Chilmark holiday lettings

We found 478 holiday rentals — enter your dates for availability

Select from 61 homes, 10 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:29 May - 5 Jun

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 £2,117
for 7 nights, 1 home
£302 per night
includes taxes & fees
Private cottage nestled in center of the Vineyard

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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.

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.

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

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.

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)
  • 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)
  • 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)
  • Inkwell Beach (12.5 mi / 20.1 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 best area to stay in Chilmark when booking a holiday rental?
When considering a holiday rental in Chilmark, Massachusetts, the area offers a delightful blend of scenic beauty and local charm. One of the most appealing neighbourhoods is near Menemsha, a quaint fishing village known for its stunning sunsets and picturesque harbour. Staying here provides easy access to the renowned Menemsha Beach, great for a relaxing day by the water or enjoying fresh seafood from local vendors.

Another great option is the area around Chilmark's scenic countryside, where you can find charming properties that offer a peaceful retreat. This location is close to the beautiful Chilmark Community Centre, which hosts various events and activities throughout the year, making it a lively spot for both locals and visitors.

While the exact number of properties can fluctuate, the offerings in these neighbourhoods typically range from cosy cottages to larger family homes, ensuring that there's something to suit every preference.
How much does it cost to rent a holiday home in Chilmark?
Prices for holiday 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 holiday 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 areas along the northern shores of Martha's Vineyard. The region near Menemsha, with its charming fishing village vibe, offers beachfront properties that provide stunning views of the sunset over the water. Many of these rentals come equipped with amenities such as outdoor decks, barbecue facilities, and fully furnished kitchens, great for families and friends looking to enjoy a seaside getaway.

Additionally, the area surrounding Squibnocket Beach is top for its serene atmosphere and access to beautiful sandy shores. Here, you can find spacious homes featuring private pools, landscaped gardens, and direct access to the beach, allowing for a relaxing retreat. The local charm is enhanced by nearby artisanal shops and seafood eateries, offering a taste of the island's culinary delights.

For those interested in outdoor activities, Chilmark's proximity to hiking trails and nature reserves allows for exploration of the island's natural beauty.
What is the most popular type of holiday rental accomodation in Chilmark?
In Chilmark, holiday houses are the most popular type of holiday rental, with around 220 available throughout the area. These houses typically feature spacious layouts, multiple bedrooms, fully equipped kitchens, and often come with outdoor spaces such as decks or gardens, allowing guests to enjoy the picturesque surroundings. Additionally, there are about 36 charming cottages that provide a quaint and cosy atmosphere, great for those looking for a more intimate stay. While there are several apartments available, they are less common compared to the other options.
Are there any family house rentals in Chilmark?
In Chilmark, Massachusetts, families will find a variety of house rentals, with around 46 options available. This charming area is known for its picturesque landscapes and proximity to stunning beaches, making it an ideal choice for family getaways. Many of these homes feature spacious living areas, fully equipped kitchens for preparing meals together, and outdoor decks or gardens for enjoying the serene surroundings.

Visitors can explore nearby attractions such as the beautiful Menemsha Beach, superb for a day of sun and sand, or the scenic trails of the Chilmark Reservation, which offer opportunities for hiking and wildlife observation. With amenities like Wi-Fi, air conditioning, and often laundry facilities, these properties ensure a comfortable stay for families looking to relax and explore the natural beauty of Martha's Vineyard.
Can I rent a holiday home with a pool or hot tub in Chilmark?
In Chilmark, there are several holiday homes available for rent that feature pools and hot tubs. This charming town on Martha's Vineyard is ideal for travellers seeking a relaxing getaway amidst stunning natural scenery. Many of the properties come equipped with private pools, hot tubs, and outdoor patios, superb for enjoying the tranquil surroundings. Additionally, you can expect amenities such as fully equipped kitchens, spacious living areas, and easy access to nearby beaches, making these rentals suitable for both families and groups looking to unwind in comfort.
Can I find long-stay holiday rentals in Chilmark?
A long-stay holiday rental in Chilmark is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your travel dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Are there pet-friendly house rentals in Chilmark?
In Chilmark, Massachusetts, there are numerous pet-friendly house rentals available, with around 32 options to choose from. This picturesque area on Martha's Vineyard is known for its stunning landscapes and tranquil beaches, making it an excellent destination for travellers with pets. Many of the holiday rentals here feature spacious outdoor areas, ideal for pets to roam, as well as amenities such as fully equipped kitchens, comfortable living spaces, and sometimes even private decks or patios for relaxation.

Chilmark is close to several beautiful beaches, including Menemsha Beach and Squibnocket Beach, which are often favoured by pet owners for their scenic views and less crowded atmosphere. Additionally, the surrounding nature trails and open spaces provide ample opportunities for walks and outdoor adventures with pets.
Are there any remote work holiday rentals in Chilmark?
In Chilmark, Massachusetts, there are an impressive 240 remote work holiday rentals available, making it an excellent choice for those looking to balance work and leisure. Many of these properties are equipped with essential amenities for remote work, including high-speed Wi-Fi, dedicated workspaces, and comfortable desk chairs. Some even offer additional features like computer monitors, printers, and fax machines to ensure a productive environment.

With its picturesque landscapes and serene surroundings, Chilmark provides a tranquil setting for remote working. Besides the work-friendly amenities, visitors can enjoy the stunning natural beauty of the area, including nearby beaches and hiking trails. The charming local community also offers delightful shops and restaurants, great for unwinding after a day of work. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Chilmark holiday rentals with parking?
Vrbo offers a wide selection of holiday rentals in Chilmark with parking available—perfect for families or travellers 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 rental amenities include fully equipped kitchens, which allow guests to prepare their own meals and enjoy dining at home. Many properties also feature decks or patios, providing outdoor spaces to relax and soak in the tranquil surroundings. Additional amenities often include blenders for making smoothies or cocktails, onsite parking for convenience, and fireplaces that create a warm, inviting atmosphere, especially during cooler evenings.
When is the best time to visit Chilmark for a holiday rental?
The best time to visit Chilmark for a holiday rental is during the peak season from June to August, with July being particularly popular. This vibrant period attracts visitors eager to soak in the sun, partake in outdoor activities, and explore the picturesque landscapes of Martha's Vineyard.

During these summer months, you'll enjoy warm temperatures averaging around 25 to 30 degrees Celsius, great for beach outings, hiking, or simply relaxing by the shore. The charming coastal town buzzes with energy, providing ample opportunities for sightseeing and local events, making it an ideal time for travellers.

For those looking for a more budget-friendly option, October presents a wonderful opportunity to visit Chilmark. The fall foliage showcases stunning autumn colours, creating a serene backdrop for leisurely strolls and scenic drives. Plus, the crowds have thinned, allowing for a more tranquil experience while still enjoying the beautiful scenery.

Ultimately, the best time to book your holiday rental in Chilmark hinges on your preferences: whether you favour the lively summer atmosphere filled with activities or the peaceful charm of autumn.
How early should I book a Chilmark holiday rental?
Book your Chilmark holiday 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 holiday 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 engage in the natural beauty and charm of Martha's Vineyard. The area is renowned for its stunning landscapes, including the picturesque Menemsha Hills, which offer scenic hiking trails and breathtaking views of the coastline. The quaint fishing village of Menemsha is a highlight, where travellers can enjoy fresh seafood and watch the sunset over the harbour.

Chilmark is also home to the serene Lucy Vincent Beach, a great spot for relaxation and swimming, although it's worth noting that access is restricted to residents and their guests. For those interested in art and culture, the nearby community offers galleries showcasing local artists and craftspeople.
Can I change or cancel my Chilmark home rental booking on Vrbo?
To find Chilmark holiday 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 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 travellers 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 cosy cabin or a beach house, 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 holiday 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, such as last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to support you every step of the way.

Vrbo also offers support via live chat through our Help Centre, 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 organising 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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