Chestertown hotels

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Chestertown, MD
Jan 23 — Jan 242
Chestertown, MD
Sun 1/23
Mon 1/24

Good to know

Low season

June

High season

December

Average price (weeknight)

$145

Average price (weekend night)

$187
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.

Best Chestertown hotels

Most recommended Chestertown hotels

Show all
Brampton Bed and Breakfast Inn - Chestertown - Bedroom
$292+
Free Wi-Fi
Pet friendly
Driftwood Inn - Chestertown - Building
Driftwood Inn
5.7 Okay
$72+
$72+
Parking
Free Wi-Fi
Pet friendly
Great Oak Manor - Chestertown - Dining room
Great Oak Manor - Chestertown - Dining room
Great Oak Manor
9.1 Excellent
$228+
$228+
Parking
Free Wi-Fi
Pet friendly
Spa

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.
  • How long should you stay? KAYAK users usually book their accommodation in Chestertown for 2 days.

FAQs when booking a hotel in Chestertown

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.

Accommodations in Chestertown