Hotels in Chestertown

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Aug 3 - Aug 4
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Check prices in Chestertown for tonight, Aug 3 - Aug 4
Aug 4 - Aug 5
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Top Rated Chestertown Hotels

Comfort Inn & Suites Chestertown

Comfort Inn & Suites Chestertown

2.5 out of 5
150 Scheeler Road Chestertown MD
Free Cancellation
0.64 mi from city center
$103 nightly
The price is $115 total per night
$115 total
Aug 23 - Aug 24
Total with taxes and fees
Comfort Inn & Suites Chestertown features a gym, free WiFi in public areas, and a business center. If you drive, put free parking to good use. The 24-hour front desk has staff always at the ready. Additional amenities include a seasonal outdoor pool, coffee/tea in a common area, and a meeting room.
Pool
Breakfast included
The Lodge at Great Oak Landing

The Lodge at Great Oak Landing

3 out of 5
22170 Great Oak Landing Rd Chestertown MD
Free Cancellation
7.76 mi from city center
$124 nightly
The price is $137 total per night
$137 total
Aug 4 - Aug 5
Total with taxes and fees
Guests staying at The Lodge at Great Oak Landing enjoy access to a golf course, a 24-hour gym, and free WiFi in public areas. You can put free parking to good use if you drive. Other amenities at this beach lodge include a seasonal outdoor pool, coffee/tea in a common area, and laundry facilities.
Pool
Parking included
Red Roof Inn & Suites Chestertown

Red Roof Inn & Suites Chestertown

2 out of 5
160 Scheeler Rd Chestertown MD
Free Cancellation
Reserve now, pay when you stay
0.58 mi from city center
$63 nightly
The price is $70 total per night
$70 total
Aug 9 - Aug 10
Total with taxes and fees
Red Roof Inn & Suites Chestertown features free WiFi in public areas, coffee in a common area, and free newspapers. You can put free parking to good use if you drive. The 24-hour front desk has staff always at the ready. Additional amenities include laundry facilities, a fireplace in the lobby, and a vending machine.
Pet friendly
Parking included
Historic Inns of Annapolis

Historic Inns of Annapolis

3.5 out of 5
58 State Circle Annapolis MD
Free Cancellation
Reserve now, pay when you stay
27.98 mi from city center
$132 nightly
The price is $150 total per night
$150 total
Aug 9 - Aug 10
Total with taxes and fees
At Historic Inns of Annapolis, guests have access to a 24-hour gym, free WiFi in public areas, and meeting rooms. Valet parking is available for USD 50.00 per night, and there's also limo/town car service. The front desk has multilingual staff on hand 24/7 to help with luggage storage, tours or tickets, and securing valuables. Other amenities at this historic hotel include conference space, coffee/tea in a common area, and express check-in.
Annapolis Waterfront Hotel, Autograph Collection

Annapolis Waterfront Hotel, Autograph Collection

4 out of 5
80 Compromise St Annapolis MD
Free Cancellation
Reserve now, pay when you stay
27.93 mi from city center
$199 nightly
The price is $227 total per night
$227 total
Aug 16 - Aug 17
Total with taxes and fees
Annapolis Waterfront Hotel, Autograph Collection offers a 24-hour gym, a rooftop terrace, and free WiFi in public areas. Valet parking is available for USD 39 per day. The 24-hour front desk has staff standing by to help with dry cleaning/laundry, luggage storage, and concierge services. If you like to take your furry friend along on your adventures, this pet-friendly property offers food and water bowls. Additional amenities include meeting rooms, conference space, and a 24-hour business center.
Pet friendly
Free WiFi
Pendry Baltimore

Pendry Baltimore

5 out of 5
1715 Thames St. Baltimore MD
Free Cancellation
Reserve now, pay when you stay
28.3 mi from city center
$470 nightly
The price is $552 total per night
$552 total
Aug 31 - Sep 1
Total with taxes and fees
Guests of Pendry Baltimore enjoy a 24-hour gym, free WiFi in public areas, and meeting rooms. Valet parking is USD 65 per night if you plan to drive, or hop aboard the airport shuttle (available 24 hours) for USD 108.39 per vehicle one-way. The 24-hour front desk has staff standing by to help with dry cleaning/laundry, luggage storage, and securing valuables. If you like to take your furry friend along on your adventures, this pet-friendly property offers food and water bowls. Other amenities at this luxury hotel include a business center, a seasonal outdoor pool, and a terrace.
Pool
Spa
Best Western Plus Hotel & Conference Center

Best Western Plus Hotel & Conference Center

2.5 out of 5
5625 O'Donnell Street Baltimore MD
Free Cancellation
Reserve now, pay when you stay
25.92 mi from city center
$111 nightly
The price is $131 total per night
$131 total
Aug 30 - Aug 31
Total with taxes and fees
Guests of Best Western Plus Hotel & Conference Center have access to an indoor pool, a gym, and free WiFi in public areas. There's free parking and a cruise ship terminal shuttle. The 24-hour front desk has multilingual staff ready to assist with concierge services, dry cleaning/laundry, and luggage storage. Additional amenities include a hot tub, meeting rooms, and a conference center.
Pool
Hot Tub
La Quinta Inn & Suites by Wyndham Baltimore N / White Marsh

La Quinta Inn & Suites by Wyndham Baltimore N / White Marsh

3 out of 5
4 Philadelphia Ct Rosedale MD
Free Cancellation
Reserve now, pay when you stay
24.05 mi from city center
$75 nightly
The price is $87 total per night
$87 total
Sep 2 - Sep 3
Total with taxes and fees
Guests of La Quinta Inn & Suites by Wyndham Baltimore N / White Marsh enjoy a gym, free WiFi in public areas, and a business center. Free parking is included with your stay. The 24-hour front desk has multilingual staff ready to assist with concierge services and securing valuables. Additional amenities include coffee/tea in a common area, express check-in, and express check-out.
Breakfast included
Pet friendly
Quality Inn & Suites Bel Air I-95 Exit 77A

Quality Inn & Suites Bel Air I-95 Exit 77A

2.5 out of 5
2112a Emmorton Park Road Edgewood MD
Free Cancellation
Reserve now, pay when you stay
20.67 mi from city center
$63 nightly
The price is $70 total per night
$70 total
Sep 1 - Sep 2
Total with taxes and fees
Guests of Quality Inn & Suites Bel Air I-95 Exit 77A have access to free WiFi in public areas. Free parking is included with your stay. Front-desk staff are standing by 24/7 to assist with any requests.
Breakfast included
Parking included
Hyatt Place Kent Narrows & Marina

Hyatt Place Kent Narrows & Marina

3 out of 5
3028 KENT NARROW WAY S Grasonville MD
Free Cancellation
Reserve now, pay when you stay
19.68 mi from city center
$169 nightly
The price is $188 total per night
$188 total
Aug 9 - Aug 10
Total with taxes and fees
Guests staying at Hyatt Place Kent Narrows & Marina enjoy an indoor pool, a 24-hour gym, and free WiFi in public areas. If you drive, put free parking to good use. The front desk is staffed 24/7 to help secure valuables, and answer any questions about the accommodations. Additional amenities include a business center, coffee/tea in a common area, and a microwave in a common area.
Pool
Breakfast included
Best Western Kent Narrows Inn

Best Western Kent Narrows Inn

2.5 out of 5
3101 Main Street Grasonville MD
Free Cancellation
Reserve now, pay when you stay
19.64 mi from city center
$119 nightly
The price is $133 total per night
$133 total
Aug 5 - Aug 6
Total with taxes and fees
At Best Western Kent Narrows Inn, guests enjoy an indoor pool, a gym, and a sauna. There's free parking if you drive. The 24-hour front desk has staff standing by to help secure valuables, and answer any questions about the accommodations. Additional amenities include free WiFi in public areas, a hot tub, and a 24-hour business center.
La Quinta Inn & Suites by Wyndham Aberdeen-APG

La Quinta Inn & Suites by Wyndham Aberdeen-APG

3 out of 5
793 W Bel Air Ave Aberdeen MD
Free Cancellation
Reserve now, pay when you stay
21.94 mi from city center
$88 nightly
The price is $99 total per night
$99 total
Aug 9 - Aug 10
Total with taxes and fees
La Quinta Inn & Suites by Wyndham Aberdeen-APG features a gym, free WiFi in public areas, and conference space. You can put free parking to good use if you drive. The 24-hour front desk has staff standing by to help with luggage storage and dry cleaning/laundry. Additional amenities include a 24-hour business center, a seasonal outdoor pool, and a computer station.
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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.

Stay near popular Chestertown attractions

Washington College

8.6/10 (87 reviews)
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.
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Cheap Chestertown hotels options

    Driftwood Inn

    Driftwood Inn

    609 Washington Avenue Chestertown MD
    $64 nightly
    The price is $70 total per night from Aug 4 to Aug 5
    $70 total
    Aug 4 - Aug 5
    Total with taxes and fees
    Comfort Inn & Suites Chestertown

    Comfort Inn & Suites Chestertown

    150 Scheeler Road Chestertown MD
    $103 nightly
    The price is $115 total per night from Aug 23 to Aug 24
    $115 total
    Aug 23 - Aug 24
    Total with taxes and fees
    8.6/10 Excellent! (943 reviews)

Where should you stay in Chestertown?

What are some of the best hotels to stay with the kids in Chestertown?

Book one of these hotels for you and the kids in Chestertown. Comfort Inn & Suites Chestertown is a hotel offering free parking, free full breakfast, and laundry facilities. You and your family can also consider Red Roof Inn & Suites Chestertown, a hotel offering free parking, laundry facilities, and free WiFi.

What are the best hotels in central Chestertown?

These are some of the most popular hotels in the center of Chestertown:

Close to central Chestertown, you'll find interesting places to visit like Chestertown Historic District.

Chestertown hotels essential information

Accommodation
1,091 hotels
Lowest Price
$70
Highest Price
$552
Popular hotels
Comfort Inn & Suites Chestertown, The Lodge at Great Oak Landing, Red Roof Inn & Suites Chestertown, Historic Inns of Annapolis, Annapolis Waterfront Hotel, Autograph Collection, Pendry Baltimore, Best Western Plus Hotel & Conference Center, La Quinta Inn & Suites by Wyndham Baltimore N / White Marsh, Quality Inn & Suites Bel Air I-95 Exit 77A, Hyatt Place Kent Narrows & Marina, Best Western Kent Narrows Inn, La Quinta Inn & Suites by Wyndham Aberdeen-APG

Recent Reviews

Annapolis Waterfront Hotel, Autograph Collection

Annapolis Waterfront Hotel, Autograph Collection

5/5 Excellent
"Wonderful stay! Excellent location on the water. Had a room with a balcony. Staff and restaurants were all very nice."
A verified traveler stayed at Annapolis Waterfront Hotel, Autograph Collection
Posted 15 hours ago
Annapolis Waterfront Hotel, Autograph Collection

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