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Chestertown hotels from HK$461

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Check prices for these dates

Tonight
15 Apr - 16 Apr
Tomorrow
16 Apr - 17 Apr
This weekend
18 Apr - 20 Apr
Next weekend
25 Apr - 27 Apr

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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, (756)
"Inside the building it was clean, quiet and nice. In the back parking lot, it was very dirty. The grounds surrounding the lot was littered with trash and debris. One person looked to be sleeping in his car. I did appreciate the very bright lighting in that lot. A small clean up of the back lot would make a big difference in first impressions!!"
The price is HK$833
HK$925 total
includes taxes & fees
24 Apr - 25 Apr
Comfort Inn & Suites Chestertown
Red Roof Inn & Suites Chestertown
Desk, laptop workspace, blackout curtains, iron/ironing board

Red Roof Inn & Suites Chestertown

2.0 star property
7.4 out of 10, Good, (343)
"I stayed here one night and got a stripper pregnant. 10/10 will book again. "
The price is HK$530
HK$589 total
includes taxes & fees
22 Apr - 23 Apr
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
7.8 out of 10, Good, (47)
"Generally okay, Clean but property could use some upgrade"
The price is HK$838
HK$930 total
includes taxes & fees
29 Apr - 30 Apr
The Lodge at Great Oak Landing
Driftwood Inn
Lobby

Driftwood Inn

2.0 star property
5.2 out of 10, (169)
"Rooms were clean. Check-in was a breeze, and the housekeeping lady is the best left her a nice tip"
The price is HK$492
HK$547 total
includes taxes & fees
16 Apr - 17 Apr
Driftwood Inn
Quality Inn
Exterior

Quality Inn

2.5 star property
7.6 out of 10, Good, (996)
"Comfortable and clean"
The price is HK$698
HK$775 total
includes taxes & fees
16 Apr - 17 Apr
Quality Inn
Relax Inn Smyrna
Premium bedding, down duvets, individually furnished, desk

Relax Inn Smyrna

2.0 star property
8.0 out of 10, Very good, (75)
"The room was clean and the bed was quite comfortable. It is a bit dated, and could use a bit of paint and sprucing up. Our room had only a blind on the window, so it was pretty bright overnight. I slept well and that was the purpose of ghe room. It was easy to get to and close to my final destination. Plenty of places to get food nearby. Friendly staff and cheap rate"
The price is HK$690
HK$768 total
includes taxes & fees
16 Apr - 17 Apr
Relax Inn Smyrna
Hampton Inn Middletown
Indoor pool

Hampton Inn Middletown

2.5 star property
8.8 out of 10, Excellent, (783)
"Wounderful"
The price is HK$965
HK$1,071 total
includes taxes & fees
20 Apr - 21 Apr
Hampton Inn Middletown
Holiday Inn Express And Suites Middletown by IHG
Exterior

Holiday Inn Express And Suites Middletown by IHG

2.5 star property
9.2 out of 10, Wonderful, (555)
"Beautiful hotel. Great service. I didn’t like that the suite was small and was not a separate room suite. The pool and fitness room was also too small."
The price is HK$969
HK$1,076 total
includes taxes & fees
20 Apr - 21 Apr
Holiday Inn Express And Suites Middletown by IHG
Fairfield Inn & Suites by Marriott Middletown
Lobby

Fairfield Inn & Suites by Marriott Middletown

2.5 star property
9.2 out of 10, Wonderful, (217)
"Never had a problem with Fairfield Inn. Very nicely done. Free breakfast if you want. Comfortable beds & clean rooms. "
The price is HK$853
HK$947 total
includes taxes & fees
5 May - 6 May
Fairfield Inn & Suites by Marriott Middletown
First Floor Standard Deluxe King
Miscellaneous

First Floor Standard Deluxe King

2.5 star property
The price is HK$2,719
HK$3,869 total
includes taxes & fees
24 Apr - 25 Apr
First Floor Standard Deluxe King
First Floor Standard Suite
Miscellaneous

First Floor Standard Suite

2.0 star property
The price is HK$2,873
HK$4,032 total
includes taxes & fees
24 Apr - 25 Apr
First Floor Standard Suite
Top Floor Standard Deluxe Bay View
Miscellaneous

Top Floor Standard Deluxe Bay View

2.5 star property
The price is HK$2,925
HK$4,087 total
includes taxes & fees
24 Apr - 25 Apr
Top Floor Standard Deluxe Bay View
Top Floor Family Deluxe Bay View
Miscellaneous

Top Floor Family Deluxe Bay View

2.5 star property
The price is HK$2,925
HK$4,087 total
includes taxes & fees
17 Apr - 18 Apr
Top Floor Family Deluxe Bay View
Top Floor Standard Deluxe
Miscellaneous

Top Floor Standard Deluxe

2.5 star property
10.0 out of 10, Exceptional, (1)
"Very relaxing and peaceful love it can’t wait to be there again….."
The price is HK$2,719
HK$3,869 total
includes taxes & fees
17 Apr - 18 Apr
Top Floor Standard Deluxe
Spectacular Top Floor Deluxe Suite With Beautiful View & More!
Miscellaneous

Spectacular Top Floor Deluxe Suite With Beautiful View & More!

2.5 star property
The price is HK$2,925
HK$4,087 total
includes taxes & fees
17 Apr - 18 Apr
Spectacular Top Floor Deluxe Suite With Beautiful View & More!
First Floor East Standard Deluxe
Miscellaneous

First Floor East Standard Deluxe

2.5 star property
The price is HK$2,719
HK$3,869 total
includes taxes & fees
17 Apr - 18 Apr
First Floor East Standard Deluxe
Fantastic Suite With King Bed and Beautiful Bay View!
Miscellaneous

Fantastic Suite With King Bed and Beautiful Bay View!

2.0 star property
The price is HK$2,925
HK$4,087 total
includes taxes & fees
24 Apr - 25 Apr
Fantastic Suite With King Bed and Beautiful Bay View!
First Floor Standard Deluxe
Miscellaneous

First Floor Standard Deluxe

2.0 star property
The price is HK$2,719
HK$3,869 total
includes taxes & fees
16 Apr - 17 Apr
First Floor Standard Deluxe
Second Floor Standard Deluxe
Miscellaneous

Second Floor Standard Deluxe

2.0 star property
The price is HK$2,719
HK$3,869 total
includes taxes & fees
17 Apr - 18 Apr
Second Floor Standard Deluxe
Second East Family Deluxe
Miscellaneous

Second East Family Deluxe

2.5 star property
The price is HK$2,719
HK$3,869 total
includes taxes & fees
17 Apr - 18 Apr
Second East Family Deluxe
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, boating 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. Reviews from our site also recommend The Lodge at Great Oak Landing and Red Roof Inn & Suites Chestertown as top options for your stay. See all available top hotels, or vacation rentals in Chestertown.

What are some of the best holiday rentals that Chestertown has to offer?

Directly Across from USNA Gate One & Steps from the Waterfront and Main Street! : This holiday home rental outside of Chestertown is located in the city centre, and has a fireplace, a patio and a BBQ to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You and your friends and family can relax into your holiday with amenities such as a selection of games. See all 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?

Red Roof Inn & Suites Chestertown is a hotel with free parking and laundry facilities, and it's a top choice on Expedia for families. Comfort 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?

Red Roof Inn & Suites Chestertown is a top LGBTQ-friendly hotel that features free Wi-Fi and free parking. The Lodge at Great Oak Landing and Comfort 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?

Red Roof Inn & Suites Chestertown is a top hotel for people travelling with their pets, and offers laundry facilities and free newspapers for its human guests. Other good options for you and your pet include Comfort 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. See more options for historical stays in Chestertown.

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 Crumpton Auction. 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.