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Search Guest Houses in Chestertown

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Guest Houses in Chestertown

No exact matches found, but these alternatives could be just right

Recommended hotels in Chestertown

Lobby
Comfort Inn & Suites Chestertown

Comfort Inn & Suites Chestertown

2.5 star property
Chestertown
8.6 out of 10, Excellent, (848)
"The room was a great size and very clean. The staff were very accommodating and friendly. The amenities were very good. We would definitely recommend this hotel. "
United States
Santa
$102 nightly
The price is $113
Nov 23 - Nov 24
Total with taxes and fees
Comfort Inn & Suites Chestertown
Private beach nearby, sun loungers, beach volleyball
The Lodge at Great Oak Landing

The Lodge at Great Oak Landing

3.5 star property
Chestertown
8.0 out of 10, Very Good, (75)
"Very nice rooms, "
United States
Stephania
$113 nightly
The price is $126
Nov 19 - Nov 20
Total with taxes and fees
The Lodge at Great Oak Landing
Suite, Multiple Beds, Non Smoking | 1 bedroom, desk, laptop workspace, blackout drapes
Red Roof Inn & Suites Chestertown

Red Roof Inn & Suites Chestertown

2.0 star property
Chestertown
7.2 out of 10, Good, (416)
"This property was clean but dated. The carpet was stained, the furniture and fixtures were worn and broken, towels were washed but old and in need of replacement."
United States
Derek
$72 nightly
The price is $80
Nov 30 - Dec 1
Total with taxes and fees
Red Roof Inn & Suites Chestertown
Property grounds
First Floor Studio Apartment in Historic Chestertown

First Floor Studio Apartment in Historic Chestertown

Chestertown
9.6 out of 10, Exceptional, (106)
"Amazing and neat and very private "
United States
Alexander M.
$144 nightly
The price is $159
Nov 19 - Nov 20
Total with taxes and fees
First Floor Studio Apartment in Historic Chestertown
Restaurant
Hampton Inn & Suites Edgewood/Aberdeen-South

Hampton Inn & Suites Edgewood/Aberdeen-South

2.5 star property
Edgewood
9.4 out of 10, Exceptional, (1004)
"Would stay again"
United States
Dena
$82 nightly
The price is $91
Nov 25 - Nov 26
Total with taxes and fees
Hampton Inn & Suites Edgewood/Aberdeen-South
Exterior
La Quinta Inn & Suites by Wyndham Aberdeen-APG

La Quinta Inn & Suites by Wyndham Aberdeen-APG

3.0 star property
Aberdeen
9.0 out of 10, Wonderful, (1006)
"The room was nice the bed comfy, the staff was friendly "
United States
Kenya
$93 nightly
The price is $104
Nov 23 - Nov 24
Total with taxes and fees
La Quinta Inn & Suites by Wyndham Aberdeen-APG
Lobby
Fairfield Inn & Suites by Marriott Middletown

Fairfield Inn & Suites by Marriott Middletown

2.5 star property
Middletown
9.2 out of 10, Wonderful, (305)
"Great overall experience "
United States
Clement
$108 nightly
The price is $120
Nov 23 - Nov 24
Total with taxes and fees
Fairfield Inn & Suites by Marriott Middletown
Free daily self-serve breakfast
Quality Inn

Quality Inn

2.5 star property
Smyrna
7.6 out of 10, Good, (1000)
"Everything was great!! Checked in with ease and staff was great!!"
United States
Tonya
$68 nightly
The price is $75
Dec 18 - Dec 19
Total with taxes and fees
Quality Inn
Restaurant
Hampton Inn & Suites Baltimore/Aberdeen

Hampton Inn & Suites Baltimore/Aberdeen

2.5 star property
Aberdeen
9.0 out of 10, Wonderful, (590)
"Wonderful room and location "
United States
Caren
$90 nightly
The price is $101
Nov 25 - Nov 26
Total with taxes and fees
Hampton Inn & Suites Baltimore/Aberdeen
Exterior
Holiday Inn Express Edgewood-Aberdeen-Bel Air by IHG

Holiday Inn Express Edgewood-Aberdeen-Bel Air by IHG

2.5 star property
Edgewood
9.0 out of 10, Wonderful, (539)
"Super clean, a great place to stay"
United States
Diana
$87 nightly
The price is $97
Dec 8 - Dec 9
Total with taxes and fees
Holiday Inn Express Edgewood-Aberdeen-Bel Air by IHG
View from property
TownePlace Suites by Marriott Edgewood Aberdeen

TownePlace Suites by Marriott Edgewood Aberdeen

3.0 star property
Aberdeen
9.0 out of 10, Wonderful, (90)
"Breakfast was good."
United States
Romelle
$97 nightly
The price is $109
Dec 8 - Dec 9
Total with taxes and fees
TownePlace Suites by Marriott Edgewood Aberdeen
Desk, free WiFi, bed sheets, alarm clocks
Quality Inn & Suites Bel Air I-95 Exit 77A

Quality Inn & Suites Bel Air I-95 Exit 77A

2.5 star property
Edgewood
7.4 out of 10, Good, (1017)
"Nice place to stay"
United States
Patrick
$63 nightly
The price is $71
Nov 19 - Nov 20
Total with taxes and fees
Quality Inn & Suites Bel Air I-95 Exit 77A
Lobby lounge
Courtyard Aberdeen at Ripken Stadium

Courtyard Aberdeen at Ripken Stadium

3.0 star property
Aberdeen
8.6 out of 10, Excellent, (214)
"Excellent place to stay. A wonderful maid helped us. Room great and food excellent evening and morning."
United States
Bartley
$84 nightly
The price is $94
Dec 4 - Dec 5
Total with taxes and fees
Courtyard Aberdeen at Ripken Stadium
Basic Single Room | Desk, free WiFi, bed sheets
Motel Edgewood

Motel Edgewood

2.0 star property
Edgewood
7.6 out of 10, Good, (9)
"Bed was clean and crisply made. Occupants were respectful of sleeping hours. Check-in and check-out were simple. Parking was convenient and had easy access to the highway."
United States
Nancy
$60 nightly
The price is $68
Nov 19 - Nov 20
Total with taxes and fees
Motel Edgewood
Reception
Hampton Inn Middletown

Hampton Inn Middletown

2.5 star property
Middletown
8.8 out of 10, Excellent, (854)
"Enjoyed the amenities and great location for shops nearby "
United States
Erica
$103 nightly
The price is $115
Dec 1 - Dec 2
Total with taxes and fees
Hampton Inn Middletown
Studio Suite, 1 King Bed with Sofa bed, Non Smoking | Free WiFi, bed sheets
La Quinta Inn & Suites by Wyndham Bel Air/I-95 Exit 77A

La Quinta Inn & Suites by Wyndham Bel Air/I-95 Exit 77A

3.0 star property
Edgewood
8.2 out of 10, Very Good, (1000)
"Our stay was very good enjoyed the continental breakfast and how close the hotel was to other amenities "
United States
ANNIE
$79 nightly
The price is $88
Nov 19 - Nov 20
Total with taxes and fees
La Quinta Inn & Suites by Wyndham Bel Air/I-95 Exit 77A
Terrace/patio
Hilton Garden Inn Kent Island Marina

Hilton Garden Inn Kent Island Marina

3.0 star property
Grasonville
9.0 out of 10, Wonderful, (1000)
"Easy parking and check in. Conveniently located within walking distance of some great seafood restaurants. Always an enjoyable stay"
United States
Roberta
$95 nightly
The price is $106
Nov 25 - Nov 26
Total with taxes and fees
Hilton Garden Inn Kent Island Marina
Suite, 1 Queen Bed, Non Smoking | In-room safe, iron/ironing board, free WiFi, bed sheets
Quality Inn

Quality Inn

2.5 star property
Grasonville
7.8 out of 10, Good, (851)
"room was nice breakfast was good and the staff was very friendly and helpful. "
United States
Esai
$95 nightly
The price is $105
Dec 10 - Dec 11
Total with taxes and fees
Quality Inn
Lake
Inn at Huntingfield Creek

Inn at Huntingfield Creek

3.5 star property
Rock Hall
10.0 out of 10, Exceptional, (56)
"We stayed one night for our Anniversary, and the stay was so peaceful. The grounds are beautiful, the staff so nice, and the main house is amazing. We definitely plan on making this an annual thing!"
United States
Aaron
$144 nightly
The price is $160
Dec 1 - Dec 2
Total with taxes and fees
Inn at Huntingfield Creek
Exterior
Holiday Inn Express & Suites Middletown by IHG

Holiday Inn Express & Suites Middletown by IHG

2.5 star property
Middletown
9.2 out of 10, Wonderful, (639)
"This was a great relaxing stay"
United States
Pamela
$116 nightly
The price is $129
Nov 23 - Nov 24
Total with taxes and fees
Holiday Inn Express & Suites Middletown by IHG
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.
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Top Chestertown Hotel Reviews

Historic Inns of Annapolis

Historic Inns of Annapolis

10/10 Excellent
"."
Kristine 1-night trip
Posted 20 hours ago
Historic Inns of Annapolis

Find out more about Chestertown

Chestertown Guest Houses information

Number of reviews
11,606
Accommodation
17 Guest Houses
Lowest Price
$68
Highest Price
$160

Frequently asked questions

What is the nightly rate for a guest house in Chestertown?
Rates for Chestertown guest houses vary, but travelers can find great-value prices from $68 with Expedia. A range of factors can affect nightly rates, such as the location, the breakfast offering, and the range of amenities. Travelers looking for a good deal should consider looking for a midweek stay, as weekend rates at Chestertown guest houses tend to be higher. Remember to also use our filters to sort prices from low to high.
What's the difference between a Chestertown guest house and a B&B?
A guest house in Chestertown is typically a larger establishment with more rooms, offering a more hotel-like experience, and may provide additional amenities including luxury bedding. In contrast, a B&B is usually a smaller property that focuses primarily on providing a room and breakfast. A B&B is often more personal, and breakfast is typically included as part of the stay, but other services might be more limited compared to a guest house.

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