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Chestertown Hotels from S$76

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12 Jul - 13 Jul
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Top 10 trending Chestertown hotels

Comfort Inn & Suites Chestertown
Lobby

Comfort Inn & Suites Chestertown

2.5 star property
8.6 out of 10, Excellent, (778)
"Comfortable room, friendly staff. "
The price is S$160
includes taxes & fees
3 Aug - 4 Aug
Comfort Inn & Suites Chestertown
Red Roof Inn & Suites Chestertown
1 bedroom, desk, laptop workspace, blackout curtains

Red Roof Inn & Suites Chestertown

2.0 star property
7.4 out of 10, Good, (372)
"Had a good time and enjoyed the quietness at the hotel. "
The price is S$97
includes taxes & fees
20 Jul - 21 Jul
Red Roof Inn & Suites Chestertown
The Lodge at Great Oak Landing
Private beach nearby, sun-loungers, beach volleyball

The Lodge at Great Oak Landing

3.5 star property
8.0 out of 10, Very good, (53)
"not super fancy but really well done. comfy beds and a first rate chef. plus great for the boating crowd"
The price is S$188
includes taxes & fees
14 Jul - 15 Jul
The Lodge at Great Oak Landing
Driftwood Inn
Front of property – evening/night

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 S$90
includes taxes & fees
14 Jul - 15 Jul
Driftwood Inn
Holiday Inn Express Annapolis East-Kent Island by IHG
Exterior

Holiday Inn Express Annapolis East-Kent Island by IHG

2.5 star property
9.2 out of 10, Wonderful, (867)
"Great place"
The price is S$169
includes taxes & fees
21 Jul - 22 Jul
Holiday Inn Express Annapolis East-Kent Island by IHG
La Quinta Inn & Suites by Wyndham Baltimore N / White Marsh
Free daily buffet breakfast

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

3.0 star property
7.0 out of 10, Good, (1016)
"Great place to stay with good pricing and clean. "
The price is S$112
includes taxes & fees
14 Jul - 15 Jul
La Quinta Inn & Suites by Wyndham Baltimore N / White Marsh
Hyatt Place Kent Narrows & Marina
Terrace/patio

Hyatt Place Kent Narrows & Marina

3.0 star property
9.4 out of 10, Exceptional, (579)
"Great place to stay. "
The price is S$216
includes taxes & fees
4 Aug - 5 Aug
Hyatt Place Kent Narrows & Marina
Hilton Garden Inn Kent Island Marina
Terrace/patio

Hilton Garden Inn Kent Island Marina

3.0 star property
9.0 out of 10, Wonderful, (958)
"Great stay. We have stayed multiple times throughout the years and the quality has always been excellent."
The price is S$216
includes taxes & fees
28 Jul - 29 Jul
Hilton Garden Inn Kent Island Marina
Country Inn & Suites by Radisson, Baltimore North, MD
Exterior

Country Inn & Suites by Radisson, Baltimore North, MD

3.0 star property
7.4 out of 10, Good, (1003)
"It was a very nice stay. I enjoyed the peaceful atmosphere. Thank you. "
The price is S$144
includes taxes & fees
4 Aug - 5 Aug
Country Inn & Suites by Radisson, Baltimore North, MD
Quality Inn & Suites Bel Air I-95 Exit 77A
Desk, free WiFi, bed sheets, alarm clocks

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

2.5 star property
7.2 out of 10, Good, (1013)
"Everything is great, best place to stay"
The price is S$85
includes taxes & fees
12 Aug - 13 Aug
Quality Inn & Suites Bel Air I-95 Exit 77A
Super 8 by Wyndham Aberdeen MD
Exterior

Super 8 by Wyndham Aberdeen MD

2.0 star property
6.8 out of 10, (816)
"Staff is great & rooms always good "
The price is S$80
includes taxes & fees
10 Aug - 11 Aug
Super 8 by Wyndham Aberdeen MD
Best Western Plus Hotel & Conference Center
Lobby

Best Western Plus Hotel & Conference Center

2.5 star property
7.8 out of 10, Good, (1001)
"It’s always a Great time here "
The price is S$167
includes taxes & fees
20 Jul - 21 Jul
Best Western Plus Hotel & Conference Center
Hampton Inn & Suites Edgewood/Aberdeen-South
Restaurant

Hampton Inn & Suites Edgewood/Aberdeen-South

2.5 star property
9.2 out of 10, Wonderful, (1013)
"Great stay at a great price "
The price is S$139
includes taxes & fees
20 Jul - 21 Jul
Hampton Inn & Suites Edgewood/Aberdeen-South
Americas Best Value Inn Edgewood
Lobby sitting area

Americas Best Value Inn Edgewood

2.0 star property
5.4 out of 10, (944)
"The staff was great."
The price is S$82
includes taxes & fees
27 Jul - 28 Jul
Americas Best Value Inn Edgewood
Super 8 by Wyndham Havre De Grace Aberdeen Area
In-room safe, desk, soundproofing, rollaway beds

Super 8 by Wyndham Havre De Grace Aberdeen Area

2.0 star property
6.8 out of 10, (923)
"This is a terrible place to stay. "
The price is S$76
includes taxes & fees
10 Aug - 11 Aug
Super 8 by Wyndham Havre De Grace Aberdeen Area
Super 8 by Wyndham Baltimore/Essex Area
Exterior

Super 8 by Wyndham Baltimore/Essex Area

2.0 star property
5.4 out of 10, (373)
"My every need was meet and the staff was pleasant.."
The price is S$126
includes taxes & fees
13 Jul - 14 Jul
Super 8 by Wyndham Baltimore/Essex Area
Historic Inns of Annapolis
Terrace/patio

Historic Inns of Annapolis

3.5 star property
9.0 out of 10, Wonderful, (1803)
"Wonderful stay!"
Historic Inns of Annapolis
Annapolis Waterfront Hotel, Autograph Collection
Premium bedding, down duvets, pillow-top beds, in-room safe

Annapolis Waterfront Hotel, Autograph Collection

4.0 star property
8.8 out of 10, Excellent, (837)
"Front desk staff was very friendly and helpful."
The price is S$309
includes taxes & fees
11 Aug - 12 Aug
Annapolis Waterfront Hotel, Autograph Collection
Hampton Inn & Suites Baltimore/Aberdeen
Restaurant

Hampton Inn & Suites Baltimore/Aberdeen

2.5 star property
9.0 out of 10, Wonderful, (549)
"Liked everything about this hotel. Would definitely stay here again"
The price is S$151
includes taxes & fees
20 Jul - 21 Jul
Hampton Inn & Suites Baltimore/Aberdeen
Fairfield Inn & Suites by Marriott White Marsh
Free daily buffet breakfast

Fairfield Inn & Suites by Marriott White Marsh

2.5 star property
8.6 out of 10, Excellent, (1003)
"Excellent stay. "
The price is S$149
includes taxes & fees
11 Aug - 12 Aug
Fairfield Inn & Suites by Marriott White Marsh
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.
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Learn more about Chestertown

Quaint Chestertown awaits: its sports, university life, art and more!

See all hotels in Chestertown
Photo by Assya A
Open Photo by Assya A

Frequently asked questions

Where is the best place for a stay in Chestertown?

Comfort Inn & Suites Chestertown is a favourite property for Expedia customers. This hotel offers free breakfast and free parking. Red Roof Inn & Suites Chestertown is another top choice for your stay based on reviews. See all available top hotels, or vacation rentals in Chestertown.

If I need to cancel my hotel reservation in Chestertown, will I receive a refund?

Yes! You'll find that most hotel bookings are fully refundable as long as you cancel prior to the accommodation's cancellation deadline, which in most cases is within 24 or 48 hours of your check-in date. If you booked a non-refundable reservation, you may still be able to cancel and get a refund within a 24-hour period of your booking. Filter your search by fully refundable to find flexible hotel deals in Chestertown.

What's the best accommodation for a budget-friendly stay in Chestertown?

Based on reviews, Red Roof Inn & Suites Chestertown is a popular 2-star hotel for our travellers looking for an economical choice, and features free WiFi and free parking. Another top choice for your budget-friendly stay is Driftwood Inn. View all budget hotels in Chestertown.

What's the best family accommodation in Chestertown?

Comfort Inn & Suites Chestertown is a hotel with free parking and free full breakfast, and it's a top choice on Expedia for families. Red Roof Inn & Suites Chestertown is another good option for your stay with the kids. Also, children of all ages will enjoy a visit to Crumpton Auction. Find more child-friendly accommodations in Chestertown.

What's the best place to stay for couples in Chestertown?

Red Roof Inn & Suites Chestertown is a favourite hotel for couples, and features free WiFi and free parking. See all romantic hotels in Chestertown.

What is the top LGBTQ-friendly hotel in Chestertown?

Comfort Inn & Suites Chestertown is a top LGBTQ-friendly hotel, and features free breakfast and free WiFi. The Lodge at Great Oak Landing and Red Roof Inn & Suites Chestertown are two other good options for your stay. See all available hotels listed as LGBTQ-friendly in Chestertown.

What's the best dog-friendly accommodation option in Chestertown?

Comfort Inn & Suites Chestertown is a top hotel for people travelling with their pets, and offers a seasonal outdoor pool and a fitness centre for its human guests. Other good options for you and your pet include Red Roof Inn & Suites Chestertown and Driftwood Inn. See more pet-friendly hotel accommodations in Chestertown.

What's the best hotel to stay near the beach in Chestertown?

The Lodge at Great Oak Landing is a top lodge with a seasonal outdoor pool and 3 bars/lounges, and it's located near a private beach . See more stays near the beach in Chestertown.

What's the best hotel in Chestertown to learn about local history?

Based on our travel expertise, Comfort Inn & Suites Chestertown is a top hotel on Expedia for those interested in history, and it features free breakfast and free WiFi. Also, notable landmarks to visit include Historical Society of Kent County Maryland.

What are some accommodation options with pools in Chestertown?

The Lodge at Great Oak Landing is a top lodge with a seasonal outdoor pool, 3 bars/lounges and free WiFi. View all hotels with pools in Chestertown.

What is the best spa hotel in Chestertown?

Great Oak Manor is a top spa hotel featuring a private beach and a fitness centre. See all spa hotels in Chestertown.

How is it to stay in Chestertown?

Visitors to Chestertown will definitely enjoy the university setting. Tourists can also enjoy the city's sporting events, festivals and art. In Chestertown, there are 41 hotels and other accommodation options to choose from. Find out more about Chestertown.

What should I see while I'm in Chestertown?

Cultural venues include Historical Society of Kent County Maryland and Garfield Center for the Arts at the Prince Theater. University life is a highlight and campuses to tour include Washington College and River Arts Chestertown. A couple of additional sights to add to your itinerary are Rolphs Wharf Marina and Chestertown Historic District. Take a look at what more there is to see and do in Expedia's Chestertown guide.

What's the seasonal weather like in Chestertown?

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.