Chestertown Rentals By Owner

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 Vacation Rentals in Chestertown:

• Eagles Nest at Loon Lake near Gore Mountain
• TRIPP LAKE RETREAT sleeps 7 and is a great place to make Adirondack memories!
• Secluded and Cozy Townhome at Tripp Lake
• Welcome home!
• The Roost, a lakefront 4 season home in the Adirondack Mountains
• Relax at Our River Retreat
• Rustic Adirondack Retreat on Tripp Lake
• Lakefront home steps away from a private, gentle sloping sandy beach & fire pit.
• Modern Cabin w/Hot Tub-Minutes to Lakes & Skiing
• Same local favorite, an even better nightly rate, and now with NO CLEANING FEE!

There are many large, family-friendly vacation homes available in Chestertown; however, here are the most popular family rentals listed on our site:

• 21 Mi to Gore Mtn: Adirondack Oasis w/Sauna
• Loon Lake Lakefront 4 Bedroom Four Season retreat
• Comfortable year round Lake house on Loon Lake perfect for a getaway
• Elizabeth. A Guest House Near Lake George.
• Solitude at Lake's End
• Lakefront cabin with beautiful views, lake and beach access
• Two Houses on One Magnificent Property

Yes, there are 3 self-catering vacation homes in Chestertown that have hot tubs, swimming pools, & other amenities.

There are more than 3 luxury villas and vacation homes in or near Chestertown. Filter by price to compare find the most expensive places to stay on Unpluggedweekend.

Yes, there are 3 pet friendly vacation homes and places to stays that are available in or near Chestertown that you may consider.