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Find hotels in Chestertown, MD from $62

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Check Chestertown hotel prices

Tonight
May 31 - Jun 1
Tomorrow night
Jun 1 - Jun 2
This weekend
May 31 - Jun 2

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Compare 993 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
8.6 out of 10, Excellent, (677)
"Breakfast area and food was below expectations"
The price is $127
$141 total
includes taxes & fees
Jun 4 - Jun 5
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, (273)
"nice hotel. helpful staff. stores and dining are walkable distances."
The price is $107
$119 total
includes taxes & fees
Jun 9 - Jun 10
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
3.0 star property
7.6 out of 10, Good, (4)
"The place is beautiful. The rooms are little small and could use updating. When I turned the air on the windows rattled so loud. I had to keep it on low to avoid the noise. No microwave in the room and be prepared for the slamming door at 6am. Other than those things we really enjoyed our time. "
The price is $132
$151 total
includes taxes & fees
Jun 5 - Jun 6
The Lodge at Great Oak Landing
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Driftwood Inn
Lobby
Driftwood Inn
2.0 star property
5.0 out of 10, (159)
"It was clean and everything worked--more than I could say for many other more expensive rooms I've stayed in. The shower was exceptionally good. Watch out for the hot water: very hot! The TV had Netflix, Hulu, Roku, & Vudu. And they worked. On the downside, the furnishings and carpet were worn, but not terrible. "
The price is $64
$70 total
includes taxes & fees
Jun 2 - Jun 3
Driftwood Inn
Inn at Huntingfield Creek
Lake
Inn at Huntingfield Creek
3.5 star property
10.0 out of 10, Exceptional, (44)
"Lovely property with wonderful owners and staff, including three very welcoming dogs. We had a perfect weekend getaway."
The price is $230
$255 total
includes taxes & fees
Jun 18 - Jun 19
Inn at Huntingfield Creek
Mariners Motel
Outdoor pool
Mariners Motel
2.0 star property
9.4 out of 10, Exceptional, (85)
"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 $167
$185 total
includes taxes & fees
Jun 2 - Jun 3
Mariners Motel
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
$272 total
includes taxes & fees
Jun 2 - Jun 3
BAYSIDE BUNGALOW
First Floor Studio Apartment in Historic Chestertown
Property grounds
First Floor Studio Apartment in Historic Chestertown
9.8 out of 10, Exceptional, (59)
"This was the perfect place to rest our heads along our trip down the east coast. Very comfortable, clean and quiet. We made time to visit the beautiful town and I’m glad we did!"
The price is $110
$164 total
includes taxes & fees
Jun 11 - Jun 12
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)
"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, (75)
"Great stay over Memorial Day weekend. Loved the location of the house...so close to the water and not crowded at all. We will definitely be back!"
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, (38)
"This was our second stay at your lovely cottage. I’m sure it won’t be our last. Great location!"
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!
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, (77)
"We had a great stay and the property is well maintained. They had a lot of extras for our convenience such as toothbrushes, snacks, and more. The dock and view was beautiful and relaxing. We plan to come back soon!"
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, (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
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, oven, stovetop
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
$396 total
includes taxes & fees
Jun 2 - Jun 3
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, (35)
"Nice place with everything I could want. Would stay there again!"
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, (26)
"This was our second stay here. The property is well appointed for a relaxing stay with 5-star views! Lots of room for family to spread out and relax, and the kitchen has everything you need to make delicious meals. Betterton is extra relaxing with its beautiful views and quiet stillness. We'll be back!"
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, (59)
"This is a great place to relax. The house had everything we needed and was very comfortable."
Charming Chestertown Waterfront Cottage
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

La Quinta Inn & Suites by Wyndham Baltimore N / White Marsh

La Quinta Inn & Suites by Wyndham Baltimore N / White Marsh

4 Philadelphia Ct, Rosedale, MD
The price is $95 per night from Jun 2 to Jun 3
$95
$109 total
includes taxes & fees
Jun 2 - Jun 3
7.2/10 Good! (1,004 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
5,581
Accommodation
993 hotels
Highest price
$230
Lowest price
$62
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

Fairfield Inn & Suites by Marriott White Marsh

Fairfield Inn & Suites by Marriott White Marsh

5/5 Excellent
"This is the second time I've stayed here and both experiences were extemely positive. I don't have one bad thing to say!"
A verified traveler stayed at Fairfield Inn & Suites by Marriott White Marsh
Posted 1 day ago
Fairfield Inn & Suites by Marriott White Marsh