Photo by Wen C.

Chilmark cottages

We found 27 cottages — enter your dates for availability

Find spaces that suit your style

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    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

Frequently asked questions

Are there any cottage rentals in Chilmark?
Check out our 27 cottage rentals and begin organising your trip to Chilmark. Whether you want to be in Makonikey, Lagoon Heights, Katama or another well-known neighbourhood, Vrbo's charming and cosy cottages give you more room to spread out compared to a hotel.
How much does it cost to stay in a cottage rental in Chilmark?
One of the only things that can top spending your next holiday in a comfy cottage rental in Chilmark is getting it for an amazing price. Stay on the lookout for any accommodation offering discounts to guests who stay a full week. Some properties offer even better discounts if you stay a whole month. You can also make use of Vrbo's price filter to look for cottages that match your budget.
When is the best time to rent a cottage in Chilmark?
Follow the crowds and consider booking your cottage rental in August. With temperatures that range between 21 ºC (70 ºF) and 23 ºC (73 ºF), this is the most popular month to travel to Chilmark. For a more relaxed atmosphere, it's worth looking at the shoulder seasons. No matter when you decide to visit this part of Martha's Vineyard, a Vrbo cottage will guarantee your holiday is a memorable experience.
Where can I rent a Chilmark holiday cottage with great views?
Vrbo has a range of awesome cottage rentals in Chilmark, including properties with nature views. Before and after seeing the sights, relax and gaze at scenes that are an attraction in themselves.
Does Chilmark have any lakeside cottages?
For a refreshing getaway, you can't beat our lakeside cottage rentals. Try our convenient "Location" filter and then tick the box marked "Lake" to see if you can find any cosy stays that'll place you near the water in Chilmark. Spend your days being adventurous or just enjoy the magnificent sunrises and sunsets glittering off the lake.
What are the top things to do in Chilmark?
When you want to travel beyond the picturesque surroundings of your cottage rental, you'll discover lots to experience in Chilmark, starting with Martha's Vineyard Museum. Searching for more things that will keep the whole family occupied? Martha's Vineyard Film Centre and Aquinnah Cliffs are other leading attractions worth visiting.
Why should I book my holiday cottage with Vrbo?
Booking your cottage rental with Vrbo means you get the whole place to yourselves — your own private retreat, without any distractions from others. Not only that, our flexible payment and cancellation policies allow you to change your plans if necessary.