Monthly Rentals in Chilmark

Discover long-term rentals that feel like home for stays of a month or longer.

Nearby monthly rentals

Superhost
Condo in Tisbury
4.77 out of 5 average rating, 13 reviews

Martha’s Vineyard Condo * Near Ferry

AnthonyRating, 5 stars7 months ago
Great location and a nice quaint spot for one or two ! Great value for the area as well
Guest favorite
Home in Chilmark
4.99 out of 5 average rating, 97 reviews

Renovated Barn in Chilmark 3BR

VickyRating, 5 stars6 months ago
As always, we had a wonderful time in Alexia's pristine, charming, well laid-out home. It suits our family perfectly, with its separate "wings" and its open common space. It's close to Menemsha and great walking trails. As a host, Alexia is always available and helpful. We had a relaxed and happy stay there!
Guest favorite
Guesthouse in Chilmark
4.98 out of 5 average rating, 215 reviews

Beautiful Guest House in Chilmark

TomRating, 5 stars7 months ago
We loved our stay at Stephanie’s place in Chilmark. Her place is in an amazing part of The Vineyard near to the best beaches on the Island. The listing accurately reflects the space and it was very clean and nice and just as we expected. Stephanie was also very accommodating, allowing us to check in early and check out late. In short, it made for a perfect island getaway and we will definitely be back.
Guest favorite
Cottage in Chilmark
5 out of 5 average rating, 47 reviews

Walk to the beach: Charming Menemsha Cottage

NatalieRating, 5 stars7 months ago
Whitney was very helpful and extremely responsive. We loved her charming cottage on a quiet lane just a short walk to scenic Menemsha. The house is very comfortable and well supplied with kitchen basics, beach going essentials and a nice BBQ. Good selection of guide books and beach reads too. We had some issues with the AC, but she responded promptly and sent the HVAC experts to reset the system. We especially appreciated the bag of ground coffee she provided to get us going the first morning!

Amenities and perks for longer stays

Furnished rentals

Fully furnished rentals include a kitchen and the amenities you need to live comfortably for a month or longer. It’s the perfect alternative to a sublet.

Flexibility you need

Choose your exact move-in and move-out dates and easily book online, without any additional commitment or paperwork.*

Simple monthly prices

Special rates for long-term vacation rentals and a single monthly payment without additional charges.*

Book with confidence

Reviewed by our trusted community of guests and 24/7 support during your extended stay.

Work-friendly spaces for digital nomads

Traveling professional? Find a long-term stay with high-speed wifi and dedicated working spaces.

Looking for corporate housing?

Airbnb has fully furnished apartment homes ideal for staffing, corporate housing, and relocation needs.

Stay near Chilmark's top sights

Martha's Vineyard102 locals recommend
State Road60 locals recommend
Gay Head Lighthouse48 locals recommend
Larsen's Fish Market48 locals recommend
Menemsha Beach35 locals recommend
7aFoods33 locals recommend

Destinations to explore

*Some exclusions may apply in certain geographies and for some properties.
  1. Airbnb
  2. United States
  3. Massachusetts
  4. Dukes County
  5. Chilmark
  6. Monthly Rentals