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Chestertown Hotels

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Check prices for these dates

Tonight
Mar 26 - Mar 27
Tomorrow
Mar 27 - Mar 28
This weekend
Mar 28 - Mar 30
Next weekend
Apr 4 - Apr 6

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Top 10 trending Chestertown hotels

Comfort Inn & Suites Chestertown
Lobby

Comfort Inn & Suites Chestertown

2.5 star property
8.6 out of 10, Excellent, (749)
"It was fine and served our needs."
The price is P6,000
P6,660 total
includes taxes & fees
Apr 20 - Apr 21
Comfort Inn & Suites Chestertown
Red Roof Inn & Suites Chestertown
Desk, laptop workspace, blackout drapes, iron/ironing board

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 P3,554
P3,945 total
includes taxes & fees
Mar 27 - Mar 28
Red Roof Inn & Suites Chestertown
The Lodge at Great Oak Landing
Private beach nearby, sun loungers, beach volleyball

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 P6,218
P6,902 total
includes taxes & fees
Apr 9 - Apr 10
The Lodge at Great Oak Landing
Driftwood Inn
Lobby

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 P3,640
P4,040 total
includes taxes & fees
Mar 30 - Mar 31
Driftwood Inn
Quality Inn
Exterior

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 P5,124
P5,688 total
includes taxes & fees
Mar 27 - Mar 28
Quality Inn
Relax Inn Smyrna
Premium bedding, down comforters, individually furnished, desk

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 P5,101
P5,675 total
includes taxes & fees
Apr 8 - Apr 9
Relax Inn Smyrna
Hampton Inn Middletown
Indoor pool

Hampton Inn Middletown

2.5 star property
8.8 out of 10, Excellent, (781)
"Would definitely stay again"
The price is P6,095
P6,766 total
includes taxes & fees
Apr 20 - Apr 21
Hampton Inn Middletown
Holiday Inn Express And Suites Middletown by IHG
Exterior

Holiday Inn Express And Suites Middletown by IHG

2.5 star property
9.2 out of 10, Wonderful, (550)
"Great"
The price is P7,165
P7,953 total
includes taxes & fees
Apr 2 - Apr 3
Holiday Inn Express And Suites Middletown by IHG
Fairfield Inn & Suites by Marriott Middletown
Lobby

Fairfield Inn & Suites by Marriott Middletown

2.5 star property
9.2 out of 10, Wonderful, (210)
"The staff was courteous and professional, made you feel welcome and the property was clean. A pleasure to stay there"
The price is P6,045
P6,710 total
includes taxes & fees
Apr 7 - Apr 8
Fairfield Inn & Suites by Marriott Middletown
Top Floor Standard Deluxe
Miscellaneous

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 P18,284
P26,705 total
includes taxes & fees
Mar 29 - Mar 30
Top Floor Standard Deluxe
First Floor Standard Deluxe King
Miscellaneous

First Floor Standard Deluxe King

2.5 star property
The price is P18,284
P26,705 total
includes taxes & fees
Mar 29 - Mar 30
First Floor Standard Deluxe King
Top Floor Standard Deluxe
Miscellaneous

Top Floor Standard Deluxe

2.0 star property
The price is P18,284
P26,705 total
includes taxes & fees
Mar 29 - Mar 30
Top Floor Standard Deluxe
First Floor Standard Deluxe
Miscellaneous

First Floor Standard Deluxe

2.0 star property
The price is P18,284
P26,705 total
includes taxes & fees
Mar 29 - Mar 30
First Floor Standard Deluxe
Top Floor Family Deluxe Bay View
Miscellaneous

Top Floor Family Deluxe Bay View

2.5 star property
The price is P21,712
P30,338 total
includes taxes & fees
Apr 9 - Apr 10
Top Floor Family Deluxe Bay View
First Floor East Standard Deluxe
Miscellaneous

First Floor East Standard Deluxe

2.5 star property
The price is P18,284
P26,705 total
includes taxes & fees
Mar 29 - Mar 30
First Floor East Standard Deluxe
Top Floor Family Deluxe
Miscellaneous

Top Floor Family Deluxe

2.5 star property
The price is P18,203
P26,586 total
includes taxes & fees
Mar 27 - Mar 28
Top Floor Family Deluxe
Second Floor Standard Deluxe
Miscellaneous

Second Floor Standard Deluxe

2.0 star property
The price is P18,284
P26,705 total
includes taxes & fees
Mar 29 - Mar 30
Second Floor Standard Deluxe
First Floor Standard Suite
Miscellaneous

First Floor Standard Suite

2.0 star property
The price is P19,427
P27,916 total
includes taxes & fees
Mar 29 - Mar 30
First Floor Standard Suite
Second East Family Deluxe
Miscellaneous

Second East Family Deluxe

2.5 star property
The price is P20,189
P28,724 total
includes taxes & fees
Apr 9 - Apr 10
Second East Family Deluxe
Second Conference Family Deluxe Bay View
Miscellaneous

Second Conference Family Deluxe Bay View

2.5 star property
The price is P21,712
P30,338 total
includes taxes & fees
Apr 9 - Apr 10
Second Conference Family Deluxe 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!

See all hotels in Chestertown
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 favorite 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 trip. See all available top hotels, or 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 place to stay on a budget in Chestertown?

Based on reviews, Red Roof Inn & Suites Chestertown is a popular 2-star hotel for our travelers 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 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 accommodation for a romantic vacation to Chestertown?

Red Roof Inn & Suites Chestertown is a favorite hotel for couples, and features free WiFi and free parking. See all romantic hotels 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 fitness center and laundry facilities 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's the best place to stay in Chestertown to absorb the 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.

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 is the best spa hotel in Chestertown?

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