Chilmark holiday homes

We found 500 holiday rentals — enter your dates for availability
Select from 66 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:11 Dec - 18 Dec

Entering from the driveway
Living room with loft space above
West wing with futon/sleeper
Spacious wrap around deck with all day sun and shade
Exceptional
(45 reviews)

Striking 5BR/4BA Chilmark Contemporary with Views of the Sound

Chilmark

8% off
NZ$8,840
for 7 nights, 1 home
NZ$1,263 per night
includes taxes & fees
Striking 5BR/4BA Chilmark Contemporary with Views of the Sound
Interior
Terrace/patio
Dining
Private kitchen
Exceptional
(7 reviews)

BRAND NEW!

Oak Bluffs

8% off
NZ$14,070
for 7 nights, 1 home
NZ$2,010 per night
includes taxes & fees
BRAND NEW!
Exterior
Living area
Living area
Outdoor dining
Exceptional
(17 reviews)

THE PARK ESTATE! Your Martha's Vineyard Getaway!

Oak Bluffs

9% off
NZ$96,493
for 7 nights, 1 home
NZ$13,785 per night
includes taxes & fees
THE PARK ESTATE! Your Martha's Vineyard Getaway!
Kitchen & stairs to upper level
Exterior
Living room
Upstairs bedroom with queen bed
Exceptional
(76 reviews)

Beachfront Aquinnah home. Beautiful views!

Aquinnah

8% off
NZ$6,782
for 7 nights, 1 home
NZ$969 per night
includes taxes & fees
Beachfront Aquinnah home. Beautiful views!
Exterior
Living area
Chef's kitchen
Screened-in porch
Exceptional
(10 reviews)

Lovely Chilmark home on Abel's Hill with private beach, pond, tennis, and trails

Chilmark

8% off
NZ$16,481
for 7 nights, 1 home
NZ$2,354 per night
includes taxes & fees
Lovely Chilmark home on Abel's Hill with private beach, pond, tennis, and trails
Outdoor relaxing!
Exterior
Sun room off the kitchen.
Double sinks for busy kitchens.
Exceptional
(5 reviews)

WALK TO VILLAGE LOCATION, NEW POOL, FAMILY COMPOUND!

Edgartown

9% off
NZ$42,704
for 7 nights, 1 home
NZ$6,101 per night
includes taxes & fees
WALK TO VILLAGE LOCATION, NEW POOL, FAMILY COMPOUND!
Outdoor dining
Property grounds
Private kitchen
Room
Exceptional
(93 reviews)

Martha's Vineyard Cozy Getaway Near Picturesque Philbin Beach

Aquinnah

7% off
NZ$6,010
for 7 nights, 1 home
NZ$859 per night
includes taxes & fees
Martha's Vineyard Cozy Getaway Near Picturesque Philbin Beach
Exterior
The garden gate
Living area
Terrace/patio
Exceptional
(39 reviews)

Walk to private beach from beautiful Abels Hill house

Chilmark

8% off
NZ$9,100
for 7 nights, 1 home
NZ$1,300 per night
includes taxes & fees
Walk to private beach from beautiful Abels Hill house
Exterior
Outdoor dining
Living area
Private kitchen
Exceptional
(127 reviews)

On HGTV! New w/ Hot Tub, Bocce Court, AC, WALK to Town & Beach!

Edgartown

7% off
NZ$7,115
for 7 nights, 1 home
NZ$1,016 per night
includes taxes & fees
On HGTV! New w/ Hot Tub, Bocce Court, AC, WALK to Town & Beach!
Dining area can seat 8-10 and looks onto patio and water views.
Meals on the patio are a daily delight- sparkly mornings to ocean dipped sunsets
Newly built cedar and mahogany with rain head shower.
Large, farmhouse fireplace perfect for chillier seasons.
Exceptional
(42 reviews)

Sanctuary House: An ocean-view farmhouse retreat

Vineyard Haven

8% off
NZ$8,840
for 7 nights, 1 home
NZ$1,263 per night
includes taxes & fees
Sanctuary House: An ocean-view farmhouse retreat
Living room / Dining area
Approach to our home
Loft area
Rear view of our home
Exceptional
(16 reviews)

Katama Edgartown... bike to South Beach, bike to Town

Edgartown

8% off
NZ$6,260
for 7 nights, 1 home
NZ$894 per night
includes taxes & fees
Katama Edgartown... bike to South Beach, bike to Town
Living area
Outdoor dining
Living area
Exterior
Exceptional
(16 reviews)

Guest House In Edgartown

Edgartown

8% off
NZ$5,080
for 7 nights, 1 home
NZ$726 per night
includes taxes & fees
Guest House In Edgartown
Exterior
Outdoor dining
Private kitchen
Dining
Exceptional
(8 reviews)

Charming 4-bedroom house with AC and WiFi in beautiful Edgartown

Edgartown

8% off
NZ$4,707
for 7 nights, 1 home
NZ$672 per night
includes taxes & fees
Charming 4-bedroom house with AC and WiFi in beautiful Edgartown
Living area
South view to Pond and Atlantic Ocean from master bedroom
Hallway to master suite
Exterior
Exceptional
(14 reviews)

Walk to Beach, Kayak from Backyard Dock, Ocean & Squibnocket Pond Views

Chilmark

8% off
NZ$10,979
for 7 nights, 1 home
NZ$1,568 per night
includes taxes & fees
Walk to Beach, Kayak from Backyard Dock, Ocean & Squibnocket Pond Views
Private kitchen
Living area
Dining
Interior
Exceptional
(6 reviews)

Spacious home for entertaining, centrally located to beach, ferry, and airport.

Edgartown

8% off
NZ$38,825
for 7 nights, 1 home
NZ$5,546 per night
includes taxes & fees
Spacious home for entertaining, centrally located to beach, ferry, and airport.
Room
Property grounds
Interior
Living area
Exceptional
(54 reviews)

Amazing Views!!! Sunsets!!! Larger Roof Deck!!! Historic Martha’s Vineyard Gem!!

Aquinnah

8% off
NZ$3,943
for 7 nights, 1 home
NZ$563 per night
includes taxes & fees
Amazing Views!!! Sunsets!!! Larger Roof Deck!!! Historic Martha’s Vineyard Gem!!
Exterior
Terrace/patio
Living area
Living area
Exceptional
(13 reviews)

Charming Katama Home in Prime Edgartown Location!

Edgartown

16% off
NZ$10,991
for 7 nights, 1 home
NZ$1,570 per night
includes taxes & fees
Charming Katama Home in Prime Edgartown Location!
Front view of main entrance
Front of main house at 47 Cooke St Edgartown MA
Kitchen
Entryway
Exceptional
(55 reviews)

Edgartown close to beach and town 6BD with Pool and Hot Tub

Edgartown

8% off
NZ$26,073
for 7 nights, 1 home
NZ$3,725 per night
includes taxes & fees
Edgartown close to beach and town 6BD with Pool and Hot Tub
House exterior and front yard
House exterior
Bedroom with queen bed
Kitchen
Exceptional
(19 reviews)

Charming Family Home in the Heart of Martha's Vineyard

Vineyard Haven

8% off
NZ$7,875
for 7 nights, 1 home
NZ$1,125 per night
includes taxes & fees
Charming Family Home in the Heart of Martha's Vineyard
Private kitchen
Living area
Outdoor dining
Dining
Exceptional
(31 reviews)

The Seashell Cove - Martha's Vineyard

Edgartown

12% off
NZ$10,568
for 7 nights, 1 home
NZ$1,510 per night
includes taxes & fees
The Seashell Cove - Martha's Vineyard

  • Peace of mind

    Our Book with Confidence guarantee gives you 24/7 support

  • More quality time

    From booking to staying, the whole process is simple and enjoyable

  • All the privacy of home

    Enjoy full kitchens, laundry, pools, gardens and more

  • More for less

    More space, more privacy, more amenities — more value

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:

  • 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)
  • 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.
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.
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 Bookabach.
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.
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.
Are all fees included in the Chilmark holiday homes prices shown on Bookabach?
Bookabach 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.
Are there any Chilmark holiday homes with parking?
Bookabach offers a wide selection of holiday homes 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 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.
Are there any discounts for Chilmark holiday homes?
You can find great discounts on holiday homes in Chilmark on Bookabach, 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.
Can I change or cancel my Chilmark holiday home booking on Bookabach?
To find Chilmark holiday rentals with free cancellation, just use Bookabach'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". Whether you're adjusting your plans or looking for flexible payment options, Bookabach makes it easy to book with confidence.
Can I find long-stay holiday homes in Chilmark?
A long-stay holiday home 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 vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Can I plan a group trip on Bookabach?
Bookabach'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 favourites, and build the perfect itinerary together.
How early should I book a Chilmark holiday home?
Book your Chilmark holiday home 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 Bookabach booking and occupancy data for 2024 stays.
How much does it cost to rent a holiday home in Chilmark?
Prices for holiday homes 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 travelling solo, as a couple, with family, or in a group. Bookabach offers something for every taste and budget, from affordable homes in Chilmark to more spacious homes.
What can I expect from Bookabach customer service and Bookabach Care™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, Bookabach Care™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, Bookabach customer service is available 24/7 to support you every step of the way. Bookabach 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.
What is Bookabach Care™ and how does it work?
Bookabach's mission is to help guests relax, reconnect, and enjoy precious time together. With Bookabach Care™, 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.
Why should I join Bookabach as a host?
Joining Bookabach 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, Bookabach 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 Bookabach handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.

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