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Chestertown MD Hotels

Search among 52 available hotels and places to stay in Chestertown from 50+ providers

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8.2
Great61 reviews
Map
1.3 mi from City Center317 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
Bed & Breakfast
8.8
Great33 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$ 337 /nightSelect
7.0
Very good48 reviews
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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
Great53 reviews
Map
21.2 mi from Chestertown21.2 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$ 189 /nightSelect
8.4
Great78 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
Great36 reviews
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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$ 159 /nightSelect
8.6
Great72 reviews
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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$ 499 /nightSelect
7.8
Very good46 reviews
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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$ 51 /nightSelect
8.4
Great82 reviews
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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$ 70 /nightSelect
7.8
Very good98 reviews
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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$ 92 /nightSelect
8.2
Great67 reviews
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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$ 118 /nightSelect
8.2
Great105 reviews
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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
8.6
Great54 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
Great70 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$ 110 /nightSelect
8.2
Great57 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
8.2
Great110 reviews
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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$ 159 /nightSelect
8.2
Great53 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
8.4
Great50 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$ 188 /nightSelect
8.0
Great41 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$ 124 /nightSelect
7.8
Very good59 reviews
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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$ 47 /nightSelect
8.0
Great40 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
8.6
Great39 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$ 234 /nightSelect
7.8
Very good66 reviews
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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$ 58 /nightSelect
8.2
Great56 reviews
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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$ 101 /nightSelect
8.4
Great84 reviews
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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
8.0
Great81 reviews
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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
8.2
Great61 reviews
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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
8.0
Great43 reviews
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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
Great55 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
7.8
Very good40 reviews
Map
21.2 mi from Chestertown21.2 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$ 100 /nightSelect
8.4
Great66 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$ 139 /nightSelect
8.2
Great67 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$ 175 /nightSelect
8.0
Great97 reviews
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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$ 62 /nightSelect
8.4
Great44 reviews
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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
8.4
Great112 reviews
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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
8.2
Great89 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
8.2
Great13 reviews
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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$ 141 /nightSelect
7.6
Very good25 reviews
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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
8.4
Great73 reviews
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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$ 105 /nightSelect
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10.8 mi from Chestertown10.8 mi from City Center
The Mainstay is about 0.3 miles from the 2-star Mariners Motel, while Wesley Chapel United Methodist Church is 10 minutes' walk away.
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8.2
Great16 reviews
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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$ 145 /nightSelect
7.8
Very good7 reviews
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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
8.6
Great7 reviews
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21.2 mi from Chestertown21.2 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
8.4
Great24 reviews
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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
7.8
Very good32 reviews
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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
8.0
Great5 reviews
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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.
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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$ 202 /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
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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
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21.2 mi from Chestertown21.2 mi from City Center
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8.6
Great1 review
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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.
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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 1860 rated 8.8/10 at the cost of 337US$ per night with a picnic area, concierge service, board games. Go here to check other popular 5-star places to stay in Chestertown.

What are the best romantic hotels in Chestertown?

According to Booked.net travel data, there are 4 deals for couples. Check Quality Suites rated 8.0/10 with an indoor swimming pool, newspaper service, a gym. It’s set 1.3 miles from Emmanuel Episcopal Church and costs about 75US$ per night. To see more romantic hotels click here.

What are the top pet-friendly hotels in Chestertown?

Another most recommended Chestertown place to stay with pets is Comfort Inn & Suites with a golf course, a business center, free private parking. It offers rooms for 92US$ per night. See more pet-friendly hotels here.

Which hotels are the best ones to stay at in Chestertown?

For instance, book Driftwood Inn rated 7.0/10 for 57US$ per night. It's set 0.7 miles from Kent Plaza Shopping Center and provides a photocopy machine, 24-hour reception, free parking. As an alternative, check Comfort Inn & Suites rated 8.2/10 with a golf course, a business center, free private parking on site.

Which hotels in Chestertown offer an especially good breakfast?

You may like Quality Suites rated 8.0/10 with an indoor swimming pool, newspaper service, a gym. It costs 75US$ per night.

How much is it to stay a night in Chestertown?

According to Booked.net travel data, the average prices for Chestertown hotels are:
A 3-star hotel room costs about 75US$ per night. Check Quality Suites (rating: 8.0/10).
If you're searching for something really special, a 5-star hotel can be found for 337US$ per night. Check Brampton 1860 with rating 8.8/10.

What are the best accommodations close to Washington College?

On Booked.net you will find 3 great accommodations close to Washington College in Chestertown. Also, you may like Comfort Inn & Suites rated 8.2/10 with a golf course, a business center, laundry. It costs 92US$ 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.

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Chestertown hotels essential information

🏨 Hotels in Chestertown 52
👛 Lowest price 47 USD
✍️ Hotels Reviews 2 595