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Chilmark vacation rentals

We found 521 vacation rentals — enter your dates for availability

Select from 76 homes, 10 cottages, and other vacation rentals in Chilmark to find one that's perfect for your trip. Vacation homes provide the best amenities for you and your friends, family, or even pets, like air conditioning and cable TV. At the end of the day, you'll find a rental for everyone's needs, including accessible or non-smoking choices.

Vacation rentals with weekly discounts - Chilmark

Showing deals for:Feb 20 - Feb 27

Image gallery for Relax & Renew at Luxury Villa with Heated Pool & Hot Tub,Tennis,Bikes,Firepit!

Pool
9.4 out of 10, Exceptional, (13 reviews)
Exceptional
(13 reviews)

Relax & Renew at Luxury Villa with Heated Pool & Hot Tub,Tennis,Bikes,Firepit!

Oak Bluffs, MA

8% off
Price is CA $2,032
CA $17,952 total
includes taxes & fees
Relax & Renew at Luxury Villa with Heated Pool & Hot Tub,Tennis,Bikes,Firepit!

Find spaces that suit your style

  • 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, yards and more

  • More for less

    More space, more privacy, more amenities — more value

Find out more about Chilmark

Explore the beachside setting in Chilmark

The area's wineries and festivals are just a few of the reasons to vacation in Chilmark. Well-liked for its beaches, hiking and local tours, this city is both relaxing and scenic. If you're looking for accommodations with space to entertain friends and family, Vrbo 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

Are you searching for attractions to see while you're in town? Although it can be tempting to stay in your comfortable vacation rental, you'll want to check out everything that makes Chilmark a one-of-a-kind vacation spot. These are some of the top attractions to see, all within 30 miles (48.2 km) of the city center:

  • 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 looking for adventure or just want to take in the scenery, Chilmark is a great spot to appreciate mother nature. These are a few of the area's noteworthy natural features, all within 30 miles (48.2 km) of the city center:

  • 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)

Transportation 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 center. 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 vacation rental?
When considering a vacation rental in Chilmark, Massachusetts, a popular area to stay is near Menemsha. This charming fishing village offers a picturesque setting with its iconic beach and stunning sunsets, making it a favourite among visitors. Menemsha is known for its quaint atmosphere, seafood shacks, and access to the Menemsha Pond, superb for kayaking and paddleboarding. The proximity to the beach creates a wonderful opportunity for relaxation and beachcombing, while the village itself boasts a handful of shops and dining options that highlight the local culinary scene.

Another excellent option is the area surrounding Chilmark's beautiful beaches, such as Squibnocket Beach. This area is renowned for its natural beauty and tranquil surroundings, offering a more secluded experience away from the bustle of larger towns. Visitors can enjoy scenic walks along the coastline, with opportunities for birdwatching and exploring the local flora and fauna. The nearby Chilmark Community Centre often hosts events and activities that can provide a glimpse into the local culture.
How much does it cost to rent a vacation home in Chilmark?
Prices for vacation 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 travelling 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.
Are there any discounts for Chilmark vacation 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, travellers should explore the picturesque coastline along the Atlantic Ocean, particularly near Menemsha Beach. This area offers a selection of charming beach cottages and luxurious homes, many of which come with amenities such as expansive decks, outdoor dining areas, and stunning ocean views, great for enjoying sunrises and sunsets.

The nearby Chilmark Pond area is also a delightful option, where visitors can find properties with private access to the water. Many of these rentals feature modern kitchens for self-catering, spacious living rooms, and sometimes even private docks for boating or kayaking, allowing for a truly immersive seaside experience.
What is the most popular type of vacation rental accomodation in Chilmark?
In Chilmark, vacation houses are the most popular type of rental accommodation, with around 63 available in the area. These houses are typically situated in serene locations, providing a superb retreat to enjoy the natural beauty of Martha's Vineyard. Most of these rentals come with ample space, featuring multiple bedrooms, fully equipped kitchens, and outdoor areas such as decks or patios for relaxing and dining al fresco. Additionally, there are about 10 cottages, which offer a quaint and charming atmosphere, often with rustic decor and proximity to nature trails. While there are several apartments, they tend to be less common.
Are there any family house rentals in Chilmark?
In Chilmark, Massachusetts, there are numerous family-friendly vacation rentals available—specifically, around 51 options for visitors to choose from. This charming town on Martha's Vineyard is known for its stunning coastal views and serene atmosphere, making it an excellent destination for families seeking a relaxing getaway.

Properties in this area often feature spacious living rooms, fully equipped kitchens for preparing family meals, and outdoor areas where children can play and adults can unwind. Many homes come with amenities such as Wi-Fi and air conditioning, ensuring a comfortable stay for all guests.
Can I rent a vacation home with a pool or hot tub in Chilmark?
In Chilmark, Massachusetts, there are several vacation homes available for rent that feature pools or hot tubs. This picturesque area on Martha's Vineyard is known for its scenic views and tranquil atmosphere, making it an ideal destination for relaxation. Many of the properties come equipped with private pools, hot tubs, and spacious outdoor areas great for enjoying the beautiful surroundings. Travellers can expect amenities such as fully equipped kitchens, generous living spaces, and sometimes even access to nearby beaches, enhancing the overall vacation experience.
Can I find long-stay vacation rentals in Chilmark?
A long-stay vacation 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, making it an excellent choice for travellers looking to bring their furry companions along. Many of these properties offer amenities such as spacious outdoor areas, fully equipped kitchens, and comfortable living spaces, providing a cozy feel during your stay.
Are there any remote work vacation rentals in Chilmark?
In Chilmark, Massachusetts, there are numerous vacation rentals suitable for remote work, with around 69 options available. This picturesque town on Martha's Vineyard offers a tranquil environment ideal for productivity. Many properties feature dedicated workspaces equipped with desks, ergonomic chairs, and high-speed Wi-Fi, ensuring a comfortable setup for those working remotely. Additionally, some rentals may include amenities such as computer monitors and safes for added convenience and security. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Chilmark vacation rentals with parking?
Vrbo offers a wide selection of vacation 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 vacation 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.
How early should I book a Chilmark vacation rental?
Book your Chilmark vacation 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 vacation 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 vacation 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 vacation 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.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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