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Find hotels in Chestertown, MD from NT$1,687

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Compare 1,079 hotels, room rates, hotel reviews and availability. Most hotels are fully refundable.

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 NT$4,554
NT$5,055 total
includes taxes & fees
Aug 19 - Aug 20
Mariners Motel

Inn at Haven Harbour

3.0 star property
The price is NT$6,487
NT$7,788 total
includes taxes & fees
Jul 31 - Aug 1
Inn at Haven Harbour

Vandiver Inn

3.5 star property
9.4 out of 10, Exceptional, (506)
"Staff was very friendly. We had a very relaxing stay. "
Vandiver Inn

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 NT$3,881
NT$4,308 total
includes taxes & fees
Jul 27 - Jul 28
The Lodge at Great Oak Landing

Comfort Inn & Suites Chestertown

2.5 star property
8.6 out of 10, Excellent, (787)
"It was a clean comfortable spot to rest for the night. "
The price is NT$3,358
NT$3,727 total
includes taxes & fees
Aug 17 - Aug 18
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 NT$2,244
NT$2,491 total
includes taxes & fees
Aug 3 - Aug 4
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 NT$1,863
NT$2,068 total
includes taxes & fees
Jul 30 - Jul 31
Driftwood Inn

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 NT$3,726
NT$4,136 total
includes taxes & fees
Jul 31 - Aug 1
Holiday Inn Express Annapolis East-Kent Island by IHG

The Inn at Chesapeake Bay Beach Club

4.0 star property
9.4 out of 10, Exceptional, (403)
"Staff was very polite and friendly. "
The price is NT$6,014
NT$7,422 total
includes taxes & fees
Aug 24 - Aug 25
The Inn at Chesapeake Bay Beach Club

Motel Edgewood

2.0 star property
8.0 out of 10, Very Good, (4)
The price is NT$1,716
NT$1,922 total
includes taxes & fees
Aug 3 - Aug 4
Motel Edgewood

Fairfield Inn & Suites by Marriott Middletown

2.5 star property
9.2 out of 10, Wonderful, (255)
"Nice place to stay"
The price is NT$3,374
NT$3,745 total
includes taxes & fees
Aug 4 - Aug 5
Fairfield Inn & Suites by Marriott Middletown

Country Inn & Suites by Radisson, Bel Air/Aberdeen, MD

3.0 star property
8.8 out of 10, Excellent, (1002)
"This hotel was very convenient and comfortable. The breakfast was very good. I would definitely stay here again,"
The price is NT$2,910
NT$3,259 total
includes taxes & fees
Jul 27 - Jul 28
Country Inn & Suites by Radisson, Bel Air/Aberdeen, MD

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

Relax Inn Smyrna

2.0 star property
7.8 out of 10, Good, (84)
"Owner was very nice. "
The price is NT$2,350
NT$2,614 total
includes taxes & fees
Aug 4 - Aug 5
Relax Inn Smyrna

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 NT$2,873
NT$3,189 total
includes taxes & fees
Aug 24 - Aug 25
Quality Inn

Holiday Inn Express And Suites Middletown by IHG

2.5 star property
9.2 out of 10, Wonderful, (595)
"Easy to navigate and nice, helpful staff "
The price is NT$3,403
NT$3,777 total
includes taxes & fees
Aug 17 - Aug 18
Holiday Inn Express And Suites Middletown 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 NT$3,696
NT$4,102 total
includes taxes & fees
Aug 10 - Aug 11
Best Western Kent Narrows Inn

La Quinta Inn & Suites by Wyndham Bel Air/I-95 Exit 77A

3.0 star property
8.2 out of 10, Very Good, (1008)
"Great stay, would do it again. "
The price is NT$2,200
NT$2,464 total
includes taxes & fees
Jul 27 - Jul 28
La Quinta Inn & Suites by Wyndham Bel Air/I-95 Exit 77A

SpringHill Suites Baltimore White Marsh/Middle River

2.5 star property
9.0 out of 10, Wonderful, (710)
"Great stay"
The price is NT$3,595
NT$4,152 total
includes taxes & fees
Aug 17 - Aug 18
SpringHill Suites Baltimore White Marsh/Middle River

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 NT$2,934
NT$3,256 total
includes taxes & fees
Aug 3 - Aug 4
Quality Inn
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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Stay near popular Chestertown attractions

Learn more about Chestertown

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

Somewhere over the rainbow... Terrific view on the plane back to the North.
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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 favorite 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 trip. 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, most hotel bookings are fully refundable as long as you cancel before the hotel’s cancellation deadline, which often is within 24-48 hours of your scheduled arrival. If your reservation is non-refundable, 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.

Where can I learn more about changing or cancelling my trip to Chestertown?

For more details about rescheduling or cancelling your trip to Chestertown, click here.

What's the best place to stay on a budget in Chestertown?

Based on reviews, Red Roof Inn & Suites Chestertown is a popular 2-star hotel for our travelers 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 hotel for families 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 kid-friendly vacation. Kids of all ages will also enjoy a visit to Crumpton Auction. Find more child-friendly accommodations in Chestertown.

What's the best accommodation for a romantic vacation to Chestertown?

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

What's the best LGBTQ-friendly accommodation 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 other good options for your trip. See all available hotels listed as LGBTQ-friendly in Chestertown.

What's the best pet-friendly hotel in Chestertown?

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

Where is the best hotel to stay near Washington College?

Adjacent to Washington College, Driftwood Inn is one of the top choices for your stay based on our traveler data, and this property offers free parking and free WiFi. Other good options close by include Comfort Inn & Suites Chestertown and Red Roof Inn & Suites Chestertown.

What about the best place to stay near Rolphs Wharf Marina?

One of the top choices for your stay is Comfort Inn & Suites Chestertown, located 4.1 mi (6.6 km) from Rolphs Wharf Marina, and this hotel offers free breakfast and free parking. Driftwood Inn and Red Roof Inn & Suites Chestertown are two other good options within a few miles.

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 place to stay in Chestertown to absorb the 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 accommodations with pools in Chestertown?

The Lodge at Great Oak Landing is a top lodge with a seasonal outdoor pool, 3 bars, 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 center. See all spa hotels in Chestertown.

What's the best hotel for staying near Salisbury - Ocean City Wicomico Regional Airport (SBY)?

Country Inn & Suites by Radisson, Salisbury, MD is one of the top choices for your stay and is a popular 3-star hotel featuring free breakfast and an indoor pool. It's located 2.2 mi (3.6 km) from Salisbury - Ocean City Wicomico Regional Airport. Other options close to the airport include Microtel Inn & Suites by Wyndham Salisbury and Sleep Inn Salisbury.

How is it to stay in Chestertown?

Visitors to Chestertown are sure to enjoy the university setting. Tourists can also enjoy the city's sporting events, festivals, and art. In Chestertown, there are 44 hotels and other accommodations to choose from. Find out more about Chestertown.

What are the top places to visit 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 agenda are Rolphs Wharf Marina and Chestertown Historic District. Check out what more 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 temp of 74°F, while the coldest months are January and February with an average of 39°F. Average annual precipitation for Chestertown is 48 inches.