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Find hotels in Chestertown, MD from $67

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Check Chestertown hotel prices

Tonight
Jul 26 - Jul 27
Tomorrow night
Jul 27 - Jul 28
This weekend
Jul 26 - Jul 28

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Compare 991 hotels, room rates, hotel reviews and availability. Most hotels are fully refundable.

Comfort Inn & Suites Chestertown
Lobby
Comfort Inn & Suites Chestertown
2.5 star property
8.4 out of 10, Very Good, 693 reviews
"Nice hotel amid a small town "
The price is $136
includes taxes & fees
$122 per night
Jul 28 - Jul 29
Comfort Inn & Suites Chestertown
Red Roof Inn & Suites Chestertown
Suite, Multiple Beds, Non Smoking | Desk, laptop workspace, blackout drapes, iron/ironing board
Red Roof Inn & Suites Chestertown
2.0 star property
7.4 out of 10, Good, 288 reviews
"Na"
The price is $85
includes taxes & fees
$76 per night
Aug 11 - Aug 12
Red Roof Inn & Suites Chestertown
The Lodge at Great Oak Landing
Private beach nearby, sun loungers, beach volleyball, beach bar
The Lodge at Great Oak Landing
3.5 star property
8.8 out of 10, Excellent, 13 reviews
". "
The price is $152
includes taxes & fees
$136 per night
Jul 30 - Jul 31
The Lodge at Great Oak Landing
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Driftwood Inn
Lobby
Driftwood Inn
2.0 star property
5.0 out of 10, 162 reviews
"I decided to go low-budget for my two-night stay in Chestertown (in town for the Rock Hall Triathlons). This place is convenient and an excellent choice for someone who doesn't plan to spend a lot of time in their room. Rooms are spare w/no frills. Basically four lights in the entire room (overhead, wall, bathroom, shower). Bed was reasonably comfortable. I did notice that the shower temperature control looked a little grungy on the inside; otherwise, the room was clean and fit for purpose. I...
The price is $70
includes taxes & fees
$64 per night
Jul 28 - Jul 29
Driftwood Inn
Inn at Huntingfield Creek
Lake
Inn at Huntingfield Creek
3.5 star property
10.0 out of 10, Exceptional, 45 reviews
"Lovely property with wonderful owners and staff, including three very welcoming dogs. We had a perfect weekend getaway."
The price is $267
includes taxes & fees
$241 per night
Jul 28 - Jul 29
Inn at Huntingfield Creek
Mariners Motel
Outdoor pool
Mariners Motel
2.0 star property
9.4 out of 10, Exceptional, 86 reviews
"Really cute property and rooms. The rooms are small but exceptionally clean and nicely decorated. Pretty grounds with a pool, fire pit, hammocks and yard games available. Easy walking distance to a few restaurants. Staff was very pleasant. "
The price is $185
includes taxes & fees
$167 per night
Jul 31 - Aug 1
Mariners Motel
BAYSIDE BUNGALOW
Fridge, microwave, coffee/tea maker, toaster
BAYSIDE BUNGALOW
10.0 out of 10, Exceptional, 22 reviews
"Such a lovely place and perfect for what we needed! In town for weekend with our virual yacht club."
The price is $272
includes taxes & fees
$257 per night
Jul 28 - Jul 29
BAYSIDE BUNGALOW
First Floor Studio Apartment in Historic Chestertown
Property grounds
First Floor Studio Apartment in Historic Chestertown
9.8 out of 10, Exceptional, 62 reviews
"A comfortable, charming getaway in a great location"
The price is $164
includes taxes & fees
$155 per night
Jul 29 - Jul 30
First Floor Studio Apartment in Historic Chestertown
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 reviews
"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
200 steps to the beach!
Interior
200 steps to the beach!
10.0 out of 10, Exceptional, 80 reviews
"So close to beach and a great restaurant, The Blue Heron, with outside bar. Chairs and bikes included were a bonus!"
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, 41 reviews
"Very quiet area, close to beach. We enjoyed our stay. Great beach for kids. Clean and comfortable rental. A bad storm caused lots of branches to block driveway. Host and owner quickly resolved issue. Outside shower is planned, this will be a nice addition to this rental. Thank you"
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 reviews
"I raced the Waterman's tri and this location was perfect, well equipped, comfortable, clean, easy."
Cute waterfront apartment -- 8 min from the beach!
Chester River Waterfront, Magnificent Views, Dock, Beach, close 2 town
2 bedrooms, iron/ironing board, free WiFi, bed sheets
Chester River Waterfront, Magnificent Views, Dock, Beach, close 2 town
9.8 out of 10, Exceptional, 79 reviews
"House was even better than the photos showed. We spent evenings out on the dock watvhing the river and beautiful views. The hosts thought of every detail for a perfect stay."
Chester River Waterfront, Magnificent Views, Dock, Beach, close 2 town
Waterfront Oasis w/ Private Dock, 3BR/2BA
Pool
Waterfront Oasis w/ Private Dock, 3BR/2BA
9.8 out of 10, Exceptional, 21 reviews
"We loved this rental. Beautiful view of the river. Sunsets were amazing. Quite area. Lovely walk in the neighborhood for our dog. Loved sitting outside in the mornings and watching the birds. Was a easy drive to Baltimore - went to the baseball game. My only negative point is that carpet in the bedrooms need to be professionally cleaned or replaced. Thank you."
Waterfront Oasis w/ Private Dock, 3BR/2BA
This is truly a Baydream!
Exterior
This is truly a Baydream!
10.0 out of 10, Exceptional, 29 reviews
"Very welcoming and enjoyable"
This is truly a Baydream!
Bayside Cottage steps from Rock Hall Harbor
Fridge, microwave, oven, stovetop
Bayside Cottage steps from Rock Hall Harbor
10.0 out of 10, Exceptional, 1 review
"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 $441
includes taxes & fees
$416 per night
Jul 28 - Jul 29
Bayside Cottage steps from Rock Hall Harbor
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, 36 reviews
"A must book!"
Serene Waterfront Cottage with dock and gorgeous views.
Historic Waterfront Home with Chesapeake Bay View. Sleeps 9. Close to the Beach
Beach nearby, sun loungers, beach towels
Historic Waterfront Home with Chesapeake Bay View. Sleeps 9. Close to the Beach
9.4 out of 10, Exceptional, 30 reviews
"Buena Vista is a charming historic home with modern updates overlooking a beautiful river view. The house is comfortable and generously stocked. The hostess is quick to reply to inquiries. I enjoyed swimming and watching sunsets at the beach which is a 5 minute walk away."
Historic Waterfront Home with Chesapeake Bay View. Sleeps 9. Close to the Beach
Charming Chestertown Waterfront Cottage
Beach towels
Charming Chestertown Waterfront Cottage
10.0 out of 10, Exceptional, 60 reviews
"Our second stay at this home was just as delightful as the first. The house is clean, well-stocked and comfortable with a gorgeous view out the back windows. We have family nearby and look forward to coming again!"
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, 5 reviews
"Lovely property, cool history beautiful decor"
Cozy, unique, historic registered cottage on the Corsica River!
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 $115 per night from Aug 18 to Aug 19
$115
includes taxes & fees
$98 per night
Aug 18 - Aug 19
7.6/10 Good! (1,001 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

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

Hyatt Place Kent Narrows & Marina

Hyatt Place Kent Narrows & Marina

5/5 Excellent
Perfectly fine
"Totally fine. This isn't luxury: the room is spacious and clean and new and mostly comfortable (oddly soft bed) but kind of a cross between a dorm room and a hotel. Sort of weird they don't take more advantage of being on the water and water culture (e.g., no kayaks or canoes for guests to even give the illusion of being connected to the bay). The pool is small, indoors, and honestly not inviting. It's probably perfectly fine but didn't scream the cleanest in the world. All else being equal, given that it's a gagillion degrees out, I would have chosen the hotel across the way with the outdoor pool."
A verified traveler stayed at Hyatt Place Kent Narrows & Marina
Posted 2 days ago
Hyatt Place Kent Narrows & Marina

Chestertown Travel Info

Number of reviews
5,712
Accommodation
991 hotels
Highest price
$441
Lowest price
$67
Reasons to visit
Historical Society of Kent County Maryland, Garfield Center for the Arts at the Prince Theater and Washington College