Find hotels in Chestertown, MD from ฿1,951

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Check prices for these dates

Next weekend
12 Jun - 14 Jun
In two weeks
19 Jun - 21 Jun

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Our top choices for Chestertown hotels

Private beach nearby, sun-loungers, beach volleyball

The Lodge at Great Oak Landing

The Lodge at Great Oak Landing
3.0 star property
Chestertown
7.8 out of 10, Good, (86 reviews)
"Peaceful and beautiful location. Such a relaxing spot. Very clean throughout the whole property. Staff very pleasant and attentive. Would stay here again "
United States
Nicola
The price is ฿4,323
฿4,942 total
includes taxes & fees
18 Jun - 19 Jun
The Lodge at Great Oak Landing
Free daily full breakfast

Comfort Inn & Suites Chestertown

Comfort Inn & Suites Chestertown
2.5 star property
Chestertown
8.6 out of 10, Excellent, (921 reviews)
"Great visit"
United States
Danielle
The price is ฿3,784
฿4,200 total
includes taxes & fees
17 Jun - 18 Jun
Comfort Inn & Suites Chestertown
Lobby lounge

Red Roof Inn & Suites Chestertown

Red Roof Inn & Suites Chestertown
2.0 star property
Chestertown
7.2 out of 10, Good, (453 reviews)
"Nothing special but good for the price. "
United States
Andreas
The price is ฿2,361
฿2,621 total
includes taxes & fees
25 Jun - 26 Jun
Red Roof Inn & Suites Chestertown
Front of property – evening/night

Driftwood Inn

Driftwood Inn
2.0 star property
Chestertown
5.2 out of 10, (177 reviews)
"Terrible !!! Dirty not clean the owner was rude and didn’t care about the conditions of the room. I asked for partial refund and was denied. Rat poop in the heaters. Dog hair in tubs dead bugs. Body fluids everywhere! Also drug dealers outside with guns. The owner still didn’t care what they were doing. Don’t go to this place it should be shut down !"
United States
Gabriel
The price is ฿2,075
฿2,303 total
includes taxes & fees
15 Jun - 16 Jun
Driftwood Inn
Standard Room, 2 Queen Beds | In-room safe, desk, soundproofing, rollaway beds

Super 8 by Wyndham Havre De Grace Aberdeen Area

Super 8 by Wyndham Havre De Grace Aberdeen Area
2.0 star property
Havre De Grace
6.6 out of 10, (996 reviews)
"Everything was good"
United States
Bree
The price is ฿1,742
฿1,951 total
includes taxes & fees
9 Jun - 10 Jun
Super 8 by Wyndham Havre De Grace Aberdeen Area
Indoor pool

Best Western Kent Narrows Inn

Best Western Kent Narrows Inn
2.5 star property
Grasonville
8.0 out of 10, Very good, (1,005 reviews)
"Good hotel for the price"
United States
Brenda
The price is ฿3,581
฿3,975 total
includes taxes & fees
15 Jun - 16 Jun
Best Western Kent Narrows Inn
Lobby

Days Inn by Wyndham Aberdeen

Days Inn by Wyndham Aberdeen
2.0 star property
Aberdeen
7.0 out of 10, Good, (971 reviews)
"It's better than Red Roof but definitely spend the money for better if with the Family"
United States
Christopher
The price is ฿2,493
฿2,792 total
includes taxes & fees
9 Jun - 10 Jun
Days Inn by Wyndham Aberdeen
Basic Single Room | Premium bedding, down duvets, individually furnished, desk

Relax Inn Smyrna Dover Coastal Gateway

Relax Inn Smyrna Dover Coastal Gateway
2.0 star property
Smyrna
7.8 out of 10, Good, (99 reviews)
"I was in town for just one night and ended up booking this last minute. I’ve never stayed at a motel before because of the stigma, but I was pleasantly surprised. Everything was very clean, and the owner at the front desk was extremely friendly and welcoming. A nice bonus was the smart TV, which let me log into my own accounts and relax. Overall, a great experience and definitely changed my perspective on motels."
United States
Michael
The price is ฿2,591
฿3,316 total
includes taxes & fees
10 Jun - 11 Jun
Relax Inn Smyrna Dover Coastal Gateway
Suite, 1 Queen Bed, Non Smoking | In-room safe, iron/ironing board, free WiFi, bed sheets

Quality Inn Grasonville near Kent Island

Quality Inn Grasonville near Kent Island
2.5 star property
Grasonville
7.8 out of 10, Good, (917 reviews)
"Room was clean and staff took very good care of us"
United States
Carol
The price is ฿3,485
฿3,868 total
includes taxes & fees
29 Jun - 30 Jun
Quality Inn Grasonville near Kent Island
Reception

Kent Island Resort

Kent Island Resort
3.5 star property
Stevensville
9.2 out of 10, Wonderful, (142 reviews)
"We loved the quaintness of the room, complete with a gas fireplace and floor to ceiling drapes. Having a restaurant right on site was incredible. I especially loved the girl dinner deal! We enjoyed the stay and the property was beautiful."
United States
Kiana
The price is ฿5,029
฿6,692 total
includes taxes & fees
10 Jun - 11 Jun
Kent Island Resort
Exterior

134 Prince - Luxury Boutique Hotel

134 Prince - Luxury Boutique Hotel
2.5 star property
Annapolis
9.8 out of 10, Exceptional, (37 reviews)
"Great property and super friendly staff!!"
United States
Chris
The price is ฿6,992
฿7,970 total
includes taxes & fees
10 Jun - 11 Jun
134 Prince - Luxury Boutique Hotel
Lobby

Country Inn & Suites by Radisson, Bel Air/Aberdeen, MD

Country Inn & Suites by Radisson, Bel Air/Aberdeen, MD
3.0 star property
Bel Air
8.8 out of 10, Excellent, (1,005 reviews)
"We had a very nice stay."
United States
Aimee
The price is ฿3,253
฿3,643 total
includes taxes & fees
10 Jun - 11 Jun
Country Inn & Suites by Radisson, Bel Air/Aberdeen, MD
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, (1,007 reviews)
"Great place to stay"
United States
Harry
The price is ฿3,398
฿3,806 total
includes taxes & fees
15 Jun - 16 Jun
La Quinta Inn & Suites by Wyndham Aberdeen-APG
Lobby sitting area

Comfort Inn & Suites Aberdeen near APG

Comfort Inn & Suites Aberdeen near APG
2.5 star property
Aberdeen
8.0 out of 10, Very good, (916 reviews)
"Room was clean and staff were friendly! Will definitely stay here again."
United States
Krithivasan
The price is ฿2,860
฿3,203 total
includes taxes & fees
5 Jul - 6 Jul
Comfort Inn & Suites Aberdeen near APG
Terrace/patio

Home2 Suites by Hilton Baltimore / Aberdeen, MD

Home2 Suites by Hilton Baltimore / Aberdeen, MD
3.0 star property
Aberdeen
8.8 out of 10, Excellent, (380 reviews)
"Great stay at this"
United States
Wilson
The price is ฿3,200
฿3,584 total
includes taxes & fees
14 Jun - 15 Jun
Home2 Suites by Hilton Baltimore / Aberdeen, MD
Exterior

Super 8 by Wyndham Aberdeen MD

Super 8 by Wyndham Aberdeen MD
2.0 star property
Aberdeen
6.8 out of 10, (874 reviews)
"Room was dirty, housekeeping ignored the do not disturb sign and barged in when trying to get dressed and would not leave. Roaches in room."
United States
Farrah
The price is ฿1,923
฿2,154 total
includes taxes & fees
17 Jun - 18 Jun
Super 8 by Wyndham Aberdeen MD
Combined shower/bathtub, free toiletries, hair dryer, towels

Ramada Hotel & Conference Center by Wyndham Edgewood

Ramada Hotel & Conference Center by Wyndham Edgewood
2.0 star property
Edgewood
6.6 out of 10, (531 reviews)
"the breakfast was simple bagels juice, cereal they should have better breakfast choices"
United States
Andrea
The price is ฿2,916
฿3,266 total
includes taxes & fees
15 Jun - 16 Jun
Ramada Hotel & Conference Center by Wyndham Edgewood
Exterior detail

Vandiver Inn

Vandiver Inn
3.5 star property
Havre De Grace
9.4 out of 10, Exceptional, (549 reviews)
"A beautiful and romantic Victorian B&B with friendly staff and delicious breakfast. We absolutely loved our stay and would go back again if we were ever in the area."
United States
Shannon
The price is ฿4,739
฿5,308 total
includes taxes & fees
17 Jun - 18 Jun
Vandiver Inn
Desk, laptop workspace, iron/ironing board, free WiFi

Quality Inn Smyrna

Quality Inn Smyrna
2.5 star property
Smyrna
7.6 out of 10, Good, (1,004 reviews)
"The people helpfull,clean place.morning scrambled and make your own waffles great.coffee can use some improvements."
United States
Stephen
The price is ฿2,952
฿3,276 total
includes taxes & fees
1 Jul - 2 Jul
Quality Inn Smyrna
Bar (on property)

Travelodge by Wyndham Aberdeen

Travelodge by Wyndham Aberdeen
2.0 star property
Aberdeen
6.4 out of 10, (565 reviews)
"Easy access to all nearby businesses."
United States
Grady
The price is ฿1,804
฿2,020 total
includes taxes & fees
7 Jun - 8 Jun
Travelodge by Wyndham Aberdeen
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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Stay near popular Chestertown attractions

Washington College

4.3/5 (87 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

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

Top Chestertown Hotel Reviews

Hampton Inn Baltimore Bayview Campus

Hampton Inn Baltimore Bayview Campus

10/10 Excellent
"Great breakfast"
Michel 2-night trip
Posted less than an hour ago
Hampton Inn Baltimore Bayview Campus

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 ฿2,124 per night from 8 Jun to 9 Jun
฿2,124
฿2,378 total
8 Jun - 9 Jun
includes taxes & fees
7.4/10 Good! (1,133 reviews)

Frequently asked questions

Where is the best place for a stay in Chestertown?
Based on our traveller data, Comfort Inn & Suites Chestertown is one of the top choices for your stay. This hotel offers free breakfast and free parking. Other good options for your trip include Red Roof Inn & Suites Chestertown and The Lodge at Great Oak Landing. 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 free WiFi, 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, free WiFi and free self-parking. 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 43 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. Natural beauty is on display at Northern Chesapeake Bay, Chesapeake Bay and Chestertown Dog Park. 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.