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Search Luxury Hotels in Chestertown

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Check availability on Chestertown Luxury Hotels

Tonight
25 Jun - 26 Jun
Tomorrow
26 Jun - 27 Jun
This weekend
27 Jun - 29 Jun
Next weekend
4 Jul - 6 Jul

Top Chestertown Luxury Hotels

We don't have any properties that match your exact search

Recommended hotels in Chestertown

The Lodge at Great Oak Landing
Private beach nearby, sun-loungers, beach volleyball

The Lodge at Great Oak Landing

3.5 star property
7.8 out of 10, Good, (52)
"not super fancy but really well done. comfy beds and a first rate chef. plus great for the boating crowd"
The price is 3.460.571 ₫
3.841.233 ₫ total
includes taxes & fees
26 Jun - 27 Jun
The Lodge at Great Oak Landing
Comfort Inn & Suites Chestertown
Lobby

Comfort Inn & Suites Chestertown

2.5 star property
8.6 out of 10, Excellent, (773)
"Comfortable room, friendly staff. "
The price is 2.979.282 ₫
3.307.003 ₫ total
includes taxes & fees
24 Jul - 25 Jul
Comfort Inn & Suites Chestertown
Red Roof Inn & Suites Chestertown
Suite, Multiple Beds, Non Smoking | 1 bedroom, desk, laptop workspace, blackout curtains

Red Roof Inn & Suites Chestertown

2.0 star property
7.4 out of 10, Good, (368)
"Was a decent place to stay for the price. "
The price is 1.789.139 ₫
1.985.944 ₫ total
includes taxes & fees
2 Jul - 3 Jul
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 1.778.676 ₫
1.974.330 ₫ total
includes taxes & fees
26 Jun - 27 Jun
Driftwood Inn
Quality Inn
Free daily self-service breakfast

Quality Inn

2.5 star property
7.6 out of 10, Good, (1000)
"2nd time staying here no major issues "
The price is 2.615.700 ₫
2.903.427 ₫ total
includes taxes & fees
29 Jun - 30 Jun
Quality Inn
Relax Inn Smyrna
Reception

Relax Inn Smyrna

2.0 star property
7.8 out of 10, Good, (80)
"The owner/staff were so sweet and helpful "
The price is 2.327.973 ₫
2.589.637 ₫ total
includes taxes & fees
26 Jun - 27 Jun
Relax Inn Smyrna
Hampton Inn Middletown
Reception

Hampton Inn Middletown

2.5 star property
8.8 out of 10, Excellent, (805)
"Good location. Breakfast was great and plenty of parking. "
The price is 3.417.674 ₫
3.793.617 ₫ total
includes taxes & fees
29 Jun - 30 Jun
Hampton Inn Middletown
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, (586)
"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 3.426.567 ₫
3.803.489 ₫ total
includes taxes & fees
30 Jun - 1 Jul
Holiday Inn Express And Suites Middletown by IHG
Fairfield Inn & Suites by Marriott Middletown
Lobby

Fairfield Inn & Suites by Marriott Middletown

2.5 star property
9.2 out of 10, Wonderful, (245)
"Clean, friendly staff on checkin and checkout. "
The price is 3.609.666 ₫
4.006.729 ₫ total
includes taxes & fees
6 Jul - 7 Jul
Fairfield Inn & Suites by Marriott Middletown
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.

Frequently asked questions

Are you searching for the perfect hotel for your luxury trip to Chestertown?
Use Expedia to help you arrange a flight to Baltimore, MD (MTN-Martin State) airport or Easton, MD (ESN-Easton - Newnam) airport, and then choose from a variety of places to stay that will deliver the luxury you want. Amenities are important when you plan a trip, so we make it easy to find what you need to make your stay relaxing and comfortable. If you want an upscale hotel with a spa, an indoor pool or luxury bedding, Expedia can assist you in finding the best luxury hotel experience that Chestertown offers. During your visit, you might want to enjoy the university which Chestertown is known for.
How many luxury hotels will I be able to find in Chestertown?
Lie in the lap of luxury during your getaway to Chestertown in one of Expedia's 6 luxury hotels.
When can I expect good weather in Chestertown?
Planning for the weather is an important factor for making your trip to Chestertown a success, especially when you're splurging. 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.
What's there to see and do in Chestertown?
When you're in Chestertown, enjoy exploring the sights and attractions here including Historical Society of Kent County Maryland, Rolphs Wharf Marina and Garfield Center for the Arts at the Prince Theater. If you have extra time while you're in the area, you might want to see Chestertown Historic District and Sumner Hall.