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Jun 5 - Jun 7
In two weeks
Jun 12 - Jun 14

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Our top choices for Chestertown hotels

Private beach nearby, sun loungers, beach volleyball

The Lodge at Great Oak Landing

The Lodge at Great Oak Landing
3.0 star property
Chestertown
7.8 out of 10, Good, (83 reviews)
"Peaceful and beautiful location. Such a relaxing spot. Very clean throughout the whole property. Staff very pleasant and attentive. Would stay here again "
United States
Nicola
The price is ￥21,071
￥24,092 total
includes taxes & fees
Jun 3 - Jun 4
The Lodge at Great Oak Landing
Lobby lounge

Red Roof Inn & Suites Chestertown

Red Roof Inn & Suites Chestertown
2.0 star property
Chestertown
7.2 out of 10, Good, (449 reviews)
"Nothing special but good for the price. "
United States
Andreas
The price is ￥11,466
￥12,727 total
includes taxes & fees
Jun 8 - Jun 9
Red Roof Inn & Suites Chestertown
Free daily full breakfast

Comfort Inn & Suites Chestertown

Comfort Inn & Suites Chestertown
2.5 star property
Chestertown
8.6 out of 10, Excellent, (914 reviews)
"Great visit"
United States
Danielle
The price is ￥16,908
￥18,769 total
includes taxes & fees
Jun 21 - Jun 22
Comfort Inn & Suites Chestertown
Front of property - evening/night

Driftwood Inn

Driftwood Inn
2.0 star property
Chestertown
5.2 out of 10, (177 reviews)
"Terrible !!! Dirty not clean the owner was rude and didn’t care about the conditions of the room. I asked for partial refund and was denied. Rat poop in the heaters. Dog hair in tubs dead bugs. Body fluids everywhere! Also drug dealers outside with guns. The owner still didn’t care what they were doing. Don’t go to this place it should be shut down !"
United States
Gabriel
The price is ￥10,114
￥11,227 total
includes taxes & fees
Jun 1 - Jun 2
Driftwood Inn
Suite, 1 Queen Bed, Non Smoking | In-room safe, iron/ironing board, free WiFi, bed sheets

Quality Inn Grasonville near Kent Island

Quality Inn Grasonville near Kent Island
2.5 star property
Grasonville
7.8 out of 10, Good, (913 reviews)
"Room was clean and staff took very good care of us"
United States
Carol
The price is ￥16,922
￥18,784 total
includes taxes & fees
Jun 29 - Jun 30
Quality Inn Grasonville near Kent Island
Standard Room, 2 Queen Beds | In-room safe, desk, soundproofing, rollaway beds

Super 8 by Wyndham Havre De Grace Aberdeen Area

Super 8 by Wyndham Havre De Grace Aberdeen Area
2.0 star property
Havre De Grace
6.6 out of 10, (992 reviews)
"Cold air dark room great staff!"
United States
Marc
The price is ￥8,726
￥9,774 total
includes taxes & fees
Jun 3 - Jun 4
Super 8 by Wyndham Havre De Grace Aberdeen Area
Reception

Kent Island Resort

Kent Island Resort
3.5 star property
Stevensville
9.2 out of 10, Wonderful, (141 reviews)
"We loved the quaintness of the room, complete with a gas fireplace and floor to ceiling drapes. Having a restaurant right on site was incredible. I especially loved the girl dinner deal! We enjoyed the stay and the property was beautiful."
United States
Kiana
The price is ￥24,839
￥32,971 total
includes taxes & fees
Jun 15 - Jun 16
Kent Island Resort
Basic Single Room | Premium bedding, down comforters, individually furnished, desk

Relax Inn Smyrna Dover Coastal Gateway

Relax Inn Smyrna Dover Coastal Gateway
2.0 star property
Smyrna
7.8 out of 10, Good, (98 reviews)
"I was in town for just one night and ended up booking this last minute. I’ve never stayed at a motel before because of the stigma, but I was pleasantly surprised. Everything was very clean, and the owner at the front desk was extremely friendly and welcoming. A nice bonus was the smart TV, which let me log into my own accounts and relax. Overall, a great experience and definitely changed my perspective on motels."
United States
Michael
The price is ￥11,575
￥14,816 total
includes taxes & fees
Jun 2 - Jun 3
Relax Inn Smyrna Dover Coastal Gateway
Exterior detail

Vandiver Inn

Vandiver Inn
3.5 star property
Havre De Grace
9.4 out of 10, Exceptional, (547 reviews)
"A beautiful and romantic Victorian B&B with friendly staff and delicious breakfast. We absolutely loved our stay and would go back again if we were ever in the area."
United States
Shannon
The price is ￥23,014
￥25,776 total
includes taxes & fees
Jun 1 - Jun 2
Vandiver Inn
Exterior

Haven Point Inn and Gallery

Haven Point Inn and Gallery
2.0 star property
Rock Hall
10.0 out of 10, Exceptional, (1 review)
"Room was very clean and the owner was very helpful will definitely stay there again"
United States
John
The price is ￥21,551
￥23,922 total
includes taxes & fees
Jun 16 - Jun 17
Haven Point Inn and Gallery
Lake

Inn at Huntingfield Creek

Inn at Huntingfield Creek
3.5 star property
Rock Hall
10.0 out of 10, Exceptional, (63 reviews)
"The owners and staff were very courteous and nice. The room layout was great and thoughtfully designed and decorated."
United States
Sandra
The price is ￥28,363
￥31,482 total
includes taxes & fees
Jun 10 - Jun 11
Inn at Huntingfield Creek
Indoor pool

Best Western Kent Narrows Inn

Best Western Kent Narrows Inn
2.5 star property
Grasonville
8.0 out of 10, Very Good, (1,005 reviews)
"Good hotel for the price"
United States
Brenda
The price is ￥18,329
￥20,345 total
includes taxes & fees
Jun 8 - Jun 9
Best Western Kent Narrows Inn
Exterior

La Quinta Inn & Suites by Wyndham Aberdeen-APG

La Quinta Inn & Suites by Wyndham Aberdeen-APG
3.0 star property
Aberdeen
9.0 out of 10, Wonderful, (1,001 reviews)
"Great place to stay"
United States
Harry
The price is ￥14,079
￥15,769 total
includes taxes & fees
Jun 30 - Jul 1
La Quinta Inn & Suites by Wyndham Aberdeen-APG
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, (1,001 reviews)
"Great location and very clean!"
United States
Neille
The price is ￥22,139
￥24,574 total
includes taxes & fees
Jun 24 - Jun 25
Holiday Inn Express Annapolis East-Kent Island by IHG
Desk, laptop workspace, iron/ironing board, free WiFi

Quality Inn Smyrna

Quality Inn Smyrna
2.5 star property
Smyrna
7.6 out of 10, Good, (1,003 reviews)
"The rooms were clean and the staff was very kind and helpful. Overall, it was a great value for us!"
United States
Jesse
The price is ￥13,680
￥15,184 total
includes taxes & fees
Jun 30 - Jul 1
Quality Inn Smyrna
Lobby

Hampton Inn & Suites Baltimore/Aberdeen

Hampton Inn & Suites Baltimore/Aberdeen
2.5 star property
Aberdeen
9.0 out of 10, Wonderful, (660 reviews)
"Clean, comfortable, decent breakfast."
United States
Diane
The price is ￥15,019
￥16,821 total
includes taxes & fees
Jun 8 - Jun 9
Hampton Inn & Suites Baltimore/Aberdeen
Terrace/patio

Home2 Suites by Hilton Baltimore / Aberdeen, MD

Home2 Suites by Hilton Baltimore / Aberdeen, MD
3.0 star property
Aberdeen
8.8 out of 10, Excellent, (378 reviews)
"Great stay at this"
United States
Wilson
The price is ￥15,542
￥17,406 total
includes taxes & fees
Jun 28 - Jun 29
Home2 Suites by Hilton Baltimore / Aberdeen, MD
Reception

Hampton Inn & Suites Edgewood/Aberdeen-South

Hampton Inn & Suites Edgewood/Aberdeen-South
2.5 star property
Edgewood
9.4 out of 10, Exceptional, (1,003 reviews)
"Best place to stay"
United States
Victor
The price is ￥14,756
￥16,526 total
includes taxes & fees
Jun 14 - Jun 15
Hampton Inn & Suites Edgewood/Aberdeen-South
Exterior

Super 8 by Wyndham Aberdeen MD

Super 8 by Wyndham Aberdeen MD
2.0 star property
Aberdeen
7.0 out of 10, Good, (873 reviews)
"Breakfast could be better. "
United States
Joseph V
The price is ￥8,664
￥9,704 total
includes taxes & fees
Jun 8 - Jun 9
Super 8 by Wyndham Aberdeen MD
Meeting facility

Historic Inns of Annapolis

Historic Inns of Annapolis
3.5 star property
Historic District
9.0 out of 10, Wonderful, (1,853 reviews)
"Great hotel..will definitely be back"
United States
Randy
The price is ￥17,429
￥25,317 total
includes taxes & fees
Jun 8 - Jun 9
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

4.3/5 (87 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

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
Aerial summer view of colonial Chestertown on the Chesapeake Bay in Maryland USA

Top Chestertown Hotel Reviews

Historic Inns of Annapolis

Historic Inns of Annapolis

8/10 Good
"Great location with views all the way to the Bay Bridge from some rooms. Comfortable and spacious room."
nicole 2-night trip
Posted 5 hours ago
Historic Inns of Annapolis

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 ￥9,722 per night from Jun 7 to Jun 8
￥9,722
￥10,888 total
Jun 7 - Jun 8
includes taxes & fees
7.4/10 Good! (1,123 reviews)

Frequently asked questions

Where is the best place for a stay in Chestertown?
Based on our traveler data, Comfort Inn & Suites Chestertown is one of the top choices for your stay. This hotel offers free breakfast and free parking. Other good options for your stay include Red Roof Inn & Suites Chestertown and The Lodge at Great Oak Landing. See all available top hotels, or vacation rentals in Chestertown.
What are some of the best vacation rentals that Chestertown has to offer?
NEW! Charming Farm House in Historic Kent Island: This vacation home rental outside of Chestertown is located on a river and has a balcony, 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. 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 free WiFi, 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, free WiFi, and free parking. 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 45 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. Natural beauty is on display at Northern Chesapeake Bay, Chesapeake Bay, and Chestertown Dog Park. 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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