Discover the 2 Best Resorts in Chestertown
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About Chestertown Cottage Resorts on Vacation Cottage
Looking for accommodations? Numerous resorts offer condos and apartment-style units for reservation. Chestertown boasts a variety of nearby resorts, offering plentiful options for travelers. Access over 2 options resorts in the vicinity of Chestertown, along with exciting activities to enjoy during your stay.
In the Chestertown region, you'll find multiple resorts equipped with amenities such as gyms, WiFi, spas, private pools, and pet-friendly rooms. These resorts cater to various types of travelers: from honeymooners seeking romance to couples planning destination weddings, golf enthusiasts, or those attending conferences and business meetings.
Additionally, all-inclusive resorts in Chestertown cater to couples, families, and groups, accommodating both short-term and long-term stays. Vacation Cottage offers a wide array of resorts in or near Chestertown, serving as an excellent alternative to traditional vacation rentals and ensuring you discover the perfect lodging for your next trip.
Frequently Asked Questions About Chestertown Cottage Resorts
What is the best all-inclusive resort for families in Chestertown?
Most of our listed resorts are suitable for families in Chestertown. Filter your all-inclusive resorts Chestertown with a family-friendly option to see which ones are right for you.
Are there pools in resorts near Chestertown?
Yes, there are more than 2 resorts in Chestertown that have indoor and private swimming pools. Check out our filter option and find your best resort near Chestertown.
What is the price for luxury resorts in Chestertown?
At Vacation Cottage, the rate for luxury resorts in Chestertown per night starts from $56. Our partner provides these prices & we calculated the average daily rate in Chestertown. Please see our partner's price for more details.
Do you have resorts in Chestertown that allow pets?
Yes. We have all-inclusive resorts in Chestertown that allow pets. Some of the top pet-friendly resorts in Chestertown are:
- Three Bears, Immaculate 2 Bed/2.5 bath suite, Heat/AC & Washer/dryer
- Private room ∙ 2 guests
- Start your Adirondack escape at Cape Cotter! Near Gore Mountain and Lake George!
- Rustic Adirondacks Home with Hot Tub and Lake Access!
- 185 m² House ∙ 3 bedrooms ∙ 8 guests
- The Fern Lodge
You can see all pet-friendly places to stayin Chestertown on Vacation Cottage
What are the best resorts in Chestertown?
Most of the resorts are perfect for travelers, but based on guest reviews in 2025, the best resorts in or near Chestertown are:
- Three Bears, Immaculate 2 Bed/2.5 bath suite, Heat/AC & Washer/dryer
- Private room ∙ 2 guests
- Start your Adirondack escape at Cape Cotter! Near Gore Mountain and Lake George!
- Rustic Adirondacks Home with Hot Tub and Lake Access!
- 185 m² House ∙ 3 bedrooms ∙ 8 guests
- The Fern Lodge
Which resorts in Chestertown are romantic?
Some of the resorts in Chestertown have been described as romantic by other travelers:
