Chestertown Hotels from ₹5,692

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Our top choices for Chestertown hotels

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)
"clean, comfortable, and staff was friendly and helpful. "
United States
Gail
The price is ₹9,715
₹11,107 total
includes taxes & fees
29 Apr - 30 Apr
The Lodge at Great Oak Landing

Comfort Inn & Suites Chestertown

Comfort Inn & Suites Chestertown
2.5 star property
Chestertown
8.6 out of 10, Excellent, (907 reviews)
"Great visit"
United States
Danielle
The price is ₹11,409
₹12,664 total
includes taxes & fees
3 May - 4 May
Comfort Inn & Suites Chestertown

Red Roof Inn & Suites Chestertown

Red Roof Inn & Suites Chestertown
2.0 star property
Chestertown
7.2 out of 10, Good, (440 reviews)
"A significant improvement compared to my previous stays in terms of cleanliness and upkeep. The receptionists were also helpful."
United States
Thomas
The price is ₹6,782
₹7,528 total
includes taxes & fees
5 May - 6 May
Red Roof Inn & Suites Chestertown

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
The price is ₹5,981
₹6,640 total
includes taxes & fees
23 May - 24 May
Driftwood Inn

Haven Point Inn and Gallery

Haven Point Inn and Gallery
2.0 star property
Rock Hall
The price is ₹13,943
₹15,477 total
includes taxes & fees
6 May - 7 May
Haven Point Inn and Gallery

Kent Island Resort

Kent Island Resort
3.5 star property
Stevensville
9.2 out of 10, Wonderful, (137 reviews)
"Very nice room and wonderful stay."
United States
Julie
The price is ₹16,861
₹21,963 total
includes taxes & fees
4 May - 5 May
Kent Island Resort

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, (590 reviews)
"Great place to stay. "
United States
Nathan
The price is ₹8,760
₹9,811 total
includes taxes & fees
4 May - 5 May
Holiday Inn Express Edgewood-Aberdeen-Bel Air by IHG

Fairfield Inn & Suites by Marriott Middletown

Fairfield Inn & Suites by Marriott Middletown
3.0 star property
Middletown
9.2 out of 10, Wonderful, (377 reviews)
"Really nice hotel."
United States
Gerard
The price is ₹10,550
₹11,710 total
includes taxes & fees
18 May - 19 May
Fairfield Inn & Suites by Marriott Middletown

Relax Inn Smyrna

Relax Inn Smyrna
2.0 star property
Smyrna
8.0 out of 10, Very good, (94 reviews)
"Great location"
United States
Patrick
The price is ₹7,461
₹9,550 total
includes taxes & fees
27 May - 28 May
Relax Inn Smyrna

Vandiver Inn

Vandiver Inn
3.5 star property
Havre De Grace
9.4 out of 10, Exceptional, (543 reviews)
"Breakfast menu was very good, staff friendly and helpful. "
United States
JoEllen
The price is ₹12,631
₹14,147 total
includes taxes & fees
29 Apr - 30 Apr
Vandiver Inn

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, (367 reviews)
"Staff was very friendly and it was a perfect location for us"
United States
Ryan
The price is ₹9,075
₹10,164 total
includes taxes & fees
28 May - 29 May
Home2 Suites by Hilton Baltimore / Aberdeen, MD

Quality Inn Smyrna

Quality Inn Smyrna
2.5 star property
Smyrna
7.6 out of 10, Good, (1,002 reviews)
"My visit at the Hotel was amazing & peaceful."
United States
Milton
The price is ₹7,660
₹8,502 total
includes taxes & fees
19 May - 20 May
Quality Inn Smyrna

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)
"Easy night stay with restaurants close by as well!"
United States
Chad
The price is ₹9,022
₹10,105 total
includes taxes & fees
3 May - 4 May
Country Inn & Suites by Radisson, Bel Air/Aberdeen, MD

Hampton Inn & Suites Baltimore/Aberdeen

Hampton Inn & Suites Baltimore/Aberdeen
2.5 star property
Aberdeen
9.0 out of 10, Wonderful, (639 reviews)
"Good breakfast, and clean rooms"
United States
George
The price is ₹8,882
₹9,948 total
includes taxes & fees
5 May - 6 May
Hampton Inn & Suites Baltimore/Aberdeen

Amazing Getaway: Enjoy our Cozy Log Cabins on the Chesapeake Bay!

Amazing Getaway: Enjoy our Cozy Log Cabins on the Chesapeake Bay!
2.0 star property
North East
8.8 out of 10, Excellent, (3 reviews)
"Very nice cabin. By the town and easy drive to everything. "
United States
Mark
The price is ₹32,951
₹39,920 total
includes taxes & fees
30 Apr - 1 May
Amazing Getaway: Enjoy our Cozy Log Cabins on the Chesapeake Bay!

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, (1,002 reviews)
"Great place to stay"
United States
Harry
The price is ₹8,327
₹9,326 total
includes taxes & fees
7 May - 8 May
La Quinta Inn & Suites by Wyndham Aberdeen-APG

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, (677 reviews)
"Great location and nice place to stay. Walk to nearby things to do and enjoy. "
United States
Sharon
The price is ₹11,492
₹12,756 total
includes taxes & fees
3 May - 4 May
Holiday Inn Express & Suites Middletown by IHG

Fairfield Inn & Suites by Marriott Aberdeen

Fairfield Inn & Suites by Marriott Aberdeen
3.0 star property
Aberdeen
9.0 out of 10, Wonderful, (336 reviews)
"The staff was lovely and so accommodating. Definitely the best part of our stay."
United States
Maritza
The price is ₹10,312
₹11,550 total
includes taxes & fees
30 Apr - 1 May
Fairfield Inn & Suites by Marriott Aberdeen

Comfort Inn & Suites Aberdeen near APG

Comfort Inn & Suites Aberdeen near APG
2.5 star property
Aberdeen
8.0 out of 10, Very good, (886 reviews)
"Would stay again! Very great place "
United States
Mindy
The price is ₹7,714
₹8,639 total
includes taxes & fees
4 May - 5 May
Comfort Inn & Suites Aberdeen near APG

Hampton Inn & Suites Edgewood/Aberdeen-South

Hampton Inn & Suites Edgewood/Aberdeen-South
2.5 star property
Edgewood
9.4 out of 10, Exceptional, (1,008 reviews)
"nice place to stay"
United States
Paul
The price is ₹8,445
₹9,459 total
includes taxes & fees
12 May - 13 May
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

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.

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

Top Chestertown Hotel Reviews

More cheap stays in Chestertown

Frequently asked questions

Where is the best place for a stay in Chestertown?
Based on our traveller data, Comfort Inn & Suites Chestertown is one of the top choices for your stay. This hotel offers free breakfast and free parking. The Lodge at Great Oak Landing is another good option for your trip. 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. Natural beauty is on display at Northern Chesapeake Bay, Chesapeake Bay and Chestertown Dog Park. 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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