Chestertown hotels

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Chestertown, MD, United States
Oct 28 — Oct 292
Chestertown, MD, United States
Thu 28/10
Fri 29/10

Good to know

Cheapest month to stay with an average 20% drop in price.
Most expensive month to stay with an average 17% rise in price.
Average Sun - Thu price over the last 2 weeks.
Average Fri & Sat price over the last 2 weeks.

Low season

June

High season

December

Average price (weeknight)

R2 137

Average price (weekend night)

R2 759

Best Chestertown hotels

Most recommended Chestertown hotels

Show all
Comfort Inn & Suites - Chestertown - Building
Comfort Inn & Suites
8 Excellent
R124+
R124+
Parking
Free Wi-Fi
Pet-friendly
Air conditioning
Brampton Bed and Breakfast Inn - Chestertown - Bedroom
R277+
Free Wi-Fi
Pet-friendly
Air conditioning
Driftwood Inn - Chestertown - Building
Driftwood Inn - Chestertown - Building
Driftwood Inn
5.6 Okay
R72+
R72+
Parking
Free Wi-Fi
Pet-friendly
Air conditioning
Great Oak Manor - Chestertown - Dining room
Great Oak Manor - Chestertown - Dining room
Great Oak Manor
9.3 Excellent
R221+
R221+
Parking
Free Wi-Fi
Pet-friendly
Air conditioning
Beautiful Waterfront Estate - Chestertown
Beautiful Waterfront Estate - Chestertown
Beautiful Waterfront Estate
10 Excellent
R3 386+
R3 386+
Pool
Air conditioning
Manor House on Beautiful Eastern Shore Estate - Chestertown
Manor House on Beautiful Eastern Shore Estate - Chestertown
Free Wi-Fi
Pool
Pet-friendly
Air conditioning

When to book a hotel in Chestertown

Price per night / 3-star hotel. Prices are not fixed and may vary with time.
Average nightly price per month
Average nightly price

Top tips for finding perfect Chestertown hotel deals

  • If you’re looking for a cheap hotel in Chestertown, you should consider visiting during the low season. You'll find cheaper accommodations in Chestertown in June and July.
  • Hotel room prices vary depending on many factors but you’ll most likely find the best hotel deals in Chestertown if you stay on a Sunday. The opposite is true for, Tuesday, which is usually the most expensive day.

FAQs when booking a hotel in Chestertown

  • Hotels are safe environments for travellers as long as they properly implement sanitary measures in response to coronavirus (COVID-19). However, we recommend getting in touch with the local authorities regarding safety procedures for hotels in Chestertown. For more advice, please view our information page on what to know about coronavirus (COVID-19) and travel.

  • After you launch a hotel search on KAYAK, you can refine your research by neighbourhood, which allows you to pick the central Chestertown districts. You can also do a search using the city map to choose a specific location, like Chestertown city centre

  • Take a look at our extensive hotel map to find the best hotels near you.

Where to stay in Chestertown?

Our map will help you find the perfect place to stay in Chestertown by showing you the exact location of each hotel.