Chestertown Hotels from ₹5,142

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Check prices for these dates

Tonight
14 Mar - 15 Mar
Tomorrow
15 Mar - 16 Mar
Next weekend
20 Mar - 22 Mar
In two weeks
27 Mar - 29 Mar

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Our top choices for Chestertown hotels

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, (77 reviews)
"Very nice rooms, "
United States
Stephania
The price is ₹9,957
₹11,384 total
includes taxes & fees
17 Mar - 18 Mar
The Lodge at Great Oak Landing
Lobby lounge

Red Roof Inn & Suites Chestertown

Red Roof Inn & Suites Chestertown
2.0 star property
Chestertown
7.2 out of 10, Good, (429 reviews)
"Arrived earlier than expected and the staff was very accommodating and friendly which made for an excellent stay from start to finish. "
United States
Linette
The price is ₹6,554
₹7,275 total
includes taxes & fees
24 Mar - 25 Mar
Red Roof Inn & Suites Chestertown
Free daily full breakfast

Comfort Inn & Suites Chestertown

Comfort Inn & Suites Chestertown
2.5 star property
Chestertown
8.6 out of 10, Excellent, (885 reviews)
"Staying is peaceful and the rooms clean."
United States
Robert
The price is ₹9,635
₹10,695 total
includes taxes & fees
19 Mar - 20 Mar
Comfort Inn & Suites Chestertown
Front of property – evening/night

Driftwood Inn

Driftwood Inn
2.0 star property
Chestertown
5.2 out of 10, (175 reviews)
"Rooms are clean, staf was helpful "
United States
Daryl
Driftwood Inn
Indoor pool

Best Western Kent Narrows Inn

Best Western Kent Narrows Inn
2.5 star property
Grasonville
8.0 out of 10, Very good, (1,006 reviews)
"Wonderful staff,Clean rooms and comfortable bed!!"
United States
Evette
The price is ₹8,666
₹9,619 total
includes taxes & fees
17 Mar - 18 Mar
Best Western Kent Narrows Inn
Exterior

134 Prince - Luxury Boutique Hotel

134 Prince - Luxury Boutique Hotel
2.5 star property
Annapolis
9.8 out of 10, Exceptional, (34 reviews)
"Wonderful place to go, especially during the Annapolis boat show... easy access to everything beautiful property and staff"
United States
Ian
134 Prince - Luxury Boutique Hotel
Lobby lounge

Flag House Inn

Flag House Inn
3.5 star property
Historic District
9.4 out of 10, Exceptional, (87 reviews)
"The Inn is beautiful and the staff very welcoming. My room was spotless, cozy, and tastefully decorated. The location is directly across the street from the USNA. I skipped breakfast, but the offerings looked lovely. Will definitely stay here again. "
United States
Elizabeth
The price is ₹16,742
₹19,086 total
includes taxes & fees
16 Mar - 17 Mar
Flag House 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, (1,000 reviews)
"My visit at the Hotel was amazing & peaceful."
United States
Milton
The price is ₹7,073
₹7,851 total
includes taxes & fees
14 Apr - 15 Apr
Quality Inn Smyrna
Free daily continental breakfast

Holiday Inn Express Edgewood-Aberdeen-Bel Air by IHG

Holiday Inn Express Edgewood-Aberdeen-Bel Air by IHG
2.5 star property
Edgewood
9.0 out of 10, Wonderful, (576 reviews)
"A solid place to stay in the area!"
United States
Donald
The price is ₹8,482
₹9,500 total
includes taxes & fees
17 Mar - 18 Mar
Holiday Inn Express Edgewood-Aberdeen-Bel Air by IHG
Exterior

La Quinta Inn & Suites by Wyndham Aberdeen-APG

La Quinta Inn & Suites by Wyndham Aberdeen-APG
3.0 star property
Aberdeen
9.0 out of 10, Wonderful, (1,001 reviews)
"Clean room, near shopping & dining, & complimentary breakfast buffet! "
United States
Chanel
The price is ₹7,993
₹8,953 total
includes taxes & fees
30 Mar - 31 Mar
La Quinta Inn & Suites by Wyndham Aberdeen-APG
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, (355 reviews)
"Consistently a good stay here with helpful staff and comfortable rooms. "
United States
Mary
The price is ₹9,127
₹10,131 total
includes taxes & fees
22 Mar - 23 Mar
Fairfield Inn & Suites by Marriott Middletown
Property amenity

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, (976 reviews)
"There were no healthy options offered, not even hard-boiled eggs. I guess they haven't seen the new food pyramid!"
United States
Carleen Lyden
The price is ₹4,591
₹5,142 total
includes taxes & fees
17 Mar - 18 Mar
Super 8 by Wyndham Havre De Grace Aberdeen Area
Individually decorated, individually furnished, desk, blackout curtains

Ramada Hotel & Conference Center by Wyndham Edgewood

Ramada Hotel & Conference Center by Wyndham Edgewood
2.0 star property
Edgewood
6.6 out of 10, (523 reviews)
"Clean room, courteous staff, quiet area, convenient location with food and amenities nearby."
United States
Somu
The price is ₹5,808
₹6,505 total
includes taxes & fees
17 Mar - 18 Mar
Ramada Hotel & Conference Center by Wyndham Edgewood
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, (353 reviews)
"Awesome staff, very clean, great pool Awesome breakfast!!! All good things"
United States
Patty
The price is ₹9,022
₹10,105 total
includes taxes & fees
22 Mar - 23 Mar
Home2 Suites by Hilton Baltimore / Aberdeen, MD
Lobby sitting area

Comfort Inn & Suites Aberdeen near APG

Comfort Inn & Suites Aberdeen near APG
2.5 star property
Aberdeen
8.0 out of 10, Very good, (864 reviews)
"For a night to rest our heads, this stay was ok. While the floors were sticky and the hot breakfast was cold, the bed was comfortable enough for us the sleep like a rock. "
United States
Nichole
The price is ₹7,223
₹8,090 total
includes taxes & fees
30 Mar - 31 Mar
Comfort Inn & Suites Aberdeen near APG
Lobby

Country Inn & Suites by Radisson, Bel Air/Aberdeen, MD

Country Inn & Suites by Radisson, Bel Air/Aberdeen, MD
3.0 star property
Bel Air
8.8 out of 10, Excellent, (1,001 reviews)
"Very nice place to stay. They offer a good breakfast buffet Variety.Beds very comfortable they offer daily room service just all around good stay would recommend."
United States
Donald
The price is ₹7,814
₹8,751 total
includes taxes & fees
30 Mar - 31 Mar
Country Inn & Suites by Radisson, Bel Air/Aberdeen, MD
Lobby

Homewood Suites by Hilton Bel Air

Homewood Suites by Hilton Bel Air
3.0 star property
Bel Air
8.8 out of 10, Excellent, (476 reviews)
"Nice accommodation"
United States
Cecilia
The price is ₹8,997
₹10,076 total
includes taxes & fees
25 Mar - 26 Mar
Homewood Suites by Hilton Bel Air
Lobby

Quality Inn Grasonville near Kent Island

Quality Inn Grasonville near Kent Island
2.5 star property
Grasonville
7.8 out of 10, Good, (880 reviews)
"Staff was friendly and helpful and allowed me to check in early"
United States
Chad
The price is ₹8,619
₹9,568 total
includes taxes & fees
17 Mar - 18 Mar
Quality Inn Grasonville near Kent Island
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, (972 reviews)
"Check-in was great! The young man at the desk was so friendly and helpful!! Room was clean and beds were clean and comfortable!"
United States
Kelley
The price is ₹9,957
₹11,052 total
includes taxes & fees
23 Mar - 24 Mar
Holiday Inn Express Annapolis East-Kent Island by IHG
Reception

Hampton Inn & Suites Edgewood/Aberdeen-South

Hampton Inn & Suites Edgewood/Aberdeen-South
2.5 star property
Edgewood
9.2 out of 10, Wonderful, (1,002 reviews)
"Clean room, nice staff and great breakfast "
United States
Curtis
The price is ₹7,506
₹8,406 total
includes taxes & fees
19 Mar - 20 Mar
Hampton Inn & Suites Edgewood/Aberdeen-South
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)
Founded in 1782, Washington College is the first college chartered in the sovereign United States. Explore its picturesque campus with historic architecture and Chester River waterfront views.
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Historical Society of Kent County Maryland

Step inside the Geddes-Piper House, home to Kent County's historical treasures and curated exhibits. Explore Maryland's rich past through intimate galleries and knowledgeable guides who bring local stories to life.
See properties

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

Hampton Inn Baltimore/Glen Burnie

Hampton Inn Baltimore/Glen Burnie

10/10 Excellent
"Room and all surrounding areas were very clean. The staff was so kind and so friendly. It is in an amazing location and some very good choices for food right in the shopping plaza. "
Linda 2-night trip
Posted 6 hours ago
Hampton Inn Baltimore/Glen Burnie

More cheap stays in Chestertown

Americas Best Value Inn Edgewood

Americas Best Value Inn Edgewood

1709 Edgewood Road Edgewood MD
The price is ₹4,702 per night from 17 Mar to 18 Mar
₹4,702
₹5,266 total
17 Mar - 18 Mar
includes taxes & fees
5.8/10 (1,001 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. Red Roof Inn & Suites Chestertown is another top choice for your stay based on reviews. See all available top hotels, or 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 41 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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