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Chestertown Hotels

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Top 10 trending Chestertown hotels

Comfort Inn & Suites Chestertown

2.5 star property
8.6 out of 10, Excellent, (749)
"The hotel was spotless. Very clean. Comfortable and safe. "
The price is €106
includes taxes & fees
20 Apr - 21 Apr
Comfort Inn & Suites Chestertown

Red Roof Inn & Suites Chestertown

2.0 star property
7.4 out of 10, Good, (338)
"I loved the decor of my room. The king size bed was cozy. "
The price is €64
includes taxes & fees
31 Mar - 1 Apr
Red Roof Inn & Suites Chestertown

The Lodge at Great Oak Landing

3.5 star property
7.8 out of 10, Good, (46)
"Generally okay, Clean but property could use some upgrade"
The price is €111
includes taxes & fees
13 Apr - 14 Apr
The Lodge at Great Oak Landing

Driftwood Inn

2.0 star property
5.0 out of 10, (168)
"Rooms were clean. Check-in was a breeze, and the housekeeping lady is the best left her a nice tip"
The price is €65
includes taxes & fees
31 Mar - 1 Apr
Driftwood Inn

Quality Inn

2.5 star property
7.6 out of 10, Good, (991)
"It was clean and actually smelled good. It was comfortable. They may need more TV channels. But everything was good."
The price is €92
includes taxes & fees
31 Mar - 1 Apr
Quality Inn

Relax Inn Smyrna

2.0 star property
8.0 out of 10, Very good, (74)
"The gentleman in the office was very nice & professional. The room could use some repair, especially the bathroom door. I was pleased with the comfortable bed and the full size shamoo, conditioner & shower gel dispensers in the shower. Loved the big towels too!"
The price is €91
includes taxes & fees
31 Mar - 1 Apr
Relax Inn Smyrna

Hampton Inn Middletown

2.5 star property
8.8 out of 10, Excellent, (781)
"Wounderful"
The price is €108
includes taxes & fees
20 Apr - 21 Apr
Hampton Inn Middletown

Holiday Inn Express And Suites Middletown by IHG

2.5 star property
9.2 out of 10, Wonderful, (550)
"Great"
The price is €128
includes taxes & fees
20 Apr - 21 Apr
Holiday Inn Express And Suites Middletown by IHG

Fairfield Inn & Suites by Marriott Middletown

2.5 star property
9.2 out of 10, Wonderful, (210)
"Ease of check-in and quiet location."
The price is €108
includes taxes & fees
7 Apr - 8 Apr
Fairfield Inn & Suites by Marriott Middletown

Spectacular Top Floor Deluxe Suite With Beautiful View & More!

2.5 star property
The price is €487
includes taxes & fees
9 Apr - 10 Apr
Spectacular Top Floor Deluxe Suite With Beautiful View & More!

First Floor Master Suite Bay View

2.0 star property
The price is €558
includes taxes & fees
9 Apr - 10 Apr
First Floor Master Suite Bay View

Second Floor East Standard Suite

2.0 star property
The price is €480
includes taxes & fees
9 Apr - 10 Apr
Second Floor East Standard Suite

Top Floor East Family Deluxe

2.0 star property
The price is €461
includes taxes & fees
9 Apr - 10 Apr
Top Floor East Family Deluxe

First Floor East Family Deluxe

2.5 star property
The price is €461
includes taxes & fees
13 Apr - 14 Apr
First Floor East Family Deluxe

First Floor Standard Deluxe Bay View

2.5 star property
The price is €487
includes taxes & fees
9 Apr - 10 Apr
First Floor Standard Deluxe Bay View

First Floor East Standard Deluxe

2.5 star property
The price is €461
includes taxes & fees
9 Apr - 10 Apr
First Floor East Standard Deluxe

Top Floor Standard Deluxe

2.5 star property
10.0 out of 10, Exceptional, (1)
"Very relaxing and peaceful love it can’t wait to be there again….."
The price is €461
includes taxes & fees
9 Apr - 10 Apr
Top Floor Standard Deluxe

Second Floor Master Suite Bay View

3.5 star property
The price is €558
includes taxes & fees
9 Apr - 10 Apr
Second Floor Master Suite Bay View

Top Floor Handicap Accessible Bay View

2.5 star property
The price is €487
includes taxes & fees
9 Apr - 10 Apr
Top Floor Handicap Accessible Bay View

Second Conference Standard Suite Bay View

2.0 star property
The price is €506
includes taxes & fees
9 Apr - 10 Apr
Second Conference Standard Suite Bay View
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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Learn more about Chestertown

Quaint Chestertown awaits: its sports, university life, wildlife and more!

Photo by Assya A
Open Photo by Assya A

Frequently asked questions

Where is the best place for a stay in Chestertown?

Comfort Inn & Suites Chestertown is a favourite property for Expedia customers. This hotel offers free breakfast and free parking. Reviews from our site also recommend Red Roof Inn & Suites Chestertown and Driftwood Inn as top options for your stay. See all available top hotels, or vacation rentals in Chestertown.

What are some of the best holiday rentals that Chestertown has to offer?

240' Private Beachfront @Kent Island Love Point - Great for Large Groups: This holiday home rental outside of Chestertown is located on the beach, and has a fireplace, a patio and a BBQ to put you at ease in your new surroundings. It has 5 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and a selection of games. 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 accommodation for a budget-friendly stay in Chestertown?

Based on reviews, Red Roof Inn & Suites Chestertown is a popular 2-star hotel for our travellers looking for an economical choice, and features free WiFi and free parking. Another top choice for your budget-friendly stay is Driftwood Inn. View all budget hotels 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's the best place to stay for couples in Chestertown?

Red Roof Inn & Suites Chestertown is a favourite hotel for couples, and features free WiFi and free parking. See all romantic hotels 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 fitness centre and laundry facilities 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's the best hotel in Chestertown to learn about local history?

Based on our travel expertise, Comfort Inn & Suites Chestertown is a top hotel on Expedia for those interested in history, and it features free breakfast and free WiFi. Also, notable landmarks to visit include Historical Society of Kent County Maryland. See more options for historical stays 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.

What is the best spa hotel in Chestertown?

Great Oak Manor is a top spa hotel featuring a private beach and a fitness centre. See all spa hotels 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 43 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. 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 itinerary are Rolphs Wharf Marina and Urieville Park. 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.