What are the top rated Cottage Rentals in Chestertown?

There are a lot of options in Chestertown. If you plan on staying in the Chestertown area, consider making a reservation for a few nights at one of these properties as these have been rated the top Cottage Rentals in Chestertown: <a href="/property/the-roost-a-lakefront-4-season-home-in-the-adirondack-mountains/HA-3211206231" class="class="static-page-link"">The Roost, a lakefront 4 season home in the Adirondack Mountains</a> <a href="/property/relax-at-our-river-retreat/HA-3211214420" class="class="static-page-link"">Relax at Our River Retreat</a> <a href="/property/same-local-favorite-an-even-better-nightly-rate-and-now-with-no-cleaning-fee/HA-3212215004" class="class="static-page-link"">Same local favorite, an even better nightly rate, and now with NO CLEANING FEE!</a> <a href="/property/adirondack-base-camp-by-loon-lake-and-gore-mt/HA-3213406894" class="class="static-page-link"">Adirondack Base Camp by Loon Lake and Gore Mt.!</a> <a href="/property/waterfront-adirondack-home-located-between-gore-and-lake-george/HA-3214059718" class="class="static-page-link"">WaterFront Adirondack Home-located between Gore and Lake George</a> <a href="/property/family-friendly-3br-3-5ba-lodge-w-lake-beach-screened-patio-grill-sunroom/HA-3214758903" class="class="static-page-link"">Family Friendly 3BR 3.5BA Lodge w/Lake &amp; Beach, Screened Patio, Grill, Sunroom</a> <a href="/property/the-fern-lodge/BC-1093458" class="class="static-page-link"">The Fern Lodge</a> <a href="/property/4-mi-to-beach-lake-spacious-home-in-chestertown/HA-12120169536" class="class="static-page-link"">4 Mi to Beach &amp; Lake: Spacious Home in Chestertown</a> <a href="/property/whit-s-end/BC-6868488" class="class="static-page-link"">Whit&#39;s End</a> <a href="/property/4-mi-to-beach-and-lake-spacious-home-in-chestertown/BC-14502184" class="class="static-page-link"">4 Mi to Beach and Lake Spacious Home in Chestertown</a>

How much does it cost to rent a cottage in Chestertown?

The average cost for a cottage rental in Chestertown is $372 per night. Cruisesbyowner has a wide list of great cottages near Chestertown that would suit your needs. There are single and multiple rooms for solo trips or family vacations.

Are there any cottages in Chestertown that allow pets?

Yes, here are the top cottage rentals in Chestertown that allow you to bring your pet: Elizabeth. A Guest House Near Lake George. Solitude at Lake's End The Fern Lodge Lakefront cabin with beautiful views, lake and beach access <a href="/all/usa/new-york/chestertown" class="class="static-page-link"">See all pet-friendly vacation rentals in Chestertown on Cruisesbyowner</a>

Do you have any rental cottages in Chestertown that are suitable for families?

Most of our listed cottages are suitable for families. Check out the complete list of cottages in Chestertown to find one that works for you.

Are there quality cottages in Chestertown that have indoor swimming pools?

As of 2026, the data from Cruisesbyowner shows that there are Over 174 private swimming pools or cottages with indoor pools in the Chestertown area along with other great amenities.

Chestertown Cottage Rentals By Owner

Elizabeth. A Guest House Near Lake George.

From US $361

8.2 (45 Reviews)

House

Elizabeth. A Guest House Near Lake George.

Air Conditioner
Parking
Pet Friendly

Chestertown Cottage Rentals & Holiday Homes

Find the best cottages in Chestertown - We found 174 exact matches

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