Photo by Wen C.

Chilmark holiday lettings

We found 497 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:5 Dec - 12 Dec

Image gallery for Sanctuary House: An ocean-view farmhouse retreat

Sweeping view of the Vineyard Sound and Naushon Island
10 out of 10 rating
Exceptional
(32 reviews)

Sanctuary House: An ocean-view farmhouse retreat

Vineyard Haven, MA

7% off
Price is £3,611
for 7 nights, 1 home
£516 nightly
Includes taxes & fees
Sanctuary House: An ocean-view farmhouse retreat

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Find out more about Chilmark

Find out more about Chilmark

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)
  • 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 best area to stay in Chilmark when booking a holiday rental?
When considering a holiday rental in Chilmark, Massachusetts, the area around Menemsha is an excellent choice. This charming fishing village offers a picturesque setting with its beautiful harbour, making it a favourite spot for visitors seeking a quintessential New England experience. Staying in Menemsha not only provides access to stunning sunsets over the water but also places you within walking distance of local seafood shacks that serve up fresh catches. The scenic Menemsha Beach is superb for a relaxing day by the sea, offering a tranquil atmosphere and opportunities for swimming and sunbathing.

Another appealing area to explore is the vicinity of Chilmark's rural landscapes, where you can find a selection of holiday rentals located among rolling hills and wooded areas. This region is ideal for those who appreciate nature, as it is close to the Polly Hill Arboretum, a beautiful garden showcasing a diverse collection of plants and trees. The serene surroundings also offer great walking and hiking trails, allowing you to fully immerse yourself in the natural beauty of Martha's Vineyard.
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, Massachusetts, the area offers picturesque coastal landscapes and a tranquil atmosphere. The stretch along Menemsha Beach is particularly appealing, where holiday rentals provide stunning views of the ocean and easy access to sandy shores. Many properties in this region often come with amenities such as outdoor decks, private gardens, and spacious living areas, great for families or groups seeking a relaxing getaway.

Additionally, the nearby Squibnocket Beach area features charming homes with amenities like outdoor showers and expansive patios, ideal for enjoying the seaside breeze. This exclusive part of Chilmark is known for its natural beauty, and properties here often boast proximity to scenic walking paths along the coastline.
What is the most popular type of holiday rental accomodation in Chilmark?
In Chilmark, holiday houses are the most popular type of rental, with approximately 63 available throughout the area. These houses often provide spacious living arrangements, featuring multiple bedrooms, fully equipped kitchens, and outdoor spaces such as decks or patios for enjoying the beautiful coastal views. Many of these properties are situated near picturesque spots, making them ideal for families or groups seeking a relaxing getaway. Additionally, there are about 10 cottages available, which offer a more quaint, charming atmosphere, typically with well-appointed interiors and easy access to local attractions.
Are there any family house rentals in Chilmark?
In Chilmark, Massachusetts, there is a wealth of family-friendly house rentals available, with around 51 options for visitors to choose from. This picturesque area on Martha's Vineyard is ideal for families seeking a tranquil getaway. Many of the homes feature spacious living areas, fully equipped kitchens for convenient meal preparation, and outdoor spaces superb for children to play or for families to enjoy alfresco dining.

Travellers will appreciate amenities such as Wi-Fi and laundry facilities, ensuring a comfortable and practical stay. The charming surroundings boast beautiful beaches, where families can spend the day swimming or building sandcastles. Nearby attractions include the scenic views at Menemsha Beach and the vibrant arts scene in the nearby town of Oak Bluffs.
Can I rent a holiday home with a pool or hot tub in Chilmark?
In Chilmark, Massachusetts, there are several holiday homes available for rent that feature pools and hot tubs. This picturesque area on Martha's Vineyard offers a serene setting with beautiful landscapes and proximity to stunning beaches. Many of these rentals come with amenities such as private pools, hot tubs, spacious outdoor decks, and well-equipped kitchens, making them great for families or groups looking to unwind in a tranquil environment.
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, there are numerous pet-friendly house rentals available, with around 38 options for travellers seeking to bring their furry friends along. This picturesque area on Martha's Vineyard offers a delightful combination of charming coastal scenery and tranquil rural landscapes. Many of the holiday rentals feature amenities such as spacious outdoor areas, fully equipped kitchens, and comfortable living spaces, making them ideal for families and pet owners alike.
Are there any remote work holiday rentals in Chilmark?
In Chilmark, Massachusetts, there are numerous remote work holiday rentals available, with around 69 properties suiting this need. This picturesque town on Martha's Vineyard offers a serene environment, great for those looking to blend work and leisure. Many of these rentals come equipped with essential amenities for remote work, including dedicated office spaces, desks and comfortable desk chairs, high-speed Wi-Fi, and even computer monitors in some properties. 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 typically include a fully equipped kitchen featuring essential appliances such as a microwave, dishwasher, and refrigerator, along with cookware and dishware for preparing meals. Many holiday rentals are designed to provide a comfortable home-like experience, making them ideal for families or groups seeking a relaxing getaway in this picturesque area of Martha's Vineyard.
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 the most popular month. This vibrant period attracts travellers looking to soak up the sun, enjoy outdoor activities, and experience the picturesque charm of Martha's Vineyard. Visitors during these months can indulge in swimming, beachcombing, and exploring the stunning coastline while relishing the warm temperatures, often reaching the mid-20s Celsius.

In July, the atmosphere is particularly lively, with families and friends gathering to partake in a variety of local events, farmers' markets, and art exhibitions. It's an excellent time to immerse yourself in the community spirit, as well as to enjoy the beautiful landscapes and outdoor adventures that Chilmark offers, such as hiking the scenic trails of the nearby Nature Conservancy.

If you're looking for a more budget-friendly option, consider visiting in October. This month showcases the tranquil beauty of Chilmark as the summer crowds dissipate, offering a quieter experience. The autumn foliage creates a stunning backdrop for leisurely walks and photography, allowing you to appreciate the area's natural beauty without the hustle and bustle of the peak season.
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.
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 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 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.

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