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Chestertown Hotels from ₹4,643

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Top 10 Chestertown hotels and places to stay

Our top choices for Chestertown hotels

Days Inn by Wyndham Aberdeen

2.0 star property
7.0 out of 10, Good, (887)
"Good nice area "
The price is ₹5,719
₹6,406 total
includes taxes & fees
14 Sept - 15 Sept
Days Inn by Wyndham Aberdeen

Super 8 by Wyndham Havre De Grace Aberdeen Area

2.0 star property
6.6 out of 10, (950)
"It was good for the price"
The price is ₹4,351
₹4,874 total
includes taxes & fees
6 Oct - 7 Oct
Super 8 by Wyndham Havre De Grace Aberdeen Area

Vandiver Inn

3.5 star property
9.4 out of 10, Exceptional, (514)
"For an old house converted into a B&B it was very nice, well maintained and clean. Staff was friendly and breakfast was good."
Vandiver Inn

Comfort Inn & Suites Chestertown

2.5 star property
8.6 out of 10, Excellent, (812)
"Friendly staff, clean room, convenient location. "
The price is ₹9,678
₹10,743 total
includes taxes & fees
14 Sept - 15 Sept
Comfort Inn & Suites Chestertown

Red Roof Inn & Suites Chestertown

2.0 star property
7.2 out of 10, Good, (393)
"We had a great stay with our two Pups.. The room was very nice and comfortable and very clean."
The price is ₹6,751
₹7,494 total
includes taxes & fees
14 Sept - 15 Sept
Red Roof Inn & Suites Chestertown

The Lodge at Great Oak Landing

3.5 star property
8.0 out of 10, Very good, (68)
"Everything was perfect. The staff is super friendly, the room was clean and fresh. The beds were super comfy, the food is amazing and the chef was super nice!! Great friendly atmosphere. I’m definitely going back!!"
The price is ₹11,677
₹12,962 total
includes taxes & fees
9 Sept - 10 Sept
The Lodge at Great Oak Landing

Super 8 by Wyndham Aberdeen MD

2.0 star property
6.8 out of 10, (839)
"Staff is great & rooms always good "
The price is ₹4,952
₹5,547 total
includes taxes & fees
16 Sept - 17 Sept
Super 8 by Wyndham Aberdeen MD

Holiday Inn Belcamp - Aberdeen Area by IHG

3.0 star property
8.4 out of 10, Very good, (716)
"It was a good location. Workers are super friendly and attentive. "
The price is ₹7,414
₹8,304 total
includes taxes & fees
12 Sept - 13 Sept
Holiday Inn Belcamp - Aberdeen Area by IHG

Hampton Inn Baltimore/White Marsh

2.5 star property
7.8 out of 10, Good, (1009)
"Convenience to 95 and in a safe area with dining options"
The price is ₹8,544
₹9,868 total
includes taxes & fees
10 Sept - 11 Sept
Hampton Inn Baltimore/White Marsh

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

3.0 star property
8.2 out of 10, Very good, (1008)
"Good hotel, good location "
The price is ₹6,289
₹7,043 total
includes taxes & fees
10 Sept - 11 Sept
La Quinta Inn & Suites by Wyndham Bel Air/I-95 Exit 77A

Relax Inn Smyrna

2.0 star property
7.8 out of 10, Good, (88)
"Owner was very nice. "
The price is ₹7,864
₹8,748 total
includes taxes & fees
9 Sept - 10 Sept
Relax Inn Smyrna

Holiday Inn Express White Marsh by IHG

2.5 star property
9.6 out of 10, Exceptional, (920)
"The facility is very clean and quiet. The staff is very polite and accommodating. The complimentary breakfast is very good. My family and I will stay again."
The price is ₹8,826
₹10,194 total
includes taxes & fees
5 Oct - 6 Oct
Holiday Inn Express White Marsh by IHG

Village Inn

2.0 star property
6.2 out of 10, (494)
"The staff is super friendly and there is a convenient store to buy drinks and snacks within walking distance."
The price is ₹7,878
₹8,980 total
includes taxes & fees
9 Sept - 10 Sept
Village Inn

Hampton Inn Middletown

2.5 star property
8.8 out of 10, Excellent, (832)
"Decent for a Hampton Inn"
The price is ₹9,678
₹10,743 total
includes taxes & fees
14 Sept - 15 Sept
Hampton Inn Middletown

Hyatt Place Kent Narrows & Marina

3.0 star property
9.4 out of 10, Exceptional, (624)
"Great location"
The price is ₹14,299
₹15,872 total
includes taxes & fees
8 Oct - 9 Oct
Hyatt Place Kent Narrows & Marina

Motel Edgewood

2.0 star property
8.6 out of 10, Excellent, (7)
"Bed was clean and crisply made. Occupants were respectful of sleeping hours. Check-in and check-out were simple. Parking was convenient and had easy access to the highway."
The price is ₹4,877
₹5,463 total
includes taxes & fees
18 Sept - 19 Sept
Motel Edgewood

Holiday Inn Express & Suites Middletown by IHG

2.5 star property
9.2 out of 10, Wonderful, (613)
"Very beautiful and clean properly with great staff. "
The price is ₹9,444
₹10,483 total
includes taxes & fees
28 Sept - 29 Sept
Holiday Inn Express & Suites Middletown by IHG

Hampton Inn & Suites Edgewood/Aberdeen-South

2.5 star property
9.4 out of 10, Exceptional, (1003)
"Very good breakfast options Convenient parking Clean room Friendly staff"
The price is ₹7,803
₹8,739 total
includes taxes & fees
14 Sept - 15 Sept
Hampton Inn & Suites Edgewood/Aberdeen-South

Quality Inn

2.5 star property
7.8 out of 10, Good, (820)
"Great place and great staff"
The price is ₹8,625
₹9,574 total
includes taxes & fees
17 Sept - 18 Sept
Quality Inn

Fairfield Inn & Suites by Marriott Middletown

2.5 star property
9.2 out of 10, Wonderful, (273)
"Friendly staff, comfortable bed and clean room "
The price is ₹9,179
₹10,189 total
includes taxes & fees
14 Sept - 15 Sept
Fairfield Inn & Suites by Marriott Middletown
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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Accommodation near Chestertown attractions

Historical Society of Kent County Maryland

Historical Society of Kent County Maryland

You can spend an afternoon browsing the exhibits at Historical Society of Kent County Maryland during your trip to Chestertown. Amble around this family-friendly area's riverfront or experience its festivals.

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.

Photo by Assya A
Open Photo by Assya A

Top Chestertown Hotel Reviews

More cheap stays in Chestertown

More cheap stays in Chestertown

Explore a world of travel with Expedia

Explore a world of travel with Expedia

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 The Lodge at Great Oak Landing and Red Roof Inn & Suites Chestertown as top options for your stay. 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 42 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. University life is a highlight and campuses to tour include Washington College and River Arts Chestertown. A couple of additional sights to add to your itinerary are Rolphs Wharf Marina and Chestertown Historic District. 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.