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Check prices for these dates

This weekend
22 May - 24 May
Next weekend
29 May - 31 May

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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
3.5 star property
Chestertown
8.0 out of 10, Very good, (82 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 NZ$246
includes taxes & fees
1 June - 2 June
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, (441 reviews)
"Nothing special but good for the price. "
United States
Andreas
The price is NZ$136
includes taxes & fees
2 June - 3 June
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, (913 reviews)
"Great visit"
United States
Danielle
The price is NZ$211
includes taxes & fees
16 June - 17 June
Comfort Inn & Suites Chestertown
Front of property – evening/night

Driftwood Inn

Driftwood Inn
2.0 star property
Chestertown
5.2 out of 10, (176 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 NZ$120
includes taxes & fees
29 May - 30 May
Driftwood 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 NZ$281
includes taxes & fees
26 May - 27 May
Haven Point Inn and Gallery
Reception

Kent Island Resort

Kent Island Resort
3.5 star property
Stevensville
9.2 out of 10, Wonderful, (137 reviews)
"Very nice room and wonderful stay."
United States
Julie
The price is NZ$361
includes taxes & fees
26 May - 27 May
Kent Island Resort
Deluxe Room | Interior detail

Relax Inn Smyrna Dover Coastal Gateway

Relax Inn Smyrna Dover Coastal Gateway
2.0 star property
Smyrna
7.8 out of 10, Good, (97 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 NZ$154
includes taxes & fees
27 May - 28 May
Relax Inn Smyrna Dover Coastal Gateway
Room, Multiple Beds, Hot Tub (LC) | Interior

Amazing Getaway: Enjoy our Cozy Log Cabins on the Chesapeake Bay!

Amazing Getaway: Enjoy our Cozy Log Cabins on the Chesapeake Bay!
2.0 star property
North East
8.8 out of 10, Excellent, (3 reviews)
"Very nice cabin. By the town and easy drive to everything. "
United States
Mark
The price is NZ$721
includes taxes & fees
1 June - 2 June
Amazing Getaway: Enjoy our Cozy Log Cabins on the Chesapeake Bay!
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, (1,000 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 NZ$170
includes taxes & fees
1 June - 2 June
Quality Inn Smyrna
Standard Room, 2 Queen 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, (991 reviews)
"Cold air dark room great staff!"
United States
Marc
The price is NZ$115
includes taxes & fees
24 May - 25 May
Super 8 by Wyndham Havre De Grace Aberdeen Area
Exterior detail

Vandiver Inn

Vandiver Inn
3.5 star property
Havre De Grace
9.4 out of 10, Exceptional, (544 reviews)
"Breakfast menu was very good, staff friendly and helpful. "
United States
JoEllen
The price is NZ$275
includes taxes & fees
15 June - 16 June
Vandiver Inn
Indoor pool

Best Western Kent Narrows Inn

Best Western Kent Narrows Inn
2.5 star property
Grasonville
8.0 out of 10, Very good, (1,000 reviews)
"It is a nice Hotel."
United States
Dale
The price is NZ$219
includes taxes & fees
27 May - 28 May
Best Western Kent Narrows Inn
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 NZ$336
includes taxes & fees
4 June - 5 June
Inn at Huntingfield Creek
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 NZ$187
includes taxes & fees
26 May - 27 May
Home2 Suites by Hilton Baltimore / Aberdeen, MD
Lobby

Hampton Inn & Suites Baltimore/Aberdeen

Hampton Inn & Suites Baltimore/Aberdeen
2.5 star property
Aberdeen
9.0 out of 10, Wonderful, (653 reviews)
"Clean, comfortable, decent breakfast."
United States
Diane
The price is NZ$181
includes taxes & fees
27 May - 28 May
Hampton Inn & Suites Baltimore/Aberdeen
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, (1,004 reviews)
"Great place to stay"
United States
Harry
The price is NZ$170
includes taxes & fees
27 May - 28 May
La Quinta Inn & Suites by Wyndham Aberdeen-APG
Reception

Hampton Inn & Suites Edgewood/Aberdeen-South

Hampton Inn & Suites Edgewood/Aberdeen-South
2.5 star property
Edgewood
9.4 out of 10, Exceptional, (1,005 reviews)
"Best place to stay"
United States
Victor
The price is NZ$172
includes taxes & fees
31 May - 1 June
Hampton Inn & Suites Edgewood/Aberdeen-South
Property amenity

Fairfield Inn & Suites by Marriott Middletown

Fairfield Inn & Suites by Marriott Middletown
3.0 star property
Middletown
9.2 out of 10, Wonderful, (393 reviews)
"Room was clean and staff was great."
United States
Zainab
The price is NZ$209
includes taxes & fees
7 June - 8 June
Fairfield Inn & Suites by Marriott Middletown
Suite, 1 Queen Bed, Non Smoking

Quality Inn Grasonville near Kent Island

Quality Inn Grasonville near Kent Island
2.5 star property
Grasonville
7.8 out of 10, Good, (908 reviews)
"Breakfast menu had a great variety and was fresh. "
United States
Timothy
The price is NZ$201
includes taxes & fees
8 June - 9 June
Quality Inn Grasonville near Kent Island
Exterior

Super 8 by Wyndham Aberdeen MD

Super 8 by Wyndham Aberdeen MD
2.0 star property
Aberdeen
7.0 out of 10, Good, (871 reviews)
"Skipped the breakfast but there were several options. Friendly and helpful staff. Bathroom door didn’t shut properly and room table/wall surfaces could have used a little more cleaning focus. Beds were clean and nice. Bodywash in shower was empty. Room smelled VERY strong of Hawaiian air freshener. Parking was easy"
United States
Jordyn
The price is NZ$138
includes taxes & fees
21 May - 22 May
Super 8 by Wyndham Aberdeen MD
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 harbour.

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

Top Chestertown Hotel Reviews

Hampton Inn Baltimore Bayview Campus

Hampton Inn Baltimore Bayview Campus

10/10 Excellent
"This hotel was very clean and the staff was very helpful. We stayed her on 2 ocassions and will be returning"
Jose 1-night trip
Posted 10 hours ago
Hampton Inn Baltimore Bayview Campus

More cheap accommodation 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 NZ$112 per night from 21 May to 22 May
NZ$112
21 May - 22 May
includes taxes & fees
7.4/10 Good! (1,112 reviews)

Frequently asked questions

Where is the best place for a stay in Chestertown?
Based on our traveller 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 trip 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 holiday rentals that Chestertown has to offer?
NEW! Charming Farm House in Historic Kent Island: This holiday home rental outside of Chestertown is located on a river, and has a balcony, a garden and a BBQ 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 that 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! You'll find that most hotel bookings are fully refundable as long as you cancel prior to the accommodation's cancellation deadline, which in most cases is within 24 or 48 hours of your check-in date. If you booked a non-refundable reservation, 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.
What's the best family accommodation 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 stay with the kids. Also, children of all ages will enjoy a visit to Crumpton Auction. Find more child-friendly accommodations in Chestertown.
What is the top LGBTQ-friendly hotel 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 two other good options for your stay. See all available hotels listed as LGBTQ-friendly in Chestertown.
What's the best dog-friendly accommodation option in Chestertown?
Comfort Inn & Suites Chestertown is a top hotel for people travelling with their pets, and offers a seasonal outdoor pool and a fitness centre for its human guests. Other good options for you and your pet include Red Roof Inn & Suites Chestertown and Driftwood Inn. See more pet-friendly hotel accommodations in Chestertown.
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 accommodation options with pools in Chestertown?
The Lodge at Great Oak Landing is a top lodge with a seasonal outdoor pool, 3 bars/lounges and free WiFi. View all hotels with pools in Chestertown.
How is it to stay in Chestertown?
Visitors to Chestertown will definitely enjoy the university setting. Tourists can also enjoy the city's sporting events, festivals and art. In Chestertown, there are 44 hotels and other accommodation options to choose from. Find out more about Chestertown.
What should I see while I'm 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 Northern Chesapeake Bay and Chesapeake Bay exemplify the area's natural beauty. University life is a highlight and campuses to tour include Washington College and River Arts Chestertown. Take a look at what more there is 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 temperature of 23°C, while the coldest months are January and February, with an average of 4°C. Average annual precipitation for Chestertown is 1232 mm.

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