Chestertown hotels from RM240

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1 Apr - 2 Apr
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2 Apr - 3 Apr
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3 Apr - 5 Apr
Next weekend
10 Apr - 12 Apr

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Our top choices for Chestertown hotels

Free daily full breakfast

Comfort Inn & Suites Chestertown

Comfort Inn & Suites Chestertown
2.5 star property
Chestertown
8.6 out of 10, Excellent, (893 reviews)
"Best place to stay always "
United States
Robert
The price is RM524
RM582 total
includes taxes & fees
13 Apr - 14 Apr
Comfort 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
7.8 out of 10, Good, (77 reviews)
"Very nice rooms, "
United States
Stephania
The price is RM435
RM498 total
includes taxes & fees
2 Apr - 3 Apr
The Lodge at Great Oak Landing
Lobby lounge

Red Roof Inn & Suites Chestertown

Red Roof Inn & Suites Chestertown
2.0 star property
Chestertown
7.2 out of 10, Good, (433 reviews)
"Arrived earlier than expected and the staff was very accommodating and friendly which made for an excellent stay from start to finish. "
United States
Linette
The price is RM327
RM362 total
includes taxes & fees
9 Apr - 10 Apr
Red Roof Inn & Suites Chestertown
Front of property – evening/night

Driftwood Inn

Driftwood Inn
2.0 star property
Chestertown
5.2 out of 10, (175 reviews)
"Rooms are clean, staf was helpful "
United States
Daryl
The price is RM257
RM285 total
includes taxes & fees
1 May - 2 May
Driftwood 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, (1,000 reviews)
"My visit at the Hotel was amazing & peaceful."
United States
Milton
The price is RM328
RM364 total
includes taxes & fees
19 Apr - 20 Apr
Quality Inn Smyrna
Interior detail

Relax Inn Smyrna

Relax Inn Smyrna
2.0 star property
Smyrna
8.0 out of 10, Very good, (94 reviews)
"Great location"
United States
Patrick
The price is RM399
RM444 total
includes taxes & fees
5 Apr - 6 Apr
Relax Inn Smyrna
Exterior

Holiday Inn Express & Suites Middletown by IHG

Holiday Inn Express & Suites Middletown by IHG
2.5 star property
Middletown
9.2 out of 10, Wonderful, (673 reviews)
"Great location and nice place to stay. Walk to nearby things to do and enjoy. "
United States
Sharon
The price is RM407
RM452 total
includes taxes & fees
12 Apr - 13 Apr
Holiday Inn Express & Suites Middletown by IHG
Indoor pool

Hampton Inn Middletown

Hampton Inn Middletown
2.5 star property
Middletown
8.8 out of 10, Excellent, (891 reviews)
"Great place to stay"
United States
Ken
The price is RM495
RM549 total
includes taxes & fees
19 Apr - 20 Apr
Hampton Inn Middletown
Property amenity

Fairfield Inn & Suites by Marriott Middletown

Fairfield Inn & Suites by Marriott Middletown
3.0 star property
Middletown
9.2 out of 10, Wonderful, (364 reviews)
"Clean room, felt very safe and secure, free parking, staff very friendly, plenty of eating and shopping close by"
United States
Taneica
The price is RM437
RM485 total
includes taxes & fees
19 Apr - 20 Apr
Fairfield Inn & Suites by Marriott Middletown
Exterior detail

Vandiver Inn

Vandiver Inn
3.5 star property
Havre De Grace
9.4 out of 10, Exceptional, (538 reviews)
"As always we loved our stay! Definitely will be coming back "
United States
John
The price is RM543
RM608 total
includes taxes & fees
5 Apr - 6 Apr
Vandiver Inn
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, (978 reviews)
"Cleaning lady and front desk were very frindly, helpful, speedy & great at there job."
United States
Mary
The price is RM214
RM240 total
includes taxes & fees
14 Apr - 15 Apr
Super 8 by Wyndham Havre De Grace Aberdeen Area
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, (1,000 reviews)
"Beautiful area"
United States
Dan
The price is RM594
RM660 total
includes taxes & fees
29 Apr - 30 Apr
Hilton Garden Inn Kent Island Marina
Indoor pool

Best Western Kent Narrows Inn

Best Western Kent Narrows Inn
2.5 star property
Grasonville
8.0 out of 10, Very good, (1,000 reviews)
"Wonderful staff,Clean rooms and comfortable bed!!"
United States
Evette
The price is RM468
RM520 total
includes taxes & fees
26 Apr - 27 Apr
Best Western Kent Narrows Inn
Terrace/patio

Hyatt Place Kent Narrows & Marina

Hyatt Place Kent Narrows & Marina
3.0 star property
Grasonville
9.6 out of 10, Exceptional, (732 reviews)
"Clean hotel all around. Friendly stafff and comfortable environment."
United States
Jillian
The price is RM718
RM797 total
includes taxes & fees
14 Apr - 15 Apr
Hyatt Place Kent Narrows & Marina
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, (886 reviews)
"Staff was nice and room was clean "
United States
Lauren
The price is RM396
RM439 total
includes taxes & fees
5 Apr - 6 Apr
Quality Inn Grasonville near Kent Island
Lake

Inn at Huntingfield Creek

Inn at Huntingfield Creek
3.5 star property
Rock Hall
10.0 out of 10, Exceptional, (62 reviews)
"The owners and staff were very courteous and nice. The room layout was great and thoughtfully designed and decorated."
United States
Sandra
The price is RM565
RM627 total
includes taxes & fees
9 Apr - 10 Apr
Inn at Huntingfield Creek
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, (977 reviews)
"Very nice hotel, good breakfast selection, clean rooms."
United States
Linda
The price is RM445
RM494 total
includes taxes & fees
12 Apr - 13 Apr
Holiday Inn Express Annapolis East-Kent Island by IHG
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, (358 reviews)
"Staff was very friendly and it was a perfect location for us"
United States
Ryan
The price is RM393
RM441 total
includes taxes & fees
8 Apr - 9 Apr
Home2 Suites by Hilton Baltimore / Aberdeen, MD
Exterior

Haven Point Inn and Gallery

Haven Point Inn and Gallery
2.0 star property
Rock Hall
The price is RM625
RM694 total
includes taxes & fees
21 Apr - 22 Apr
Haven Point Inn and Gallery
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, (324 reviews)
"The staff was lovely and so accommodating. Definitely the best part of our stay."
United States
Maritza
The price is RM443
RM497 total
includes taxes & fees
20 Apr - 21 Apr
Fairfield Inn & Suites by Marriott 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

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

Top Chestertown Hotel Reviews

Historic Inns of Annapolis

Historic Inns of Annapolis

10/10 Excellent
"The parking valet was wonderful- so easy to park and also gave us recommendations of where to eat! Front desk personnel were also lovely. "
Sharon 1-night trip
Posted 11 hours ago
Historic Inns of Annapolis

More cheap stays in Chestertown

Americas Best Value Inn Edgewood

Americas Best Value Inn Edgewood

1709 Edgewood Road Edgewood MD
The price is RM241 per night from 2 Apr to 3 Apr
RM241
RM270 total
2 Apr - 3 Apr
includes taxes & fees
5.8/10 (1,000 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. Red Roof Inn & Suites Chestertown is another top choice for your stay based on reviews. 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 42 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 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. 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.

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