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Find hotels in Chestertown, MD from ₩91,047

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Compare 1,082 hotels, room rates, hotel reviews and availability. Most hotels are fully refundable.

Comfort Inn & Suites Chestertown
Lobby

Comfort Inn & Suites Chestertown

2.5 star property
8.6 out of 10, Excellent, (826)
"Friendly staff, clean room, convenient location. "
The price is ₩145,470
₩161,471 total
includes taxes & fees
Oct 19 - Oct 20
Comfort Inn & Suites Chestertown
Red Roof Inn & Suites Chestertown
Suite, Multiple Beds, Non Smoking | 1 bedroom, desk, laptop workspace, blackout drapes

Red Roof Inn & Suites Chestertown

2.0 star property
7.2 out of 10, Good, (401)
"We had a great stay with our two Pups.. The room was very nice and comfortable and very clean."
The price is ₩115,520
₩128,227 total
includes taxes & fees
Oct 16 - Oct 17
Red Roof 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
7.8 out of 10, Good, (70)
"Everything was perfect. The staff is super friendly, the room was clean and fresh. The beds were super comfy, the food is amazing and the chef was super nice!! Great friendly atmosphere. I’m definitely going back!!"
The price is ₩188,683
₩215,721 total
includes taxes & fees
Oct 12 - Oct 13
The Lodge at Great Oak Landing
La Quinta Inn & Suites by Wyndham Baltimore N / White Marsh
Free daily buffet breakfast

La Quinta Inn & Suites by Wyndham Baltimore N / White Marsh

3.0 star property
7.0 out of 10, Good, (1013)
"Had a nice stay "
The price is ₩108,390
₩125,191 total
includes taxes & fees
Oct 14 - Oct 15
La Quinta Inn & Suites by Wyndham Baltimore N / White Marsh
Holiday Inn Express Annapolis East-Kent Island by IHG
Exterior

Holiday Inn Express Annapolis East-Kent Island by IHG

2.5 star property
9.2 out of 10, Wonderful, (906)
"Nice Holiday Inn Express with great water views."
The price is ₩169,715
₩188,384 total
includes taxes & fees
Nov 9 - Nov 10
Holiday Inn Express Annapolis East-Kent Island by IHG
Quality Inn & Suites Bel Air I-95 Exit 77A
Desk, free WiFi, bed sheets, alarm clocks

Quality Inn & Suites Bel Air I-95 Exit 77A

2.5 star property
7.2 out of 10, Good, (1005)
"Fine would stay again"
The price is ₩88,423
₩99,034 total
includes taxes & fees
Nov 2 - Nov 3
Quality Inn & Suites Bel Air I-95 Exit 77A
Best Western Plus Hotel & Conference Center
Lobby

Best Western Plus Hotel & Conference Center

2.5 star property
7.8 out of 10, Good, (1001)
"Great stay"
The price is ₩152,302
₩178,955 total
includes taxes & fees
Nov 2 - Nov 3
Best Western Plus Hotel & Conference Center
Country Inn & Suites by Radisson, Baltimore North, MD
Exterior

Country Inn & Suites by Radisson, Baltimore North, MD

3.0 star property
7.2 out of 10, Good, (1003)
"I have been staying here for some time now and I've always been happy and every time I come in they always remember me very welcoming very helpful above and beyond service and always ask how the families doing how I'm doing it's like being home when you're away from home very happy with the place very clean rooms very nice affordable prices and staff does an amazing job working hard on keeping the place clean amazing breakfast rooms are always clean the whole place and the staff and give it a 10...
The price is ₩130,524
₩150,756 total
includes taxes & fees
Oct 26 - Oct 27
Country Inn & Suites by Radisson, Baltimore North, MD
Comfort Inn & Suites Aberdeen near APG
Lobby sitting area

Comfort Inn & Suites Aberdeen near APG

2.5 star property
7.8 out of 10, Good, (776)
"Room was clean, price is very reasonable. "
The price is ₩132,136
₩147,992 total
includes taxes & fees
Nov 9 - Nov 10
Comfort Inn & Suites Aberdeen near APG
Fairfield Inn & Suites by Marriott White Marsh
Free daily buffet breakfast

Fairfield Inn & Suites by Marriott White Marsh

2.5 star property
8.6 out of 10, Excellent, (1006)
"I loved EVERYTHING about this hotel!! We will definitely be back"
The price is ₩138,197
₩159,618 total
includes taxes & fees
Nov 2 - Nov 3
Fairfield Inn & Suites by Marriott White Marsh
Hyatt Place Kent Narrows & Marina
Terrace/patio

Hyatt Place Kent Narrows & Marina

3.0 star property
9.4 out of 10, Exceptional, (636)
"Great location and rooms. Great place!"
The price is ₩205,370
₩227,960 total
includes taxes & fees
Oct 21 - Oct 22
Hyatt Place Kent Narrows & Marina
Hampton Inn & Suites Edgewood/Aberdeen-South
Restaurant

Hampton Inn & Suites Edgewood/Aberdeen-South

2.5 star property
9.4 out of 10, Exceptional, (1004)
"Love love love this hotel they provided me with excellent care. Also helped me out with late checkout as needed. Great stay booking again very soon "
The price is ₩121,625
₩136,221 total
includes taxes & fees
Oct 16 - Oct 17
Hampton Inn & Suites Edgewood/Aberdeen-South
Americas Best Value Inn Edgewood
Lobby sitting area

Americas Best Value Inn Edgewood

2.0 star property
5.6 out of 10, (988)
"I always have a good experience with the staff. The motel might not be the greatest, but the staff is always friendly and accommodating. That's why I keep coming back."
The price is ₩81,292
₩91,047 total
includes taxes & fees
Oct 26 - Oct 27
Americas Best Value Inn Edgewood
Super 8 by Wyndham Aberdeen MD
Exterior

Super 8 by Wyndham Aberdeen MD

2.0 star property
7.0 out of 10, Good, (849)
"Parking was easy. Bed was super comfy. "
The price is ₩90,919
₩101,829 total
includes taxes & fees
Nov 10 - Nov 11
Super 8 by Wyndham Aberdeen MD
Kent Island Resort
Aerial view

Kent Island Resort

3.5 star property
9.2 out of 10, Wonderful, (114)
"Great INN super nice staff"
The price is ₩269,548
₩352,766 total
includes taxes & fees
Oct 21 - Oct 22
Kent Island Resort
Hilton Garden Inn Kent Island Marina
Terrace/patio

Hilton Garden Inn Kent Island Marina

3.0 star property
9.0 out of 10, Wonderful, (1002)
"Hotel was great, beautiful location near the water"
The price is ₩209,335
₩232,362 total
includes taxes & fees
Oct 16 - Oct 17
Hilton Garden Inn Kent Island Marina
Hampton Inn Baltimore Bayview Campus
Exterior

Hampton Inn Baltimore Bayview Campus

3.5 star property
9.0 out of 10, Wonderful, (1007)
"I loved how polite and efficient the staff was. The hotel was very clean 6nice"
The price is ₩185,945
₩218,486 total
includes taxes & fees
Oct 16 - Oct 17
Hampton Inn Baltimore Bayview Campus
Hampton Inn & Suites Baltimore/Aberdeen
Restaurant

Hampton Inn & Suites Baltimore/Aberdeen

2.5 star property
9.0 out of 10, Wonderful, (582)
"This Hotel was excellent in all ways. "
The price is ₩139,167
₩155,867 total
includes taxes & fees
Nov 2 - Nov 3
Hampton Inn & Suites Baltimore/Aberdeen
Hampton Inn Baltimore/White Marsh
Exterior

Hampton Inn Baltimore/White Marsh

2.5 star property
7.8 out of 10, Good, (1002)
"Really enjoyed my stay, the staff were nice."
The price is ₩135,658
₩156,685 total
includes taxes & fees
Oct 16 - Oct 17
Hampton Inn Baltimore/White Marsh
Historic Inns of Annapolis
Terrace/patio

Historic Inns of Annapolis

3.5 star property
9.0 out of 10, Wonderful, (1845)
"Perfect location…terrific staff…spacious room with a king sized bed! "
The price is ₩148,084
₩217,590 total
includes taxes & fees
Nov 2 - Nov 3
Historic Inns of Annapolis
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

4.1/5 (45 reviews)
Take a campus tour or just explore the area of Washington College, during your travels in Chestertown. Amble around this family-friendly area's riverfront or experience its festivals.
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Rolphs Wharf Marina

Explore the waterfront in Chestertown with a trip to Rolphs Wharf Marina. Take in the festivals in this family-friendly area.
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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 harbor.

See all hotels in Chestertown
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

Red Roof Inn & Suites Chestertown

Red Roof Inn & Suites Chestertown

10/10 Excellent
"Wish they had the pool open. The staff is great here and very helpful."
lisa 2-night trip
Posted 4 days ago
Red Roof Inn & Suites Chestertown

More cheap stays in Chestertown

Hampton Inn Baltimore/Glen Burnie

Hampton Inn Baltimore/Glen Burnie

6617 Ritchie Hwy, Glen Burnie, MD
The price is ₩145,014 per night from Nov 2 to Nov 3
₩145,014
₩165,315 total
Nov 2 - Nov 3
includes taxes & fees
8/10 Very Good! (1,005 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 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 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 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'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 41 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.

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