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Chestertown Hotels from S$75

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Check prices for these dates

Tonight
7 Jul - 8 Jul
Tomorrow
8 Jul - 9 Jul
This weekend
11 Jul - 13 Jul
Next weekend
18 Jul - 20 Jul

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Top 10 trending Chestertown hotels

Comfort Inn & Suites Chestertown
Lobby

Comfort Inn & Suites Chestertown

2.5 star property
8.6 out of 10, Excellent, (777)
"Comfortable room, friendly staff. "
The price is S$161
includes taxes & fees
3 Aug - 4 Aug
Comfort Inn & Suites Chestertown
The Lodge at Great Oak Landing
Private beach nearby, sun-loungers, beach volleyball

The Lodge at Great Oak Landing

3.5 star property
8.0 out of 10, Very good, (53)
"not super fancy but really well done. comfy beds and a first rate chef. plus great for the boating crowd"
The price is S$187
includes taxes & fees
8 Jul - 9 Jul
The Lodge at Great Oak Landing
Red Roof Inn & Suites Chestertown
1 bedroom, desk, laptop workspace, blackout curtains

Red Roof Inn & Suites Chestertown

2.0 star property
7.4 out of 10, Good, (370)
"Had a good time and enjoyed the quietness at the hotel. "
The price is S$97
includes taxes & fees
13 Jul - 14 Jul
Red Roof Inn & Suites Chestertown
Driftwood Inn
Lobby

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 S$90
includes taxes & fees
14 Jul - 15 Jul
Driftwood Inn
Fairfield Inn & Suites by Marriott Middletown
Lobby

Fairfield Inn & Suites by Marriott Middletown

2.5 star property
9.2 out of 10, Wonderful, (247)
"Nice place to stay"
The price is S$188
includes taxes & fees
27 Jul - 28 Jul
Fairfield Inn & Suites by Marriott Middletown
Holiday Inn Express White Marsh by IHG
Exterior

Holiday Inn Express White Marsh by IHG

2.5 star property
9.6 out of 10, Exceptional, (883)
"We had a great stay!"
The price is S$166
includes taxes & fees
27 Jul - 28 Jul
Holiday Inn Express White Marsh by IHG
Historic Inns of Annapolis
Exterior

Historic Inns of Annapolis

3.5 star property
9.0 out of 10, Wonderful, (1792)
"Wonderful stay!"
Historic Inns of Annapolis
Hyatt Place Kent Narrows & Marina
Terrace/patio

Hyatt Place Kent Narrows & Marina

3.0 star property
9.4 out of 10, Exceptional, (574)
The price is S$281
includes taxes & fees
8 Jul - 9 Jul
Hyatt Place Kent Narrows & Marina
Hampton Inn & Suites Baltimore/Aberdeen
Exterior

Hampton Inn & Suites Baltimore/Aberdeen

2.5 star property
9.0 out of 10, Wonderful, (547)
"Liked everything about this hotel. Would definitely stay here again"
The price is S$150
includes taxes & fees
20 Jul - 21 Jul
Hampton Inn & Suites Baltimore/Aberdeen
The Inn at Henderson's Wharf, Ascend Hotel Collection
Exterior

The Inn at Henderson's Wharf, Ascend Hotel Collection

3.0 star property
9.2 out of 10, Wonderful, (691)
"Second time staying here - absolutely lovely. "
The price is S$228
includes taxes & fees
20 Jul - 21 Jul
The Inn at Henderson's Wharf, Ascend Hotel Collection
Holiday Inn Express And Suites Middletown by IHG
Exterior

Holiday Inn Express And Suites Middletown by IHG

2.5 star property
9.2 out of 10, Wonderful, (589)
"I would like to share, the staff at the hotel was very pleasant, it felt like a home away from home, and I also enjoyed the breakfast that was offered. "
The price is S$197
includes taxes & fees
4 Aug - 5 Aug
Holiday Inn Express And Suites Middletown by IHG
Hampton Inn Middletown
Indoor pool

Hampton Inn Middletown

2.5 star property
8.8 out of 10, Excellent, (811)
"Front desk service was exceptional!!"
The price is S$176
includes taxes & fees
3 Aug - 4 Aug
Hampton Inn Middletown
Country Inn & Suites by Radisson, Bel Air/Aberdeen, MD
Lobby

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

3.0 star property
8.8 out of 10, Excellent, (1001)
"The room was huge, breakfast was delicious and the staff was friendly. I also enjoyed the swimming pool. "
The price is S$179
includes taxes & fees
20 Jul - 21 Jul
Country Inn & Suites by Radisson, Bel Air/Aberdeen, MD
Residence Inn Aberdeen at Ripken Stadium
Premium bedding, in-room safe, desk, iron/ironing board

Residence Inn Aberdeen at Ripken Stadium

3.0 star property
9.0 out of 10, Wonderful, (97)
"Convenient and private. Receptionists Tamera was excellent. Great communicator. "
The price is S$169
includes taxes & fees
15 Jul - 16 Jul
Residence Inn Aberdeen at Ripken Stadium
Kent Island Resort
Aerial view

Kent Island Resort

3.5 star property
9.2 out of 10, Wonderful, (103)
"It's only 20 min from the downtown annapolis.Clean too."
The price is S$550
includes taxes & fees
8 Jul - 9 Jul
Kent Island Resort
Hampton Inn Baltimore/Glen Burnie
Free daily continental breakfast

Hampton Inn Baltimore/Glen Burnie

2.5 star property
8.2 out of 10, Very good, (1002)
"Great Place!"
The price is S$176
includes taxes & fees
13 Jul - 14 Jul
Hampton Inn Baltimore/Glen Burnie
Courtyard Aberdeen at Ripken Stadium
Lobby

Courtyard Aberdeen at Ripken Stadium

3.0 star property
8.6 out of 10, Excellent, (207)
"The staff was very friendly, easy and quick check-in. I would chose thus hotel again, very quiet. "
The price is S$132
includes taxes & fees
27 Jul - 28 Jul
Courtyard Aberdeen at Ripken Stadium
Flag House Inn
1 bedroom, Frette Italian sheets, premium bedding, memory-foam beds

Flag House Inn

3.5 star property
9.6 out of 10, Exceptional, (70)
"Wonderfully friendly staff, great location, and beautiful property "
The price is S$253
includes taxes & fees
8 Jul - 9 Jul
Flag House Inn
Fairfield Inn & Suites by Marriott White Marsh
1 bedroom, premium bedding, desk, blackout curtains

Fairfield Inn & Suites by Marriott White Marsh

2.5 star property
8.6 out of 10, Excellent, (1009)
"Excellent stay. "
The price is S$143
includes taxes & fees
3 Aug - 4 Aug
Fairfield Inn & Suites by Marriott White Marsh
The Inn at Chesapeake Bay Beach Club
Front of property – evening/night

The Inn at Chesapeake Bay Beach Club

4.0 star property
9.4 out of 10, Exceptional, (399)
"Staff was very polite and friendly. "
The price is S$336
includes taxes & fees
22 Jul - 23 Jul
The Inn at Chesapeake Bay Beach Club
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!

See all hotels in Chestertown
Photo by Assya A
Open Photo by Assya A

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. The Lodge at Great Oak Landing and Red Roof 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?

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 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 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.