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Hotels in Chestertown

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Last Minute Hot Rate® Hotel Deals in Chestertown

We Hide Hotel Names So You Can Find 4-Star Hotels At 2-Star Prices. Choose the Location, Star Rating & Amenities. Let Hotwire Find You the Best Deal. Book Today!

Choose from 107 Chestertown Hotel Deals

Friends Lake Inn
Friends Lake Inn
4 out of 5
963 Friends Lake Rd, Chestertown, NY, 12817
  • 23 min walk from Friends Lake
The price is $176 per night from Feb 5 to Feb 6
per night
Feb 5 - Feb 6
Stay at this 4-star spa hotel in Chestertown. Enjoy free WiFi, free parking, and a full-service spa. Our guests praise the pool and the helpful staff in our ...
4.5/5 Wonderful! (75 reviews)
"Stay was off season, mid week. Quiet, Dove room was nice and cozy. Bed comfortable and warm. Breakfast offered in the am, staff friendly and helpful. Yeah nice…"

Reviewed on Sep 29, 2022

Friends Lake Inn
The Fern Lodge
The Fern Lodge
3.5 out of 5
46 Fiddlehead Bay Rd., Chestertown, NY, 12817
  • 7 min walk from Friends Lake
The price is $544 per night from Feb 3 to Feb 4
per night
Feb 3 - Feb 4
Stay at this 3.5-star beach B&B in Chestertown. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast in our reviews. Popular attractions ...
4.9/5 Exceptional! (28 reviews)
"There is not enough words to describe how amazing this place is. Wendy was very helpful and friendly. She upgraded our room so we stayed at Birch. Every little detail in that room was done very tastefully. Will definitely stay again."

Reviewed on Dec 14, 2022

The Fern Lodge
Pine Tree Motel & Cabins
Pine Tree Motel & Cabins
2 out of 5
5537 State Route 8, Chestertown, NY, 12817
  • 7 min drive from Friends Lake
Stay at this motel in Chestertown. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff and the comfy rooms in our reviews. ...
4.6/5 Wonderful! (100 reviews)
"Friendly, family owned business. Clean, neat, old style rooms with real keys."

Reviewed on Oct 17, 2022

Pine Tree Motel & Cabins
The Loft at The Remington
The Loft at The Remington
3.5 out of 5
6369 Main Street, Chestertown, NY, 12817
  • 8 min drive from Friends Lake
Stay at this 3.5-star business-friendly B&B in Chestertown. Enjoy free breakfast, free parking, and a flat-screen TV. Popular attractions Loon Lake Beach and ...
The Loft at The Remington
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

HOTW-Hotel-Deals-726-959@2x.jpg (1918×258)*Savings based on Hot Rate® hotel bookings as compared with the lowest published rates found on leading retail travel sites. Hot Rates are different from retail rates. With Hot Rates you enter the date, location and star rating. Hotel revealed only after booking. All bookings final.

Find cheap hotels in Chestertown

You’re not an average traveler—and Hotwire knows it. Your wanderlust takes you off the beaten path to discover unique adventures and every travel destination’s lesser-known tourist scenes. Hotwire has the hookup! Book your Chestertown hotel with Hotwire to complete your one-of-a-kind travel checklist.

For you, intrepid voyager, Hotwire has a large selection of the best hotels in Chestertown.

Choosing the right hotel in New York has everything to do with the way you want your trip to go. If you’ve scribbled a few obscure destinations on your itinerary, you probably already have a good sense of how your getaway is taking shape. Lean into that by booking one of Chestertown’s 107 hotels. Choose the one that best catches your trip’s tourist drift.

If you’re traveling during the week for business, Hotwire can score you a luxury hotel for as low as $109. In town for pleasure? Hotwire still has you covered. If you’re in the mood for a quick last-minute weekend getaway or spa retreat, you can get up to 60% Chestertown hotel deals at the last minute.

While traveling, where you stay plays a major role in your overall vacation enjoyment. Choosing the right hotel is just as important as making sure you book the right flight and car rental. If you’re traveling with family or friends, you may need to book a hotel with connecting rooms. If you enjoy an elegant and relaxing hotel ambiance, opt for one of Hotwire’s luxury hotels in Chestertown. No matter your reason for visiting Chestertown, with Hotwire’s large selection of hotels in the area, you’re sure to book a hotel that meets all your accommodation needs.

Frequently Asked Questions About Chestertown hotels

Where can I find the best last-minute travel deals?

If you’re traveling in the spirit of spontaneity, you’ll love the idea of leaving your exact hotel choice up to chance. With Hotwire Hot Rates, you can save up to 60% off your next flight, hotel, or car rental. Just plug in your general preferences and let Hotwire choose last-minute hotel deals in Chestertown for as low as $109.

How many hotels are there in Chestertown?

With over 107 hotels in Chestertown, you’re sure to find one that best matches your travel mood. When you book with Hotwire, you can score a stellar home away from home for as low as $109.

How to find cheap car rentals in Chestertown?

Finding a cheap car rental deal in Chestertown is as easy as scoring cheap hotels in Chestertown. Hotwire partners with top-of-the-line car rental companies to bring you a large selection of affordable options. Whether you’re in need of a large SUV for the entire family or a more compact but stylish vehicle, Hotwire has you covered. You can even save up to 60% off a car rental deal if you book a Hotwire Hot Rate at the last minute.

Is it safe to travel to Chestertown now?

With recent COVID-19 closures and reopenings, many people are wondering, “Is it safe to travel to Chestertown right now?” When it’s time to book your getaway, be sure to check out the most up-to-date information on all safety measures, any restrictions, and guidance on traveling during the coronavirus pandemic.


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