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Find hotels in Chestertown, MD from CA $85

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Check Chestertown hotel prices

Tonight
May 20 - May 21
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May 21 - May 22
This weekend
May 24 - May 26
Next weekend
May 31 - Jun 2

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Top 10 Chestertown hotels and places to stay

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 CA $313
CA $347 total
includes taxes & fees
May 22 - May 23
Inn at Huntingfield Creek
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 CA $238
CA $369 total
includes taxes & fees
May 24 - May 25
BAYSIDE BUNGALOW
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
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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!
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
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!
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
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!
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 CA $274
CA $536 total
includes taxes & fees
May 22 - May 23
Bayside Cottage steps from Rock Hall Harbor
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
Exterior
Cozy, unique, historic registered cottage on the Corsica River!
10.0 out of 10, Exceptional, (5)
"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!
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
Property grounds
Historic Downtown Garden Oasis with Private Patio
10.0 out of 10, Exceptional, (14)
"Stephen and Marianna were great hosts. The property was very clean and functional with beautiful artwork throughout the property. Great outdoor patio for relaxing plus excellent location for access to downtown Chestertown. We will be staying here again on our next visit."
Historic Downtown Garden Oasis with Private Patio
Beach nearby, sun loungers, beach towels
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
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
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!
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 CA $150
CA $224 total
includes taxes & fees
Jun 11 - Jun 12
First Floor Studio Apartment in Historic Chestertown
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
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
Fridge, microwave, oven, stovetop
Newly restored apartment in the heart of Chestertown
9.8 out of 10, Exceptional, (15)
"This was a great apartment in an excellent location. We visited Washington college and attended a sailing regatta. The Evergrain Bakery across the street was amazing. Shops and restaurants all within walking distance! Apartment was well stocked, nicely decorated and clean! Also very close to the Hodson boathouse. It was a 3 minute drive!"
Newly restored apartment in the heart of Chestertown
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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

Quality Inn & Suites Bel Air I-95 Exit 77A

Quality Inn & Suites Bel Air I-95 Exit 77A

2112a Emmorton Park Road, Edgewood, MD
The price is CA $85 per night from May 26 to May 27
CA $85
CA $95 total
includes taxes & fees
May 26 - May 27
7.4/10 Good! (1,002 reviews)

Hotels near Popular Chestertown Attractions

Image for Washington College

Washington College

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 hotels
1,005
Highest price
CA $313
Lowest price
CA $85
Known attractions
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 in Chestertown
Expedia verified reviews

Historic Inns of Annapolis

Historic Inns of Annapolis

5/5 Excellent
"Great location, beautiful, historic building within walking distance of most sights, shops and restaurants. "
A verified traveller stayed at Historic Inns of Annapolis
Posted 9 hours ago
Historic Inns of Annapolis