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Chestertown Hotels from ₹4,554

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Top 10 Chestertown hotels and places to stay

The Lodge at Great Oak Landing

3.5 star property
8.0 out of 10, Very good, (55)
"Great place to get some quiet rest by the water"
The price is ₹11,141
₹12,367 total
includes taxes & fees
27 Jul - 28 Jul
The Lodge at Great Oak Landing

Comfort Inn & Suites Chestertown

2.5 star property
8.6 out of 10, Excellent, (786)
"It was a clean comfortable spot to rest for the night. "
The price is ₹9,890
₹10,978 total
includes taxes & fees
17 Aug - 18 Aug
Comfort Inn & Suites Chestertown

Red Roof Inn & Suites Chestertown

2.0 star property
7.2 out of 10, Good, (379)
"Good location."
The price is ₹6,607
₹7,333 total
includes taxes & fees
3 Aug - 4 Aug
Red Roof Inn & Suites Chestertown

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 ₹5,485
₹6,088 total
includes taxes & fees
25 Jul - 26 Jul
Driftwood Inn

Quality Inn

2.5 star property
7.6 out of 10, Good, (1003)
"A solid, comfortable place to stay at a reasonable rate."
The price is ₹8,637
₹9,587 total
includes taxes & fees
10 Aug - 11 Aug
Quality Inn

Relax Inn Smyrna

2.0 star property
7.8 out of 10, Good, (84)
"Owner was very nice. "
The price is ₹6,922
₹7,700 total
includes taxes & fees
6 Aug - 7 Aug
Relax Inn Smyrna

Hampton Inn Middletown

2.5 star property
8.8 out of 10, Excellent, (817)
"Front desk service was exceptional!!"
The price is ₹11,021
₹12,233 total
includes taxes & fees
19 Aug - 20 Aug
Hampton Inn Middletown

Holiday Inn Express And Suites Middletown by IHG

2.5 star property
9.2 out of 10, Wonderful, (594)
"Easy to navigate and nice, helpful staff "
The price is ₹10,024
₹11,127 total
includes taxes & fees
17 Aug - 18 Aug
Holiday Inn Express And Suites Middletown by IHG

Fairfield Inn & Suites by Marriott Middletown

2.5 star property
9.2 out of 10, Wonderful, (255)
"Nice place to stay"
The price is ₹9,074
₹10,072 total
includes taxes & fees
3 Aug - 4 Aug
Fairfield Inn & Suites by Marriott Middletown

Quality Inn

2.5 star property
7.8 out of 10, Good, (793)
"The place was clean and quiet, staff was great, not much nearby to see and do. It’s a fishing town. "
The price is ₹8,462
₹9,393 total
includes taxes & fees
24 Aug - 25 Aug
Quality Inn

Vandiver Inn

3.5 star property
9.4 out of 10, Exceptional, (505)
"Loved our visit and will be back again. The rooms were comfortable and breakfast was great, and very convenient to everything "
Vandiver Inn

Super 8 by Wyndham Havre De Grace Aberdeen Area

2.0 star property
6.8 out of 10, (928)
"This is a terrible place to stay. "
The price is ₹4,554
₹5,100 total
includes taxes & fees
4 Aug - 5 Aug
Super 8 by Wyndham Havre De Grace Aberdeen Area

Hilton Garden Inn Kent Island Marina

3.0 star property
9.0 out of 10, Wonderful, (965)
"Great spot with beautiful views. "
The price is ₹14,001
₹15,541 total
includes taxes & fees
29 Jul - 30 Jul
Hilton Garden Inn Kent Island Marina

Holiday Inn Express Annapolis East-Kent Island by IHG

2.5 star property
9.2 out of 10, Wonderful, (874)
"Great place"
The price is ₹13,049
₹14,484 total
includes taxes & fees
28 Jul - 29 Jul
Holiday Inn Express Annapolis East-Kent Island by IHG

Best Western Kent Narrows Inn

2.5 star property
8.2 out of 10, Very good, (1006)
"Second time staying, it’s priced right, great staff, and amazing restaurants right across the street, quiet area right by the bay bridge. "
The price is ₹10,887
₹12,084 total
includes taxes & fees
10 Aug - 11 Aug
Best Western Kent Narrows Inn

Hyatt Place Kent Narrows & Marina

3.0 star property
9.4 out of 10, Exceptional, (595)
"Great place to stay. "
The price is ₹14,618
₹16,225 total
includes taxes & fees
28 Jul - 29 Jul
Hyatt Place Kent Narrows & Marina

Inn at Huntingfield Creek

3.5 star property
10.0 out of 10, Exceptional, (52)
"Everything was lovely. Our cottage private and very nice. Breakfast delicious. Close to town. "
Inn at Huntingfield Creek

Mariners Motel

2.0 star property
9.4 out of 10, Exceptional, (89)
"Very nice old school motel just about on the water in Rock Hall. Perfect if you’re in town for marina stuff. "
The price is ₹13,416
₹14,892 total
includes taxes & fees
10 Aug - 11 Aug
Mariners Motel

Inn at Haven Harbour

3.0 star property
The price is ₹19,110
₹22,940 total
includes taxes & fees
31 Jul - 1 Aug
Inn at Haven Harbour

Home2 Suites by Hilton Baltimore / Aberdeen, MD

3.0 star property
8.6 out of 10, Excellent, (313)
"All around good experience. The queen bed seemed small though. Looked like a full size."
The price is ₹10,294
₹11,529 total
includes taxes & fees
17 Aug - 18 Aug
Home2 Suites by Hilton Baltimore / Aberdeen, MD
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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Accommodation near Chestertown attractions

Historical Society of Kent County Maryland

Historical Society of Kent County Maryland

You can spend an afternoon browsing the exhibits at Historical Society of Kent County Maryland during your trip to Chestertown. Amble around this family-friendly area's riverfront or experience its festivals.

Learn more about Chestertown

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

Photo by Assya A
Open Photo by Assya A

Top Chestertown Hotel Reviews

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?

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. 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 44 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.