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Chestertown Hotels

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Top 10 trending Chestertown hotels

Our top choices for Chestertown hotels

Comfort Inn & Suites Chestertown

2.5 star property
8.6 out of 10, Excellent, (797)
"It was a clean comfortable spot to rest for the night. "
The price is P6,248
P6,935 total
includes taxes & fees
Sep 7 - Sep 8
Comfort Inn & Suites Chestertown

Red Roof Inn & Suites Chestertown

2.0 star property
7.2 out of 10, Good, (386)
"Good location."
The price is P4,103
P4,554 total
includes taxes & fees
Aug 28 - Aug 29
Red Roof Inn & Suites Chestertown

The Lodge at Great Oak Landing

3.5 star property
8.0 out of 10, Very Good, (65)
"Great place to get some quiet rest by the water"
The price is P7,539
P8,368 total
includes taxes & fees
Aug 24 - Aug 25
The Lodge at Great Oak Landing

Holiday Inn Express Annapolis East-Kent Island by IHG

2.5 star property
9.2 out of 10, Wonderful, (890)
"Wonderful breakfast and lovely outdoor seating next to the water! My favorite place to stay when I visit!!!"
The price is P6,781
P7,527 total
includes taxes & fees
Aug 24 - Aug 25
Holiday Inn Express Annapolis East-Kent Island by IHG

La Quinta Inn & Suites by Wyndham Baltimore N / White Marsh

3.0 star property
7.0 out of 10, Good, (1001)
"I loved my stay"
The price is P4,661
P5,383 total
includes taxes & fees
Sep 2 - Sep 3
La Quinta Inn & Suites by Wyndham Baltimore N / White Marsh

Hyatt Place Kent Narrows & Marina

3.0 star property
9.4 out of 10, Exceptional, (612)
"Great place to stay. "
The price is P9,459
P10,500 total
includes taxes & fees
Sep 16 - Sep 17
Hyatt Place Kent Narrows & Marina

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

2.5 star property
7.2 out of 10, Good, (1000)
"I liked everything about the hotel was very clean friendly staff "
The price is P3,057
P3,424 total
includes taxes & fees
Sep 7 - Sep 8
Quality Inn & Suites Bel Air I-95 Exit 77A

Country Inn & Suites by Radisson, Baltimore North, MD

3.0 star property
7.4 out of 10, Good, (1000)
"Great kid friendly place. Clean and nice breakfast buffet in the morning. Front desk staff are nice and polite. If I ever need a hotel in the area, I would be sure to stay here."
The price is P5,152
P5,951 total
includes taxes & fees
Aug 31 - Sep 1
Country Inn & Suites by Radisson, Baltimore North, MD

Hampton Inn & Suites Edgewood/Aberdeen-South

2.5 star property
9.4 out of 10, Exceptional, (1000)
"Great stay at a great price "
The price is P5,037
P5,642 total
includes taxes & fees
Sep 1 - Sep 2
Hampton Inn & Suites Edgewood/Aberdeen-South

Hilton Garden Inn Kent Island Marina

3.0 star property
9.0 out of 10, Wonderful, (986)
"How clean and polite the staff was "
The price is P8,976
P9,963 total
includes taxes & fees
Sep 14 - Sep 15
Hilton Garden Inn Kent Island Marina

Best Western Plus Hotel & Conference Center

2.5 star property
7.8 out of 10, Good, (1000)
"Nice place nice the people work over there"
The price is P6,085
P7,150 total
includes taxes & fees
Sep 7 - Sep 8
Best Western Plus Hotel & Conference Center

Kent Island Resort

3.5 star property
9.2 out of 10, Wonderful, (110)
"Hotel was great and peaceful. This hotel was water front. Nice surroundings!! I enjoyed to stay here."
The price is P9,369
P12,484 total
includes taxes & fees
Sep 1 - Sep 2
Kent Island Resort

Fairfield Inn & Suites by Marriott White Marsh

2.5 star property
8.6 out of 10, Excellent, (1002)
"Great location friendly staff "
The price is P5,764
P6,657 total
includes taxes & fees
Sep 1 - Sep 2
Fairfield Inn & Suites by Marriott White Marsh

Super 8 by Wyndham Aberdeen MD

2.0 star property
6.8 out of 10, (835)
"Everything is good for a business trip, simply sleep"
The price is P3,100
P3,472 total
includes taxes & fees
Sep 7 - Sep 8
Super 8 by Wyndham Aberdeen MD

Americas Best Value Inn Edgewood

2.0 star property
5.6 out of 10, (957)
"The staff was great."
The price is P2,906
P3,255 total
includes taxes & fees
Aug 28 - Aug 29
Americas Best Value Inn Edgewood

The Inn at Chesapeake Bay Beach Club

4.0 star property
9.4 out of 10, Exceptional, (411)
"Great location and amenities"
The price is P12,821
P15,681 total
includes taxes & fees
Sep 1 - Sep 2
The Inn at Chesapeake Bay Beach Club

Historic Inns of Annapolis

3.5 star property
9.0 out of 10, Wonderful, (1815)
"Great stay"
Historic Inns of Annapolis

Annapolis Waterfront Hotel, Autograph Collection

4.0 star property
8.8 out of 10, Excellent, (856)
"Great location and staff! The hotel is nice - wish that they had a bar and restaurant on site but plenty of options within walking distance though. Nice view of the water and updated rooms."
The price is P13,545
P15,441 total
includes taxes & fees
Sep 1 - Sep 2
Annapolis Waterfront Hotel, Autograph Collection

Hampton Inn Baltimore/White Marsh

2.5 star property
7.6 out of 10, Good, (1001)
"Clean area clean rooms friendly staff"
The price is P4,980
P5,752 total
includes taxes & fees
Aug 31 - Sep 1
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, (1002)
"Good hotel, good location "
The price is P4,060
P4,547 total
includes taxes & fees
Sep 1 - Sep 2
La Quinta Inn & Suites by Wyndham Bel Air/I-95 Exit 77A
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

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 Red Roof Inn & Suites Chestertown and Driftwood Inn 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 44 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.