Photo by Assya A

Chestertown Hotels from S$82

    calendar shield illustration
    Change your mind
    Book hotels with free cancellation
    deals illustration
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration
    Be picky
    Search almost a million properties worldwide

Check prices for these dates

Tonight
25 Jun - 26 Jun
Tomorrow
26 Jun - 27 Jun
This weekend
27 Jun - 29 Jun
Next weekend
4 Jul - 6 Jul

Filter by

Guest rating
Guest rating
Property class

Top 10 trending Chestertown hotels

Comfort Inn & Suites Chestertown
Lobby

Comfort Inn & Suites Chestertown

2.5 star property
8.6 out of 10, Excellent, (772)
"Comfortable room, friendly staff. "
The price is S$162
includes taxes & fees
24 Jul - 25 Jul
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, (368)
"Was a decent place to stay for the price. "
The price is S$97
includes taxes & fees
2 Jul - 3 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
7.8 out of 10, Good, (52)
"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
26 Jun - 27 Jun
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$97
includes taxes & fees
26 Jun - 27 Jun
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, (857)
"Good location - clean hotel."
The price is S$158
includes taxes & fees
1 Jul - 2 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, (1010)
"Great place to stay with good pricing and clean. "
The price is S$117
includes taxes & fees
30 Jun - 1 Jul
La Quinta Inn & Suites by Wyndham Baltimore N / White Marsh
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, (1000)
"Very convenient, excellent and accommodating staff."
The price is S$148
includes taxes & fees
6 Jul - 7 Jul
Country Inn & Suites by Radisson, Baltimore North, MD
Hyatt Place Kent Narrows & Marina
Terrace/patio

Hyatt Place Kent Narrows & Marina

3.0 star property
9.6 out of 10, Exceptional, (564)
"Great place to stay. "
The price is S$246
includes taxes & fees
2 Jul - 3 Jul
Hyatt Place Kent Narrows & Marina
Super 8 by Wyndham Aberdeen MD
Exterior

Super 8 by Wyndham Aberdeen MD

2.0 star property
6.8 out of 10, (808)
"Staff is great & rooms always good "
The price is S$80
includes taxes & fees
1 Jul - 2 Jul
Super 8 by Wyndham Aberdeen 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, (1009)
"Good place to stay at very reasonable rate"
The price is S$85
includes taxes & fees
29 Jun - 30 Jun
Quality Inn & Suites Bel Air I-95 Exit 77A
Hilton Garden Inn Kent Island Marina
Terrace/patio

Hilton Garden Inn Kent Island Marina

3.0 star property
9.0 out of 10, Wonderful, (943)
"Very nice place to stay. Will definitely stay there again!"
The price is S$204
includes taxes & fees
1 Jul - 2 Jul
Hilton Garden Inn Kent Island Marina
Best Western Plus Hotel & Conference Center
Lobby

Best Western Plus Hotel & Conference Center

2.5 star property
7.8 out of 10, Good, (1001)
"Best value, free parking always clean rooms."
The price is S$167
includes taxes & fees
6 Jul - 7 Jul
Best Western Plus Hotel & Conference Center
Americas Best Value Inn Edgewood
Lobby sitting area

Americas Best Value Inn Edgewood

2.0 star property
5.4 out of 10, (920)
"I recommend it to anyone weather they live in Edgewood Maryland or just coming through Edgewood "
The price is S$82
includes taxes & fees
13 Jul - 14 Jul
Americas Best Value Inn Edgewood
Hampton Inn & Suites Edgewood/Aberdeen-South
Restaurant

Hampton Inn & Suites Edgewood/Aberdeen-South

2.5 star property
9.2 out of 10, Wonderful, (1002)
"Great stay!"
The price is S$133
includes taxes & fees
30 Jun - 1 Jul
Hampton Inn & Suites Edgewood/Aberdeen-South
Super 8 by Wyndham Baltimore/Essex Area
Exterior

Super 8 by Wyndham Baltimore/Essex Area

2.0 star property
5.4 out of 10, (367)
"My every need was meet and the staff was pleasant.."
The price is S$126
includes taxes & fees
30 Jun - 1 Jul
Super 8 by Wyndham Baltimore/Essex Area
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, (912)
"Nice, clean, friendly "
The price is S$76
includes taxes & fees
1 Jul - 2 Jul
Super 8 by Wyndham Havre De Grace Aberdeen Area
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, (1000)
"Excellent stay. "
The price is S$162
includes taxes & fees
29 Jun - 30 Jun
Fairfield Inn & Suites by Marriott White Marsh
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, (829)
"Front desk staff was very friendly and helpful."
The price is S$340
includes taxes & fees
21 Jul - 22 Jul
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, (545)
"Liked everything about this hotel. Would definitely stay here again"
The price is S$151
includes taxes & fees
6 Jul - 7 Jul
Hampton Inn & Suites Baltimore/Aberdeen
Hampton Inn Baltimore Bayview Campus
Exterior

Hampton Inn Baltimore Bayview Campus

3.5 star property
9.0 out of 10, Wonderful, (1000)
"Peaceful place…easy parking…friendly staff"
The price is S$172
includes taxes & fees
3 Jul - 4 Jul
Hampton Inn Baltimore Bayview Campus
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.
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

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. 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.

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?

The Lodge at Great Oak Landing is a top LGBTQ-friendly lodge, and features a golf course and free WiFi. Comfort Inn & Suites Chestertown 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 fitness centre and laundry facilities 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.