Chestertown (MD) hotels and places to stay

Search among 54 available hotels and places to stay in Chestertown from 50+ providers

Check-in
Select date
-
Check-out
Select date
Rooms and Guests2 Guests, 1 Room
Check-in
Select date
-
Check-out
Select date
Rooms and Guests2 Guests, 1 Room
Filter & Sort
View map
Check-in
Select date
-
Check-out
Select date
Rooms and Guests2 Guests, 1 Room
1Filter & Sort
View map
View map
1-54 out of 54
Sort by: high popularity
  • Price: low to high
  • Price: high to low
  • Guest rating: high to low
  • Popularity: high to low
8.2
Great46 reviews
Map
1.3 mi from City Center284 yd from Kent Plaza Shopping Center
Offering easy access to Kent Plaza Shopping Center only 6 minutes' walk away, the 2-star Comfort Inn & Suites Chestertown provides excellent accommodation along with fitness classes and horseback riding activities.
FromUS$ 92 /nightSelect
8.0
Great49 reviews
Map
1.3 mi from City Center335 yd from Kent Plaza Shopping Center
Cassinelli Winery & Distillery is within 1.4 miles of the comfortable Quality Suites, while MassoniArt Gallery is around 1.5 miles away.
FromUS$ 75 /nightSelect
8.6
Great24 reviews
Map
1.5 mi from City Center1.5 mi from Imagination Alley
Approximately 50 miles from New Castle airport, the Brampton Bed And Breakfast Chestertown offers a spa complex for guests' enjoyment.
FromUS$ 348 /nightSelect
7.0
Very good48 reviews
Map
1692 yd from City Center276 yd from Kent Plaza Shopping Center
The pet-friendly Driftwood Inn is set 0.7 miles from Kent Plaza Shopping Center and a 25-minute walk from Chestertown Historic District.
FromUS$ 57 /nightSelect
Places to stay near Chestertown
8.4
Great60 reviews
Map
19.1 mi from Chestertown19.1 mi from City Center
Located not too far from Chesapeake Bay, the Hilton Garden Inn Kent Island Grasonville features an indoor swimming pool and 87 rooms plus it is 2.3 miles from Church of Christ.
FromUS$ 155 /nightSelect
8.4
Great38 reviews
Map
21.4 mi from Chestertown21.4 mi from City Center
Located around 2.9 miles from Cross Island Trail in Stevensville, the 4-star boutique At Chesapeake Bay Beach Club features an American-style restaurant along with fitness classes, massage therapy and various recreational opportunities.
FromUS$ 259 /nightSelect
8.6
Great61 reviews
Map
21.5 mi from Chestertown21.5 mi from City Center
While staying at the 3-star Kent Island Resort Stevensville you are invited to discover Blackwater Distilling & Tavern, set 10 minutes' drive away, or The Church of Jesus Christ of Latter-day Saints, which is 2.3 miles away.
FromUS$ 428 /nightSelect
8.4
Great44 reviews
Map
23.3 mi from Chestertown23.3 mi from City Center
While staying at the 3-star Vandiver Inn you are invited to discover Perryville Community Park, set 10 minutes away by car, or Cultural Center at the Opera House, which is 0.4 miles away.
FromUS$ 151 /nightSelect
8.6
Great27 reviews
Map
20.2 mi from Chestertown20.2 mi from City Center
The Edgewood is located 16 miles from Martin State airport and 500 feet from McDonald's bus stop.
FromUS$ 55 /nightSelect
8.4
Great55 reviews
Map
21.3 mi from Chestertown21.3 mi from City Center
The pet-friendly Homewood Suites By Hilton Bel Air boasts a location approximately 0.5 miles from Drainage Pond and offers a hot tub and an indoor pool.
FromUS$ 121 /nightSelect
7.8
Very good79 reviews
Map
22.6 mi from Chestertown22.6 mi from City Center
The 2-star Days Inn By Wyndham Aberdeen boasts a swimming pool and has 49 rooms, featuring a location near a train station.
FromUS$ 89 /nightSelect
8.2
Great58 reviews
Map
22.7 mi from Chestertown22.7 mi from City Center
The non-smoking Comfort Inn & Suites is nestled in the heart of Aberdeen and a 10-minute drive from Aberdeen Festival Park.
FromUS$ 75 /nightSelect
8.4
Great96 reviews
Map
19.1 mi from Chestertown19.1 mi from City Center
Located just 6 minutes by foot from Waterman's Monument and approximately 25 minutes' walk from Watermen's Memorial Drawbridge, the 3-star Best Western Kent Narrows Inn Grasonville features a hot tub and an indoor pool.
FromUS$ 184 /nightSelect
8.4
Great87 reviews
Map
22.7 mi from Chestertown22.7 mi from City Center
Set 2.2 miles from Swan Meadows Park, the comfortable Red Roof Inn Aberdeen features 102 rooms with private bathrooms.
FromUS$ 50 /nightSelect
8.4
Great40 reviews
Map
10.9 mi from Chestertown10.9 mi from City Center
Guests can enjoy the à la carte restaurant at the At Osprey Point Rock Hall that offers American cuisine as well as admire views of the pool.
FromUS$ 214 /nightSelect
8.2
Great48 reviews
Map
21.2 mi from Chestertown21.2 mi from City Center
Staying at the 2-star smoke free Motel 6-Edgewood, Md Edgewood means you will be about 2.1 miles from the historic Woodside House, while enjoying an outdoor swimming pool onsite.
FromUS$ 65 /nightSelect
8.6
Great54 reviews
Map
21.3 mi from Chestertown21.3 mi from City Center
Located in the business district of Bel Air, the Springhill Suites Edgewood Aberdeen offers whirlpool baths and an indoor pool along with an indoor swimming pool.
FromUS$ 169 /nightSelect
8.6
Great61 reviews
Map
22.4 mi from Chestertown22.4 mi from City Center
The 3-star Hilton Garden Inn Aberdeen is set in a business area, offering a great location a few minutes drive from Susquehanna State Park while boasting a hot tub and an indoor pool onsite.
FromUS$ 129 /nightSelect
8.0
Great47 reviews
Map
22.5 mi from Chestertown22.5 mi from City Center
Set about 1.3 miles from Aberdeen Festival Park, the rooms in the 2-star pet-friendly Super 8 By Wyndham Aberdeen Md have views of bay.
FromUS$ 53 /nightSelect
8.2
Great24 reviews
Map
23.2 mi from Chestertown23.2 mi from City Center
Located within 0.3 miles of Ripken Stadium, the Courtyard Aberdeen At Ripken Stadium has 120 rooms, and lies close to a freeway.
FromUS$ 199 /nightSelect
8.2
Great41 reviews
Map
19.0 mi from Chestertown19.0 mi from City Center
Staying at the Holiday Inn Express Annapolis East-Kent Island, An Ihg, guests can discover the rural area 7 minutes by foot from Waterman's Monument.
FromUS$ 346 /nightSelect
8.2
Great43 reviews
Map
22.6 mi from Chestertown22.6 mi from City Center
Guests can take advantage of fitness classes and entertainment activities, while staying at the 3-star Express Aberdeen-Chesapeake House, An Ihg, located 5 minutes by foot from Beards Hill Plaza Shopping Center as well as close to a freeway.
FromUS$ 102 /nightSelect
8.4
Great71 reviews
Map
22.7 mi from Chestertown22.7 mi from City Center
The 3-star La Quinta By Wyndham Aberdeen-Apg Aberdeen is located 39 minutes' drive from Martin State airport and offers a swimming pool as well as a gym.
FromUS$ 84 /nightSelect
8.4
Great42 reviews
Map
21.3 mi from Chestertown21.3 mi from City Center
Guests can have a continental breakfast and enjoy visiting Leight Park, set 10 minutes' drive from the comfortable 2-star Red Roof Inn Edgewood.
FromUS$ 73 /nightSelect
Bed & Breakfast
8.8
Great26 reviews
Map
11.0 mi from Chestertown11.0 mi from City Center
While staying at the 4-star At Huntingfield Creek you are invited to discover Rock Hall Marine Restoration & Heritage Center, set approximately 10 minutes away by car, or Ferry Park, which is about 10 minutes away by car.
FromUS$ 201 /nightSelect
8.2
Great55 reviews
Map
20.6 mi from Chestertown20.6 mi from City Center
Located approximately 25 minutes by foot from Mt Calvary FWB Church, the Home2 Suites By Hilton Baltimore/Aberdeen Md Aberdeen offers a buffet breakfast and features an indoor pool.
FromUS$ 157 /nightSelect
8.4
Great30 reviews
Map
21.1 mi from Chestertown21.1 mi from City Center
The Ramada By Wyndham Edgewood Hotel & Conference Center is a charming 2-star property set nearly a 25-minute stroll from Presbury United Methodist Church and around 2.2 miles from Trinity Lutheran Church & School.
FromUS$ 80 /nightSelect
Hotel
8.2
Great43 reviews
Map
18.6 mi from Chestertown18.6 mi from City Center
A 10-minute drive from Mears Point Marina, the perfect Quality features the outdoor swimming pool along with whirlpool baths and an outdoor swimming pool.
FromUS$ 150 /nightSelect
8.0
Great59 reviews
Map
22.7 mi from Chestertown22.7 mi from City Center
Comprising 61 rooms, the 3-star Travelodge By Wyndham Aberdeen is set near the business district of Aberdeen, about 2.3 miles from Maryland House Travel Plaza.
FromUS$ 61 /nightSelect
8.4
Great38 reviews
Map
10.9 mi from Chestertown10.9 mi from City Center
Offering a seasonal outdoor pool, the 3-star Inn At Haven Harbour is placed in the beach area of Rock Hall, approximately 0.5 miles from Rock Hall Marine Restoration & Heritage Center.
FromUS$ 199 /nightSelect
8.6
Great22 reviews
Map
23.2 mi from Chestertown23.2 mi from City Center
Set around 1.5 miles from U.S. Army Ordinance Museum, the 3-star residential Residence Inn Aberdeen At Ripken Stadium invites its guests to benefit from fitness classes, spa therapy and various recreational opportunities, plus to have a meal in an American-style restaurant.
FromUS$ 119 /nightSelect
8.0
Great30 reviews
Map
21.3 mi from Chestertown21.3 mi from City Center
While staying at the convenient 2-star Candlewood Suites Aberdeen-Bel Air, An Ihg you are invited to discover Belcamp Beach, set 1.7 miles away, or Sophia's Dairy, which is around 1.5 miles away.
FromUS$ 131 /nightSelect
8.4
Great76 reviews
Map
21.3 mi from Chestertown21.3 mi from City Center
The Quality Inn & Suites Bel Air I-95 Exit 77A is a comfortable 3-star property set within 2.8 miles of Flying Point Park and 2.3 miles from Anita C Leight Estuary Center.
FromUS$ 149 /nightSelect
8.4
Great93 reviews
Map
21.3 mi from Chestertown21.3 mi from City Center
The eco-friendly Country Inn & Suites By Radisson, Bel Air/Aberdeen, Md Bel Air is set 2.2 miles from Anita C Leight Estuary Center and approximately 1.9 miles from Cokesbury Memorial United Methodist.
FromUS$ 147 /nightSelect
8.4
Great44 reviews
Map
21.0 mi from Chestertown21.0 mi from City Center
Offering fitness classes, spa therapy and various recreational opportunities onsite, along with an American restaurant, the Holiday Inn - Belcamp - Aberdeen Area, An Ihg boasts a setting in the business district of Belcamp.
FromUS$ 148 /nightSelect
8.2
Great77 reviews
Map
23.6 mi from Chestertown23.6 mi from City Center
Featuring 60 rooms, various recreational opportunities and entertainment activities, the charming Super 8 By Wyndham Havre De Grace Aberdeen Area is approximately 1.9 miles from Frank J. Hutchins Memorial Park in Havre de Grace.
FromUS$ 77 /nightSelect
8.6
Great51 reviews
Map
21.4 mi from Chestertown21.4 mi from City Center
Located 16 miles from Martin State airport, the 3-star Hampton Inn & Suites Aberdeen/Apg South offers storage for belongings and a laundromat for guests' convenience.
FromUS$ 106 /nightSelect
8.4
Great34 reviews
Map
22.7 mi from Chestertown22.7 mi from City Center
U.S. Army Ordinance Museum is 20 minutes' stroll from the 3-star Hampton Inn & Suites By Hilton Baltimore/Aberdeen, Md Aberdeen and Lohr's Orchard is 3.1 miles away.
FromUS$ 126 /nightSelect
8.6
Great7 reviews
Map
21.3 mi from Chestertown21.3 mi from City Center
The lovely Holiday Inn Express Edgewood-Aberdeen-Bel Air is nestled in a tourist area of Edgewood and comes with a hot tub and an indoor pool.
FromUS$ 99 /nightSelect
8.2
Great11 reviews
Map
21.3 mi from Chestertown21.3 mi from City Center
Boasting a swimming pool, the Hilton Garden Inn Bel Air, Md Bel Air is about 25 minutes by foot from Harford Community Church.
FromUS$ 122 /nightSelect
8.4
Great51 reviews
Map
21.1 mi from Chestertown21.1 mi from City Center
St. Francis de Sales Catholic Church is around 1.4 miles from the Wingate By Wyndham Bel Air I-95 Exit 77A - Apg Area, while Edgewood Baptist Church is 10 minutes' drive away.
FromUS$ 147 /nightSelect
7.8
Very good7 reviews
Map
25.8 mi from Chestertown25.8 mi from City Center
Situated around 0.2 miles from Pell Gardens Park, the 3-star Inn At The Canal Bed & Breakfast features massage therapy and entertainment activities along with 6 rooms.
FromUS$ 291 /nightSelect
7.6
Very good25 reviews
Map
21.2 mi from Chestertown21.2 mi from City Center
While staying at the 2-star Super 8 By Wyndham Joppa you are invited to discover Mariner Point Park, set 2.1 miles away, or Pulaski Flea Market, which is approximately 2 miles away.
FromUS$ 70 /nightSelect
7.8
Very good32 reviews
Map
21.3 mi from Chestertown21.3 mi from City Center
Belcamp Beach is set a 25-minute walk from the pet-friendly Extended Stay America Suites - Baltimore - Bel Air - Aberdeen.
FromUS$ 102 /nightSelect
8.4
Great24 reviews
Map
11.1 mi from Chestertown11.1 mi from City Center
Guests can have a full English breakfast and enjoy visiting Rock Hall Marine Restoration & Heritage Center, set 0.6 miles from the 2-star Haven Point.
FromUS$ 175 /nightSelect
8.4
Great21 reviews
Map
25.4 mi from Chestertown25.4 mi from City Center
Featuring an indoor swimming pool, the Western Denton offers 60 rooms right in a leisure area.
FromUS$ 104 /nightSelect
8.4
Great30 reviews
Map
21.1 mi from Chestertown21.1 mi from City Center
The 3-star Bay Side Inn & Suites Aberdeen is set within a 10-minute drive of Mt Calvary FWB Church and 0.6 miles from Grace United Methodist Church.
FromUS$ 65 /nightSelect
8.2
Great16 reviews
Map
22.8 mi from Chestertown22.8 mi from City Center
While staying at the 3-star Fairfield By Marriott Inn & Suites you are invited to discover Legends of the Fog, set around 2.4 miles away, or Aberdeen Festival Park, which is 1.5 miles away.
FromUS$ 299 /nightSelect
Map
20.6 mi from Chestertown20.6 mi from City Center
The 2-star Budget Inn Of is set around 10 minutes' drive from Horizon Cinemas and within 2 miles of Aberdeen Festival Park.
FromUS$ 55 /nightSelect
7.8
Very good12 reviews
Map
19.1 mi from Chestertown19.1 mi from City Center
Watermen's Memorial Drawbridge is approximately 25 minutes' stroll from the Hyatt Place Kent Narrows And Marina Grasonville, while Mears Point Marina is 0.3 miles away.
FromUS$ 199 /nightSelect
8.2
Great8 reviews
Map
23.9 mi from Chestertown23.9 mi from City Center
While staying at the Fairfield By Marriott Inn & Suites you are invited to discover Silver Lake Park, set approximately 1.7 miles away, or Pharo House, which is about 2.4 miles away.
FromUS$ 159 /nightSelect
Map
21.3 mi from Chestertown21.3 mi from City Center
Leight Park is also set within 2.2 miles of the Towneplace Suites By Marriott Edgewood Aberdeen Belcamp.
FromUS$ 259 /nightSelect
Historic Kent Manor Inn
Hotel
8.6
Great1 review
Map
21.2 mi from Chestertown21.2 mi from City Center
The Historic Kent Manor has a swimming pool along with a lounge bar and boasts a location at a short distance from Chesapeake Bay.
Select
Mariner'S Motel
Motel
Map
10.8 mi from Chestertown10.8 mi from City Center
Located around an 11-minute walk from Rock Hall Marine Restoration & Heritage Center, the Mariner'S Motel features a seasonal outdoor swimming pool.
Select

FAQs about hotels in Chestertown

We hope that the answers to these questions will help you plan your trip

What are the finest 5-star hotels in Chestertown?

The best one is Brampton Bed And Breakfast Inn rated 8.6/10 at the cost of 348US$ per night with a picnic area, concierge service, and board games. Go here to check other popular 5-star places to stay in Chestertown.

What are the top Chestertown hotels for couples?

According to Booked.net travel data, there are 4 deals for couples. Check Comfort Inn & Suites rated 8.2/10 with a golf course, a business center, and 24-hour front desk. It’s set 0.8 miles from Chestertown Baptist Church and costs about 92US$ per night. Other suitable options for couples you can find here.

What are the top pet-friendly hotels in Chestertown?

Another most recommended Chestertown place to stay with pets is Driftwood Inn with 24 hour front desk assistance, 24-hour security service, and housekeeping service. It offers rooms for 57US$ per night. For more pet-friendly accommodations go here.

What are the most favored hotels in Chestertown?

You may like Comfort Inn & Suites rated 8.2/10 featuring a golf course, a business center, and 24 hour front desk assistance. It costs 92US$ per night. Also, you may book Brampton Bed And Breakfast Inn (rating: 8.6/10), a fantastic hotel with a picnic area, concierge service, and board games. It costs about 348US$ per night.

Which Chestertown hotels provide a good breakfast?

You may like Quality Suites rated 8.0/10 with a gym, a gym area, and a swimming pool. It costs 75US$ per night.

What is the average cost of a hotel room in Chestertown?

According to Booked.net travel data, the average prices for Chestertown properties are:
A 3-star hotel room costs about 75US$ per night. Check Quality Suites (rating: 8.0/10).
If you're looking for something really special, a 5-star hotel can be found for 348US$ per night. Check Brampton Bed And Breakfast Inn with rating 8.6/10.

What are the best hotels not far from Washington College?

On Booked.net you will find 3 great accommodations not far from Washington College in Chestertown. Also, you may check Driftwood Inn with 24-hour front desk, 24-hour security service, and housekeeping for 57US$ per night.

Where to stay in Chestertown?

Convenience of staying in hotels downtown

An option near the city center is John L Stam House next to Historical Society of Kent County Maryland.

Consider staying at Lodging At The Imperial, where you'll be within 5 minutes' walking distance of Historical Society of Kent County Maryland. Stay at Holiday Inn Express Hotel & Suites Chestertown to be within a 5-minute walk from Upper Shore Comm Hlth Ctr.

Show moreLess

Chestertown hotels essential information

🏨 Hotels in Chestertown 54
👛 Lowest price 50 USD
✍️ Hotels Reviews 2 168