Chestertown Summer Rentals, Cottages & Cabins

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 Summer Rentals in Chestertown:

• The Roost, a lakefront 4 season home in the Adirondack Mountains
• Relax at Our River Retreat
• Same local favorite, an even better nightly rate, and now with NO CLEANING FEE!
• Adirondack Base Camp by Loon Lake and Gore Mt.!
• WaterFront Adirondack Home-located between Gore and Lake George
• #7 Adirondack@Birchwood Cottages on Loon Lake. Family Friendly Waterfront
• Family Friendly 3BR 3.5BA Lodge w/Lake & Beach, Screened Patio, Grill, Sunroom
• 4 Mi to Beach & Lake: Spacious Home in Chestertown
• Historic 1860s ADK Farmhouse w/Hot Tub, Private Pond, & walkable to Chestertown.
• Forest Lake Haven close to Lake George and Gore Mountain, 5 BR spacious and NEW

In 2026, Whisperingpinescottages offers 176 summer rentals in or around Chestertown. Find unique home rentals for your summer holiday or a weekend getaway with family and friends.

The average price per night for a summer rental in Chestertown is $375. Check the full list of summer accommodations in Chestertown.

There are 176 summer rentals, cabins, cottages and properties that are available to rent. Book for your next trip with Whisperingpinescottages.

Yes, here are some popular summer holiday rentals in Chestertown that have a private or indoor pool:

• A beautiful lake view cabin on Friends Lake
• Solitude at Lake's End
• The Fern Lodge
• Elizabeth. A Guest House Near Lake George.

Check all holiday rentals with a pool in Chestertown on Whisperingpinescottages.