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Chestertown (MD) hotels and places to stay

Search among 75 available hotels and places to stay in Chestertown from 50+ providers.

If you are looking for comfortable accommodation for your next city escape in Maryland, we are always ready to indulge you with good Chestertown hotel deals. Grab Chestertown hotel deals and special offers as Booked.net works around the clock to find exclusive offers just for you. Our website is complete with search filters, filters, which you may find extremely useful when looking for 5-star hotels and places to stay in Chestertown. We’ve got modern and historical hotels with a big list of services and amenities together with other amazing accommodation options which grant you an extensive base for exploring.Hide
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06Dec2021Monday
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  • The hotel has
    • Free on-site car park
  • The hotel has
    • 24-hour reception
  • The hotel has
    • Restaurant
View on map1.3 mi from City Center400 yd from Kent Plaza Shopping Center
Located 3 km away from Chestertown city center, this hotel features 53 rooms and an outdoor swimming pool.
8.2
Great39 reviews
From   US$ 148 /nightSelect
Not available
  • The hotel has
    • On-site car park
  • The hotel has
    • Late check-in/ -out
    • 24-hour reception
  • The hotel has
    • Fitness centre
View on map1.3 mi from City Center400 yd from Kent Plaza Shopping Center
Set close to Washington College, the hotel boasts American meals served at the onsite outdoor restaurant.
8.4
Great18 reviews
From   US$ 105 /nightSelect
Not available
View on map1.5 mi from City Center1.5 mi from Imagination Alley
Located next to Historical Society of Kent County, the venue comprises 13 rooms with garden views.
8.0
Great2 reviews
From   US$ 264 /nightSelect
Not available
View on map1700 yd from City Center300 yd from Kent Plaza Shopping Center
Within easy reach of Poor Richards of Chestertown, this hotel comprises 28 rooms with private bathrooms.
5.4
Guest rating19 reviews
From   US$ 65 /nightSelect
Not available
A few meters away you can enjoy River Arts Chestertown.
From   US$ 143 /nightSelect
Not available
View on map1.7 mi from City Center1.5 mi from Kent Plaza Shopping Center
Situated 1.4 miles from Church of the Nazarene, the villa offers hiking, cycling and fishing.
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Not available
Similar properties near Chestertown
View on map21.5 mi from Chestertown21.5 mi from City Center
Located next to Bay Bridge Airport, the venue comprises 24 rooms with sea views.
8.6
Great26 reviews
From   US$ 203 /nightSelect
Not available
View on map19.1 mi from Chestertown19.1 mi from City Center
This hotel, featuring 90 non-smoking rooms and an air-conditioned restaurant, is centrally based in the heart of the city.
8.6
Great18 reviews
From   US$ 174 /nightSelect
Not available
View on map23.3 mi from Chestertown23.3 mi from City Center
The romantic hotel is a good starting point to Havre de Grace' sights including Susquehanna Museum at the Lock House and Concord Point Lighthouse.
7.8
Very good2 reviews
From   US$ 127 /nightSelect
Not available
View on map24.6 mi from Chestertown24.6 mi from City Center
The excellent hotel in a business area is complete with 72 rooms and an indoor pool, offering cots and a play area to guests with children.
8.2
Great14 reviews
From   US$ 138 /nightSelect
Not available
View on map21.3 mi from Chestertown21.3 mi from City Center
This suburban hotel with 119 modern rooms is located in the heart of Bel Air.
8.2
Great20 reviews
From   US$ 100 /nightSelect
Not available
View on map19.0 mi from Chestertown19.0 mi from City Center
The hotel offers easy access to Chesapeake Exploration Center, boasting 76 rooms in the heart of Grasonville.
8.6
Great5 reviews
From   US$ 161 /nightSelect
Not available
View on map21.3 mi from Chestertown21.3 mi from City Center
This conveniently located hotel in Riverside boasts 92 beautiful rooms along with a spa area and a Jacuzzi.
8.4
Great16 reviews
From   US$ 110 /nightSelect
Not available
View on map26.3 mi from Chestertown26.3 mi from City Center
This historical-style hotel serves Turkish meals prepared in the full-service restaurant on site.
6.8
Nice16 reviews
From   US$ 65 /nightSelect
Not available
View on map28.4 mi from Chestertown28.4 mi from City Center
Located next to St Michaels, the venue comprises 111 rooms with bay views.
7.0
Very good3 reviews
From   US$ 227 /nightSelect
Not available
View on map22.8 mi from Chestertown22.8 mi from City Center
Located 3 km from the center of Aberdeen, the hotel offers a night bar plus playpens, a game room and video games for children.
7.6
Very good21 reviews
From   US$ 97 /nightSelect
Not available
View on map21.1 mi from Chestertown21.1 mi from City Center
This hotel in a shopping area of Edgewood offers Greek specialties served in the onsite casual restaurant.
7.6
Very good11 reviews
From   US$ 65 /nightSelect
Not available
View on map29.1 mi from Chestertown29.1 mi from City Center
The Georgian-style building of the hotel boasts 20 rooms close to Chesapeake Bay.
8.0
Great2 reviews
From   US$ 179 /nightSelect
Not available
View on map19.1 mi from Chestertown19.1 mi from City Center
Opened in 1989, this pleasant accommodation includes an indoor swimming pool, a shared lounge and a golf course, within 30 minutes' walk from the center of Grasonville.
8.4
Great26 reviews
From   US$ 117 /nightSelect
Not available
View on map10.9 mi from Chestertown10.9 mi from City Center
The hotel features a large pool and a spectacular view, boasting great setting.
8.2
Great3 reviews
From   US$ 171 /nightSelect
Not available
View on map22.6 mi from Chestertown22.6 mi from City Center
This hotel with golf courses and a stadium onsite features 49 beautiful rooms and is perfectly located a short walk from Ripken Stadium.
5.6
Guest rating21 reviews
From   US$ 55 /nightSelect
Not available
View on map22.5 mi from Chestertown22.5 mi from City Center
The hotel was built in 1990 in a business area of Aberdeen, and nowadays has 62.
7.0
Very good12 reviews
From   US$ 71 /nightSelect
Not available
View on map22.6 mi from Chestertown22.6 mi from City Center
Boasting setting in the centre of Aberdeen, the venue offers steam baths and massage treatments plus 120 quiet rooms.
7.4
Very good5 reviews
From   US$ 134 /nightSelect
Not available
View on map21.1 mi from Chestertown21.1 mi from City Center
A seasonal outdoor pool is available onsite together with boating and fishing services, while the hotel boasts a riverside location in a busy area.
7.6
Very good6 reviews
From   US$ 97 /nightSelect
Not available
View on map22.4 mi from Chestertown22.4 mi from City Center
This hotel with a stadium and golf courses onsite features 96 luxurious rooms and is conveniently located a short walk from Ripken Stadium.
8.4
Great26 reviews
From   US$ 138 /nightSelect
Not available
View on map23.2 mi from Chestertown23.2 mi from City Center
Located 4 km from the center of Aberdeen, the hotel offers a coffee bar plus cots and a pool for children.
7.8
Very good4 reviews
From   US$ 251 /nightSelect
Not available
View on map21.4 mi from Chestertown21.4 mi from City Center
Featuring garden views, the 4-storey hotel includes an American cuisine restaurant and a café bar.
8.0
Great1 review
From   US$ 179 /nightSelect
Not available
View on map22.7 mi from Chestertown22.7 mi from City Center
Located just off Ripken Museum, this hotel is nestled in a Mexican-style building and features an indoor swimming pool.
6.6
Nice20 reviews
From   US$ 61 /nightSelect
Not available
View on map20.6 mi from Chestertown20.6 mi from City Center
This historic-style hotel is set at a short distance to Ripken Museum.
7.6
Very good
From   US$ 175 /nightSelect
Not available
View on map22.7 mi from Chestertown22.7 mi from City Center
The hotel, placed in an innovative-style building, offers location in the heart of Aberdeen, boasting 92 modern rooms and a seasonal outdoor swimming pool.
6.6
Nice14 reviews
From   US$ 149 /nightSelect
Not available
View on map22.7 mi from Chestertown22.7 mi from City Center
The hotel was built in 1966 in a business area of Aberdeen, and nowadays has 61.
6.4
Nice14 reviews
From   US$ 95 /nightSelect
Not available
View on map24.2 mi from Chestertown24.2 mi from City Center
Featuring historical architecture, the venue provides 93 rooms and offers easy access to Middletown Main Street Pocket Park.
8.0
Great2 reviews
From   US$ 162 /nightSelect
Not available
View on map23.0 mi from Chestertown23.0 mi from City Center
This hotel in the business district of White Marsh is situated close to White Marsh Mall and welcomes guests since 2013.
7.6
Very good9 reviews
From   US$ 107 /nightSelect
Not available
View on map18.6 mi from Chestertown18.6 mi from City Center
Featuring 59 rooms, this hotel offers a scenic view of Chesapeake Bay and Sandy Point State Park and is located close to a motorway.
7.8
Very good14 reviews
From   US$ 185 /nightSelect
Not available
View on map27.1 mi from Chestertown27.1 mi from City Center
Featuring historical architecture, the venue provides 9 rooms and offers easy access to Historic Odessa Foundation.
7.0
Very good2 reviews
From   US$ 80 /nightSelect
Not available
View on map21.4 mi from Chestertown21.4 mi from City Center
Featuring a casino, barbeque grills and a library, the property offers accommodation since 2009 in a busy area.
8.4
Great8 reviews
From   US$ 94 /nightSelect
Not available
View on map21.3 mi from Chestertown21.3 mi from City Center
The hotel offers a business accommodation with 104 rooms in the leisure area of Edgewood.
8.8
Great25 reviews
From   US$ 105 /nightSelect
Not available
View on map20.2 mi from Chestertown20.2 mi from City Center
A few meters away you can enjoy Anita C. Leight Estuary Center.
From   US$ 66 /nightSelect
Not available
View on map23.6 mi from Chestertown23.6 mi from City Center
Located close to Harford Memorial Hospital, the hotel has 60 rooms, and boasts access to a motorway.
7.0
Very good20 reviews
From   US$ 60 /nightSelect
Not available
View on map21.3 mi from Chestertown21.3 mi from City Center
Located in a business area, the hotel has 72 rooms, and it features a port nearby.
6.8
Nice8 reviews
From   US$ 81 /nightSelect
Not available
Sutton InnHotel
View on map30.2 mi from Chestertown30.2 mi from City Center
Welcoming guests in the heart of Elkton, the hotel was remodelled in 2011.
7.8
Very good8 reviews
From   US$ 110 /nightSelect
Not available
View on map21.0 mi from Chestertown21.0 mi from City Center
Boasting an infinity pool, the hotel is about 20 minutes' walk from the center of Belcamp.
8.6
Great11 reviews
From   US$ 151 /nightSelect
Not available
View on map21.3 mi from Chestertown21.3 mi from City Center
The hotel was built in 2007 in a busy area of Edgewood, and nowadays has 66.
9.0
Perfect36 reviews
From   US$ 137 /nightSelect
Not available
View on map23.2 mi from Chestertown23.2 mi from City Center
Nestled 4 km from Aberdeen city center, the hotel boasts an indoor pool and a café bar.
8.0
Great5 reviews
From   US$ 108 /nightSelect
Not available
View on map21.4 mi from Chestertown21.4 mi from City Center
Boasting accommodation with an outdoor pool and views of the garden, the venue is situated in a shopping area close to a port.
9.2
Perfect15 reviews
From   US$ 155 /nightSelect
Not available
Inn At Huntingfield CreekBed & Breakfast
View on map11.0 mi from Chestertown11.0 mi from City Center
Located 30 minutes' drive from Rock Hall city center, this hotel offers a shared lounge, barbeque grills and a library.
8.4
Great2 reviews
From   US$ 258 /nightSelect
Not available
View on map21.3 mi from Chestertown21.3 mi from City Center
Welcoming guests in the centre of Edgewood, the hotel was remodelled in 2008.
6.6
Nice7 reviews
From   US$ 151 /nightSelect
Not available
View on map21.1 mi from Chestertown21.1 mi from City Center
This hotel, boasting a 24-hour restaurant along with an outdoor swimming pool, is centrally lodged in the heart of Edgewood.
7.8
Very good12 reviews
From   US$ 144 /nightSelect
Not available
View on map25.8 mi from Chestertown25.8 mi from City Center
A few meters away you can enjoy Detwiler's Farm Market.
8.0
Great2 reviews
From   US$ 291 /nightSelect
Not available
View on map21.1 mi from Chestertown21.1 mi from City Center
Boasting accommodation with an outdoor swimming pool and views of the garden, the venue is situated in a business area close to a bus stop.
7.0
Very good7 reviews
From   US$ 70 /nightSelect
Not available
View on map25.4 mi from Chestertown25.4 mi from City Center
Set in the centre of Denton, the hotel features a seasonal outdoor pool and has a 24-hour restaurant onsite.
8.4
Great6 reviews
From   US$ 128 /nightSelect
Not available
View on map21.3 mi from Chestertown21.3 mi from City Center
Situated in a business area of Bel Air, this hotel features an outdoor swimming pool and a golf course.
7.6
Very good4 reviews
From   US$ 96 /nightSelect
Not available
View on map23.2 mi from Chestertown23.2 mi from City Center
Boasting 70 rooms and high chairs and a pool for children, the venue is settled in the heart of the city.
5.0
Guest rating9 reviews
From   US$ 80 /nightSelect
Not available
View on map21.3 mi from Chestertown21.3 mi from City Center
This eco-friendly hotel overlooks the river boasting its location in busy area.
8.6
Great39 reviews
From   US$ 127 /nightSelect
Not available
Great Oak ManorBed & Breakfast
View on map8.4 mi from Chestertown8.4 mi from City Center
The hotel offers 12 rooms with the sea views, a first floor restaurant, and a music bar.
7.6
Very good4 reviews
From   US$ 219 /nightSelect
Not available
View on map21.1 mi from Chestertown21.1 mi from City Center
At this 4-storey hotel, guests can have a buffet breakfast and enjoy visiting Urban Air Trampoline Park set within an easy reach.
7.8
Very good5 reviews
From   US$ 159 /nightSelect
Not available
View on map11.1 mi from Chestertown11.1 mi from City Center
The guests can indulge in canoeing, hiking and cycling and relax in a garden bar, while the hotel boasts a beautiful location close to Dream Charters.
9.0
Perfect1 review
From   US$ 165 /nightSelect
Not available
View on map10.9 mi from Chestertown10.9 mi from City Center
Featuring an outdoor pool, this property is set a short distance from Ferry Park and Aaron Chapel Fellowship Hall.
7.6
Very good
From   US$ 137 /nightSelect
Not available
View on map20.6 mi from Chestertown20.6 mi from City Center
Within easy reach of Heat Center, this hotel comprises 24 rooms with private bathrooms.
From   US$ 55 /nightSelect
Not available
View on map22.7 mi from Chestertown22.7 mi from City Center
Boasting an excellent location in a business area, the hotel offers staying in a historic-style building with 92 rooms available.
From   US$ 149 /nightSelect
Not available
View on map21.1 mi from Chestertown21.1 mi from City Center
This hotel with golf courses and a stadium onsite features 36 non-smoking rooms and is centrally located a short walk from Aberdeen Proving Ground.
8.0
Great8 reviews
From   US$ 65 /nightSelect
Not available
View on map22.8 mi from Chestertown22.8 mi from City Center
Located 1.6 miles away from the city center, this hotel features 84 rooms and an indoor pool.
From   US$ 149 /nightSelect
Not available
View on map21.3 mi from Chestertown21.3 mi from City Center
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Not available
View on map21.0 mi from Chestertown21.0 mi from City Center
Located just off Highway Holiness Church and 2.2 miles from Ripken Stadium, this hotel features entertainment activities and a cable flat-screen.
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Not available
View on map23.0 mi from Chestertown23.0 mi from City Center
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View on map23.1 mi from Chestertown23.1 mi from City Center
Set within walking distance of Sandy Point State Park, this villa includes 3 bedrooms and an equipped kitchenette area for guests' convenience.
From   US$ 273 /nightSelect
Not available
View on map21.2 mi from Chestertown21.2 mi from City Center
There are rooms facing the garden and the hotel is set close to Bay Bridge Airport.
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Not available
View on map21.3 mi from Chestertown21.3 mi from City Center
The hotel has an indoor pool and lies close to Generation Church which is worth visiting.
From   US$ 114 /nightSelect
Not available
View on map26.9 mi from Chestertown26.9 mi from City Center
C&D Canal Museum is 3.6 miles from this villa that offers 3 bedrooms along with a kitchen.
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Not available
View on map25.8 mi from Chestertown25.8 mi from City Center
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Not available
View on map25.7 mi from Chestertown25.7 mi from City Center
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Not available
View on map23.1 mi from Chestertown23.1 mi from City Center
Sail Selina II, St. Michaels is 12 miles from this villa that offers 4 bedrooms along with a mini-kitchen.
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Not available
View on map24.4 mi from Chestertown24.4 mi from City Center
This villa is a 10-minute drive from Saint John's Methodist Church and offers windsurfing and fishing.
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Not available
View on map18.4 mi from Chestertown18.4 mi from City Center
This 93 m² apartment gives direct access to Garnett Church and comprises 2 bedrooms.
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Not available
View on map26.6 mi from Chestertown26.6 mi from City Center
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Not available

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75 hotels found

FAQs about hotels in Chestertown

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

What are the best pet-friendly hotels in Chestertown?

Another most recommended Chestertown place to stay with pets is Driftwood Inn with housekeeping, ironing and a photocopy machine. It offers rooms for 68US$ per night. For more pet-friendly accommodations go here.

What are the top 5-star hotels in Chestertown?

The best one is Brampton Bed And Breakfast Inn rated 8.0/10 at the cost of 229US$ per night with concierge service, board games and housekeeping service. Click here to find out more 5-star hotels here.

What are the top Chestertown hotels for couples?

According to Booked.net travel data, there are 4 deals for couples. Find out Quality Suites (rating: 8.2/10) at the cost of 149US$ per one night, set 1.5 miles from Twigs & Teacups. It offers an indoor swimming pool, a business center and restaurant along with laundry facilities, housekeeping service and 24-hour front desk assistance. Visitors can book a room from 68US$ per night. Other suitable options for couples you can find here.

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.

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