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Aerial summer view of colonial Chestertown on the Chesapeake Bay in Maryland USA

Chestertown long stay rentals

Stay a week, a month or longer in a comfortable place all your own

Relax—Stayz takes the hassle out of booking monthly rentals in Chestertown. The wide selection available and useful search filters make finding your home away from home a breeze. Whether you’re looking for fast Wi-Fi for remote working, a fully equipped kitchen for home cooking or a pool where you can relax with a good book, you’re sure to find it on Stayz. Many long-term rentals in Chestertown are great for kids and welcome four-legged friends, too. What's more, some offer monthly discounts on extended-stay homes and weekly discounts on shorter-term rentals.

  • 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
Great discounts on monthly rentals in Chestertown

You’ll often find discounted rates for long stays of over 28 days on Stayz, making stays of a month or more excellent value.

Entire homes, maximum privacy

Looking for your own place to retreat to? On Stayz, you'll enjoy secluded stays with entire monthly rental homes just for you.

Pet-friendly monthly rentals

Many homes welcome guests with animal companions, so you don’t have to leave your pet at home.

Chestertown Furnished monthly rentals for remote workers

Find your perfect home office set up. There are plenty of stays on Stayz with dedicated workspaces and fast Wi-Fi so that you can take your work with you.

Monthly stays with practical kitchens

Most furnished extended-stay rentals in Chestertown come with well-equipped kitchens ideal for home cooking, so you can enjoy healthy meals in or even host your own dinner parties.

Long-term rentals with parking in Chestertown

Take advantage of the ‘amenities’ filter to find monthly stays with their very own parking spot for the ultimate in convenience.

Wheelchair-accessible holiday rentals

Stayz offers a range of monthly rental homes designed to accommodate everyone for a comfortable and inclusive extended stay.

Holiday rentals in Chestertown with pool

Stayz's handy search filters will help you find monthly holiday homes with swimming pools so that you can relax in your very own pool.

Rentals with free cancellation in Chestertown

Plans change. We get that. With Stayz, you can search, select 'free cancellation,' and see all rentals in Chestertown with flexible cancellation policies.