Hotels in Chestertown

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Check prices for these dates

Tonight
May 3 - May 4
Tomorrow
May 4 - May 5
Next weekend
May 8 - May 10
In two weeks
May 15 - May 17

Where to stay in Chestertown?

Private beach nearby, sun loungers, beach volleyball
The Lodge at Great Oak Landing
The Lodge at Great Oak Landing
3.5 star property
Chestertown
7.8 out of 10, Good, (80 reviews)
Escape to this waterfront retreat featuring a seasonal outdoor pool and private beach with chairs and umbrellas. Play a round at the 9-hole golf course, dine at the restaurant, or relax at one of 3 bars before exploring nearby attractions.
The price is $132
$151 total
includes taxes & fees
May 14 - May 15
The Lodge at Great Oak Landing
Free daily full breakfast
Comfort Inn & Suites Chestertown
Comfort Inn & Suites Chestertown
2.5 star property
Chestertown
8.6 out of 10, Excellent, (909 reviews)
Tucked in peaceful Chestertown, this hotel welcomes guests with spotless rooms and an attentive staff. Swim in the seasonal outdoor pool, maintain your routine in the fitness center, and start each day with complimentary breakfast, all within reach of local attractions.
The price is $114
$126 total
includes taxes & fees
May 25 - May 26
Comfort Inn & Suites Chestertown
Lobby lounge
Red Roof Inn & Suites Chestertown
Red Roof Inn & Suites Chestertown
2.0 star property
Chestertown
7.2 out of 10, Good, (440 reviews)
This quiet Chestertown retreat offers free parking and WiFi to make your stay stress-free. Explore nearby Rolling Road Park and Historical Society of Kent County Maryland, with 24-hour staff ready to assist throughout your visit.
The price is $72
$80 total
includes taxes & fees
May 10 - May 11
Red Roof Inn & Suites Chestertown
Front of property - evening/night
Driftwood Inn
Driftwood Inn
2.0 star property
Chestertown
5.2 out of 10, (175 reviews)
Wake up refreshed at this comfortable Chestertown motel near Rolling Road Park. Enjoy convenient amenities like free WiFi and parking while exploring local attractions including the Historical Society of Kent County Maryland.
The price is $64
$70 total
includes taxes & fees
May 23 - May 24
Driftwood Inn
Desk, laptop workspace, iron/ironing board, free WiFi
Quality Inn Smyrna
Quality Inn Smyrna
2.5 star property
Smyrna
7.6 out of 10, Good, (1,001 reviews)
Experience small-town charm at this Smyrna hotel, just a short drive from Dover Downs Casino and International Speedway. Take a morning dip in the outdoor pool, stay fit at the on-site gym, and enjoy complimentary breakfast, WiFi, and parking.
The price is $82
$91 total
includes taxes & fees
May 10 - May 11
Quality Inn Smyrna
Deluxe Room | Interior detail
Relax Inn Smyrna
Relax Inn Smyrna
2.0 star property
Smyrna
8.0 out of 10, Very Good, (95 reviews)
This inviting hotel in Smyrna offers free WiFi and self parking for hassle-free convenience. The 24-hour front desk ensures assistance whenever needed. Clean rooms provide a comfortable retreat after exploring nearby Snowland attraction.
The price is $89
$114 total
includes taxes & fees
May 19 - May 20
Relax Inn Smyrna
Exterior
Holiday Inn Express & Suites Middletown by IHG
Holiday Inn Express & Suites Middletown by IHG
2.5 star property
Middletown
9.2 out of 10, Wonderful, (678 reviews)
Mornings are brighter at this Middletown hotel where free breakfast starts your day. Take advantage of the 24-hour fitness center, complimentary WiFi, and parking. Clean rooms await near Westown attractions and Everett Theatre.
The price is $110
$122 total
includes taxes & fees
May 31 - Jun 1
Holiday Inn Express & Suites Middletown by IHG
Indoor pool
Hampton Inn Middletown
Hampton Inn Middletown
2.5 star property
Middletown
8.8 out of 10, Excellent, (897 reviews)
This Hampton Inn offers free breakfast, parking, and WiFi near Westown and Everett Theatre. Relax in the indoor pool and hot tub after exploring local attractions, or enjoy a meal at one of the 20 nearby restaurants.
The price is $111
$123 total
includes taxes & fees
May 28 - May 29
Hampton Inn Middletown
Property amenity
Fairfield Inn & Suites by Marriott Middletown
Fairfield Inn & Suites by Marriott Middletown
3.0 star property
Middletown
9.2 out of 10, Wonderful, (380 reviews)
Take a refreshing dip in the indoor pool at this welcoming Middletown hotel. Enjoy free continental breakfast daily and WiFi access. Located near Westown and Everett Theatre, with friendly staff ready to assist you 24 hours a day.
The price is $104
$115 total
includes taxes & fees
May 10 - May 11
Fairfield Inn & Suites by Marriott Middletown
Property grounds
First Floor Standard Deluxe Bay View
First Floor Standard Deluxe Bay View
2.5 star property
North East
The price is $374
$523 total
includes taxes & fees
May 14 - May 15
First Floor Standard Deluxe Bay View
Exterior detail
Vandiver Inn
Vandiver Inn
3.5 star property
Havre De Grace
9.4 out of 10, Exceptional, (543 reviews)
Discover Havre De Grace from this cozy inn offering free WiFi, parking, and daily cooked-to-order breakfast. Explore nearby hiking trails and kayaking, or visit the Maritime and Decoy Museums. Guests rave about the helpful staff and garden setting.
The price is $169
$189 total
includes taxes & fees
May 4 - May 5
Vandiver Inn
Standard Room, 2 Queen Beds | In-room safe, desk, soundproofing, rollaway beds
Super 8 by Wyndham Havre De Grace Aberdeen Area
Super 8 by Wyndham Havre De Grace Aberdeen Area
2.0 star property
Havre De Grace
6.6 out of 10, (986 reviews)
Discover Havre De Grace from this hotel offering free continental breakfast, WiFi, and parking. Clean rooms provide a comfortable base to visit Susquehanna Museum and Millard Tydings Memorial Park. Guests consistently praise the attentive staff and well-maintained property.
The price is $54
$60 total
includes taxes & fees
May 5 - May 6
Super 8 by Wyndham Havre De Grace Aberdeen Area
Terrace/patio
Hilton Garden Inn Kent Island Marina
Hilton Garden Inn Kent Island Marina
3.0 star property
Grasonville
9.0 out of 10, Wonderful, (1,000 reviews)
Overlooking the bay in Grasonville, this hotel offers a refreshing indoor pool, restaurant, and bar. Unwind on the terrace after exploring nearby Chesapeake Bay Environmental Center, with convenient room service and in-room microwaves for added comfort.
The price is $147
$163 total
includes taxes & fees
May 10 - May 11
Hilton Garden Inn Kent Island Marina
Indoor pool
Best Western Kent Narrows Inn
Best Western Kent Narrows Inn
2.5 star property
Grasonville
8.0 out of 10, Very Good, (1,001 reviews)
Embrace coastal charm at this hotel in Grasonville, where superior rooms frame magical sunset vistas over the water. After exploring nearby walking trails, unwind in the indoor pool, hot tub, or sauna. Free breakfast fuels adventures to local restaurants.
The price is $107
$119 total
includes taxes & fees
May 10 - May 11
Best Western Kent Narrows Inn
Suite, 1 Queen Bed, Non Smoking | In-room safe, iron/ironing board, free WiFi, bed sheets
Quality Inn Grasonville near Kent Island
Quality Inn Grasonville near Kent Island
2.5 star property
Grasonville
7.8 out of 10, Good, (900 reviews)
Discover quiet comfort at this Grasonville hotel with complimentary buffet breakfast, WiFi, and parking. Take a refreshing swim in the seasonal outdoor pool after exploring nearby Chesapeake Bay Environmental Center. Friendly staff and clean rooms await just 50 minutes from BWI Airport.
The price is $106
$118 total
includes taxes & fees
May 25 - May 26
Quality Inn Grasonville near Kent Island
Terrace/patio
Hyatt Place Kent Narrows & Marina
Hyatt Place Kent Narrows & Marina
3.0 star property
Grasonville
9.4 out of 10, Exceptional, (751 reviews)
Experience coastal luxury at this modern Kent Narrows hotel with marina access. A 24-hour fitness center, bar, and café await after exploring nearby Chesapeake Bay Environmental Center. The helpful staff and convenient location make for an exceptional stay.
The price is $169
$188 total
includes taxes & fees
May 10 - May 11
Hyatt Place Kent Narrows & Marina
Exterior
Holiday Inn Express Annapolis East-Kent Island by IHG
Holiday Inn Express Annapolis East-Kent Island by IHG
2.5 star property
Grasonville
9.2 out of 10, Wonderful, (997 reviews)
Wake up to tranquil Chesapeake Bay vistas at this quiet waterfront retreat. Steps from the scenic bike trail with an inviting seasonal pool for afternoon dips. Complimentary breakfast fuels adventures to nearby Environmental Center and Queenstown Harbor Golf Club.
The price is $134
$149 total
includes taxes & fees
May 27 - May 28
Holiday Inn Express Annapolis East-Kent Island by IHG
Lake
Inn at Huntingfield Creek
Inn at Huntingfield Creek
3.5 star property
Rock Hall
10.0 out of 10, Exceptional, (63 reviews)
Surrounded by garden landscapes, this waterfront B&B features in-room refrigerators and laundry amenities. After enjoying the complimentary breakfast, relax by the outdoor pool or book a massage at the spa, just minutes from Rock Hall Harbor.
The price is $200
$223 total
includes taxes & fees
May 5 - May 6
Inn at Huntingfield Creek
Terrace/patio
Home2 Suites by Hilton Baltimore / Aberdeen, MD
Home2 Suites by Hilton Baltimore / Aberdeen, MD
3.0 star property
Aberdeen
8.8 out of 10, Excellent, (369 reviews)
This all-suite Aberdeen hotel offers spacious accommodations with a 24-hour fitness center near Cal Ripken Museum. After exploring nearby attractions, unwind in the indoor pool. Free parking and helpful staff ensure a comfortable business or leisure stay.
The price is $98
$109 total
includes taxes & fees
May 10 - May 11
Home2 Suites by Hilton Baltimore / Aberdeen, MD
Property grounds
First Floor Master Suite Bay View
First Floor Master Suite Bay View
2.0 star property
North East
The price is $443
$597 total
includes taxes & fees
May 14 - May 15
First Floor Master Suite Bay View
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.
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When is the best time to visit Chestertown?

Our prices for hotels in Chestertown are cheapest in January
Price trends for hotels in Chestertown
Pricing is based on two traveler single night rates
View properties in May
Currently viewing crowd sizes and weather for May.
Typical weather for Chestertown
May
High 22°C / low 14°C. Sunny most days.
View properties in May
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May, no crowd data, average high temperature 22 degrees Celsius, average low temperature 14 degrees Celsius. Sunny most days.
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26°
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June, no crowd data, average high temperature 26 degrees Celsius, average low temperature 18 degrees Celsius. Sunny most days.
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29°
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July, no crowd data, average high temperature 29 degrees Celsius, average low temperature 22 degrees Celsius. Sunny most days.
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28°
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August, no crowd data, average high temperature 28 degrees Celsius, average low temperature 21 degrees Celsius. Sunny most days.
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25°
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September, no crowd data, average high temperature 25 degrees Celsius, average low temperature 17 degrees Celsius. Sunny most days.
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October, no crowd data, average high temperature 19 degrees Celsius, average low temperature 12 degrees Celsius. Sunny most days.
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November, no crowd data, average high temperature 12 degrees Celsius, average low temperature 5 degrees Celsius. Sunny most days.
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8°
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December, no crowd data, average high temperature 8 degrees Celsius, average low temperature 2 degrees Celsius. Partly sunny.
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January, no crowd data, average high temperature 4 degrees Celsius, average low temperature -2 degrees Celsius. Partly sunny.
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6°
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February, no crowd data, average high temperature 6 degrees Celsius, average low temperature -1 degrees Celsius. Partly sunny.
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11°
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March, no crowd data, average high temperature 11 degrees Celsius, average low temperature 3 degrees Celsius. Partly sunny.
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17°
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April, no crowd data, average high temperature 17 degrees Celsius, average low temperature 8 degrees Celsius. Sunny most days.
8°
Monthly weather averages (˚C)

Top landmarks in Chestertown

Washington College

4.3/5 (87 reviews)
If you'd like to get a taste of Chestertown student life, check out Washington College, in the heart of the town.
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Learn more about Chestertown

Cobblestone streets wind past Federal-era mansions in this Chesapeake Bay gem where history feels less like a museum and more like a neighbor who won't stop talking. The Chester River waterfront invites sailing adventures aboard traditional skipjacks, while Washington College students add youthful energy to the centuries-old town. High Street's galleries showcase local artists who've captured the distinctive Eastern Shore light. The Garfield Center for the Arts occupies a lovingly restored 1920s theater where performances continue in a space that's seen everything from vaudeville to indie films. Don't miss First Fridays when galleries stay open late and locals debate whether the best crab cakes come from waterfront restaurants or roadside shacks.

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Aerial summer view of colonial Chestertown on the Chesapeake Bay in Maryland USA

Check out reviews of Chestertown hotels guests love

Pendry Baltimore

Pendry Baltimore

8/10 Good
"property is very beautiful. Everything perfect from the robes, to the marble in the showers to the thread count of sheets. only thing that could be better is size of rooms ,are a bit small. However, interior of room is very high-end amazing millwork location is great. It’s in charm city. If you’re looking for Luxury in Baltimore, you have this or The Four Seasons that is your only two options. This property is about 1/2 the price of The Four Seasons if you can find good price Expedia. On website, the prices are the same as four seasons 700-800 night. With Expedia, you can get an amazing price 375 a night w/ VIP benefits. However, be careful property does not want to acknowledge benefits unless you point out. They also charged me a few extra fees that are not disclosed on Expedia.Also by accident, I was charged for a few extra valet parking nights, which by the way is highly overpriced @ $65 a night. But pointed out, they were happy to correct. By mistake I used debit card instead of credit card to check in, they billed me around 4k because they include $150 nightly incidentals + the room fee for 6 nights. I ended up checking out two days earlier. My total bill was around $2700 because ordered 2 movies & room service once, &Valet park each night. They promised to refund balance, but instead the following morning charged me another 4k . Now total been billed over 8K. I called to rectify They did fix. They are helpful when you ask, place beautiful but be careful on charges."
Jennifer 6-night trip
Posted 8 hours ago
Pendry Baltimore

Frequently asked questions

What hotels do travelers recommend in Chestertown?
Guests like Comfort Inn & Suites Chestertown and The Lodge at Great Oak Landing.
Can I book a refundable hotel in Chestertown?
If you're looking for the flexibility to change your plans to Chestertown, most properties offer refundable* rates you can book. You can find these properties by searching our site and using the "fully refundable" filter to narrow the results down.
Where can I stay in Chestertown if I want a vacation home instead of a hotel?
If you want to find a good alternative to a hotel, review our selection of 26 vacation homes. You can also consider one of the 6 apartments or 5 cottages.
What will the weather in Chestertown be like during my trip?
July and August are typically the warmest months in Chestertown when the average temp is 74°F. January and February are the coldest months when the average temperature is 39°F. August and July are the months with the most rain.
Why should I book my Chestertown hotel with Hotels.com?
There are lots of reasons to book your Chestertown trip with us: our free cancellations on selected hotels gives you flexibility, and with One Key™, our rewards program, you will be able to earn and use OneKeyCash™* on all eligible bookings such as hotels, car rentals, flights, vacation rentals and more on Hotels.com, Expedia and Vrbo.