Chestertown Hotels

Start date: Check-in selected.
To Date
End date: Check-out
  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

Filter by

Guest rating
Guest rating
Star rating

Top 10 trending Chestertown hotels

Comfort Inn & Suites Chestertown

2.5 star property
Chestertown
8.6 out of 10, Excellent, (847)
"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
The price is P6,024
P6,686 total
includes taxes & fees
Nov 19 - Nov 20
Comfort 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
The price is P4,252
P4,720 total
includes taxes & fees
Nov 30 - Dec 1
Red Roof Inn & Suites Chestertown

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
The price is P5,846
P6,684 total
includes taxes & fees
Nov 17 - Nov 18
The Lodge at Great Oak Landing

La Quinta Inn & Suites by Wyndham Baltimore N / White Marsh

3.0 star property
Rosedale
7.0 out of 10, Good, (1060)
"Easy check in and out. "
United States
Andrew
The price is P3,969
P4,584 total
includes taxes & fees
Dec 9 - Dec 10
La Quinta Inn & Suites by Wyndham Baltimore N / White Marsh

Holiday Inn Express Annapolis East-Kent Island by IHG

2.5 star property
Grasonville
9.2 out of 10, Wonderful, (921)
"The hotel was nice and clean and the staff was always polite and helpful. "
United States
William
The price is P6,319
P7,014 total
includes taxes & fees
Dec 15 - Dec 16
Holiday Inn Express Annapolis East-Kent Island by IHG

Country Inn & Suites by Radisson, Baltimore North, MD

3.0 star property
Rossville
7.2 out of 10, Good, (1003)
"The reason I booked this hotel was because it had a hot tub and pool. These were both closed for "the season" without notification. If I knew that, I would have booked elsewhere. Everything else was just ok."
Canada
Brian
The price is P5,108
P5,899 total
includes taxes & fees
Dec 7 - Dec 8
Country Inn & Suites by Radisson, Baltimore North, MD

Best Western Plus Hotel & Conference Center

2.5 star property
Medford
7.8 out of 10, Good, (1003)
"Great stay"
United States
Diedre
The price is P6,832
P8,028 total
includes taxes & fees
Dec 1 - Dec 2
Best Western Plus Hotel & Conference Center

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

2.5 star property
Edgewood
7.4 out of 10, Good, (1004)
"It was good for the price and a convenient location, for what I needed to do. Staff was friendly and helpful. Room was clean, bed very comfortable."
United States
Clyde
The price is P3,720
P4,167 total
includes taxes & fees
Nov 17 - Nov 18
Quality Inn & Suites Bel Air I-95 Exit 77A

Hampton Inn & Suites Edgewood/Aberdeen-South

2.5 star property
Edgewood
9.4 out of 10, Exceptional, (1001)
"Very good breakfast options Convenient parking Clean room Friendly staff"
United States
Alexander
The price is P4,819
P5,397 total
includes taxes & fees
Nov 23 - Nov 24
Hampton Inn & Suites Edgewood/Aberdeen-South

Fairfield Inn & Suites by Marriott White Marsh

2.5 star property
Nottingham
8.6 out of 10, Excellent, (1005)
"Great place to stay"
United States
Teresa
The price is P5,150
P5,948 total
includes taxes & fees
Nov 29 - Nov 30
Fairfield Inn & Suites by Marriott White Marsh

Super 8 by Wyndham Baltimore/Essex Area

2.0 star property
Essex
5.4 out of 10, (404)
"disgusting hotel cockroaches, bed bugs, and mice. The worst customer service, which refused to let us check out or get a refund. "
United States
tamer
The price is P4,665
P5,388 total
includes taxes & fees
Nov 30 - Dec 1
Super 8 by Wyndham Baltimore/Essex Area

Americas Best Value Inn Edgewood

2.0 star property
Edgewood
5.6 out of 10, (1003)
"I love staying here. The prices are always reasonable, the staff are always so nice & helpful. The area is kept clean there's stores close to this hotel all around so convient! "
United States
Christeena
The price is P3,012
P3,373 total
includes taxes & fees
Nov 17 - Nov 18
Americas Best Value Inn Edgewood

Comfort Inn & Suites Aberdeen near APG

2.5 star property
Aberdeen
7.8 out of 10, Good, (796)
"Friendly staff; great sized room & walk in shower. Great for traveling through stay! Thank you!"
United States
Nancy
The price is P5,220
P5,847 total
includes taxes & fees
Nov 23 - Nov 24
Comfort Inn & Suites Aberdeen near APG

Hyatt Place Kent Narrows & Marina

3.0 star property
Grasonville
9.4 out of 10, Exceptional, (655)
"My favorite hotel "
United States
Jen
The price is P9,390
P10,423 total
includes taxes & fees
Nov 17 - Nov 18
Hyatt Place Kent Narrows & Marina

Hampton Inn Baltimore Bayview Campus

3.5 star property
Pulaski Industrial Area
8.8 out of 10, Excellent, (1004)
"Great stay as always!"
United States
Eunice
The price is P6,567
P7,716 total
includes taxes & fees
Nov 23 - Nov 24
Hampton Inn Baltimore Bayview Campus

Hampton Inn & Suites Baltimore/Aberdeen

2.5 star property
Aberdeen
9.0 out of 10, Wonderful, (590)
"Great stay!"
United States
Barbara
The price is P5,339
P5,979 total
includes taxes & fees
Dec 8 - Dec 9
Hampton Inn & Suites Baltimore/Aberdeen

Hampton Inn Baltimore/White Marsh

2.5 star property
Nottingham
7.8 out of 10, Good, (1002)
"Breakfast lady fabulous Staff very friendly "
United Kingdom
Alan
The price is P5,150
P5,948 total
includes taxes & fees
Nov 23 - Nov 24
Hampton Inn Baltimore/White Marsh

Kent Island Resort

3.5 star property
Stevensville
9.2 out of 10, Wonderful, (124)
"The property is very charming and the staff was extremely attentive and friendly. It's a beautiful area. Close to Annapolis and a lot of fun things to do."
United States
Michael
The price is P10,571
P13,928 total
includes taxes & fees
Dec 1 - Dec 2
Kent Island Resort

Hilton Garden Inn Kent Island Marina

3.0 star property
Grasonville
9.0 out of 10, Wonderful, (1000)
"Our view was spectacular and the room was immaculate. Staff was friendly and welcoming. It was close to several restaurants. "
United States
Patricia
The price is P6,009
P6,670 total
includes taxes & fees
Nov 23 - Nov 24
Hilton Garden Inn Kent Island Marina

Super 8 by Wyndham Aberdeen MD

2.0 star property
Aberdeen
7.0 out of 10, Good, (854)
"Nice and clean. Staff was friendly. I had no problems whatsoever, and I would stay here again."
United States
Shelly
The price is P3,062
P3,429 total
includes taxes & fees
Dec 15 - Dec 16
Super 8 by Wyndham Aberdeen MD
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.
Save an average of 15% on thousands of hotels when you're signed in

Stay near popular Chestertown attractions

Learn more about Chestertown

Colonial charm meets Chesapeake Bay beauty in this historic waterfront town where 18th-century buildings house art galleries and boutiques. Rent kayaks to explore the Chester River or time your visit for the Downrigging Weekend Festival when tall ships transform the harbor.

Aerial summer view of colonial Chestertown on the Chesapeake Bay in Maryland USA

Top Chestertown Hotel Reviews

More cheap stays in Chestertown

Frequently asked questions

Where is the best place for a stay in Chestertown?
Comfort Inn & Suites Chestertown is a favorite property for Expedia customers. This hotel offers free breakfast and free parking. Reviews from our site also recommend The Lodge at Great Oak Landing and Red Roof Inn & Suites Chestertown as top options for your trip. See all available top hotels, or vacation rentals in Chestertown.
If I need to cancel my hotel reservation in Chestertown, will I receive a refund?
Yes, most hotel bookings are fully refundable as long as you cancel before the hotel's cancellation deadline, which often is within 24-48 hours of your scheduled arrival. If your reservation is non-refundable, you may still be able to cancel and get a refund within a 24-hour period of your booking. Filter your search by fully refundable to find flexible hotel deals in Chestertown.
What's the best hotel for families in Chestertown?
Comfort Inn & Suites Chestertown is a hotel with free parking and free full breakfast, and it's a top choice on Expedia for families. Red Roof Inn & Suites Chestertown is another good option for your kid-friendly vacation. Kids of all ages will also enjoy a visit to Crumpton Auction. Find more child-friendly accommodations in Chestertown.
What's the best LGBTQ-friendly accommodation in Chestertown?
Comfort Inn & Suites Chestertown is a top LGBTQ-friendly hotel, and features free breakfast and free WiFi. Red Roof Inn & Suites Chestertown and The Lodge at Great Oak Landing are other good options for your trip. See all available hotels listed as LGBTQ-friendly in Chestertown.
What's the best pet-friendly hotel in Chestertown?
Comfort Inn & Suites Chestertown is a top hotel for people traveling with their pets, and offers a seasonal outdoor pool and a fitness center for its human guests. Other good options to stay with your pet include Red Roof Inn & Suites Chestertown and Driftwood Inn. See more pet-friendly hotel accommodations in Chestertown.
What's the best hotel to stay near the beach in Chestertown?
The Lodge at Great Oak Landing is a top lodge with a seasonal outdoor pool and 3 bars/lounges, and it's located near a private beach. See more stays near the beach in Chestertown.
What are some accommodations with pools in Chestertown?
The Lodge at Great Oak Landing is a top lodge with a seasonal outdoor pool, 3 bars, and free WiFi. View all hotels with pools in Chestertown.
How is it to stay in Chestertown?
Visitors to Chestertown are sure to enjoy the university setting. Tourists can also enjoy the city's sporting events, festivals, and art. In Chestertown, there are 39 hotels and other accommodations to choose from. Find out more about Chestertown.
What are the top places to visit in Chestertown?
Cultural venues include Historical Society of Kent County Maryland and Garfield Center for the Arts at the Prince Theater. The picturesque setting of Northern Chesapeake Bay and Chesapeake Bay exemplify the area's natural beauty. University life is a highlight and campuses to tour include Washington College and River Arts Chestertown. Check out what more to see and do in Expedia's Chestertown guide.
What's the seasonal weather like in Chestertown?
The hottest months are usually July and August with an average temp of 74°F, while the coldest months are January and February with an average of 39°F. Average annual precipitation for Chestertown is 48 inches.

Explore a world of travel with Expedia