Find hotels in Chestertown, MD from ฿1,823

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Check prices for these dates

This weekend
29 May - 31 May
Next weekend
5 Jun - 7 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
8.0 out of 10, Very good, (82 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 ฿4,295
฿4,911 total
includes taxes & fees
28 May - 29 May
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, (913 reviews)
"Great visit"
United States
Danielle
The price is ฿3,611
฿4,008 total
includes taxes & fees
22 Jun - 23 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, (444 reviews)
"Nothing special but good for the price. "
United States
Andreas
The price is ฿2,337
฿2,594 total
includes taxes & fees
4 Jun - 5 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, (176 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 ฿2,062
฿2,288 total
includes taxes & fees
28 May - 29 May
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, (991 reviews)
"Cold air dark room great staff!"
United States
Marc
The price is ฿1,628
฿1,823 total
includes taxes & fees
31 May - 1 Jun
Super 8 by Wyndham Havre De Grace Aberdeen Area
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, (911 reviews)
"Room was clean and staff took very good care of us"
United States
Carol
The price is ฿3,449
฿3,828 total
includes taxes & fees
28 May - 29 May
Quality Inn Grasonville near Kent Island
Deluxe Room | Interior detail

Relax Inn Smyrna Dover Coastal Gateway

Relax Inn Smyrna Dover Coastal Gateway
2.0 star property
Smyrna
7.8 out of 10, Good, (98 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 ฿2,565
฿3,283 total
includes taxes & fees
2 Jun - 3 Jun
Relax Inn Smyrna Dover Coastal Gateway
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, (1,077 reviews)
"Clean and helpful staff"
United States
Ana Sofía
The price is ฿2,156
฿2,415 total
includes taxes & fees
4 Jun - 5 Jun
La Quinta Inn & Suites by Wyndham Bel Air/I-95 Exit 77A
Reception

Kent Island Resort

Kent Island Resort
3.5 star property
Stevensville
9.2 out of 10, Wonderful, (140 reviews)
"Very nice room and wonderful stay."
United States
Julie
The price is ฿5,041
฿6,702 total
includes taxes & fees
1 Jun - 2 Jun
Kent Island Resort
Meeting facility

Historic Inns of Annapolis

Historic Inns of Annapolis
3.5 star property
Historic District
9.0 out of 10, Wonderful, (1,855 reviews)
"Great location"
United States
Stephanie
The price is ฿3,798
฿5,447 total
includes taxes & fees
16 Jun - 17 Jun
Historic Inns of Annapolis
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, (600 reviews)
"Great place to stay. "
United States
Nathan
The price is ฿3,117
฿3,491 total
includes taxes & fees
1 Jun - 2 Jun
Holiday Inn Express Edgewood-Aberdeen-Bel Air by IHG
Indoor pool

Best Western Kent Narrows Inn

Best Western Kent Narrows Inn
2.5 star property
Grasonville
8.0 out of 10, Very good, (1,002 reviews)
"It is a nice Hotel."
United States
Dale
The price is ฿3,736
฿4,147 total
includes taxes & fees
7 Jun - 8 Jun
Best Western Kent Narrows Inn
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, (378 reviews)
"Great stay at this"
United States
Wilson
The price is ฿3,168
฿3,548 total
includes taxes & fees
4 Jun - 5 Jun
Home2 Suites by Hilton Baltimore / Aberdeen, MD
Superior Room, 1 King Bed (Smoke Free) | In-room safe, desk, blackout curtains, free WiFi

Red Roof Inn Aberdeen

Red Roof Inn Aberdeen
2.0 star property
Aberdeen
6.4 out of 10, (1,000 reviews)
"Ordinarily you probably wouldn't think to highly of a Red Roof. However, it was surprisingly clean and well maintained. The bed was extremely comfortable. I'd stay here again."
United States
Adam
The price is ฿1,797
฿2,013 total
includes taxes & fees
28 May - 29 May
Red Roof Inn Aberdeen
Exterior

Super 8 by Wyndham Aberdeen MD

Super 8 by Wyndham Aberdeen MD
2.0 star property
Aberdeen
7.0 out of 10, Good, (873 reviews)
"Breakfast could be better. "
United States
Joseph V
The price is ฿1,766
฿1,978 total
includes taxes & fees
4 Jun - 5 Jun
Super 8 by Wyndham Aberdeen MD
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, (1,000 reviews)
"The rooms were clean and the staff was very kind and helpful. Overall, it was a great value for us!"
United States
Jesse
The price is ฿2,922
฿3,243 total
includes taxes & fees
7 Jun - 8 Jun
Quality Inn Smyrna
Terrace/patio

Fairfield Inn & Suites by Marriott Aberdeen

Fairfield Inn & Suites by Marriott Aberdeen
3.0 star property
Aberdeen
9.0 out of 10, Wonderful, (340 reviews)
"Very sweet young lady who checked us in. Nice property, great location!"
United States
Andrea
The price is ฿3,554
฿3,981 total
includes taxes & fees
8 Jun - 9 Jun
Fairfield Inn & Suites by Marriott Aberdeen
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, (1,003 reviews)
"Great place to stay"
United States
Harry
The price is ฿2,870
฿3,214 total
includes taxes & fees
17 Jun - 18 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, (911 reviews)
"The property was clean and the staff is friendly and welcoming. The breakfast buffet was well done and offered a lot of breakfast choices. The lobby offers 24-hour coffee and tea which is a nice touch. Overall, a nice stay and I would recommend to travelers."
United States
Patricia
The price is ฿2,677
฿2,998 total
includes taxes & fees
7 Jun - 8 Jun
Comfort Inn & Suites Aberdeen near APG
Desk, laptop workspace, iron/ironing board, free WiFi

SpringHill Suites by Marriott Edgewood/Aberdeen

SpringHill Suites by Marriott Edgewood/Aberdeen
3.0 star property
Bel Air
8.8 out of 10, Excellent, (383 reviews)
"Nice clean property that was well staffed. I used Expedia to book the room and that always seems to help."
United States
Joe
The price is ฿3,766
฿4,218 total
includes taxes & fees
8 Jun - 9 Jun
SpringHill Suites by Marriott Edgewood/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 staff Breakfast options were great"
AbdulRauf 4-night trip
Posted 8 hours 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 ฿1,843 per night from 31 May to 1 Jun
฿1,843
฿2,064 total
31 May - 1 Jun
includes taxes & fees
7.4/10 Good! (1,120 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 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 44 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.