1# Most popular
Driftwood Inn
$63
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How Much Does a Hotel in Chestertown Cost?
Good to know
Low Season
August
cheapest month to stay
18%
expected price decrease
High Season
October
most expensive time to stay
20%
expected price increase
Average price (weekend night):
$193
(price in the last 3 days)
Fri & Sat
(weekend night)
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
Where to stay in Chestertown?
Our Heatmaps tool will help you find the perfect place to stay in Chestertown by showing you how close hotel options are to major activities
Best Chestertown Hotels
Details
Reviews
Overall 9.8 Excellent
Based on 233 reviews
Cleanliness
10.0
Breakfast
10.0
Value for money
10.0
Service
10.0
Amenities
9.9
Food
9.6
Vibe
9.5
Location
9.4
Comfort
8.5
Room
8.5
Parking
Details
Reviews
Overall 9.6 Excellent
Based on 43 reviews
Service
10.0
Location
10.0
Amenities
9.7
Room
9.0
Breakfast
8.9
Comfort
8.8
Service
10.0
Amenities
9.7
Room
9.0
10.0 Excellent
Pros: Remote and lovely location, pet friendly, historic charm
Cons:
Parking
Details
Reviews
Overall 9.7 Excellent
Based on 28 reviews
Service
10.0
Location
9.0
Room
8.0
Breakfast
8.0
Comfort
6.7
Service
10.0
Location
8.9
Breakfast
8.0
Room
7.7
Comfort
6.2
Offering an outdoor pool and a restaurant, Inn at Osprey Point is located in Rock Hall. Free WiFi access is available. Each room here will provide you with a TV, air conditioning and cable channels. Private bathrooms also come with a bath or shower. Extras include a private pool and bed linen. A continental breakfast is offered at the Inn at Osprey Point. You will also find free bikes, meeting facilities and a children's playground. An array of activities can be enjoyed on site or in the surroundings, including kayaking and cycling. The property offers free parking. Baltimore - Washington International Airport is 22.4 miles away.
Details
Reviews
Overall 9.2 Excellent
Based on 38 reviews
Service
10.0
Location
10.0
Cleanliness
10.0
Breakfast
10.0
Amenities
8.3
Room
8.1
Comfort
7.0
Service
10.0
Location
10.0
Cleanliness
10.0
Breakfast
10.0
Amenities
8.6
Room
7.8
Showcasing a barbecue and views of the garden, Haven Point Inn is located in Rock Hall. Free private parking is available on site. The rooms are equipped with a flat-screen TV. Certain rooms feature a sitting area to relax in after a busy day. A terrace or balcony are featured in certain rooms. The rooms come with a private bathroom. For your comfort, you will find free toiletries and a hairdryer. You will find a gift shop at the property. Free use of bicycles is available at this hotel and the area is popular for biking. Baltimore is 22 miles from Haven Point Inn, and Annapolis is 17 miles from the property. Baltimore - Washington International Airport is 22 miles away.
Details
Reviews
Situated on the bay, Inn at Huntingfield Creek is a great choice for a stay in Rock Hall. Guests will have free perks like breakfast, WiFi, and self parking. Rooms offer upscale touches like fireplaces and jetted tubs, along with balconies or patios and living rooms.
Details
Reviews
Overall 8.6 Excellent
Based on 219 reviews
Food
10.0
Service
9.4
Value for money
9.3
Comfort
9.0
Location
8.8
Breakfast
8.4
Cleanliness
8.2
Room
7.9
Vibe
6.7
WiFi
6.3
Service
9.2
Comfort
9.2
Location
8.9
Cleanliness
8.5
Breakfast
8.5
Room
8.1
Service
9.5
Breakfast
8.5
Room
7.8
Service
9.3
7.7 Good
Pros: The location was very convenient to everything in Chestertown. Staff was friendly. Breakfast was pretty good.
Cons: Couldn't adjust the temp in the room. No movie rentals and no room service.
9.0 Excellent
Pros: Very nice room. Staff very helpful.
Cons: Needed a list of local restaurants.
Parking
Details
Reviews
Overall 7.9 Good
Based on 10 reviews
Situated on the bay, Mariners Motel is a great choice for a stay in Rock Hall. Guests can enjoy the outdoor pool or take advantage of nearby hiking/biking trails. Other highlights include a seasonal outdoor pool and a garden, and rooms offer refrigerators and free WiFi.
Details
Reviews
Overall 7.2 Good
Based on 58 reviews
10.0 Excellent
Pros: Breakfast was hot.
Cons: The heat lamp in bath was not working.
Parking
Details
Reviews
Overall 0.0 Poor
Based on reviews
Details
Reviews
Overall 3.7 Mediocre
Based on 131 reviews
Location
9.7
Value for money
5.9
Comfort
3.5
Service
3.3
Vibe
3.0
Room
2.5
Cleanliness
1.2
Comfort
3.4
Room
2.1
Room
2.2
Cleanliness
1.0
Room
2.6
3.4 Mediocre
Pros: Location is clise to the college within walking distance.
Cons: Room was dated. Wallpaper peeling off. The carpet needed replacement. Bathroom window would not close. Fire damaged rear section of motel.
3.1 Mediocre
Pros:
Cons: The room was not inviting or clean. There was no Wi-Fi or continental breakfast, even though both were advertised. The bed was on a slant and it was not very comfortable. It looked like a place were cops would keep their witnesses.
4.5 Okay
Pros: Leaving.
Cons: Everything. The place was dirty, disheveled and poorly maintained. The best view of the place was in the rearview mirror.
5.7 Okay
Pros: The price is right- 20-30% below surrounding motels. The room was adequately clean and quiet. I arrived at 11 PM and was gone by 7 AM - why pay more for 8 hrs?
I did not find it as bad as most negative reviews - you can't expect the Hilton at these prices.
Cons: Front desk folks were a bit unprofessional - run by a family not a business.
Parking
FAQs when booking a Hotel in Chestertown
How much is a cheap hotel in Chestertown?
KAYAK users have found double rooms in Chestertown for as cheap as $180 in the last 3 days. The average price is $57.
How can I find hotels near me?
Take a look at our extensive hotel Heatmaps to find the best hotels near you.