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Chestertown hotels from RM223

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Top 10 trending Chestertown hotels

Inn at Haven Harbour

3.0 star property
The price is RM1,646
RM1,912 total
includes taxes & fees
30 Aug - 31 Aug
Inn at Haven Harbour

The Inn at Henderson's Wharf, Ascend Hotel Collection

3.0 star property
9.2 out of 10, Wonderful, (699)
"Second time staying here - absolutely lovely. "
The price is RM604
RM794 total
includes taxes & fees
17 Aug - 18 Aug
The Inn at Henderson's Wharf, Ascend Hotel Collection

Sagamore Pendry Baltimore

5.0 star property
9.4 out of 10, Exceptional, (1000)
"Great place for staycation."
The price is RM1,457
RM1,886 total
includes taxes & fees
17 Aug - 18 Aug
Sagamore Pendry Baltimore

Red Roof Inn & Suites Chestertown

2.0 star property
7.2 out of 10, Good, (383)
"Good location."
The price is RM324
RM359 total
includes taxes & fees
5 Aug - 6 Aug
Red Roof Inn & Suites Chestertown

The Lodge at Great Oak Landing

3.5 star property
8.0 out of 10, Very good, (57)
"Great place to get some quiet rest by the water"
The price is RM560
RM622 total
includes taxes & fees
31 Jul - 1 Aug
The Lodge at Great Oak Landing

Driftwood Inn

2.0 star property
5.2 out of 10, (171)
"Rooms were clean. Check-in was a breeze, and the housekeeping lady is the best left her a nice tip"
The price is RM269
RM298 total
includes taxes & fees
31 Jul - 1 Aug
Driftwood Inn

Comfort Inn & Suites Chestertown

2.5 star property
8.6 out of 10, Excellent, (787)
"It was a clean comfortable spot to rest for the night. "
The price is RM466
RM518 total
includes taxes & fees
3 Aug - 4 Aug
Comfort Inn & Suites Chestertown

5 Mi to Downtown Baltimore: Quiet Home w/ Porch

3.0 star property
The price is RM796
RM2,003 total
includes taxes & fees
4 Aug - 5 Aug
5 Mi to Downtown Baltimore: Quiet Home w/ Porch

Relax Inn Smyrna

2.0 star property
7.8 out of 10, Good, (84)
"Owner was very nice. "
The price is RM339
RM377 total
includes taxes & fees
7 Aug - 8 Aug
Relax Inn Smyrna

Motel Edgewood

2.0 star property
8.4 out of 10, Very good, (6)
"Bed was clean and crisply made. Occupants were respectful of sleeping hours. Check-in and check-out were simple. Parking was convenient and had easy access to the highway."
The price is RM248
RM277 total
includes taxes & fees
11 Aug - 12 Aug
Motel Edgewood

86 State Circle - Luxury Boutique Hotel

2.0 star property
10.0 out of 10, Exceptional, (1)
The price is RM1,249
RM1,424 total
includes taxes & fees
3 Aug - 4 Aug
86 State Circle - Luxury Boutique Hotel

Fairfield Inn & Suites by Marriott Middletown

2.5 star property
9.2 out of 10, Wonderful, (255)
"Nice place to stay"
The price is RM474
RM526 total
includes taxes & fees
10 Aug - 11 Aug
Fairfield Inn & Suites by Marriott Middletown

Hilton Garden Inn Bel Air

3.0 star property
9.4 out of 10, Exceptional, (202)
"Convenient. Easy on/off to I-95, quiet, clean, nice rooms,nice area, close to several eateries, friendly/efficient staff, and parking."
The price is RM536
RM600 total
includes taxes & fees
24 Aug - 25 Aug
Hilton Garden Inn Bel Air

Kent Island Resort

3.5 star property
9.2 out of 10, Wonderful, (105)
"Welcoming and well-staffed property, in a lovely and tranquil setting. Staff was friendly and helpful. Restaurant/bar service and food were outstanding. Great quiet getaway weekend spot. "
The price is RM842
RM1,096 total
includes taxes & fees
12 Aug - 13 Aug
Kent Island Resort

Annapolis Waterfront Hotel, Autograph Collection

4.0 star property
8.8 out of 10, Excellent, (847)
"Front desk staff was very friendly and helpful."
The price is RM968
RM1,104 total
includes taxes & fees
24 Aug - 25 Aug
Annapolis Waterfront Hotel, Autograph Collection

Historic Inns of Annapolis

3.5 star property
9.0 out of 10, Wonderful, (1832)
"Loved the hotel-great location "
Historic Inns of Annapolis

Red Roof Inn Edgewood

2.0 star property
7.2 out of 10, Good, (833)
"Great staff , clean room better than expected for a Red Roof Inn. "
The price is RM293
RM329 total
includes taxes & fees
11 Aug - 12 Aug
Red Roof Inn Edgewood

Courtyard by Marriott Baltimore Downtown/McHenry Row

3.0 star property
9.0 out of 10, Wonderful, (636)
"Convenient for cruise port"
The price is RM529
RM622 total
includes taxes & fees
10 Aug - 11 Aug
Courtyard by Marriott Baltimore Downtown/McHenry Row

Extended Stay America Suites Baltimore Bel Air Aberdeen

2.5 star property
7.0 out of 10, Good, (699)
"Clean rooms and professional staff members "
The price is RM328
RM367 total
includes taxes & fees
17 Aug - 18 Aug
Extended Stay America Suites Baltimore Bel Air Aberdeen

Candlewood Suites Aberdeen-Bel Air by IHG

2.5 star property
8.0 out of 10, Very good, (438)
"Amazing facility! Great friendly staff! Clean room!"
The price is RM453
RM507 total
includes taxes & fees
24 Aug - 25 Aug
Candlewood Suites Aberdeen-Bel Air by IHG
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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Learn more about Chestertown

Quaint Chestertown awaits: its sports, university life, art and more!

Photo by Assya A
Open Photo by Assya A

Top Chestertown Hotel 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 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?

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'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?

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'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 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. 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 Chestertown Historic District. 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.