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Find hotels in Chestertown, MD from NT$1,559

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Compare 1,078 hotels, room rates, hotel reviews and availability. Most hotels are fully refundable.

Inn at Haven Harbour

3.0 star property
The price is NT$6,567
NT$7,883 total
includes taxes & fees
Aug 18 - Aug 19
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 NT$4,236
NT$5,568 total
includes taxes & fees
Aug 17 - Aug 18
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 NT$10,216
NT$13,225 total
includes taxes & fees
Aug 17 - Aug 18
Sagamore Pendry Baltimore

Red Roof Inn & Suites Chestertown

2.0 star property
7.2 out of 10, Good, (383)
"Good location."
The price is NT$2,263
NT$2,512 total
includes taxes & fees
Aug 5 - Aug 6
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 NT$3,914
NT$4,344 total
includes taxes & fees
Jul 31 - Aug 1
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 NT$1,879
NT$2,085 total
includes taxes & fees
Aug 8 - Aug 9
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 NT$3,270
NT$3,630 total
includes taxes & fees
Aug 3 - Aug 4
Comfort Inn & Suites Chestertown

5 Mi to Downtown Baltimore: Quiet Home w/ Porch

3.0 star property
The price is NT$5,562
NT$13,992 total
includes taxes & fees
Aug 12 - Aug 13
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 NT$2,370
NT$2,636 total
includes taxes & fees
Aug 5 - Aug 6
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 NT$1,731
NT$1,938 total
includes taxes & fees
Aug 3 - Aug 4
Motel Edgewood

86 State Circle - Luxury Boutique Hotel

2.0 star property
10.0 out of 10, Exceptional, (1)
The price is NT$8,758
NT$9,984 total
includes taxes & fees
Aug 3 - Aug 4
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 NT$3,326
NT$3,692 total
includes taxes & fees
Aug 10 - Aug 11
Fairfield Inn & Suites by Marriott Middletown

Hilton Garden Inn Bel Air

3.0 star property
9.4 out of 10, Exceptional, (201)
"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 NT$3,747
NT$4,196 total
includes taxes & fees
Aug 17 - Aug 18
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 NT$5,889
NT$7,660 total
includes taxes & fees
Aug 12 - Aug 13
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 NT$6,790
NT$7,741 total
includes taxes & fees
Aug 24 - Aug 25
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 NT$2,051
NT$2,297 total
includes taxes & fees
Aug 11 - Aug 12
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 NT$3,715
NT$4,365 total
includes taxes & fees
Aug 10 - Aug 11
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 NT$2,289
NT$2,564 total
includes taxes & fees
Aug 17 - Aug 18
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 NT$3,178
NT$3,559 total
includes taxes & fees
Aug 24 - Aug 25
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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Stay near popular Chestertown attractions

Learn more about Chestertown

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

Somewhere over the rainbow... Terrific view on the plane back to the North.
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 favorite 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 trip. 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, most hotel bookings are fully refundable as long as you cancel before the hotel’s cancellation deadline, which often is within 24-48 hours of your scheduled arrival. If your reservation is non-refundable, 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.

Where can I learn more about changing or cancelling my trip to Chestertown?

For more details about rescheduling or cancelling your trip to Chestertown, click here.

What's the best place to stay on a budget in Chestertown?

Based on reviews, Red Roof Inn & Suites Chestertown is a popular 2-star hotel for our travelers 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 hotel for families 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 kid-friendly vacation. Kids of all ages will also enjoy a visit to Crumpton Auction. Find more child-friendly accommodations in Chestertown.

What's the best accommodation for a romantic vacation to Chestertown?

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

What's the best LGBTQ-friendly accommodation 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 other good options for your trip. See all available hotels listed as LGBTQ-friendly in Chestertown.

What's the best pet-friendly hotel in Chestertown?

Comfort Inn & Suites Chestertown is a top hotel for people traveling with their pets, and offers a seasonal outdoor pool and a fitness center for its human guests. Other good options to stay with your pet include Red Roof Inn & Suites Chestertown and Driftwood Inn. See more pet-friendly hotel accommodations in Chestertown.

Where is the best hotel to stay near Washington College?

Adjacent to Washington College, Driftwood Inn is one of the top choices for your stay based on our traveler data, and this property offers free parking and free WiFi. Other good options close by include Comfort Inn & Suites Chestertown and Red Roof Inn & Suites Chestertown.

What about the best place to stay near Rolphs Wharf Marina?

One of the top choices for your stay is Comfort Inn & Suites Chestertown, located 4.1 mi (6.6 km) from Rolphs Wharf Marina, and this hotel offers free breakfast and free parking. Driftwood Inn and Red Roof Inn & Suites Chestertown are two other good options within a few miles.

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 place to stay in Chestertown to absorb the 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. See more options for historical stays in Chestertown.

What are some accommodations with pools in Chestertown?

The Lodge at Great Oak Landing is a top lodge with a seasonal outdoor pool, 3 bars, 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 center. See all spa hotels in Chestertown.

What's the best hotel for staying near Salisbury - Ocean City Wicomico Regional Airport (SBY)?

Country Inn & Suites by Radisson, Salisbury, MD is one of the top choices for your stay and is a popular 3-star hotel featuring free breakfast and an indoor pool. It's located 2.2 mi (3.6 km) from Salisbury - Ocean City Wicomico Regional Airport. Other options close to the airport include Microtel Inn & Suites by Wyndham Salisbury and Sleep Inn Salisbury.

How is it to stay in Chestertown?

Visitors to Chestertown are sure to enjoy the university setting. Tourists can also enjoy the city's sporting events, festivals, and art. In Chestertown, there are 43 hotels and other accommodations to choose from. Find out more about Chestertown.

What are the top places to visit 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 agenda are Rolphs Wharf Marina and Chestertown Historic District. Check out what more 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 temp of 74°F, while the coldest months are January and February with an average of 39°F. Average annual precipitation for Chestertown is 48 inches.