Photo by Assya A

Chestertown hotels from RM263

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Top 10 trending Chestertown hotels

Comfort Inn & Suites Chestertown

2.5 star property
8.6 out of 10, Excellent, (757)
"Inside the building it was clean, quiet and nice. In the back parking lot, it was very dirty. The grounds surrounding the lot was littered with trash and debris. One person looked to be sleeping in his car. I did appreciate the very bright lighting in that lot. A small clean up of the back lot would make a big difference in first impressions!!"
The price is RM487
RM541 total
includes taxes & fees
4 May - 5 May
Comfort Inn & Suites Chestertown

Red Roof Inn & Suites Chestertown

2.0 star property
7.4 out of 10, Good, (344)
"I stayed here one night and got a stripper pregnant. 10/10 will book again. "
The price is RM302
RM335 total
includes taxes & fees
29 Apr - 30 Apr
Red Roof Inn & Suites Chestertown

The Lodge at Great Oak Landing

3.5 star property
7.8 out of 10, Good, (47)
"Generally okay, Clean but property could use some upgrade"
The price is RM530
RM588 total
includes taxes & fees
22 Apr - 23 Apr
The Lodge at Great Oak Landing

Driftwood Inn

2.0 star property
5.2 out of 10, (170)
"Rooms were clean. Check-in was a breeze, and the housekeeping lady is the best left her a nice tip"
The price is RM280
RM311 total
includes taxes & fees
22 Apr - 23 Apr
Driftwood Inn

Mariners Motel

2.0 star property
9.4 out of 10, Exceptional, (88)
"Great location and very well cared for older motel. Updating extremely well done. We enjoyed the complimentary bikes, being so close to the water and the many good restaurants nearby. We will be back!"
The price is RM685
RM761 total
includes taxes & fees
22 Apr - 23 Apr
Mariners Motel

Inn at Huntingfield Creek

3.5 star property
10.0 out of 10, Exceptional, (50)
"We had a great stay at this nice inn. It is exactly what we are looking for: a quiet place on the eastern shore surrounded by nature. The cottage (one of seven) is spacious and well appointed. The bed is very comfortable. The tranquility of sitting on the back porch looking at the golden sunset beyond the vast field and tree line!! We took many walks across the 70 plus acre property to the shore and just absorbed the peace and sound of the wind blowing over the water. It’s amazing. The living...
The price is RM737
RM818 total
includes taxes & fees
22 Apr - 23 Apr
Inn at Huntingfield Creek

Quality Inn

2.5 star property
7.8 out of 10, Good, (745)
"Hallway carpet needs to be replaced or minimally vacuumed. "
The price is RM375
RM416 total
includes taxes & fees
22 Apr - 23 Apr
Quality Inn

Holiday Inn Express Annapolis East-Kent Island by IHG

2.5 star property
9.2 out of 10, Wonderful, (837)
"Second time staying at this hotel, very convenient and reasonable. "
The price is RM455
RM505 total
includes taxes & fees
4 May - 5 May
Holiday Inn Express Annapolis East-Kent Island by IHG

Motel Edgewood

2.0 star property
7.4 out of 10, Good, (3)
The price is RM258
RM289 total
includes taxes & fees
22 Apr - 23 Apr
Motel Edgewood

Best Western Kent Narrows Inn

2.5 star property
8.2 out of 10, Very good, (1003)
"Like the area. Was put in the backside of hotel overlooking a busy highway."
The price is RM430
RM478 total
includes taxes & fees
22 Apr - 23 Apr
Best Western Kent Narrows Inn

Hyatt Place Kent Narrows & Marina

3.0 star property
9.4 out of 10, Exceptional, (523)
"My hotel room was beautiful, the view was amazing and the hotel staff was very friendly. Although I was there in pouring rain there are many dining choices within walking distance"
The price is RM569
RM632 total
includes taxes & fees
22 Apr - 23 Apr
Hyatt Place Kent Narrows & Marina

Hilton Garden Inn Kent Island Marina

3.0 star property
9.0 out of 10, Wonderful, (906)
"Excellent "
The price is RM634
RM704 total
includes taxes & fees
30 Apr - 1 May
Hilton Garden Inn Kent Island Marina

Home2 Suites by Hilton Baltimore / Aberdeen, MD

3.0 star property
8.6 out of 10, Excellent, (305)
"Stayed overnight to visit our son. Have stayed here a few times before with no issue. This time, however, it seemed the hotel has gone downhill. The air conditioner would not go under 72 degrees (very stuffy in the room), No vent in the bathroom (again stuffy and mold inducing), and they did not have any decaf coffee for breakfast. With the variety of hotels in the area, we probably will not stay here again"
The price is RM446
RM500 total
includes taxes & fees
27 Apr - 28 Apr
Home2 Suites by Hilton Baltimore / Aberdeen, MD

SpringHill Suites Baltimore White Marsh/Middle River

2.5 star property
9.0 out of 10, Wonderful, (661)
"Clean and friendly staff"
The price is RM541
RM625 total
includes taxes & fees
22 Apr - 23 Apr
SpringHill Suites Baltimore White Marsh/Middle River

Holiday Inn Belcamp - Aberdeen Area by IHG

3.0 star property
8.2 out of 10, Very good, (682)
"Peaceful area, clean property and amicable staff. Good places to eat near by."
The price is RM410
RM460 total
includes taxes & fees
27 Apr - 28 Apr
Holiday Inn Belcamp - Aberdeen Area by IHG

Wingate by Wyndham Bel Air I-95 Exit 77A / APG Area

2.5 star property
7.2 out of 10, Good, (896)
"Enjoyed stay"
The price is RM270
RM303 total
includes taxes & fees
28 Apr - 29 Apr
Wingate by Wyndham Bel Air I-95 Exit 77A / APG Area

Americas Best Value Inn Edgewood

2.0 star property
5.2 out of 10, (862)
"Great for a 2 star hotel"
The price is RM263
RM295 total
includes taxes & fees
1 May - 2 May
Americas Best Value Inn Edgewood

Ramada Hotel & Conference Center by Wyndham Edgewood

2.0 star property
6.6 out of 10, (485)
"For the price you pay, it's a very good room. Mine was a King size bedroom. I found everything neat and well kept. Was happy with the stay. There was Microwave, mini fridge, ironing table and room was spacious as well. Will visit again. "
The price is RM394
RM441 total
includes taxes & fees
2 May - 3 May
Ramada Hotel & Conference Center by Wyndham Edgewood

TownePlace Suites by Marriott Edgewood Aberdeen

3.0 star property
9.0 out of 10, Wonderful, (60)
"Breakfast was a really great surprise! Far superior to any stay I’ve ever had! Very clean. Friendly and helpful staff who made us feel at home!"
The price is RM521
RM583 total
includes taxes & fees
7 May - 8 May
TownePlace Suites by Marriott Edgewood Aberdeen

Homewood Suites by Hilton Bel Air

3.0 star property
8.8 out of 10, Excellent, (404)
"Angela was extremely accommodating to us and the guests who were in town for our son’s wedding. "
The price is RM559
RM847 total
includes taxes & fees
27 Apr - 28 Apr
Homewood Suites by Hilton Bel Air
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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Quaint Chestertown awaits: its sports, university life, boating and more!

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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 accommodation for a budget-friendly stay in Chestertown?

Based on reviews, Red Roof Inn & Suites Chestertown is a popular 2-star hotel for our travellers looking for an economical choice, and features free WiFi and free parking. Another top choice for your budget-friendly stay is Driftwood Inn. View all budget hotels in Chestertown.

What's the best family accommodation in Chestertown?

Red Roof Inn & Suites Chestertown is a hotel with free parking and laundry facilities, and it's a top choice on Expedia for families. Comfort 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's the best place to stay for couples in Chestertown?

Red Roof Inn & Suites Chestertown is a favourite hotel for couples, and features free WiFi and free parking. See all romantic hotels in Chestertown.

What is the top LGBTQ-friendly hotel in Chestertown?

Red Roof Inn & Suites Chestertown is a top LGBTQ-friendly hotel that features free Wi-Fi and free parking. The Lodge at Great Oak Landing and Comfort Inn & Suites Chestertown 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?

Red Roof Inn & Suites Chestertown is a top hotel for people travelling with their pets, and offers laundry facilities and free newspapers for its human guests. Other good options for you and your pet include Comfort 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's the best hotel in Chestertown to learn about local history?

Based on our travel expertise, Comfort Inn & Suites Chestertown is a top hotel on Expedia for those interested in history, and it features free breakfast and free WiFi. Also, notable landmarks to visit include Historical Society of Kent County Maryland.

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.

What is the best spa hotel in Chestertown?

Great Oak Manor is a top spa hotel featuring a private beach and a fitness centre. See all spa hotels 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 41 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. University life is a highlight and campuses to tour include Washington College and River Arts Chestertown. A couple of additional sights to add to your itinerary are Rolphs Wharf Marina and Crumpton Auction. 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.