Photo by Patricia Knorr

Find hotels in Chestertown, MD from ฿1,970

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
2 Nov - 3 Nov
Tomorrow
3 Nov - 4 Nov
Next weekend
7 Nov - 9 Nov
In two weeks
14 Nov - 16 Nov

Filter by

Guest rating
Guest rating
Star rating

Top 10 Chestertown hotels and places to stay

Lobby
Comfort Inn & Suites Chestertown
Comfort Inn & Suites Chestertown
2.5 star property
8.6 out of 10, Excellent, (835)
"Very helpful front desk woman. On first perusal property appears a erase but clean, helpful, reasonable for a short stay. "
United States
Freda
The price is ฿3,298
฿3,660 total
includes taxes & fees
4 Nov - 5 Nov
Comfort Inn & Suites Chestertown
Suite, Multiple Beds, Non Smoking | 1 bedroom, desk, laptop workspace, blackout curtains
Red Roof Inn & Suites Chestertown
Red Roof Inn & Suites Chestertown
2.0 star property
7.2 out of 10, Good, (409)
"Food stains on the carpets, spots throughout the carpets in commons and in rooms."
United States
Allen
The price is ฿2,328
฿2,584 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
8.0 out of 10, Very good, (73)
"For the price off season the room should have had better amenities "
United States
Daniel
The price is ฿3,201
฿3,659 total
includes taxes & fees
4 Nov - 5 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
7.0 out of 10, Good, (1043)
"Quiet location , clean environment. The stay was pleasant."
United States
Rasheed
The price is ฿2,379
฿2,748 total
includes taxes & fees
2 Dec - 3 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
9.2 out of 10, Wonderful, (913)
"Excellent, pet friendly, clean, convenient, and beautiful "
United States
John
The price is ฿2,554
฿2,835 total
includes taxes & fees
3 Dec - 4 Dec
Holiday Inn Express Annapolis East-Kent Island by IHG
Lobby
Best Western Plus Hotel & Conference Center
Best Western Plus Hotel & Conference Center
2.5 star property
7.8 out of 10, Good, (1001)
"Great stay"
United States
Diedre
The price is ฿3,740
฿4,395 total
includes taxes & fees
9 Nov - 10 Nov
Best Western Plus Hotel & Conference Center
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
7.4 out of 10, Good, (1013)
"This is an older hotel, however they have been doing upgrades and every time I stay here I see people cleaning different areas of the hotel. I appreciate the continental breakfast options and how friendly the staff is. "
United States
Christina
The price is ฿2,037
฿2,281 total
includes taxes & fees
9 Nov - 10 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
7.2 out of 10, Good, (1004)
"I have been staying here for some time now and I've always been happy and every time I come in they always remember me very welcoming very helpful above and beyond service and always ask how the families doing how I'm doing it's like being home when you're away from home very happy with the place very clean rooms very nice affordable prices and staff does an amazing job working hard on keeping the place clean amazing breakfast rooms are always clean the whole place and the staff and give it a 10...
United States
Michael
The price is ฿2,968
฿3,428 total
includes taxes & fees
9 Nov - 10 Nov
Country Inn & Suites by Radisson, Baltimore North, MD
Free daily buffet breakfast
Fairfield Inn & Suites by Marriott White Marsh
Fairfield Inn & Suites by Marriott White Marsh
2.5 star property
8.6 out of 10, Excellent, (1006)
"Great place to stay"
United States
Teresa
The price is ฿3,050
฿3,523 total
includes taxes & fees
23 Nov - 24 Nov
Fairfield Inn & Suites by Marriott White Marsh
Restaurant
Hampton Inn & Suites Edgewood/Aberdeen-South
Hampton Inn & Suites Edgewood/Aberdeen-South
2.5 star property
9.4 out of 10, Exceptional, (1006)
"Very good breakfast options Convenient parking Clean room Friendly staff"
United States
Alexander
The price is ฿2,704
฿3,029 total
includes taxes & fees
11 Nov - 12 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
7.8 out of 10, Good, (790)
"Friendly staff; great sized room & walk in shower. Great for traveling through stay! Thank you!"
United States
Nancy
The price is ฿2,721
฿3,047 total
includes taxes & fees
9 Nov - 10 Nov
Comfort Inn & Suites Aberdeen near APG
Lobby sitting area
Americas Best Value Inn Edgewood
Americas Best Value Inn Edgewood
2.0 star property
5.6 out of 10, (1003)
"Stayed 3 nights. The beds were comfortable, the rooms were clean. "
Canada
Michelle
The price is ฿1,940
฿2,173 total
includes taxes & fees
3 Nov - 4 Nov
Americas Best Value Inn Edgewood
Exterior
Super 8 by Wyndham Baltimore/Essex Area
Super 8 by Wyndham Baltimore/Essex Area
2.0 star property
5.4 out of 10, (401)
"Good"
Canada
Hoa Thai
The price is ฿3,007
฿3,473 total
includes taxes & fees
9 Nov - 10 Nov
Super 8 by Wyndham Baltimore/Essex Area
Terrace/patio
Hyatt Place Kent Narrows & Marina
Hyatt Place Kent Narrows & Marina
3.0 star property
9.4 out of 10, Exceptional, (643)
"Great location and rooms. Great place!"
United States
Ana
The price is ฿4,365
฿4,845 total
includes taxes & fees
9 Nov - 10 Nov
Hyatt Place Kent Narrows & Marina
Aerial view
Kent Island Resort
Kent Island Resort
3.5 star property
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 ฿5,787
฿7,625 total
includes taxes & fees
1 Dec - 2 Dec
Kent Island Resort
Exterior
Super 8 by Wyndham Aberdeen MD
Super 8 by Wyndham Aberdeen MD
2.0 star property
7.0 out of 10, Good, (853)
"Nice and clean. Staff was friendly. I had no problems whatsoever, and I would stay here again."
United States
Shelly
The price is ฿1,759
฿1,970 total
includes taxes & fees
9 Nov - 10 Nov
Super 8 by Wyndham Aberdeen MD
Exterior
Hampton Inn Baltimore Bayview Campus
Hampton Inn Baltimore Bayview Campus
3.5 star property
8.8 out of 10, Excellent, (1004)
"We’ve stayed here two times already and always enjoyed it! Clean rooms, friendly staff, free parking and many shopping options close by!"
United States
Alexander
The price is ฿3,685
฿4,330 total
includes taxes & fees
23 Nov - 24 Nov
Hampton Inn Baltimore Bayview Campus
Restaurant
Hampton Inn & Suites Baltimore/Aberdeen
Hampton Inn & Suites Baltimore/Aberdeen
2.5 star property
9.0 out of 10, Wonderful, (588)
"Great stay!"
United States
Barbara
The price is ฿3,022
฿3,385 total
includes taxes & fees
30 Nov - 1 Dec
Hampton Inn & Suites Baltimore/Aberdeen
Exterior
Hampton Inn Baltimore/White Marsh
Hampton Inn Baltimore/White Marsh
2.5 star property
7.8 out of 10, Good, (1017)
"Really enjoyed my stay, the staff were nice."
United States
KaTerra
The price is ฿2,890
฿3,338 total
includes taxes & fees
23 Nov - 24 Nov
Hampton Inn Baltimore/White Marsh
Lobby
Americas Best Value Inn Baltimore
Americas Best Value Inn Baltimore
2.0 star property
6.8 out of 10, (1000)
"Super staff and service. Good location and easy to reach. All basic facilities available. Friendly staff and easy check in. No breakfast(only coffee). "
United States
Anoop
The price is ฿2,683
฿3,153 total
includes taxes & fees
9 Nov - 10 Nov
Americas Best Value Inn Baltimore
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

River Arts Chestertown

Chestertown RiverArts celebrates creativity with monthly themed exhibits and workshops. Explore rotating galleries, meet local artists, and time your visit for the spring "Paint the Town" event or October's Studio Tour.
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

Best Western Plus Hotel & Conference Center

Best Western Plus Hotel & Conference Center

10/10 Excellent
"We went on a family weekend getaway. The hotel is a few minutes drive from the harbor. The pool was a favorite with the kids . We loved the fact the comedy club and safari night club was conveniently located on the property. The breakfast needed other meat options other than pork sausage, a beef or turkey bacon would’ve been better options . The hotel was clean , security was phenomenal especially during event times keeping hotel guest secure. I would definitely stay here again "
Jannelle 2-night trip
Posted 7 days ago
Best Western Plus Hotel & Conference Center
Americas Best Value Inn Edgewood

Americas Best Value Inn Edgewood

10/10 Excellent
"Staff"
Wayne 1-night trip
Posted 11 days ago
Americas Best Value Inn Edgewood

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 ฿2,037 per night from 9 Nov to 10 Nov
฿2,037
฿2,281 total
9 Nov - 10 Nov
includes taxes & fees
7.2/10 Good! (1,005 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 37 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