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Chestertown Hotels

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Check Chestertown hotel prices

Tonight
May 23 - May 24
Tomorrow night
May 24 - May 25
This weekend
May 24 - May 26
Next weekend
May 31 - Jun 2

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Top 10 trending Chestertown hotels

Lobby
Comfort Inn & Suites Chestertown
2.5 star property
8.6 out of 10, Excellent, (674)
"The onsite manager was very helpful. The staff was very nice. "
The price is P6,885
P7,642 total
includes taxes & fees
May 28 - May 29
Comfort Inn & Suites Chestertown
Desk, laptop workspace, blackout drapes, iron/ironing board
Red Roof Inn & Suites Chestertown
2.0 star property
7.4 out of 10, Good, (267)
"Sometimes, you don’t need a fancy place; just a clean place. That’s what this is. Maybe there weren’t the newest finishes, but we really appreciated having the extra pull-out couch and space in the room. It was perfect for traveling with my 3 teenagers."
The price is P4,441
P4,930 total
includes taxes & fees
May 30 - May 31
Red Roof Inn & Suites Chestertown
Private beach nearby, sun loungers, beach volleyball, beach bar
The Lodge at Great Oak Landing
3.0 star property
7.6 out of 10, Good, (4)
"The place is beautiful. The rooms are little small and could use updating. When I turned the air on the windows rattled so loud. I had to keep it on low to avoid the noise. No microwave in the room and be prepared for the slamming door at 6am. Other than those things we really enjoyed our time. "
The price is P7,683
P8,741 total
includes taxes & fees
May 28 - May 29
The Lodge at Great Oak Landing
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Lobby
Driftwood Inn
2.0 star property
5.0 out of 10, (159)
"It was clean and everything worked--more than I could say for many other more expensive rooms I've stayed in. The shower was exceptionally good. Watch out for the hot water: very hot! The TV had Netflix, Hulu, Roku, & Vudu. And they worked. On the downside, the furnishings and carpet were worn, but not terrible. "
The price is P3,687
P4,093 total
includes taxes & fees
May 26 - May 27
Driftwood Inn
Lake
Inn at Huntingfield Creek
3.5 star property
10.0 out of 10, Exceptional, (44)
"Lovely property with wonderful owners and staff, including three very welcoming dogs. We had a perfect weekend getaway."
The price is P13,331
P14,798 total
includes taxes & fees
May 27 - May 28
Inn at Huntingfield Creek
Outdoor pool
Mariners Motel
2.0 star property
9.4 out of 10, Exceptional, (85)
"Really cute property and rooms. The rooms are small but exceptionally clean and nicely decorated. Pretty grounds with a pool, fire pit, hammocks and yard games available. Easy walking distance to a few restaurants. Staff was very pleasant. "
The price is P9,682
P10,747 total
includes taxes & fees
May 27 - May 28
Mariners Motel
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See all available properties in Chestertown
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.

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 P3,628 per night from May 26 to May 27
P3,628
per night
26 May - 27 May
7.4/10 Good! (1,000 reviews)

Near an Attraction

Image for Washington College

Washington College

Take a campus tour or just explore the area of Washington College, during your travels in Chestertown. Amble around this family-friendly area's riverfront or experience its festivals.

See properties
Washington College

Chestertown hotels information

Number of reviews
5,560
Accommodation
1,002 hotels
Lowest Price
P3,628
Highest Price
P13,331

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 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. 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 fitness center and laundry facilities 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 located on the beach. Great Oak Manor is another good option to stay near the 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.

Recent Reviews in Chestertown
Expedia verified reviews

Historic Inns of Annapolis

Historic Inns of Annapolis

5/5 Excellent
"Beautiful, central location, well appointed! Heating/cooling system is way loud."
A verified traveler stayed at Historic Inns of Annapolis
Posted 2 days ago
Historic Inns of Annapolis