Photo by Assya A

Find hotels in Chestertown, MD from $67

    Plan, book, stay with confidence
    bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    one key icon
    Treat yourself
    Save instantly and earn perks with One Key
    Learn about One Key
    today icon
    Change your mind
    Book hotels with free cancellation

Check Chestertown hotel prices

Tonight
May 3 - May 4
Tomorrow night
May 4 - May 5
This weekend
May 3 - May 5

Filter by

Popular filters
Popular filters
Guest rating
Guest rating
Star rating
Payment type
Payment type
Property type
Property type
Neighborhood
Neighborhood
Popular locations
Popular locations
Meal plans available
Meal plans available
Amenities
Amenities
Accessibility
Accessibility
Traveler experience
Traveler experience

Compare 996 hotels, room rates, hotel reviews and availability. Most hotels are fully refundable.

Inn at Huntingfield Creek
Lake
Inn at Huntingfield Creek
3.5 star property
10.0 out of 10, Exceptional, (43)
"Beautiful inn, staff is friendly, beautiful location and friendly dogs but since we were there in the off season the town Rock hall wasn’t very interesting "
The price is $230
$255 total
includes taxes & fees
May 5 - May 6
Inn at Huntingfield Creek
BAYSIDE BUNGALOW
Fridge, microwave, coffee/tea maker, toaster
BAYSIDE BUNGALOW
10.0 out of 10, Exceptional, (16)
"We have been coming to Rock Hall for years and have stayed at the cottage the last two times and we have really enjoyed it. We will be back again and we will stay at this cottage again. My husband loves the sauna. Bill and Hannah"
The price is $175
$271 total
includes taxes & fees
May 5 - May 6
BAYSIDE BUNGALOW
Carriage House Hideaway in Middle of Chestertown
Iron/ironing board, travel crib, free WiFi, bed sheets
Carriage House Hideaway in Middle of Chestertown
10.0 out of 10, Exceptional, (76)
"Bob and Beth's apartment was absolutely perfect for us. It was the cleanest VRBO that we have ever stayed in. All of the amenities were above and beyond what we expected. The apartment is in a great location and walkable into town and the WC campus. We will definitely stay again when we come back to town."
Carriage House Hideaway in Middle of Chestertown
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free
200 steps to the beach!
Interior
200 steps to the beach!
10.0 out of 10, Exceptional, (73)
"My husband and I love visiting Rock Hall and this was our first time staying at this home. It is very nicely decorated and has all of the necessary amenities. We were so pleased with this stay, this will definitely be on our favorites list"
200 steps to the beach!
Welcome to Bayside Breeze! One Block From Town Beach, Walk to Waterfront Dining
Outdoor dining
Welcome to Bayside Breeze! One Block From Town Beach, Walk to Waterfront Dining
10.0 out of 10, Exceptional, (37)
"This was the perfect landing pad for us and our dog during out 4 night visit. Very clean kitchen and bathrooms, and conveniently located. Well-stocked with all the comforts and conveniences of home. We really loved our meals out at Harbor Shack. We would definitely stay here again!"
Welcome to Bayside Breeze! One Block From Town Beach, Walk to Waterfront Dining
Cute waterfront apartment -- 8 min from the beach!
Property grounds
Cute waterfront apartment -- 8 min from the beach!
10.0 out of 10, Exceptional, (5)
"I raced the Waterman's tri and this location was perfect, well equipped, comfortable, clean, easy."
Cute waterfront apartment -- 8 min from the beach!
Rambling Victorian Beach House on Maryland's Eastern Shore
Beach nearby, sun loungers, beach towels
Rambling Victorian Beach House on Maryland's Eastern Shore
10.0 out of 10, Exceptional, (13)
"Our group of couples + kids enjoyed our getaway to the Eastern Shore. Betterton was a great home base to visit our alma mater, Washington College, in Chestertown. There, we visited the farmers market and waterfront park & playground with the kids. Back in Betterton, the house fit our group well. Plenty of bedrooms, bathrooms and space for each family. The kids & adults enjoyed spending time lounging in the third floor living room. We were pleased that the house had plenty of games, kids toys,...
Rambling Victorian Beach House on Maryland's Eastern Shore
This is truly a Baydream!
Exterior
This is truly a Baydream!
10.0 out of 10, Exceptional, (27)
"Close to everything. Cute quiet neighborhood. Well equipped kitchen."
This is truly a Baydream!
Bayside Cottage steps from Rock Hall Harbor
Fridge, microwave, stovetop, dishwasher
Bayside Cottage steps from Rock Hall Harbor
10.0 out of 10, Exceptional, (1)
"Property was nicely refurbished and furnished and well equipped. The younger set especially enjoyed the 5 bikes in good condition and the large yard to play sports. All in all, a great weekend stay!"
The price is $201
$394 total
includes taxes & fees
May 5 - May 6
Bayside Cottage steps from Rock Hall Harbor
Charming Chestertown Waterfront Cottage
Beach towels
Charming Chestertown Waterfront Cottage
10.0 out of 10, Exceptional, (58)
"This is a great place to relax. The house had everything we needed and was very comfortable."
Charming Chestertown Waterfront Cottage
Cozy, unique, historic registered cottage on the Corsica River!
Exterior
Cozy, unique, historic registered cottage on the Corsica River!
10.0 out of 10, Exceptional, (4)
"Very nice property. Enjoy the weekend. Would recommend to anyone visiting the Chestertown and Centreville area."
Cozy, unique, historic registered cottage on the Corsica River!
Stunning 9-Bedroom Villa on the Chesapeake Bay: Pool, Hot Tub, Boat Dock & Sauna
Balcony
Stunning 9-Bedroom Villa on the Chesapeake Bay: Pool, Hot Tub, Boat Dock & Sauna
10.0 out of 10, Exceptional, (28)
"I organized a large (15 person) bachelorette weekend at this property in early April. It is an absolutely gorgeous house and the host had a number of thoughtful touches - like extra firewood for the firepit, coffee supplies, and a bottle of bubbly for our bride! The beds were comfortable (even the twins!), which was lucky because one bedroom on the breakdown was not really usable, so a handful of guests relocated to one of the 'kid rooms.' We found Ashleigh very responsive both before and...
Stunning 9-Bedroom Villa on the Chesapeake Bay: Pool, Hot Tub, Boat Dock & Sauna
Historic Downtown Garden Oasis with Private Patio
Property grounds
Historic Downtown Garden Oasis with Private Patio
10.0 out of 10, Exceptional, (13)
"I reserved the space the day before and the hosts were very accommodating. The space was very comfortable with a great table and reliable WiFi for me to work. Garden is beautiful! Wish I could've stayed longer."
Historic Downtown Garden Oasis with Private Patio
BEACH WITHOUT THE BUSTLE
Beach nearby, sun loungers
BEACH WITHOUT THE BUSTLE
10.0 out of 10, Exceptional, (21)
"We needed tranquility after returning from a deployment in the Mideast. All was perfect for my team and I."
BEACH WITHOUT THE BUSTLE
Beautiful home & short walk to beach, restaurants, and marinas in Rock Hall, MD
Aerial view
Beautiful home & short walk to beach, restaurants, and marinas in Rock Hall, MD
10.0 out of 10, Exceptional, (14)
"We enjoyed our stay. The home was well stocked and clean and spacious. Perfect for our family"
Beautiful home & short walk to beach, restaurants, and marinas in Rock Hall, MD
Beautiful, spacious, quiet waterfront house!
Fridge, microwave, oven, stovetop
Beautiful, spacious, quiet waterfront house!
10.0 out of 10, Exceptional, (39)
"We had plenty of room for our family of 8. The weather didn't let us enjoy the outdoor activities and spaces that this house has to offer, which was disappointing, but you can't control Mother Nature! Having grown up in the area, it was fun to get to some of the local spots that have been around for years."
Beautiful, spacious, quiet waterfront house!
First Floor Studio Apartment in Historic Chestertown
Property grounds
First Floor Studio Apartment in Historic Chestertown
9.8 out of 10, Exceptional, (56)
"This was our second stay and we will most definitely be repeat visitors. Spacious room, easy check in and communication with owner, lovely property and area!"
The price is $98
$152 total
includes taxes & fees
May 6 - May 7
First Floor Studio Apartment in Historic Chestertown
Waterfront Oasis w/ Private Dock, 3BR/2BA
Pool
Waterfront Oasis w/ Private Dock, 3BR/2BA
9.8 out of 10, Exceptional, (19)
"We really enjoyed our stay. We were in town to celebrate my Dad's 80th birthday and the house was convenient to Parkville and Towson. The view from the sunroom was gorgeous. It was everything we needed for a quick weekend stay. Thank you."
Waterfront Oasis w/ Private Dock, 3BR/2BA
Newly restored apartment in the heart of Chestertown
Fridge, microwave, oven, stovetop
Newly restored apartment in the heart of Chestertown
9.8 out of 10, Exceptional, (14)
"The location was great. The decor was pretty and all very comfortable"
Newly restored apartment in the heart of Chestertown
Serene Waterfront Cottage with dock and gorgeous views.
Fridge, microwave, dishwasher, coffee/tea maker
Serene Waterfront Cottage with dock and gorgeous views.
9.6 out of 10, Exceptional, (35)
"Nice place with everything I could want. Would stay there again!"
Serene Waterfront Cottage with dock and gorgeous views.
Don't see what you're looking for?
See all available properties in Chestertown
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.

More cheap stays in Chestertown

Best Western Plus Hotel & Conference Center

Best Western Plus Hotel & Conference Center

5625 O'Donnell Street, Baltimore, MD
The price is $107 per night from May 12 to May 13
$107
$125 total
includes taxes & fees
May 12 - May 13
7.6/10 Good! (1,000 reviews)

Stay near popular Chestertown attractions

Image for Washington College

Washington College

4/5(13 reviews)

Take a campus tour or just explore the area of Washington College, during your travels in Chestertown. Amble around this family-friendly area's riverfront or experience its festivals.

See properties
Washington College

Chestertown Travel Info

Number of reviews
5,515
Accommodation
996 hotels
Highest price
$230
Lowest price
$67
Reasons to visit
Historical Society of Kent County Maryland, Garfield Center for the Arts at the Prince Theater and Washington College

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.

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

Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably: This vacation home rental outside of Chestertown offers a balcony, a garden, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. It has 6 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. Make the most of the spa tub in this rental home to help you unwind. 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 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 located on the beach. Great Oak Manor is another good option to stay near the beach. See more stays near the beach in Chestertown.

Recent reviews of Chestertown hotels
Expedia verified reviews

Holiday Inn Express White Marsh, An IHG Hotel

Holiday Inn Express White Marsh, An IHG Hotel

5/5 Excellent
"Great stay"
A verified traveler stayed at Holiday Inn Express White Marsh, An IHG Hotel
Posted 2 days ago
Holiday Inn Express White Marsh, An IHG Hotel