Chestertown Hotels

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Check prices for these dates

Tonight
28 Nov - 29 Nov
Tomorrow
29 Nov - 30 Nov
This weekend
28 Nov - 30 Nov
Next weekend
5 Dec - 7 Dec

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Top 10 trending Chestertown hotels

Lobby
Comfort Inn & Suites Chestertown

Comfort Inn & Suites Chestertown

2.5 star property
Chestertown
8.6 out of 10, Excellent, (857)
"The room was a great size and very clean. The staff were very accommodating and friendly. The amenities were very good. We would definitely recommend this hotel. "
United States
Santa
The price is €103
includes taxes & fees
9 Dec - 10 Dec
Comfort Inn & Suites Chestertown
Suite, Multiple Beds, Non Smoking
Red Roof Inn & Suites Chestertown

Red Roof Inn & Suites Chestertown

2.0 star property
Chestertown
7.2 out of 10, Good, (417)
"This property was clean but dated. The carpet was stained, the furniture and fixtures were worn and broken, towels were washed but old and in need of replacement."
United States
Derek
The price is €69
includes taxes & fees
11 Dec - 12 Dec
Red Roof Inn & Suites 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
8.0 out of 10, Very good, (76)
"Very nice rooms, "
United States
Stephania
The price is €98
includes taxes & fees
11 Dec - 12 Dec
The Lodge at Great Oak Landing
Front of property – evening/night
Driftwood Inn

Driftwood Inn

2.0 star property
Chestertown
5.2 out of 10, (175)
"Rooms are clean, staf was helpful "
United States
Daryl
The price is €61
includes taxes & fees
24 Dec - 25 Dec
Driftwood Inn
Free daily buffet breakfast
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, (1075)
"Easy check in and out. "
United States
Andrew
The price is €64
includes taxes & fees
9 Dec - 10 Dec
La Quinta Inn & Suites by Wyndham Baltimore N / White Marsh
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, (925)
"nice, clean, up to date, budget friendly hotel"
United States
mike
The price is €76
includes taxes & fees
14 Dec - 15 Dec
Holiday Inn Express Annapolis East-Kent Island by IHG
Exterior
Country Inn & Suites by Radisson, Baltimore North, MD

Country Inn & Suites by Radisson, Baltimore North, MD

3.0 star property
Rossville
7.2 out of 10, Good, (1004)
"The reason I booked this hotel was because it had a hot tub and pool. These were both closed for "the season" without notification. If I knew that, I would have booked elsewhere. Everything else was just ok."
Canada
Brian
The price is €84
includes taxes & fees
29 Dec - 30 Dec
Country Inn & Suites by Radisson, Baltimore North, MD
Restaurant
Hampton Inn & Suites Edgewood/Aberdeen-South

Hampton Inn & Suites Edgewood/Aberdeen-South

2.5 star property
Edgewood
9.4 out of 10, Exceptional, (1011)
"Would stay again"
United States
Dena
The price is €79
includes taxes & fees
28 Dec - 29 Dec
Hampton Inn & Suites Edgewood/Aberdeen-South
Desk, free WiFi, bed sheets, alarm clocks
Quality Inn & Suites Bel Air I-95 Exit 77A

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

2.5 star property
Edgewood
7.4 out of 10, Good, (1024)
"Staff was very friendly. "
United States
Ashlee
The price is €61
includes taxes & fees
7 Dec - 8 Dec
Quality Inn & Suites Bel Air I-95 Exit 77A
Lobby
Best Western Plus Hotel & Conference Center

Best Western Plus Hotel & Conference Center

2.5 star property
Medford
7.8 out of 10, Good, (1002)
"Yes I love how the room was, I had an amazing stay, the staff was nice and easy to manage I loved it thank you "
United States
Carmen
The price is €90
includes taxes & fees
28 Dec - 29 Dec
Best Western Plus Hotel & Conference Center
Lobby sitting area
Comfort Inn & Suites Aberdeen near APG

Comfort Inn & Suites Aberdeen near APG

2.5 star property
Aberdeen
7.8 out of 10, Good, (800)
"The front desk staff were friendly and welcoming!"
United States
Bonnie
The price is €74
includes taxes & fees
21 Dec - 22 Dec
Comfort Inn & Suites Aberdeen near APG
Restaurant
Hampton Inn & Suites Baltimore/Aberdeen

Hampton Inn & Suites Baltimore/Aberdeen

2.5 star property
Aberdeen
9.0 out of 10, Wonderful, (595)
"Wonderful room and location "
United States
Caren
The price is €87
includes taxes & fees
7 Dec - 8 Dec
Hampton Inn & Suites Baltimore/Aberdeen
Lobby sitting area
Americas Best Value Inn Edgewood

Americas Best Value Inn Edgewood

2.0 star property
Edgewood
5.6 out of 10, (1006)
"I love staying here. The prices are always reasonable, the staff are always so nice & helpful. The area is kept clean there's stores close to this hotel all around so convient! "
United States
Christeena
The price is €49
includes taxes & fees
17 Dec - 18 Dec
Americas Best Value Inn Edgewood
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, (1004)
"Easy parking and check in. Conveniently located within walking distance of some great seafood restaurants. Always an enjoyable stay"
United States
Roberta
The price is €114
includes taxes & fees
4 Dec - 5 Dec
Hilton Garden Inn Kent Island Marina
Terrace/patio
Hyatt Place Kent Narrows & Marina

Hyatt Place Kent Narrows & Marina

3.0 star property
Grasonville
9.4 out of 10, Exceptional, (666)
"My favorite hotel "
United States
Jen
The price is €111
includes taxes & fees
1 Dec - 2 Dec
Hyatt Place Kent Narrows & Marina
Exterior
Super 8 by Wyndham Aberdeen MD

Super 8 by Wyndham Aberdeen MD

2.0 star property
Aberdeen
7.0 out of 10, Good, (856)
"Nice and clean. Staff was friendly. I had no problems whatsoever, and I would stay here again."
United States
Shelly
The price is €48
includes taxes & fees
15 Dec - 16 Dec
Super 8 by Wyndham Aberdeen MD
Free daily buffet breakfast
Fairfield Inn & Suites by Marriott White Marsh

Fairfield Inn & Suites by Marriott White Marsh

2.5 star property
Nottingham
8.6 out of 10, Excellent, (1007)
"Great place to stay"
United States
brian
The price is €91
includes taxes & fees
7 Dec - 8 Dec
Fairfield Inn & Suites by Marriott White Marsh
Exterior
Super 8 by Wyndham Baltimore/Essex Area

Super 8 by Wyndham Baltimore/Essex Area

2.0 star property
Essex
5.4 out of 10, (407)
"Just a nice quiet cool place clean rooms and the bed is away from the door lol"
United States
Jamelle
The price is €75
includes taxes & fees
4 Dec - 5 Dec
Super 8 by Wyndham Baltimore/Essex Area
Exterior
Hampton Inn Baltimore/White Marsh

Hampton Inn Baltimore/White Marsh

2.5 star property
Nottingham
7.6 out of 10, Good, (1008)
"Breakfast lady fabulous Staff very friendly "
United Kingdom
Alan
The price is €87
includes taxes & fees
9 Dec - 10 Dec
Hampton Inn Baltimore/White Marsh
Terrace/patio
Holiday Inn Express Aberdeen by IHG

Holiday Inn Express Aberdeen by IHG

2.5 star property
Aberdeen
8.6 out of 10, Excellent, (425)
"Kid friendly for sure! The room and hotel is clean and comfy, no complaints! Chlorine smell a bit strong in pool area but it didn’t bother me. We missed breakfast so not sure about that but everything else was great!"
United States
Gabrielle
The price is €106
includes taxes & fees
29 Nov - 30 Nov
Holiday Inn Express Aberdeen by IHG
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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Stay near popular Chestertown attractions

Washington College

4.1/5 (45 reviews)
Enjoy the student vibe when you visit Washington College during your travels in Chestertown. Amble around this family-friendly area's riverfront or experience its festivals.
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Rolphs Wharf Marina

Explore the waterfront in Chestertown with a trip to Rolphs Wharf Marina. Take in the festivals in this family-friendly area.
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Learn more about Chestertown

Colonial charm meets Chesapeake Bay beauty in this historic waterfront town where 18th-century buildings house art galleries and boutiques. Rent kayaks to explore the Chester River or time your visit for the Downrigging Weekend Festival when tall ships transform the harbour.

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

Top Chestertown Hotel Reviews

Best Western Plus Hotel & Conference Center

Best Western Plus Hotel & Conference Center

10/10 Excellent
"Amazing staff. Clean room."
Cindy 1-night trip
Posted 23 hours ago
Best Western Plus Hotel & Conference Center

More cheap stays in Chestertown

Best Western Plus Hotel & Conference Center

Best Western Plus Hotel & Conference Center

5625 O'Donnell Street Baltimore MD
The price is €90 per night from 28 Dec to 29 Dec
€90
28 Dec - 29 Dec
includes taxes & fees
7.8/10 Good! (1,002 reviews)

Frequently asked questions

Where is the best place for a stay in Chestertown?
Comfort Inn & Suites Chestertown is a favourite 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 stay. See all available top hotels, or vacation rentals in Chestertown.
What are some of the best holiday rentals that Chestertown has to offer?
Upper Chesapeake Bay 5 bedroom, 3 bath, Hot Tub, Waterfront: This holiday home rental outside of Chestertown is located on a river, and has a patio, a garden and a BBQ to put you at ease in your new surroundings. It has 5 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You can relax into your holiday with a selection of games and 1 hot tub. See all vacation rentals in Chestertown.
If I need to cancel my hotel reservation in Chestertown, will I receive a refund?
Yes! You'll find that most hotel bookings are fully refundable as long as you cancel prior to the accommodation's cancellation deadline, which in most cases is within 24 or 48 hours of your check-in date. If you booked a non-refundable reservation, 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.
What's the best family accommodation 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 stay with the kids. Also, children of all ages will enjoy a visit to Crumpton Auction. Find more child-friendly accommodations in Chestertown.
What is the top LGBTQ-friendly hotel 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 two other good options for your stay. See all available hotels listed as LGBTQ-friendly in Chestertown.
What's the best dog-friendly accommodation option in Chestertown?
Comfort Inn & Suites Chestertown is a top hotel for people travelling with their pets, and offers a seasonal outdoor pool and a fitness centre for its human guests. Other good options for you and your pet include Red Roof Inn & Suites Chestertown and Driftwood Inn. See more pet-friendly hotel accommodations in Chestertown.
What's the best hotel to stay near the beach in Chestertown?
The Lodge at Great Oak Landing is a top lodge with a seasonal outdoor pool and 3 bars/lounges, and it's located near a private beach . See more stays near the beach in Chestertown.
What are some accommodation options with pools in Chestertown?
The Lodge at Great Oak Landing is a top lodge with a seasonal outdoor pool, 3 bars/lounges and free WiFi. View all hotels with pools in Chestertown.
How is it to stay in Chestertown?
Visitors to Chestertown will definitely enjoy the university setting. Tourists can also enjoy the city's sporting events, festivals and art. In Chestertown, there are 39 hotels and other accommodation options to choose from. Find out more about Chestertown.
What should I see while I'm in Chestertown?
Cultural venues include Historical Society of Kent County Maryland and Garfield Center for the Arts at the Prince Theater. The picturesque setting of Northern Chesapeake Bay and Chesapeake Bay exemplify the area's natural beauty. University life is a highlight and campuses to tour include Washington College and River Arts Chestertown. Take a look at what more there is to see and do in Expedia's Chestertown guide.
What's the seasonal weather like in Chestertown?
The hottest months are usually July and August, with an average temperature of 23°C, while the coldest months are January and February, with an average of 4°C. Average annual precipitation for Chestertown is 1232 mm.

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