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Find hotels in Chestertown, MD from ￥8,762

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Compare 1,086 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
Chestertown
8.6 out of 10, Excellent, (843)
"This property is clean and welcoming. We were pleasantly surprised. Check in was easy, and the room was great. Breakfast was wonderful! Great place to stay."
United States
Paula
The price is ￥15,649
￥17,371 total
includes taxes & fees
Nov 13 - Nov 14
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
Chestertown
7.2 out of 10, Good, (414)
"This property was clean but dated. The carpet was stained, the furniture and fixtures were worn and broken, towels were washed but old and in need of replacement."
United States
Derek
The price is ￥11,047
￥12,262 total
includes taxes & fees
Nov 30 - Dec 1
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
Chestertown
8.0 out of 10, Very Good, (75)
"Very nice rooms, "
United States
Stephania
The price is ￥15,188
￥17,365 total
includes taxes & fees
Nov 12 - Nov 13
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
Rosedale
7.0 out of 10, Good, (1055)
"Easy check in and out. "
United States
Andrew
The price is ￥10,433
￥12,050 total
includes taxes & fees
Dec 9 - Dec 10
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
Grasonville
9.2 out of 10, Wonderful, (916)
"The hotel was nice and clean and the staff was always polite and helpful. "
United States
William
The price is ￥15,189
￥16,861 total
includes taxes & fees
Nov 16 - Nov 17
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
Edgewood
7.4 out of 10, Good, (1010)
"It was good for the price and a convenient location, for what I needed to do. Staff was friendly and helpful. Room was clean, bed very comfortable."
United States
Clyde
The price is ￥9,665
￥10,823 total
includes taxes & fees
Nov 11 - Nov 12
Quality Inn & Suites Bel Air I-95 Exit 77A
Exterior
Country Inn & Suites by Radisson, Baltimore North, MD

Country Inn & Suites by Radisson, Baltimore North, MD

3.0 star property
Rossville
7.2 out of 10, Good, (1004)
"The reason I booked this hotel was because it had a hot tub and pool. These were both closed for "the season" without notification. If I knew that, I would have booked elsewhere. Everything else was just ok."
Canada
Brian
The price is ￥13,269
￥15,326 total
includes taxes & fees
Dec 7 - Dec 8
Country Inn & Suites by Radisson, Baltimore North, MD
Lobby
Best Western Plus Hotel & Conference Center

Best Western Plus Hotel & Conference Center

2.5 star property
Medford
7.8 out of 10, Good, (1003)
"Great stay"
United States
Diedre
The price is ￥17,749
￥20,855 total
includes taxes & fees
Nov 16 - Nov 17
Best Western Plus Hotel & Conference Center
Restaurant
Hampton Inn & Suites Edgewood/Aberdeen-South

Hampton Inn & Suites Edgewood/Aberdeen-South

2.5 star property
Edgewood
9.4 out of 10, Exceptional, (1002)
"Very good breakfast options Convenient parking Clean room Friendly staff"
United States
Alexander
The price is ￥12,519
￥14,021 total
includes taxes & fees
Nov 17 - Nov 18
Hampton Inn & Suites Edgewood/Aberdeen-South
Lobby sitting area
Comfort Inn & Suites Aberdeen near APG

Comfort Inn & Suites Aberdeen near APG

2.5 star property
Aberdeen
7.8 out of 10, Good, (794)
"Friendly staff; great sized room & walk in shower. Great for traveling through stay! Thank you!"
United States
Nancy
The price is ￥14,214
￥15,918 total
includes taxes & fees
Nov 16 - Nov 17
Comfort Inn & Suites Aberdeen near APG
Lobby sitting area
Americas Best Value Inn Edgewood

Americas Best Value Inn Edgewood

2.0 star property
Edgewood
5.6 out of 10, (1005)
"Stayed 3 nights. The beds were comfortable, the rooms were clean. "
Canada
Michelle
The price is ￥7,824
￥8,762 total
includes taxes & fees
Nov 16 - Nov 17
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
Nottingham
8.6 out of 10, Excellent, (1007)
"Great place to stay"
United States
Teresa
The price is ￥14,475
￥16,718 total
includes taxes & fees
Nov 23 - Nov 24
Fairfield Inn & Suites by Marriott White Marsh
Terrace/patio
Hyatt Place Kent Narrows & Marina

Hyatt Place Kent Narrows & Marina

3.0 star property
Grasonville
9.4 out of 10, Exceptional, (650)
"My favorite hotel "
United States
Jen
The price is ￥20,712
￥22,990 total
includes taxes & fees
Nov 16 - Nov 17
Hyatt Place Kent Narrows & Marina
Exterior
Super 8 by Wyndham Baltimore/Essex Area

Super 8 by Wyndham Baltimore/Essex Area

2.0 star property
Essex
5.4 out of 10, (403)
"disgusting hotel cockroaches, bed bugs, and mice. The worst customer service, which refused to let us check out or get a refund. "
United States
tamer
The price is ￥12,887
￥14,885 total
includes taxes & fees
Dec 11 - Dec 12
Super 8 by Wyndham Baltimore/Essex Area
Exterior
Super 8 by Wyndham Aberdeen MD

Super 8 by Wyndham Aberdeen MD

2.0 star property
Aberdeen
7.0 out of 10, Good, (854)
"Nice and clean. Staff was friendly. I had no problems whatsoever, and I would stay here again."
United States
Shelly
The price is ￥7,824
￥8,762 total
includes taxes & fees
Dec 7 - Dec 8
Super 8 by Wyndham Aberdeen MD
Aerial view
Kent Island Resort

Kent Island Resort

3.5 star property
Stevensville
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 ￥26,938
￥35,582 total
includes taxes & fees
Nov 11 - Nov 12
Kent Island Resort
Restaurant
Hampton Inn & Suites Baltimore/Aberdeen

Hampton Inn & Suites Baltimore/Aberdeen

2.5 star property
Aberdeen
9.0 out of 10, Wonderful, (588)
"Great stay!"
United States
Barbara
The price is ￥13,869
￥15,533 total
includes taxes & fees
Nov 23 - Nov 24
Hampton Inn & Suites Baltimore/Aberdeen
Terrace/patio
Hilton Garden Inn Kent Island Marina

Hilton Garden Inn Kent Island Marina

3.0 star property
Grasonville
9.0 out of 10, Wonderful, (1002)
"Our view was spectacular and the room was immaculate. Staff was friendly and welcoming. It was close to several restaurants. "
United States
Patricia
The price is ￥15,612
￥17,330 total
includes taxes & fees
Nov 17 - Nov 18
Hilton Garden Inn Kent Island Marina
Exterior
Hampton Inn Baltimore/White Marsh

Hampton Inn Baltimore/White Marsh

2.5 star property
Nottingham
7.8 out of 10, Good, (1001)
"Really enjoyed my stay, the staff were nice."
United States
KaTerra
The price is ￥13,378
￥15,452 total
includes taxes & fees
Nov 30 - Dec 1
Hampton Inn Baltimore/White Marsh
Exterior
Hampton Inn Baltimore Bayview Campus

Hampton Inn Baltimore Bayview Campus

3.5 star property
Hopkins Bayview
8.8 out of 10, Excellent, (1006)
"Great stay as always!"
United States
Eunice
The price is ￥17,060
￥20,044 total
includes taxes & fees
Nov 30 - Dec 1
Hampton Inn Baltimore Bayview Campus
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.
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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

Garner Hotel Glen Burnie BWI Airport Area by IHG

Garner Hotel Glen Burnie BWI Airport Area by IHG

10/10 Excellent
"Clean rooms and great service"
Thomas 1-night trip
Posted 2 days ago
Garner Hotel Glen Burnie BWI Airport Area by IHG

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 ￥9,665 per night from Nov 11 to Nov 12
￥9,665
￥10,823 total
Nov 11 - Nov 12
includes taxes & fees
7.2/10 Good! (1,022 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?
Woodland Retreat on Kent Island: 5 beds, 5 miles from Bay Bridge, on 5 acres.: This vacation home rental outside of Chestertown is located next to a golf course and has a patio, a garden, and a barbecue grill to put you at ease in your new surroundings. It has 4 bedrooms as well as a kitchen with a fridge, a stovetop, and a microwave, so you can cook with friends or family. You and your friends and family can relax into your vacation with amenities like a pool table. 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. 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 39 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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