Hotels in Chestertown

Free cancellation options if plans change

Earn rewards on every night you stay

Save more with Member Prices

Check prices for these dates

Tonight
Oct 27 - Oct 28
Tomorrow
Oct 28 - Oct 29
This weekend
Oct 30 - Nov 1
Next weekend
Nov 6 - Nov 8

Where to stay in Chestertown?

A historic brick building with a corner turret and multiple windows, located on a city street with flags and street lamps.

1. Historic Inns of Annapolis

Historic Inns of Annapolis
3.5 star property
Historic District
9.0 out of 10, Wonderful, (2,060 reviews)
Nestled in the heart of Annapolis, this historic hotel offers easy access to the Naval Academy. Unwind in comfortable beds after exploring nearby attractions, or enjoy a drink at the bar. The helpful staff and clean rooms earn high praise from travelers.
The price is $86
$132 total
includes taxes & fees
Nov 9 - Nov 10
Historic Inns of Annapolis
A hotel lobby with a fireplace, seating area, and a television.

2. Comfort Inn & Suites Chestertown

Comfort Inn & Suites Chestertown
2.5 star property
Chestertown
8.6 out of 10, Excellent, (995 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 $98
$109 total
includes taxes & fees
Nov 18 - Nov 19
Comfort Inn & Suites Chestertown
A resort with a large pool, a water slide, and a building with multiple windows.

3. Great Wolf Lodge Perryville

Great Wolf Lodge Perryville
2.0 star property
Perryville
8.6 out of 10, Excellent, (361 reviews)
Splash into adventure at this exciting hotel with a water park in Perryville. Four restaurants and a bar/lounge provide ample dining choices. Located near Hollywood Casino and Garrett Island Beach, with free WiFi and convenient access to Perryville Station just a 9-minute drive away.
The price is $207
$232 total
includes taxes & fees
Oct 28 - Oct 29
Great Wolf Lodge Perryville
A living room with a fireplace, a television, and a stone accent wall.

4. Red Roof Inn & Suites Chestertown

Red Roof Inn & Suites Chestertown
2.0 star property
Chestertown
7.2 out of 10, Good, (511 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
Nov 2 - Nov 3
Red Roof Inn & Suites Chestertown
A campfire in a stone fire pit by a lakeside at sunset.

5. The Lodge at Great Oak Landing

The Lodge at Great Oak Landing
3.5 star property
Chestertown
8.0 out of 10, Very good, (124 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 $120
$137 total
includes taxes & fees
Oct 28 - Oct 29
The Lodge at Great Oak Landing
A row of motel rooms with stone walls and red doors.

6. Driftwood Inn

Driftwood Inn
2.0 star property
Chestertown
5.4 out of 10, (183 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
Oct 28 - Oct 29
Driftwood Inn
A reception area with two reception desks, a cityscape mural, and a clock on the wall.

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

La Quinta Inn & Suites by Wyndham Baltimore N / White Marsh
3.0 star property
Rossville
7.0 out of 10, Good, (1,243 reviews)
Stay close to White Marsh Mall at this comfortable hotel offering free daily breakfast, WiFi, and parking. The fitness center keeps routines on track while Johns Hopkins Hospital and Baltimore Cruise Terminal are within easy driving distance.
The price is $70
$81 total
includes taxes & fees
Nov 2 - Nov 3
La Quinta Inn & Suites by Wyndham Baltimore N / White Marsh
A marina with numerous boats docked, a prominent building with a dome in the background, and a clear view of the water.

8. Graduate by Hilton Annapolis

Graduate by Hilton Annapolis
4.0 star property
Annapolis
9.4 out of 10, Exceptional, (1,012 reviews)
This quiet Annapolis hotel offers a peaceful atmosphere near shopping and dining options. Enjoy the 24-hour fitness center, comfortable beds, and friendly bar/lounge. Borrow free bicycles to explore nearby attractions while the helpful staff ensures a comfortable stay.
The price is $139
$158 total
includes taxes & fees
Nov 22 - Nov 23
Graduate by Hilton Annapolis
Lobby

9. Hilton Garden Inn Annapolis Downtown

Hilton Garden Inn Annapolis Downtown
3.0 star property
Annapolis
8.6 out of 10, Excellent, (1,012 reviews)
Explore downtown Annapolis from this stylish Art Deco hotel with Kitchen on West St serving regional cuisine. The 24-hour fitness center, in-room refrigerators, and microwaves enhance your stay near Annapolis Civil Rights Plaque.
The price is $102
$116 total
includes taxes & fees
Nov 22 - Nov 23
Hilton Garden Inn Annapolis Downtown
A rooftop terrace with wicker furniture, a fire pit, and a view of a marina.

10. Hyatt Place Kent Narrows & Marina

Hyatt Place Kent Narrows & Marina
3.0 star property
Grasonville
9.4 out of 10, Exceptional, (847 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 $139
$154 total
includes taxes & fees
Nov 24 - Nov 25
Hyatt Place Kent Narrows & Marina
A modern hotel lobby with a long dining table, several chairs, and a bar area.

11. Hampton Inn & Suites Edgewood/Aberdeen-South

Hampton Inn & Suites Edgewood/Aberdeen-South
2.5 star property
Edgewood
9.4 out of 10, Exceptional, (1,007 reviews)
Wake up to free breakfast at this Edgewood hotel before swimming in the indoor pool or working out at the health club. Business travelers appreciate the free WiFi and parking, while nearby CopperPlex and Emmorton Recreation offer local entertainment.
The price is $85
$96 total
includes taxes & fees
Nov 2 - Nov 3
Hampton Inn & Suites Edgewood/Aberdeen-South
An indoor swimming pool with clear water, a changing room, and exercise equipment.

12. Hilton Garden Inn Baltimore/White Marsh

Hilton Garden Inn Baltimore/White Marsh
3.0 star property
Nottingham
7.8 out of 10, Good, (1,003 reviews)
This lively Baltimore hotel offers an indoor pool and The Great American Grill restaurant/bar for dining options. With free parking and WiFi, plus in-room refrigerators and microwaves, you're minutes from Essex Marina and local attractions.
The price is $102
$117 total
includes taxes & fees
Nov 2 - Nov 3
Hilton Garden Inn Baltimore/White Marsh
A Hampton Inn with a 'Welcome' sign under a covered entrance, surrounded by greenery.

13. Hampton Inn Baltimore/White Marsh

Hampton Inn Baltimore/White Marsh
2.5 star property
Nottingham
7.8 out of 10, Good, (1,003 reviews)
This Baltimore hotel sits next to a train station with restaurants nearby. Take a refreshing swim in the seasonal outdoor pool or squeeze in a workout at the fitness center. White Marsh Mall and Essex Marina are a short drive away, and guests love the helpful staff.
The price is $102
$117 total
includes taxes & fees
Nov 8 - Nov 9
Hampton Inn Baltimore/White Marsh
A hotel entrance with a stone facade, large glass doors, and a sign indicating it is The Inn.

14. The Inn at Chesapeake Bay Beach Club

The Inn at Chesapeake Bay Beach Club
4.0 star property
Stevensville
9.4 out of 10, Exceptional, (504 reviews)
Escape to this serene Chesapeake retreat featuring an outdoor pool and indulgent spa treatments. Just minutes from Northern Chesapeake Bay and Paul Reed Smith Guitars, the hotel offers a cafe, 24-hour fitness center, and attentive staff that guests consistently praise.
The price is $214
$263 total
includes taxes & fees
Nov 15 - Nov 16
The Inn at Chesapeake Bay Beach Club
A hotel room with a bed, a desk with a chair, a sofa, and a coffee table. There is a TV on the desk and a window with curtains.

15. La Quinta Inn & Suites by Wyndham Bel Air/I-95 Exit 77A

La Quinta Inn & Suites by Wyndham Bel Air/I-95 Exit 77A
3.0 star property
Edgewood
8.2 out of 10, Very good, (1,141 reviews)
Start your day with complimentary buffet breakfast at this convenient Edgewood hotel. Located near CopperPlex and Emmorton Recreation Center, with free WiFi and parking. Just 6 minutes from Edgewood Station and praised for its helpful staff.
The price is $79
$89 total
includes taxes & fees
Nov 24 - Nov 25
La Quinta Inn & Suites by Wyndham Bel Air/I-95 Exit 77A
A gazebo with a view of a lake at dusk.

16. 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, (1,004 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 $105
$117 total
includes taxes & fees
Nov 15 - Nov 16
Holiday Inn Express Annapolis East-Kent Island by IHG
A balcony with a table set for two, overlooking a marina with boats.

17. Annapolis Waterfront Hotel, Autograph Collection

Annapolis Waterfront Hotel, Autograph Collection
4.0 star property
Historic District
8.8 out of 10, Excellent, (1,003 reviews)
Wake up to shimmering harbor vistas at this waterfront gem steps from U.S. Naval Academy. After breakfast at Pussers Caribbean Grille, explore nearby Ego Alley or work out in the 24-hour fitness center while luxury yachts drift by.
The price is $215
$245 total
includes taxes & fees
Nov 8 - Nov 9
Annapolis Waterfront Hotel, Autograph Collection
A lobby with a reception desk, seating area, and a fireplace.

18. Fairfield Inn & Suites by Marriott White Marsh

Fairfield Inn & Suites by Marriott White Marsh
3.0 star property
Nottingham
8.8 out of 10, Excellent, (1,005 reviews)
Dive into the seasonal outdoor pool or maintain your routine in the 24-hour fitness center at this Baltimore hotel. Located within 15 minutes of Towson University and near White Marsh Mall, it offers free breakfast, WiFi, and parking.
The price is $101
$117 total
includes taxes & fees
Nov 22 - Nov 23
Fairfield Inn & Suites by Marriott White Marsh
A balcony with a view of a body of water, a row of buildings, and a chair.

19. Hilton Garden Inn Kent Island Marina

Hilton Garden Inn Kent Island Marina
3.0 star property
Grasonville
9.0 out of 10, Wonderful, (1,002 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 $131
$146 total
includes taxes & fees
Nov 22 - Nov 23
Hilton Garden Inn Kent Island Marina
A boat deck with a white bench and a view of a calm lake and distant trees.

20. Inn at Huntingfield Creek

Inn at Huntingfield Creek
3.5 star property
Rock Hall
10.0 out of 10, Exceptional, (74 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 $156
$173 total
includes taxes & fees
Nov 16 - Nov 17
Inn at Huntingfield Creek
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.
View all properties

Go beyond your typical stay in Chestertown

pet friendly image
Pet friendly
Pet friendly
hot tub image
Hot tub
Hot tub

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 October
Currently viewing crowd sizes and weather for October.

October

High 19°C / low 12°C. Sunny most days.
19°
weather_sun
October, no crowd data, average high temperature 19 degrees Celsius, average low temperature 12 degrees Celsius. Sunny most days.
12°
12°
weather_sun
November, no crowd data, average high temperature 12 degrees Celsius, average low temperature 5 degrees Celsius. Sunny most days.
5°
8°
weather_partly_sunny
December, no crowd data, average high temperature 8 degrees Celsius, average low temperature 2 degrees Celsius. Partly sunny.
2°
4°
weather_partly_sunny
January, no crowd data, average high temperature 4 degrees Celsius, average low temperature -2 degrees Celsius. Partly sunny.
-2°
6°
weather_partly_sunny
February, no crowd data, average high temperature 6 degrees Celsius, average low temperature -1 degrees Celsius. Partly sunny.
-1°
11°
weather_partly_sunny
March, no crowd data, average high temperature 11 degrees Celsius, average low temperature 3 degrees Celsius. Partly sunny.
3°
17°
weather_sun
April, no crowd data, average high temperature 17 degrees Celsius, average low temperature 8 degrees Celsius. Sunny most days.
8°
22°
weather_sun
May, no crowd data, average high temperature 22 degrees Celsius, average low temperature 14 degrees Celsius. Sunny most days.
14°
26°
weather_sun
June, no crowd data, average high temperature 26 degrees Celsius, average low temperature 18 degrees Celsius. Sunny most days.
18°
29°
weather_sun
July, no crowd data, average high temperature 29 degrees Celsius, average low temperature 22 degrees Celsius. Sunny most days.
22°
28°
weather_sun
August, no crowd data, average high temperature 28 degrees Celsius, average low temperature 21 degrees Celsius. Sunny most days.
21°
25°
weather_sun
September, no crowd data, average high temperature 25 degrees Celsius, average low temperature 17 degrees Celsius. Sunny most days.
17°
Monthly weather averages (˚C)

Top landmarks in Chestertown

Washington College

8.6/10 (87 reviews)
If you'd like to get a taste of Chestertown student life, check out Washington College, in the heart of the town.
See properties

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.

See all hotels in Chestertown
A lakeside town with a marina, a bridge, and a mix of residential and commercial buildings.

Check out reviews of Chestertown hotels guests love

A boat deck with a white bench and a view of a calm lake and distant trees.
Inn at Huntingfield Creek

Inn at Huntingfield Creek

Inn at Huntingfield Creek
Rock Hall

10/10 Exceptional

Quaint property - very laid-back. Exactly what we were looking for.
United States
George
Reviewed February 28, 2023
Inn at Huntingfield Creek

Frequently Asked Questions

What hotels do travelers recommend in Chestertown?

Guests like Red Roof Inn & Suites Chestertown, The Lodge at Great Oak Landing and Comfort Inn & Suites Chestertown.

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 29 vacation homes. You can also consider one of the 5 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.