Photo by Patricia Knorr

Chestertown hotels from RM232

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
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

Tonight
12 Nov - 13 Nov
Tomorrow
13 Nov - 14 Nov
This weekend
14 Nov - 16 Nov
Next weekend
21 Nov - 23 Nov

Filter by

Guest rating
Guest rating
Star rating

Top 10 trending Chestertown hotels

Lobby
Comfort Inn & Suites Chestertown

Comfort Inn & Suites Chestertown

2.5 star property
Chestertown
8.6 out of 10, Excellent, (845)
"This property is clean and welcoming. We were pleasantly surprised. Check in was easy, and the room was great. Breakfast was wonderful! Great place to stay."
United States
Paula
The price is RM422
RM469 total
includes taxes & fees
16 Nov - 17 Nov
Comfort Inn & Suites Chestertown
1 bedroom, desk, laptop workspace, blackout curtains
Red Roof Inn & Suites Chestertown

Red Roof Inn & Suites Chestertown

2.0 star property
Chestertown
7.2 out of 10, Good, (414)
"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 RM298
RM331 total
includes taxes & fees
30 Nov - 1 Dec
Red Roof 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
The price is RM410
RM468 total
includes taxes & fees
16 Nov - 17 Nov
The Lodge at Great Oak Landing
Free daily buffet breakfast
La Quinta Inn & Suites by Wyndham Baltimore N / White Marsh

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

3.0 star property
Rosedale
7.0 out of 10, Good, (1058)
"Easy check in and out. "
United States
Andrew
The price is RM278
RM321 total
includes taxes & fees
11 Dec - 12 Dec
La Quinta Inn & Suites by Wyndham Baltimore N / White Marsh
Exterior
Holiday Inn Express Annapolis East-Kent Island by IHG

Holiday Inn Express Annapolis East-Kent Island by IHG

2.5 star property
Grasonville
9.2 out of 10, Wonderful, (917)
"The hotel was nice and clean and the staff was always polite and helpful. "
United States
William
The price is RM426
RM473 total
includes taxes & fees
16 Nov - 17 Nov
Holiday Inn Express Annapolis East-Kent Island by IHG
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, (1011)
"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 RM261
RM292 total
includes taxes & fees
16 Nov - 17 Nov
Quality Inn & Suites Bel Air I-95 Exit 77A
Exterior
Country Inn & Suites by Radisson, Baltimore North, MD

Country Inn & Suites by Radisson, Baltimore North, MD

3.0 star property
Rossville
7.2 out of 10, Good, (1000)
"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 RM375
RM433 total
includes taxes & fees
23 Nov - 24 Nov
Country Inn & Suites by Radisson, Baltimore North, MD
Lobby
Best Western Plus Hotel & Conference Center

Best Western Plus Hotel & Conference Center

2.5 star property
Medford
7.8 out of 10, Good, (1002)
"Great stay"
United States
Diedre
The price is RM479
RM563 total
includes taxes & fees
16 Nov - 17 Nov
Best Western Plus Hotel & Conference Center
Restaurant
Hampton Inn & Suites Edgewood/Aberdeen-South

Hampton Inn & Suites Edgewood/Aberdeen-South

2.5 star property
Edgewood
9.4 out of 10, Exceptional, (1002)
"Very good breakfast options Convenient parking Clean room Friendly staff"
United States
Alexander
The price is RM338
RM378 total
includes taxes & fees
20 Nov - 21 Nov
Hampton Inn & Suites Edgewood/Aberdeen-South
Lobby sitting area
Comfort Inn & Suites Aberdeen near APG

Comfort Inn & Suites Aberdeen near APG

2.5 star property
Aberdeen
7.8 out of 10, Good, (795)
"Friendly staff; great sized room & walk in shower. Great for traveling through stay! Thank you!"
United States
Nancy
The price is RM366
RM410 total
includes taxes & fees
17 Nov - 18 Nov
Comfort Inn & Suites Aberdeen near APG
Lobby sitting area
Americas Best Value Inn Edgewood

Americas Best Value Inn Edgewood

2.0 star property
Edgewood
5.6 out of 10, (1002)
"It was great"
United States
J Dacari
The price is RM211
RM236 total
includes taxes & fees
16 Nov - 17 Nov
Americas Best Value Inn Edgewood
Free daily buffet breakfast
Fairfield Inn & Suites by Marriott White Marsh

Fairfield Inn & Suites by Marriott White Marsh

2.5 star property
Nottingham
8.6 out of 10, Excellent, (1000)
"Great place to stay"
United States
Teresa
The price is RM391
RM451 total
includes taxes & fees
23 Nov - 24 Nov
Fairfield Inn & Suites by Marriott White Marsh
Terrace/patio
Hyatt Place Kent Narrows & Marina

Hyatt Place Kent Narrows & Marina

3.0 star property
Grasonville
9.4 out of 10, Exceptional, (652)
"My favorite hotel "
United States
Jen
The price is RM559
RM620 total
includes taxes & fees
18 Nov - 19 Nov
Hyatt Place Kent Narrows & Marina
Exterior
Super 8 by Wyndham Baltimore/Essex Area

Super 8 by Wyndham Baltimore/Essex Area

2.0 star property
Essex
5.4 out of 10, (403)
"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 RM348
RM402 total
includes taxes & fees
11 Dec - 12 Dec
Super 8 by Wyndham Baltimore/Essex Area
Exterior
Super 8 by Wyndham Aberdeen MD

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 RM208
RM232 total
includes taxes & fees
7 Dec - 8 Dec
Super 8 by Wyndham Aberdeen MD
Aerial view
Kent Island Resort

Kent Island Resort

3.5 star property
Stevensville
9.2 out of 10, Wonderful, (123)
"Hotel was great and peaceful. This hotel was water front. Nice surroundings!! I enjoyed to stay here."
United States
Chi
The price is RM741
RM976 total
includes taxes & fees
8 Dec - 9 Dec
Kent Island Resort
Restaurant
Hampton Inn & Suites Baltimore/Aberdeen

Hampton Inn & Suites Baltimore/Aberdeen

2.5 star property
Aberdeen
9.0 out of 10, Wonderful, (589)
"Great stay!"
United States
Barbara
The price is RM374
RM419 total
includes taxes & fees
25 Nov - 26 Nov
Hampton Inn & Suites Baltimore/Aberdeen
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)
"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 RM421
RM468 total
includes taxes & fees
19 Nov - 20 Nov
Hilton Garden Inn Kent Island Marina
Exterior
Hampton Inn Baltimore/White Marsh

Hampton Inn Baltimore/White Marsh

2.5 star property
Nottingham
7.8 out of 10, Good, (1004)
"Really enjoyed my stay, the staff were nice."
United States
KaTerra
The price is RM361
RM417 total
includes taxes & fees
30 Nov - 1 Dec
Hampton Inn Baltimore/White Marsh
Exterior
Hampton Inn Baltimore Bayview Campus

Hampton Inn Baltimore Bayview Campus

3.5 star property
Pulaski Industrial Area
8.8 out of 10, Excellent, (1002)
"Great stay as always!"
United States
Eunice
The price is RM460
RM541 total
includes taxes & fees
23 Nov - 24 Nov
Hampton Inn Baltimore Bayview Campus
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Stay near popular Chestertown attractions

Washington College

4.1/5 (45 reviews)
Founded in 1782, Washington College is the first college chartered in the sovereign United States. Explore its picturesque campus with historic architecture and Chester River waterfront views.
See properties

Historical Society of Kent County Maryland

Step inside the Geddes-Piper House, home to Kent County's historical treasures and curated exhibits. Explore Maryland's rich past through intimate galleries and knowledgeable guides who bring local stories to life.
See properties

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 harbour.

See all hotels in Chestertown
Eastern Shore small towns in Maryland, USA. Traveling the Eastern Shore points o f Maryland this weekend, we came across this local church with gravestones. We found several of these local churches along with the many farms and inlets leading to the Chesapeake bay.
Photo by Patricia Knorr
Open Photo by Patricia Knorr

Top Chestertown Hotel Reviews

Historic Inns of Annapolis

Historic Inns of Annapolis

10/10 Excellent
"Excellent stay. Can’t wait to return. "
Kristen 1-night trip
Posted 2 days ago
Historic Inns of Annapolis

More cheap stays in Chestertown

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

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

2112a Emmorton Park Road, Edgewood, MD
The price is RM261 per night from 16 Nov to 17 Nov
RM261
RM292 total
16 Nov - 17 Nov
includes taxes & fees
7.2/10 Good! (1,010 reviews)

Frequently asked questions

Where is the best place for a stay in Chestertown?
Comfort Inn & Suites Chestertown is a favourite 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 stay. 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! You'll find that most hotel bookings are fully refundable as long as you cancel prior to the accommodation's cancellation deadline, which in most cases is within 24 or 48 hours of your check-in date. If you booked a non-refundable reservation, 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 family accommodation 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 stay with the kids. Also, children of all ages will enjoy a visit to Crumpton Auction. Find more child-friendly accommodations in Chestertown.
What is the top LGBTQ-friendly hotel 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 two other good options for your stay. See all available hotels listed as LGBTQ-friendly in Chestertown.
What's the best dog-friendly accommodation option in Chestertown?
Comfort Inn & Suites Chestertown is a top hotel for people travelling with their pets, and offers a seasonal outdoor pool and a fitness centre for its human guests. Other good options for you and 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 accommodation options with pools in Chestertown?
The Lodge at Great Oak Landing is a top lodge with a seasonal outdoor pool, 3 bars/lounges and free WiFi. View all hotels with pools in Chestertown.
How is it to stay in Chestertown?
Visitors to Chestertown will definitely enjoy the university setting. Tourists can also enjoy the city's sporting events, festivals and art. In Chestertown, there are 39 hotels and other accommodation options to choose from. Find out more about Chestertown.
What should I see while I'm 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 Chesapeake Bay and Chestertown Dog Park exemplify the area's natural beauty. University life is a highlight and campuses to tour include Washington College and River Arts Chestertown. Take a look at what more there is 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 temperature of 23°C, while the coldest months are January and February, with an average of 4°C. Average annual precipitation for Chestertown is 1232 mm.

Explore a world of travel with Expedia