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Find hotels in Chestertown, MD from $53

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Compare 597 hotels, room rates, hotel reviews and availability. Most hotels are fully refundable.

Comfort Inn & Suites Chestertown
2.5 out of 5
150 Scheeler Road, Chestertown, MD, 21620
Fully refundableReserve now, pay when you stay
The price is $141 per night from Jun 4 to Jun 5
$141
per night
Jun 4 - Jun 5
0.64 mi from city center
8.4/10 Very Good! (597 reviews)
"Beautiful rooms, beautiful property! Continental breakfast was the best we have ever had. So much variety & great products"

Reviewed on May 21, 2023

Comfort Inn & Suites Chestertown
Red Roof Inn & Suites Chestertown
2 out of 5
160 Scheeler Rd, Chestertown, MD, 21620
Fully refundableReserve now, pay when you stay
The price is $119 per night from Jun 4 to Jun 5
$119
per night
Jun 4 - Jun 5
0.58 mi from city center
7.2/10 Good! (199 reviews)
"The check in staff was terrific & was able to change rooms quickly as I had mistakenly booked a rm. w/one bed instead of 2. Explained why there was no breakfast area & their inability to change the website. We were fine as there was coffee maker in room :-)"

Reviewed on May 15, 2023

Red Roof Inn & Suites Chestertown
Driftwood Inn
2 out of 5
609 Washington Avenue, Chestertown, MD, 21620
The price is $72 per night from May 31 to Jun 1
$72
per night
May 31 - Jun 1
0.25 mi from city center
4.8/10 (150 reviews)
"Very cleaned and reasonable"

Reviewed on Jun 27, 2022

Driftwood Inn

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Inn at Huntingfield Creek
3.5 out of 5
4928 Eastern Neck Rd, Rock Hall, MD, 21661
The price is $236 per night from Jun 12 to Jun 13
$236
per night
Jun 12 - Jun 13
11.32 mi from city center
10/10 Exceptional! (41 reviews)
"Many activity options."

Reviewed on May 15, 2023

Inn at Huntingfield Creek
Mariners Motel
2 out of 5
5681 South Hawthorne Avenue, Rock Hall, MD, 21661
The price is $167 per night from Jun 5 to Jun 6
$167
per night
Jun 5 - Jun 6
11.02 mi from city center
9.2/10 Wonderful! (81 reviews)
"Very glad we found this place."

Reviewed on May 13, 2023

Mariners Motel
Carriage House Hideaway in Middle of Chestertown
The price is $125 per night from Jun 1 to Jun 2
$125
per night
Jun 1 - Jun 2
0.5 mi from city center
10/10 Exceptional! (51 reviews)
"Fantastic location, gorgeous space, and great host!"

Reviewed on May 26, 2023

Carriage House Hideaway in Middle of Chestertown
First Floor Studio Apartment in Historic Chestertown
The price is $110 per night from May 31 to Jun 1
$110
per night
May 31 - Jun 1
2.18 mi from city center
9.8/10 Exceptional! (40 reviews)
Beautiful, Clean and Tranquil
"This was our second stay at this Vrbo in Chestertown. It was just as perfect for our second stay. It is very clean, quiet and comfortable and in a beautiful location."

Reviewed on May 18, 2023

First Floor Studio Apartment in Historic Chestertown
Creek Cottage at Reed Creek Farm - Idyllic, Pet-Friendly Waterfront Farm - Pool,
10/10 Exceptional! (2 reviews)
Paradise
"Everything was wonderful & we didn't want to leave! What a Gem! Thank you!"

Reviewed on Jul 5, 2022

Creek Cottage at Reed Creek Farm - Idyllic, Pet-Friendly Waterfront Farm - Pool,
Welcome to Bayside Breeze! One Block From Town Beach, Walk to Waterfront Dining
10/10 Exceptional! (25 reviews)
Rock Hall
"A very nice property"

Reviewed on Oct 25, 2022

Welcome to Bayside Breeze! One Block From Town Beach, Walk to Waterfront Dining
Waterfront Oasis w/ Private Dock, 3BR/2BA
19.06 mi from city center
10/10 Exceptional! (12 reviews)
Beautiful location
"This house met our goal- peace and relaxation on the water. Huge beautiful birds and water activities you can engage in."

Reviewed on Apr 21, 2023

Waterfront Oasis w/ Private Dock, 3BR/2BA
This is truly a Baydream!
10.75 mi from city center
10/10 Exceptional! (22 reviews)
Downrigging weekend October 2022
"Stayed in Rock Hall so we could go to Chesterton for the Sultana Downrigging weekend. Fun weekend seeing the tall ships. House was immaculate. Very comfortable. Highly recommend this house if you are looking in the area for a rental."

Reviewed on Nov 14, 2022

This is truly a Baydream!
Bayside Cottage steps from Rock Hall Harbor
The price is $201 per night from May 31 to Jun 1
$201
per night
May 31 - Jun 1
11.01 mi from city center
Bayside Cottage steps from Rock Hall Harbor
Entire Townhouse in Rock Hall
10.71 mi from city center
10/10 Exceptional! (8 reviews)
Great support from manager
"We had a small hiccup during check in The manager responded quickly and resolved the problem to our satisfaction"

Reviewed on May 8, 2023

Entire Townhouse in Rock Hall
Great Oak Manor
3.5 out of 5
10568 Cliff Rd, Chestertown, MD, 21620
7.88 mi from city center
9.4/10 Exceptional! (44 reviews)
"Plenty of privacy"

Reviewed on Feb 15, 2022

Great Oak Manor
200 steps to the beach!
11.49 mi from city center
10/10 Exceptional! (62 reviews)
Perfect getaway
"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"

Reviewed on Apr 18, 2023

200 steps to the beach!
Beautiful, spacious, quiet waterfront house!
18.4 mi from city center
9.8/10 Exceptional! (34 reviews)
Great place for a family vacation
"Good setup for a family get together. 2 grandparents in big bedroom on the main floor. 2 parents and 2 kids in 3 upstairs bedrooms. Table big enough to seat entire family and a few guests. Great open kitchen. Big family room and rear deck have great water views. We enjoyed the kayaks, inflatable ..."

Reviewed on May 15, 2023

Beautiful, spacious, quiet waterfront house!
Spacious Victorian close to everything in RH - Wheelchair friendly.
10/10 Exceptional! (3 reviews)
Sailing through History.....
"We were five retired teachers traveling to the Eastern Shore of Maryland with scheduled stops for Annapolis, St. Michaels, and Easton. Rock Hall was a perfect spot to make day trips to enjoy these locations. The house itself is perfect, five bedrooms so we each had our own room, two full baths, and ..."

Reviewed on May 6, 2023

Spacious Victorian close to everything in RH - Wheelchair friendly.
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Chestertown hotels information

Number of reviews
1,371
Accommodation
597 hotels
Lowest Price
$53
Highest Price
$236

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?

Waterfront Oasis of Annapolis Gold: This vacation home rental outside of Chestertown is located on the waterfront and has an outdoor pool, a fireplace, and air-conditioning to put you at ease in your new surroundings. Kitchen amenities include a fridge, a microwave, and kitchenware. 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?

Red Roof Inn & Suites Chestertown is a hotel with free parking and laundry facilities, and it's a top choice on Expedia for families. Driftwood Inn is another good choice for your kid-friendly vacation. Attractions in the area like Crumpton Auction and Hazel Miner Monument are also fun for kids of all ages. 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 pet-friendly hotel in Chestertown?

Driftwood Inn is a top property for people traveling with their pets, and offers free WiFi for its human guests. Comfort Inn & Suites Chestertown is another good choice for a stay with your pet. 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?

Great Oak Manor is a top 3.5-star B&B located on the 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. See more options for historical stays in Chestertown.

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