Photo by Patricia Knorr

Find hotels in Chestertown, MD from AED 241

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Check prices for these dates

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31 Oct - 1 Nov
Tomorrow
1 Nov - 2 Nov
This weekend
31 Oct - 2 Nov
Next weekend
7 Nov - 9 Nov

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Compare 1,077 hotels, room rates, hotel reviews and availability. Most hotels are fully refundable.

Lobby
Comfort Inn & Suites Chestertown
Comfort Inn & Suites Chestertown
2.5 star property
8.6 out of 10, Excellent, (835)
"Very helpful front desk woman. On first perusal property appears a erase but clean, helpful, reasonable for a short stay. "
United States
Freda
The price is AED 375
AED 416 total
includes taxes & fees
9 Nov - 10 Nov
Comfort Inn & Suites Chestertown
Suite, Multiple Beds, Non Smoking | 1 bedroom, desk, laptop workspace, blackout drapes
Red Roof Inn & Suites Chestertown
Red Roof Inn & Suites Chestertown
2.0 star property
7.2 out of 10, Good, (409)
"Food stains on the carpets, spots throughout the carpets in commons and in rooms."
United States
Allen
The price is AED 264
AED 294 total
includes taxes & fees
30 Nov - 1 Dec
Red Roof Inn & Suites Chestertown
Private beach nearby, sun loungers, beach volleyball
The Lodge at Great Oak Landing
The Lodge at Great Oak Landing
3.5 star property
7.8 out of 10, Good, (72)
"For the price off season the room should have had better amenities "
United States
Daniel
The price is AED 364
AED 416 total
includes taxes & fees
2 Nov - 3 Nov
The Lodge at Great Oak Landing
Free daily buffet breakfast
La Quinta Inn & Suites by Wyndham Baltimore N / White Marsh
La Quinta Inn & Suites by Wyndham Baltimore N / White Marsh
3.0 star property
7.0 out of 10, Good, (1042)
"Quiet location , clean environment. The stay was pleasant."
United States
Rasheed
The price is AED 273
AED 316 total
includes taxes & fees
23 Nov - 24 Nov
La Quinta Inn & Suites by Wyndham Baltimore N / White Marsh
Exterior
Holiday Inn Express Annapolis East-Kent Island by IHG
Holiday Inn Express Annapolis East-Kent Island by IHG
2.5 star property
9.2 out of 10, Wonderful, (911)
"Excellent, pet friendly, clean, convenient, and beautiful "
United States
John
The price is AED 290
AED 322 total
includes taxes & fees
12 Nov - 13 Nov
Holiday Inn Express Annapolis East-Kent Island by IHG
Desk, free WiFi, bed sheets, alarm clocks
Quality Inn & Suites Bel Air I-95 Exit 77A
Quality Inn & Suites Bel Air I-95 Exit 77A
2.5 star property
7.4 out of 10, Good, (1010)
"This is an older hotel, however they have been doing upgrades and every time I stay here I see people cleaning different areas of the hotel. I appreciate the continental breakfast options and how friendly the staff is. "
United States
Christina
The price is AED 231
AED 259 total
includes taxes & fees
3 Nov - 4 Nov
Quality Inn & Suites Bel Air I-95 Exit 77A
Lobby
Best Western Plus Hotel & Conference Center
Best Western Plus Hotel & Conference Center
2.5 star property
7.8 out of 10, Good, (1000)
"Great stay"
United States
Diedre
The price is AED 425
AED 499 total
includes taxes & fees
9 Nov - 10 Nov
Best Western Plus Hotel & Conference Center
Exterior
Country Inn & Suites by Radisson, Baltimore North, MD
Country Inn & Suites by Radisson, Baltimore North, MD
3.0 star property
7.2 out of 10, Good, (1001)
"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...
United States
Michael
The price is AED 337
AED 389 total
includes taxes & fees
13 Nov - 14 Nov
Country Inn & Suites by Radisson, Baltimore North, MD
Lobby sitting area
Comfort Inn & Suites Aberdeen near APG
Comfort Inn & Suites Aberdeen near APG
2.5 star property
7.8 out of 10, Good, (790)
"Friendly staff; great sized room & walk in shower. Great for traveling through stay! Thank you!"
United States
Nancy
The price is AED 309
AED 346 total
includes taxes & fees
9 Nov - 10 Nov
Comfort Inn & Suites Aberdeen near APG
Restaurant
Hampton Inn & Suites Edgewood/Aberdeen-South
Hampton Inn & Suites Edgewood/Aberdeen-South
2.5 star property
9.4 out of 10, Exceptional, (1005)
"Very good breakfast options Convenient parking Clean room Friendly staff"
United States
Alexander
The price is AED 307
AED 344 total
includes taxes & fees
11 Nov - 12 Nov
Hampton Inn & Suites Edgewood/Aberdeen-South
Lobby sitting area
Americas Best Value Inn Edgewood
Americas Best Value Inn Edgewood
2.0 star property
5.6 out of 10, (1000)
"Stayed 3 nights. The beds were comfortable, the rooms were clean. "
Canada
Michelle
The price is AED 220
AED 247 total
includes taxes & fees
2 Nov - 3 Nov
Americas Best Value Inn Edgewood
Free daily buffet breakfast
Fairfield Inn & Suites by Marriott White Marsh
Fairfield Inn & Suites by Marriott White Marsh
2.5 star property
8.6 out of 10, Excellent, (1003)
"Great place to stay"
United States
Teresa
The price is AED 347
AED 400 total
includes taxes & fees
23 Nov - 24 Nov
Fairfield Inn & Suites by Marriott White Marsh
Terrace/patio
Hyatt Place Kent Narrows & Marina
Hyatt Place Kent Narrows & Marina
3.0 star property
9.4 out of 10, Exceptional, (642)
"Great location and rooms. Great place!"
United States
Ana
The price is AED 496
AED 550 total
includes taxes & fees
10 Nov - 11 Nov
Hyatt Place Kent Narrows & Marina
Aerial view
Kent Island Resort
Kent Island Resort
3.5 star property
9.2 out of 10, Wonderful, (123)
"Hotel was great and peaceful. This hotel was water front. Nice surroundings!! I enjoyed to stay here."
United States
Chi
The price is AED 657
AED 866 total
includes taxes & fees
1 Dec - 2 Dec
Kent Island Resort
Exterior
Super 8 by Wyndham Baltimore/Essex Area
Super 8 by Wyndham Baltimore/Essex Area
2.0 star property
5.4 out of 10, (401)
"Good"
Canada
Hoa Thai
The price is AED 312
AED 361 total
includes taxes & fees
1 Nov - 2 Nov
Super 8 by Wyndham Baltimore/Essex Area
Exterior
Super 8 by Wyndham Aberdeen MD
Super 8 by Wyndham Aberdeen MD
2.0 star property
7.0 out of 10, Good, (853)
"Nice and clean. Staff was friendly. I had no problems whatsoever, and I would stay here again."
United States
Shelly
The price is AED 215
AED 241 total
includes taxes & fees
9 Nov - 10 Nov
Super 8 by Wyndham Aberdeen MD
Restaurant
Hampton Inn & Suites Baltimore/Aberdeen
Hampton Inn & Suites Baltimore/Aberdeen
2.5 star property
9.0 out of 10, Wonderful, (588)
"Great stay!"
United States
Barbara
The price is AED 346
AED 388 total
includes taxes & fees
30 Nov - 1 Dec
Hampton Inn & Suites Baltimore/Aberdeen
Exterior
Hampton Inn Baltimore/White Marsh
Hampton Inn Baltimore/White Marsh
2.5 star property
7.8 out of 10, Good, (1013)
"Really enjoyed my stay, the staff were nice."
United States
KaTerra
The price is AED 328
AED 379 total
includes taxes & fees
23 Nov - 24 Nov
Hampton Inn Baltimore/White Marsh
Exterior
Hampton Inn Baltimore Bayview Campus
Hampton Inn Baltimore Bayview Campus
3.5 star property
8.8 out of 10, Excellent, (1001)
"We’ve stayed here two times already and always enjoyed it! Clean rooms, friendly staff, free parking and many shopping options close by!"
United States
Alexander
The price is AED 419
AED 492 total
includes taxes & fees
23 Nov - 24 Nov
Hampton Inn Baltimore Bayview Campus
Terrace/patio
Hilton Garden Inn Kent Island Marina
Hilton Garden Inn Kent Island Marina
3.0 star property
9.0 out of 10, Wonderful, (1001)
"Hotel was great, beautiful location near the water"
United States
Daniel
The price is AED 509
AED 565 total
includes taxes & fees
10 Nov - 11 Nov
Hilton Garden Inn Kent Island Marina
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)
Founded in 1782, Washington College is the first college chartered in the sovereign United States. Explore its picturesque campus with historic architecture and Chester River waterfront views.
See properties

River Arts Chestertown

Chestertown RiverArts celebrates creativity with monthly themed exhibits and workshops. Explore rotating galleries, meet local artists, and time your visit for the spring "Paint the Town" event or October's Studio Tour.
See properties

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
Eastern Shore small towns in Maryland, USA. Traveling the Eastern Shore points o f Maryland this weekend, we came across this local church with gravestones. We found several of these local churches along with the many farms and inlets leading to the Chesapeake bay.
Photo by Patricia Knorr
Open Photo by Patricia Knorr

Top Chestertown Hotel Reviews

La Quinta Inn & Suites by Wyndham Bel Air/I-95 Exit 77A

La Quinta Inn & Suites by Wyndham Bel Air/I-95 Exit 77A

10/10 Excellent
"Consistency with every visit twice a year for 4 years"
Edward 1-night trip
Posted 2 days ago
La Quinta Inn & Suites by Wyndham Bel Air/I-95 Exit 77A

More cheap stays in Chestertown

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

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

2112a Emmorton Park Road, Edgewood, MD
The price is AED 231 per night from Nov 3 to Nov 4
AED 231
AED 259 total
3 Nov - 4 Nov
includes taxes & fees
7.2/10 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.
What are some of the best vacation rentals that Chestertown has to offer?
Waterfront Oasis w/ Private Dock, 3BR/2BA: This vacation home rental outside of Chestertown is located on a river and has a patio, a garden, and a barbecue grill to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. Make the most of the arcade game room in this rental home to help you unwind. See all 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.
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 37 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. The picturesque setting of Chesapeake Bay and Chestertown Dog Park exemplify the area's natural beauty. University life is a highlight and campuses to tour include Washington College and River Arts Chestertown. 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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