightful outdoor family fun.

Things to do recommended for groups

Indulge in delightful treats at Chilmark Chocolates, enjoy captivating performances at The Yard theatre, and embark on an adventurous hike through the scenic Waskosim's Rock Reservation. These activities promise a memorable experience for your group in the charming community of Chilmark.

Booking with Vrbo is a breeze

Are you hoping to cut costs on your next getaway? Being flexible with your travel dates can make a real difference, as prices often fluctuate. Additionally, you can enjoy substantial savings by opting for a longer stay. To discover a Vrbo property that aligns with your budget, take advantage of our filters to sort by price, location, and type of holiday rental.

Where to stay near Chilmark

Chilmark, nestled on the picturesque Martha's Vineyard, is an idyllic destination for those seeking tranquillity and stunning scenery. Explore its lovely beaches, charming neighbourhoods, and welcoming community, perfect for relaxation and outdoor adventures. Nearby, the vibrant atmosphere offers a delightful mix of history and recreation, making it ideal for a memorable getaway. Discover the unique charm of Chilmark and its surrounding areas for an unforgettable holiday experience.

  • Martha's Vineyard: Nestled just 3.7km from Chilmark, Martha's Vineyard is a picturesque island renowned for its stunning outdoor scenery and beautiful beaches. The island offers a plethora of activities for visitors, including music concerts and golf at local resorts. With its charming coastal landscape, Martha's Vineyard features inviting family beaches and serene lakes, making it an ideal spot for relaxation and exploration. Whether you fancy a scenic walk along the shore or a day spent soaking up the sun, the island is sure to enchant you with its natural beauty.
  • Falmouth: Located 13.7km away from Chilmark, Falmouth is a vibrant town that beckons outdoor enthusiasts and beach lovers. Its scenic coastline is dotted with family-friendly beaches, providing ample opportunities for swimming and sunbathing. Falmouth is also home to a prestigious golf course and a private country club, perfect for those looking to enjoy a round of golf amidst stunning vistas. Additionally, the town's educational centres offer insight into the local culture and history, making it a well-rounded destination for visitors.
  • Edgartown: Just 7.5km from Chilmark, Edgartown is a charming city that combines coastal beauty with a rich history. Known for its stunning scenery and inviting beaches, Edgartown is the perfect place for outdoor pursuits. The city features excellent golf courses and exclusive country clubs, making it a hit with avid golfers. Close to family-friendly beaches and tranquil lakes, Edgartown offers a delightful mix of relaxation and recreation, ensuring a memorable visit for all who come.

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

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

If you’re travelling with a group, family, pets, or planning an extended stay, it’s important to prioritise your preferences when filtering options. Here are some helpful booking tips for using Vrbo.

  • Traveling to Chilmark with a group: Think about the number of bedrooms you'll require, as well as additional features like a fully equipped kitchen or outdoor space for group gatherings. Thankfully, you can easily filter for all these options and much more on Vrbo.
  • Traveling to Chilmark with young kids: Travelling with young children can present its challenges. It’s important to prioritise their comfort and safety, along with suitable amenities, like a private swimming 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 holiday wouldn’t feel complete without their beloved pet by their side. If this resonates with you, explore Vrbo properties that welcome pets. The majority of pet-friendly accommodations offer feeding bowls and beds, ensuring that every member of the family feels comfortable and at home.
  • Planning for a long term stay visiting Chilmark: If you're seeking holiday rentals with discounts for stays of a month or more, you've come to the right place. By using the appropriate filters, you'll be able to effortlessly discover and save on monthly rentals. Don't forget to include options such as a parking space, a well-equipped kitchen, or a private pool in your search as well.

Vrbo Trips: Planning as easy as it gets

Vrbo's Trip Board offers a handy platform to plan new journeys, continue from where you last stopped, or organise your existing arrangements. You'll discover your saved or booked properties neatly sorted into categories such as Potential, Upcoming, or Current Trips. To begin making use of Trip Boards, please visit: https://www.vrbo.com/en-gb/trips.

**Based on Vrbo properties bookings.

Explore the beachside setting in Chilmark

The area's wineries and festivals are just some of the reasons to come on holiday to Chilmark. Revered for its beaches, hiking and local tours, this city is both relaxing and scenic. If you're looking for accommodation options with space to entertain friends and family, HomeAway 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

Do you want to find things to do in the area? Although it can be tempting to stay in your comfortable holiday rental, you'll want to check out everything that makes Chilmark a fun place to get away to. These are some of the most popular attractions to explore, all within 30 miles (48.2 km) of the city centre:

  • 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 an adventurous traveller or just want to take in the scenery, Chilmark is a great place to get outside. These are some of the area's most enchanting sights, all within 30 miles (48.2 km) of the city centre:

  • 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)

Transport 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 centre. 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 most popular type of holiday rental accommodation in Chilmark?
Houses are the most popular type of holiday rental in Chilmark, according to our data. Even if you have a different idea about what you want, Vrbo has properties in many sizes and shapes. Browse our options to find your ideal fit.
How much does it cost to rent a holiday rental in Chilmark?
Property type, length of stay and season are some factors that can affect the price of a holiday home. Simply add your dates of travel to find your perfect fit. From quaint country cottages to plush villas, all Vrbo holiday rentals offer incredible value.
How much does it cost to rent a beach house in Chilmark?
Prices for beach houses in Chilmark differ depending on the size and type of the property and when you're travelling. Simply enter your dates of travel into Vrbo and the number of guests to view your rental options and prices. From there you can use the filters to tailor your search by amenities, nearby activities, ratings and more.
Are there pet-friendly holiday rentals in Chilmark?
Yes. There are. You'll have your pick of 63 holiday rentals that cater to pets in Chilmark. Several of our pet-friendly holiday rentals have a garden for your fur baby to play in, doggie beds, complimentary treats and proximity to parks. Apply the "Pets allowed" filter to find your pawfect pad on Vrbo.
Can I rent a house with a pool in Chilmark?
Check the "pool" box in our handy filter tool and you'll find eight houses with private pools in Chilmark on Vrbo. Morning dip, sunset soak or midnight swim? Leisure time is up to you when your holiday home comes with its own pool.
What are popular rental amenities in Chilmark?
When it comes to rental amenities that people are on the lookout for in Chilmark, a chef, a water view and tennis rank the highest. With Vrbo holiday homes, you'll have options to suit your taste and style, whether you're taking a trip with your partner, your friends or even pets.
Are there large group holiday rentals in Chilmark?
With 14 properties that can host 10 guests or more in Chilmark, you don't have to limit the invite list. From fun family get-togethers to special events like birthday parties and weddings, Vrbo will help you find a large group rental that fits the occasion.
Are there holiday rentals in Chilmark that welcome kids?
Bring the whole group together for the adventure of a lifetime in Chilmark at one of our 61 family-friendly holiday rentals. A lot of these stays feature amenities that are suitable for getaways with the little ones, such as laundry facilities, living rooms and swimming pools. Simply check the "Properties good for families" filter and choose your favourite.
What are the top attractions for families in Chilmark?
Keeping the kids entertained during your holiday in Chilmark is simple with these leading family-friendly attractions:

  • Lamberts Cove Beach
  • Menemsha Beach
  • Lucy Vincent Beach

Are there one-bedroom holiday rentals in Chilmark?
Chilmark has two one-bedroom rentals on offer. Usually situated in sought-after areas thanks to their smaller size, a one-bedroom holiday rental is great if you're travelling with a pal or your partner. And with home comforts like kitchens and more privacy than a standard hotel, you'll be able to kick back while sightseeing around this fabulous destination.
Can I find two-bedroom holiday rentals in Chilmark?
You can pick from 10 two-bedroom homes in Chilmark. Settle the kids into the second room or fill it with a couple of your besties. There's enough space for whoever's fortunate enough to be coming along for the ride.
Are there holiday rentals with WiFi in Chilmark?
Choose from 26 holiday rentals with WiFi in Chilmark. If you want to disconnect from daily life on your holiday, but still want to be connected to the internet, these properties are just what you need. Narrow your search by applying the WiFi filter on Vrbo.
How can I find holiday rentals with air conditioning in Chilmark?
Pick your travel dates and then use the filter tool to find holiday rentals with air conditioning in Chilmark on Vrbo. With 45 air-conditioned properties on offer here, you can enjoy a cool and comfortable trip.
How old do you have to be to rent a holiday rental in Chilmark?
The minimum age allowed can vary across properties on Vrbo, so check the rules of the holiday home in Chilmark you're interested in. But in general, it's 16, 18 or 21.
How long can I rent a holiday rental in Chilmark for?
The amount of time you can rent a Chilmark holiday home for differs depending on the property. Just enter your travel dates to view options that offer extended stays. They come with all the things you need to make your extended holiday more comfortable such as laundries and air conditioning. Some holiday homes may also offer discounted weekly or monthly prices, so you can stick around for longer for less.

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