Photo by Patricia Knorr

Chestertown Hotels from ₹5,771

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25 Oct - 26 Oct
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26 Oct - 27 Oct
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31 Oct - 2 Nov
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7 Nov - 9 Nov

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Top 10 Chestertown hotels and places to stay

Lobby
Comfort Inn & Suites Chestertown
Comfort Inn & Suites Chestertown
2.5 star property
8.6 out of 10, Excellent, (834)
"The thermostat controls were easy to adjust. Night desk lady was friendly and pleasant. "
United States
Charlie
The price is ₹8,961
₹9,947 total
includes taxes & fees
29 Oct - 30 Oct
Comfort Inn & Suites Chestertown
Suite, Multiple Beds, Non Smoking | 1 bedroom, desk, laptop workspace, blackout curtains
Red Roof Inn & Suites Chestertown
Red Roof Inn & Suites Chestertown
2.0 star property
7.2 out of 10, Good, (406)
"We had a great stay with our two Pups.. The room was very nice and comfortable and very clean."
United States
Cynthia
The price is ₹7,116
₹7,899 total
includes taxes & fees
2 Nov - 3 Nov
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
7.8 out of 10, Good, (72)
"For the price off season the room should have had better amenities "
United States
Daniel
The price is ₹11,623
₹13,288 total
includes taxes & fees
27 Oct - 28 Oct
The Lodge at Great Oak Landing
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
7.0 out of 10, Good, (1031)
"Had a nice stay "
United States
Tammy
The price is ₹6,466
₹7,468 total
includes taxes & fees
23 Nov - 24 Nov
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
9.2 out of 10, Wonderful, (907)
"Nice Holiday Inn Express with great water views."
United States
Michael
The price is ₹9,752
₹10,824 total
includes taxes & fees
16 Nov - 17 Nov
Holiday Inn Express Annapolis East-Kent Island by IHG
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
7.2 out of 10, Good, (1002)
"Nice place to stay"
United States
Patrick
The price is ₹5,535
₹6,199 total
includes taxes & fees
11 Nov - 12 Nov
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
7.8 out of 10, Good, (1003)
"We always stay here when in Baltimore."
United States
Leslie
The price is ₹9,382
₹11,024 total
includes taxes & fees
2 Nov - 3 Nov
Best Western Plus Hotel & Conference Center
Exterior
Country Inn & Suites by Radisson, Baltimore North, MD
Country Inn & Suites by Radisson, Baltimore North, MD
3.0 star property
7.2 out of 10, Good, (1003)
"I have been staying here for some time now and I've always been happy and every time I come in they always remember me very welcoming very helpful above and beyond service and always ask how the families doing how I'm doing it's like being home when you're away from home very happy with the place very clean rooms very nice affordable prices and staff does an amazing job working hard on keeping the place clean amazing breakfast rooms are always clean the whole place and the staff and give it a 10...
United States
Michael
The price is ₹8,040
₹9,287 total
includes taxes & fees
26 Oct - 27 Oct
Country Inn & Suites by Radisson, Baltimore North, MD
Lobby sitting area
Comfort Inn & Suites Aberdeen near APG
Comfort Inn & Suites Aberdeen near APG
2.5 star property
7.8 out of 10, Good, (787)
"The front desk staff were friendly and welcoming!"
United States
Bonnie
The price is ₹7,766
₹8,698 total
includes taxes & fees
28 Oct - 29 Oct
Comfort Inn & Suites Aberdeen near APG
Restaurant
Hampton Inn & Suites Edgewood/Aberdeen-South
Hampton Inn & Suites Edgewood/Aberdeen-South
2.5 star property
9.4 out of 10, Exceptional, (1002)
"Would stay again"
United States
Dena
The price is ₹7,348
₹8,230 total
includes taxes & fees
3 Nov - 4 Nov
Hampton Inn & Suites Edgewood/Aberdeen-South
Lobby sitting area
Americas Best Value Inn Edgewood
Americas Best Value Inn Edgewood
2.0 star property
5.6 out of 10, (997)
"Stayed 3 nights. The beds were comfortable, the rooms were clean. "
Canada
Michelle
The price is ₹5,271
₹5,904 total
includes taxes & fees
26 Oct - 27 Oct
Americas Best Value Inn Edgewood
Free daily buffet breakfast
Fairfield Inn & Suites by Marriott White Marsh
Fairfield Inn & Suites by Marriott White Marsh
2.5 star property
8.6 out of 10, Excellent, (1002)
"It waa great for the price and at a great location"
United States
John
The price is ₹8,289
₹9,574 total
includes taxes & fees
23 Nov - 24 Nov
Fairfield Inn & Suites by Marriott White Marsh
Terrace/patio
Hyatt Place Kent Narrows & Marina
Hyatt Place Kent Narrows & Marina
3.0 star property
9.4 out of 10, Exceptional, (642)
"Nice location and restaurants galore in area. "
United States
David
The price is ₹13,090
₹14,530 total
includes taxes & fees
23 Nov - 24 Nov
Hyatt Place Kent Narrows & Marina
Aerial view
Kent Island Resort
Kent Island Resort
3.5 star property
9.2 out of 10, Wonderful, (118)
"Great INN super nice staff"
United States
Eric
The price is ₹16,604
₹21,730 total
includes taxes & fees
28 Oct - 29 Oct
Kent Island Resort
Exterior
Super 8 by Wyndham Baltimore/Essex Area
Super 8 by Wyndham Baltimore/Essex Area
2.0 star property
5.4 out of 10, (400)
"Just a nice quiet cool place clean rooms and the bed is away from the door lol"
United States
Jamelle
The price is ₹6,940
₹8,016 total
includes taxes & fees
26 Oct - 27 Oct
Super 8 by Wyndham Baltimore/Essex Area
Exterior
Super 8 by Wyndham Aberdeen MD
Super 8 by Wyndham Aberdeen MD
2.0 star property
7.0 out of 10, Good, (852)
"Parking was easy. Bed was super comfy. "
United States
Martha J.
The price is ₹5,153
₹5,771 total
includes taxes & fees
16 Nov - 17 Nov
Super 8 by Wyndham Aberdeen MD
Terrace/patio
Hilton Garden Inn Kent Island Marina
Hilton Garden Inn Kent Island Marina
3.0 star property
9.0 out of 10, Wonderful, (1002)
"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 ₹11,886
₹13,194 total
includes taxes & fees
29 Oct - 30 Oct
Hilton Garden Inn Kent Island Marina
Restaurant
Hampton Inn & Suites Baltimore/Aberdeen
Hampton Inn & Suites Baltimore/Aberdeen
2.5 star property
9.0 out of 10, Wonderful, (587)
"This Hotel was excellent in all ways. "
United States
Denny
The price is ₹8,487
₹9,505 total
includes taxes & fees
25 Nov - 26 Nov
Hampton Inn & Suites Baltimore/Aberdeen
Terrace/patio
Historic Inns of Annapolis
Historic Inns of Annapolis
3.5 star property
9.0 out of 10, Wonderful, (1853)
"The hotel was absolutely clean and close to the shops and restaurants. "
United States
Trudy
Historic Inns of Annapolis
Exterior
Hampton Inn Baltimore Bayview Campus
Hampton Inn Baltimore Bayview Campus
3.5 star property
9.0 out of 10, Wonderful, (1001)
"We’ve stayed here two times already and always enjoyed it! Clean rooms, friendly staff, free parking and many shopping options close by!"
United States
Alexander
The price is ₹10,515
₹12,355 total
includes taxes & fees
24 Nov - 25 Nov
Hampton Inn Baltimore Bayview Campus
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.
See properties

Rolphs Wharf Marina

Explore the waterfront in Chestertown with a trip to Rolphs Wharf Marina. Take in the festivals in this family-friendly area.
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
Eastern Shore small towns in Maryland, USA. Traveling the Eastern Shore points o f Maryland this weekend, we came across this local church with gravestones. We found several of these local churches along with the many farms and inlets leading to the Chesapeake bay.
Photo by Patricia Knorr
Open Photo by Patricia Knorr

Top Chestertown Hotel Reviews

SpringHill Suites Baltimore White Marsh/Middle River

SpringHill Suites Baltimore White Marsh/Middle River

10/10 Excellent
"It was a great experience "
Pamela 2-night trip
Posted 16 hours ago
SpringHill Suites Baltimore White Marsh/Middle River

More cheap stays in Chestertown

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

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

2112a Emmorton Park Road, Edgewood, MD
The price is ₹5,535 per night from 11 Nov to 12 Nov
₹5,535
₹6,199 total
11 Nov - 12 Nov
includes taxes & fees
7.2/10 Good! (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. 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?
Red Roof Inn & Suites Chestertown is a hotel with free parking and laundry facilities, and it's a top choice on Expedia for families. Comfort 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?
Red Roof Inn & Suites Chestertown is a top hotel for people travelling with their pets, and offers laundry facilities and free newspapers for its human guests. Other good options for you and your pet include Comfort 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 38 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 Chesapeake Bay and Chestertown Dog Park 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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