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Chestertown Winter Rentals & Holiday Homes
Discover winter rentals Chestertown - We found 175 exact matches
When do you want to travel?
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- Private Beach
- Air Conditioner
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Frequently Asked Questions About Chestertown Winter Rental
What are the top rated Winter 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 Winter 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
- Lakefront Home - 20 Min from Gore Mountain w/Hot Tub
- Historic 1860s Farmhouse, Private Fishing Pond, Canoe, Hot Tub, Walk to Town.
- #7 Adirondack@Birchwood Cottages on Loon Lake. Family Friendly Waterfront
- Family Friendly 3BR 3.5BA Lodge w/Lake & Beach, Screened Patio, Grill, Sunroom
- Forest Lake Haven close to Lake George and Gore Mountain, 5 BR spacious and NEW
How much does it cost to rent a place to stay near Chestertown in the wintertime?
The average cost for winter rentals in Chestertown is $375 per night. Whisperingpinescottages has a wide list of great winter places to stay near Chestertown that would suit your preferences. There are single and multiple rooms for solo trips or family vacations.
Are there any winter cottages/chalets in Chestertown that allow pets?
Yes, here are the top cottage/chalet rentals in Chestertown that allow you to bring your pet or dog:
- A beautiful lake view cabin on Friends Lake
- Two Houses on One Magnificent Property
- The Fern Lodge
- Elizabeth. 15 minutes to Lake George.
See all pet-friendly vacation rentals in Chestertown on Whisperingpinescottages
Do you have any winter rentals in Chestertown that are suitable for families?
Most of our rentals homes are suitable for families. Check out the complete list of places to stay in Chestertown to find what works for you.
Are there winter accommodations in Chestertown that have indoor swimming pools?
As of 2026, the data from Whisperingpinescottages shows that there are over 175 private swimming pools or indoor pools accommodations near Chestertown along with other great amenities.