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
R124+R124+
Parking
Free Wi-Fi
Pet-friendly
Air conditioning
R277+
Free Wi-Fi
Pet-friendly
Air conditioning
Red Roof Inn & Suites Chestertown - Chestertown - Living room![Red Roof Inn & Suites Chestertown - Chestertown - Living room]()
R131+
Parking
Free Wi-Fi
Pool
Pet-friendly
Driftwood Inn - Chestertown - Building![Driftwood Inn - Chestertown - Building]()
Driftwood Inn
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
R221+R221+
Parking
Free Wi-Fi
Pet-friendly
Air conditioning
Inn At Mitchell House - Chestertown![Inn At Mitchell House - Chestertown]()
R167+
Free Wi-Fi
Carriage House Hideaway in Middle of Chestertown - Chestertown![Carriage House Hideaway in Middle of Chestertown - Chestertown]()
Free Wi-Fi
Pet-friendly
John L Stam House - Chestertown - Bedroom![John L Stam House - Chestertown - Bedroom]()
John L Stam House
R211+R211+
Free Wi-Fi
Air conditioning
Chester River Waterfront, Magnificent Views, Dock, Beach, Close 2 Town - Chestertown![Chester River Waterfront, Magnificent Views, Dock, Beach, Close 2 Town - Chestertown]()
Parking
Free Wi-Fi
Pet-friendly
Air conditioning
Chestertown's Pet-Friendly Little Red Cottage - Chestertown![Chestertown's Pet-Friendly Little Red Cottage - Chestertown]()
Pet-friendly
Air conditioning
Charming Chestertown Waterfront Cottage - Chestertown![Charming Chestertown Waterfront Cottage - Chestertown]()
R425+
Air conditioning
Beautiful home for a family vacation - Chestertown![Beautiful home for a family vacation - Chestertown]()
R681+
Free Wi-Fi
Pet-friendly
Air conditioning
Water Front Retreat - Sunrise and Sunset Water Views - Chestertown![Water Front Retreat - Sunrise and Sunset Water Views - Chestertown]()
Free Wi-Fi
Pet-friendly
Air conditioning
Beautiful Waterfront Estate - Chestertown![Beautiful Waterfront Estate - Chestertown]()
Beautiful Waterfront Estate
R3 386+R3 386+
Pool
Air conditioning
Cottage within walking distance to the Bay! - Chestertown![Cottage within walking distance to the Bay! - Chestertown]()
Air conditioning
Manor House on Beautiful Eastern Shore Estate - Chestertown![Manor House on Beautiful Eastern Shore Estate - Chestertown]()
R1 491+
Free Wi-Fi
Pool
Pet-friendly
Air conditioning
Country Estate in Historic District - Chestertown![Country Estate in Historic District - Chestertown]()
R354+
Pet-friendly
Air conditioning
Carefree Elegance on the Bay, Chestertown MD - Chestertown![Carefree Elegance on the Bay, Chestertown MD - Chestertown]()
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.