What are the top rated Luxury 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 Luxury Rentals in Chestertown: <a href="/property/tripp-lake-retreat-sleeps-7-and-is-a-great-place-to-make-adirondack-memories/HA-1214313390" class="class="static-page-link"">TRIPP LAKE RETREAT sleeps 7 and is a great place to make Adirondack memories!</a> <a href="/property/secluded-and-cozy-townhome-at-tripp-lake/HA-3213714313" class="class="static-page-link"">Secluded and Cozy Townhome at Tripp Lake</a> <a href="/property/loon-lake-chestertown-spotless-bright-chalet-sleeps-6-8-13-mi-to-ski-gore/HA-3213348" class="class="static-page-link"">Loon Lake, Chestertown - Spotless, bright chalet, sleeps 6-8, 13 mi. to ski Gore</a> <a href="/property/welcome-home/HA-3212363736" class="class="static-page-link"">Welcome home!</a> <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/rustic-adirondack-retreat-on-tripp-lake/HA-3212516613" class="class="static-page-link"">Rustic Adirondack Retreat on Tripp Lake</a> <a href="/property/modern-cabin-w-hot-tub-minutes-to-lakes-skiing/HA-3213018595" class="class="static-page-link"">Modern Cabin w/Hot Tub-Minutes to Lakes &amp; Skiing</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>

What are the best pet-friendly luxury rentals in Chestertown?

We have many pet-friendly luxury rentals in the Chestertown. The top pet-friendly rentals in Chestertown are: Spectacular Lakefront Cabin on 12 acres on Friends Lake Unique Lakefront House with Sandy Beach and Dock - Sweeping Views Lakefront home steps away from a private, gentle sloping sandy beach & fire pit. Mimi’s by the lake See all <a href="/all/usa/new-york/chestertown" class="class=&#34;static-page-link&#34;">pet-friendly rentals in Chestertown</a> on 7oceanvacation

Do any luxury resorts or villas in Chestertown have a pool?

Yes, there are more than 172 luxury resorts & villas rentals in Chestertown that have indoor/outdoor and private swimming pools. Check out our filter option and find your best places to stay near Chestertown.