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Chestertown Hotels

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Top 10 trending Chestertown hotels

The Lodge at Great Oak Landing

3.5 star property
7.8 out of 10, Good, (70)
"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 P7,693
P8,540 total
includes taxes & fees
Oct 5 - Oct 6
The Lodge at Great Oak Landing

Red Roof Inn & Suites Chestertown

2.0 star property
7.2 out of 10, Good, (399)
"We had a great stay with our two Pups.. The room was very nice and comfortable and very clean."
The price is P4,710
P5,228 total
includes taxes & fees
Oct 8 - Oct 9
Red Roof Inn & Suites Chestertown

Comfort Inn & Suites Chestertown

2.5 star property
8.6 out of 10, Excellent, (825)
"Friendly staff, clean room, convenient location. "
The price is P6,663
P7,396 total
includes taxes & fees
Nov 2 - Nov 3
Comfort Inn & Suites Chestertown

Driftwood Inn

2.0 star property
5.2 out of 10, (174)
"Rooms are clean, staf was helpful "
The price is P3,693
P4,099 total
includes taxes & fees
Nov 1 - Nov 2
Driftwood Inn

Vandiver Inn

3.5 star property
9.4 out of 10, Exceptional, (518)
"Been to the Vandiver many times and are always pleasantly pleased."
Vandiver Inn

Super 8 by Wyndham Havre De Grace Aberdeen Area

2.0 star property
6.6 out of 10, (957)
"Front desk lady was super friendly helpfull dollor general close clean room great value"
The price is P3,572
P4,000 total
includes taxes & fees
Oct 8 - Oct 9
Super 8 by Wyndham Havre De Grace Aberdeen Area

Hyatt Place Kent Narrows & Marina

3.0 star property
9.4 out of 10, Exceptional, (633)
"Great location and rooms. Great place!"
The price is P8,665
P9,618 total
includes taxes & fees
Oct 26 - Oct 27
Hyatt Place Kent Narrows & Marina

TownePlace Suites by Marriott Edgewood Aberdeen

3.0 star property
9.0 out of 10, Wonderful, (86)
"Breakfast was good."
The price is P6,402
P7,170 total
includes taxes & fees
Oct 19 - Oct 20
TownePlace Suites by Marriott Edgewood Aberdeen

Quality Inn

2.5 star property
7.8 out of 10, Good, (832)
"Great place and great staff"
The price is P5,684
P6,310 total
includes taxes & fees
Nov 2 - Nov 3
Quality Inn

Holiday Inn Express Annapolis East-Kent Island by IHG

2.5 star property
9.2 out of 10, Wonderful, (903)
"The BEAUTIFUL backyard on the water, the walking trail, and the walkability to several restaurants were so nice!"
The price is P7,385
P8,198 total
includes taxes & fees
Oct 30 - Oct 31
Holiday Inn Express Annapolis East-Kent Island by IHG

Inn at Huntingfield Creek

3.5 star property
10.0 out of 10, Exceptional, (53)
"Everything was lovely. Our cottage private and very nice. Breakfast delicious. Close to town. "
Inn at Huntingfield Creek

Kent Island Resort

3.5 star property
9.2 out of 10, Wonderful, (114)
"Great INN super nice staff"
The price is P11,572
P15,052 total
includes taxes & fees
Oct 15 - Oct 16
Kent Island Resort

Hilton Garden Inn Bel Air

3.0 star property
9.2 out of 10, Wonderful, (214)
"The staff was amazing"
The price is P7,859
P8,802 total
includes taxes & fees
Nov 2 - Nov 3
Hilton Garden Inn Bel Air

The Inn at Chesapeake Bay Beach Club

4.0 star property
9.4 out of 10, Exceptional, (420)
"Beautiful hotel with friendly staff and great food! Comfortable bed, stayed at the Barn. "
The price is P11,339
P14,066 total
includes taxes & fees
Nov 2 - Nov 3
The Inn at Chesapeake Bay Beach Club

Candlewood Suites Aberdeen-Bel Air by IHG

2.5 star property
8.0 out of 10, Very Good, (454)
"Very quiet room, very friendly staff "
The price is P5,408
P6,057 total
includes taxes & fees
Nov 2 - Nov 3
Candlewood Suites Aberdeen-Bel Air by IHG

SpringHill Suites by Marriott Edgewood/Aberdeen

3.0 star property
8.8 out of 10, Excellent, (355)
"Location was great and staff very nice"
The price is P7,792
P8,727 total
includes taxes & fees
Nov 2 - Nov 3
SpringHill Suites by Marriott Edgewood/Aberdeen

Super 8 by Wyndham Baltimore/Essex Area

2.0 star property
5.4 out of 10, (393)
"Just a nice quiet cool place clean rooms and the bed is away from the door lol"
The price is P4,249
P4,907 total
includes taxes & fees
Oct 5 - Oct 6
Super 8 by Wyndham Baltimore/Essex Area

Best Western Kent Narrows Inn

2.5 star property
8.0 out of 10, Very Good, (1002)
"Clean well appointed room. Very pet friendly with a reasonable pet fee of $30."
The price is P7,326
P8,132 total
includes taxes & fees
Nov 2 - Nov 3
Best Western Kent Narrows Inn

Hilton Garden Inn Kent Island Marina

3.0 star property
9.0 out of 10, Wonderful, (1000)
"Hotel was great, beautiful location near the water"
The price is P9,160
P10,168 total
includes taxes & fees
Nov 2 - Nov 3
Hilton Garden Inn Kent Island Marina

Hampton Inn & Suites Baltimore/Aberdeen

2.5 star property
9.0 out of 10, Wonderful, (579)
"This Hotel was excellent in all ways. "
The price is P5,674
P6,355 total
includes taxes & fees
Nov 2 - Nov 3
Hampton Inn & Suites Baltimore/Aberdeen
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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Near an Attraction

Sumner Hall

Sumner Hall

You can spend time studying the exhibits at Sumner Hall in Chestertown. Experience the area's festivals and art scene.

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 harbor.

Photo by Assya A
Open Photo by Assya A

Top Chestertown Hotel Reviews

More cheap stays in Chestertown

More cheap stays in Chestertown

Frequently asked questions

Where is the best place for a stay in Chestertown?

Comfort Inn & Suites Chestertown is a favorite 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 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, most hotel bookings are fully refundable as long as you cancel before the hotel’s cancellation deadline, which often is within 24-48 hours of your scheduled arrival. If your reservation is non-refundable, 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.

Where can I learn more about changing or cancelling my trip to Chestertown?

For more details about rescheduling or cancelling your trip to Chestertown, click here.

What's the best hotel for families 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 kid-friendly vacation. Kids of all ages will also enjoy a visit to Crumpton Auction. Find more child-friendly accommodations in Chestertown.

What's the best LGBTQ-friendly accommodation 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 other good options for your trip. See all available hotels listed as LGBTQ-friendly in Chestertown.

What's the best pet-friendly hotel in Chestertown?

Comfort Inn & Suites Chestertown is a top hotel for people traveling with their pets, and offers a seasonal outdoor pool and a fitness center for its human guests. Other good options to stay with your pet include Red Roof Inn & Suites Chestertown and Driftwood Inn. See more pet-friendly hotel accommodations in Chestertown.

Where is the best hotel to stay near Washington College?

Adjacent to Washington College, Driftwood Inn is one of the top choices for your stay based on our traveler data, and this property offers free parking and free WiFi. Other good options close by include Comfort Inn & Suites Chestertown and Red Roof Inn & Suites Chestertown.

What about the best place to stay near Rolphs Wharf Marina?

One of the top choices for your stay is Comfort Inn & Suites Chestertown, located 4.1 mi (6.6 km) from Rolphs Wharf Marina, and this hotel offers free breakfast and free parking. Driftwood Inn and Red Roof Inn & Suites Chestertown are two other good options within a few miles.

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 accommodations with pools in Chestertown?

The Lodge at Great Oak Landing is a top lodge with a seasonal outdoor pool, 3 bars, and free WiFi. View all hotels with pools in Chestertown.

What's the best hotel for staying near Salisbury - Ocean City Wicomico Regional Airport (SBY)?

Country Inn & Suites by Radisson, Salisbury, MD is one of the top choices for your stay and is a popular 3-star hotel featuring free breakfast and an indoor pool. It's located 2.2 mi (3.6 km) from Salisbury - Ocean City Wicomico Regional Airport. Other options close to the airport include Microtel Inn & Suites by Wyndham Salisbury and Sleep Inn Salisbury.

How is it to stay in Chestertown?

Visitors to Chestertown are sure to enjoy the university setting. Tourists can also enjoy the city's sporting events, festivals, and art. In Chestertown, there are 42 hotels and other accommodations to choose from. Find out more about Chestertown.

What are the top places to visit 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 agenda are Rolphs Wharf Marina and Chestertown Historic District. Check out what more 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 temp of 74°F, while the coldest months are January and February with an average of 39°F. Average annual precipitation for Chestertown is 48 inches.

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Explore a world of travel with Expedia