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Chestertown Hotels

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Jul 8 - Jul 9
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Top 10 trending Chestertown hotels

Comfort Inn & Suites Chestertown
Lobby

Comfort Inn & Suites Chestertown

2.5 star property
8.6 out of 10, Excellent, (778)
"Comfortable room, friendly staff. "
The price is P6,440
P7,149 total
includes taxes & fees
Aug 3 - Aug 4
Comfort Inn & Suites Chestertown
The Lodge at Great Oak Landing
Private beach nearby, sun loungers, beach volleyball

The Lodge at Great Oak Landing

3.5 star property
8.0 out of 10, Very Good, (53)
"not super fancy but really well done. comfy beds and a first rate chef. plus great for the boating crowd"
The price is P7,500
P8,326 total
includes taxes & fees
Jul 13 - Jul 14
The Lodge at Great Oak Landing
Red Roof Inn & Suites Chestertown
1 bedroom, desk, laptop workspace, blackout drapes

Red Roof Inn & Suites Chestertown

2.0 star property
7.4 out of 10, Good, (370)
"Had a good time and enjoyed the quietness at the hotel. "
The price is P3,878
P4,304 total
includes taxes & fees
Jul 15 - Jul 16
Red Roof Inn & Suites Chestertown
Driftwood Inn
Lobby

Driftwood Inn

2.0 star property
5.2 out of 10, (171)
"Rooms were clean. Check-in was a breeze, and the housekeeping lady is the best left her a nice tip"
The price is P3,600
P3,996 total
includes taxes & fees
Jul 14 - Jul 15
Driftwood Inn
Fairfield Inn & Suites by Marriott Middletown
Lobby

Fairfield Inn & Suites by Marriott Middletown

2.5 star property
9.2 out of 10, Wonderful, (247)
"Nice place to stay"
The price is P7,540
P8,370 total
includes taxes & fees
Jul 27 - Jul 28
Fairfield Inn & Suites by Marriott Middletown
Holiday Inn Express White Marsh by IHG
Exterior

Holiday Inn Express White Marsh by IHG

2.5 star property
9.6 out of 10, Exceptional, (885)
"We had a great stay!"
The price is P6,304
P7,281 total
includes taxes & fees
Jul 20 - Jul 21
Holiday Inn Express White Marsh by IHG
Historic Inns of Annapolis
Exterior

Historic Inns of Annapolis

3.5 star property
9.0 out of 10, Wonderful, (1795)
"Wonderful stay!"
Historic Inns of Annapolis
Hyatt Place Kent Narrows & Marina
Terrace/patio

Hyatt Place Kent Narrows & Marina

3.0 star property
9.4 out of 10, Exceptional, (576)
"Great place to stay. "
The price is P8,722
P9,682 total
includes taxes & fees
Jul 14 - Jul 15
Hyatt Place Kent Narrows & Marina
Hampton Inn & Suites Baltimore/Aberdeen
Exterior

Hampton Inn & Suites Baltimore/Aberdeen

2.5 star property
9.0 out of 10, Wonderful, (548)
"Liked everything about this hotel. Would definitely stay here again"
The price is P5,975
P6,693 total
includes taxes & fees
Jul 20 - Jul 21
Hampton Inn & Suites Baltimore/Aberdeen
The Inn at Henderson's Wharf, Ascend Hotel Collection
Exterior

The Inn at Henderson's Wharf, Ascend Hotel Collection

3.0 star property
9.2 out of 10, Wonderful, (691)
"Second time staying here - absolutely lovely. "
The price is P8,144
P10,697 total
includes taxes & fees
Jul 22 - Jul 23
The Inn at Henderson's Wharf, Ascend Hotel Collection
Holiday Inn Express And Suites Middletown by IHG
Exterior

Holiday Inn Express And Suites Middletown by IHG

2.5 star property
9.2 out of 10, Wonderful, (590)
"I would like to share, the staff at the hotel was very pleasant, it felt like a home away from home, and I also enjoyed the breakfast that was offered. "
The price is P6,985
P7,753 total
includes taxes & fees
Aug 4 - Aug 5
Holiday Inn Express And Suites Middletown by IHG
Hampton Inn Middletown
Indoor pool

Hampton Inn Middletown

2.5 star property
8.8 out of 10, Excellent, (813)
"Front desk service was exceptional!!"
The price is P7,180
P7,970 total
includes taxes & fees
Aug 5 - Aug 6
Hampton Inn Middletown
Country Inn & Suites by Radisson, Bel Air/Aberdeen, MD
Lobby

Country Inn & Suites by Radisson, Bel Air/Aberdeen, MD

3.0 star property
8.8 out of 10, Excellent, (1002)
"The room was huge, breakfast was delicious and the staff was friendly. I also enjoyed the swimming pool. "
The price is P7,092
P7,943 total
includes taxes & fees
Jul 22 - Jul 23
Country Inn & Suites by Radisson, Bel Air/Aberdeen, MD
Residence Inn Aberdeen at Ripken Stadium
Premium bedding, in-room safe, desk, iron/ironing board

Residence Inn Aberdeen at Ripken Stadium

3.0 star property
9.0 out of 10, Wonderful, (98)
"Overall, excellent stay. Tamara and the rest of front desk were attentive and amazing. There was not a request they declined. There were a couple issues with room, but no deal breakers. I would definitely book again."
The price is P6,698
P7,502 total
includes taxes & fees
Jul 20 - Jul 21
Residence Inn Aberdeen at Ripken Stadium
Kent Island Resort
Aerial view

Kent Island Resort

3.5 star property
9.2 out of 10, Wonderful, (104)
"Welcoming and well-staffed property, in a lovely and tranquil setting. Staff was friendly and helpful. Restaurant/bar service and food were outstanding. Great quiet getaway weekend spot. "
The price is P13,725
P17,485 total
includes taxes & fees
Jul 22 - Jul 23
Kent Island Resort
Hampton Inn Baltimore/Glen Burnie
Free daily continental breakfast

Hampton Inn Baltimore/Glen Burnie

2.5 star property
8.2 out of 10, Very Good, (1004)
"Great Place!"
The price is P6,875
P7,837 total
includes taxes & fees
Jul 13 - Jul 14
Hampton Inn Baltimore/Glen Burnie
Courtyard Aberdeen at Ripken Stadium
Lobby

Courtyard Aberdeen at Ripken Stadium

3.0 star property
8.6 out of 10, Excellent, (207)
"The staff was very friendly, easy and quick check-in. I would chose thus hotel again, very quiet. "
The price is P5,253
P5,883 total
includes taxes & fees
Jul 27 - Jul 28
Courtyard Aberdeen at Ripken Stadium
Flag House Inn
1 bedroom, Frette Italian sheets, premium bedding, memory foam beds

Flag House Inn

3.5 star property
9.6 out of 10, Exceptional, (70)
"Wonderfully friendly staff, great location, and beautiful property "
The price is P9,886
P11,269 total
includes taxes & fees
Jul 10 - Jul 11
Flag House Inn
Fairfield Inn & Suites by Marriott White Marsh
1 bedroom, premium bedding, desk, blackout drapes

Fairfield Inn & Suites by Marriott White Marsh

2.5 star property
8.6 out of 10, Excellent, (1000)
"Excellent stay. "
The price is P5,494
P6,345 total
includes taxes & fees
Aug 3 - Aug 4
Fairfield Inn & Suites by Marriott White Marsh
The Inn at Chesapeake Bay Beach Club
Front of property - evening/night

The Inn at Chesapeake Bay Beach Club

4.0 star property
9.4 out of 10, Exceptional, (400)
"Staff was very polite and friendly. "
The price is P12,189
P14,972 total
includes taxes & fees
Jul 22 - Jul 23
The Inn at Chesapeake Bay Beach Club
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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Learn more about Chestertown

Quaint Chestertown awaits: its sports, university life, art, and more!

See all hotels in Chestertown
Photo by Assya A
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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 place to stay on a budget in Chestertown?

Based on reviews, Red Roof Inn & Suites Chestertown is a popular 2-star hotel for our travelers looking for an economical choice, and features free WiFi and free parking. Another top choice for your budget-friendly stay is Driftwood Inn. View all budget hotels in Chestertown.

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 accommodation for a romantic vacation to Chestertown?

Red Roof Inn & Suites Chestertown is a favorite hotel for couples, and features free WiFi and free parking. See all romantic hotels 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. The Lodge at Great Oak Landing and Red Roof Inn & Suites Chestertown 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's the best place to stay in Chestertown to absorb the local history?

Based on our travel expertise, Comfort Inn & Suites Chestertown is a top hotel on Expedia for those interested in history, and it features free breakfast and free WiFi. Also notable landmarks to visit include Historical Society of Kent County Maryland.

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 is the best spa hotel in Chestertown?

Great Oak Manor is a top spa hotel featuring a private beach and a fitness center. See all spa hotels 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 41 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.