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Chestertown Hotels

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Top 10 trending Chestertown hotels

Inn at Haven Harbour

3.0 star property
The price is P12,010
P14,478 total
includes taxes & fees
Aug 12 - Aug 13
Inn at Haven Harbour

Hampton Inn & Suites Edgewood/Aberdeen-South

2.5 star property
9.2 out of 10, Wonderful, (1001)
"Great stay at a great price "
The price is P5,340
P5,981 total
includes taxes & fees
Aug 6 - Aug 7
Hampton Inn & Suites Edgewood/Aberdeen-South

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 P6,317
P7,011 total
includes taxes & fees
Aug 10 - Aug 11
Comfort Inn & Suites Chestertown

Motel Edgewood

2.0 star property
8.4 out of 10, Very Good, (6)
"Bed was clean and crisply made. Occupants were respectful of sleeping hours. Check-in and check-out were simple. Parking was convenient and had easy access to the highway."
The price is P3,369
P3,773 total
includes taxes & fees
Aug 3 - Aug 4
Motel Edgewood

The Lodge at Great Oak Landing

3.5 star property
8.0 out of 10, Very Good, (57)
"Great place to get some quiet rest by the water"
The price is P7,619
P8,457 total
includes taxes & fees
Aug 3 - Aug 4
The Lodge at Great Oak Landing

Red Roof Inn & Suites Chestertown

2.0 star property
7.2 out of 10, Good, (383)
"Good location."
The price is P4,146
P4,602 total
includes taxes & fees
Aug 12 - Aug 13
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 P3,642
P4,042 total
includes taxes & fees
Aug 3 - Aug 4
Driftwood Inn

Quality Inn

2.5 star property
7.6 out of 10, Good, (1000)
"It was a nice stay, very convenient to where I needed to be."
The price is P5,759
P6,392 total
includes taxes & fees
Aug 4 - Aug 5
Quality Inn

Quality Inn

2.5 star property
7.8 out of 10, Good, (796)
"Conveniently located with overall great value."
The price is P5,791
P6,428 total
includes taxes & fees
Aug 10 - Aug 11
Quality Inn

Holiday Inn Express And Suites Middletown by IHG

2.5 star property
9.2 out of 10, Wonderful, (598)
"Easy to navigate and nice, helpful staff "
The price is P6,680
P7,415 total
includes taxes & fees
Aug 10 - Aug 11
Holiday Inn Express And Suites Middletown by IHG

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 P8,903
P9,883 total
includes taxes & fees
Aug 12 - Aug 13
Mariners Motel

Fairfield Inn & Suites by Marriott Middletown

2.5 star property
9.2 out of 10, Wonderful, (255)
"Nice place to stay"
The price is P6,450
P7,159 total
includes taxes & fees
Aug 10 - Aug 11
Fairfield Inn & Suites by Marriott Middletown

Relax Inn Smyrna

2.0 star property
7.8 out of 10, Good, (84)
"Owner was very nice. "
The price is P4,613
P5,131 total
includes taxes & fees
Aug 4 - Aug 5
Relax Inn Smyrna

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

Holiday Inn Express Annapolis East-Kent Island by IHG

2.5 star property
9.2 out of 10, Wonderful, (878)
"Great stay beautiful view"
The price is P8,235
P9,140 total
includes taxes & fees
Aug 17 - Aug 18
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, (1001)
"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 P5,769
P6,403 total
includes taxes & fees
Aug 7 - Aug 8
Best Western Kent Narrows Inn

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

TownePlace Suites by Marriott Edgewood Aberdeen

3.0 star property
9.0 out of 10, Wonderful, (76)
"3 hotels in past week… this by far exceeds the others… it was such a nice experience after the others. def. would recommend and plan on staying here again. "
The price is P6,162
P6,901 total
includes taxes & fees
Aug 18 - Aug 19
TownePlace Suites by Marriott Edgewood Aberdeen

Holiday Inn Express White Marsh by IHG

2.5 star property
9.6 out of 10, Exceptional, (902)
"Loved it! I would totally stay there again."
The price is P6,392
P7,383 total
includes taxes & fees
Aug 31 - Sep 1
Holiday Inn Express White Marsh by IHG

The Inn at Chesapeake Bay Beach Club

4.0 star property
9.4 out of 10, Exceptional, (404)
"Staff was very polite and friendly. "
The price is P11,805
P14,568 total
includes taxes & fees
Aug 24 - Aug 25
The Inn at Chesapeake Bay Beach Club
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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Near an Attraction

Sumner Hall

Sumner Hall

You can spend time studying the exhibits at Sumner Hall in Chestertown. Experience the area's festivals and art scene.

Learn more about Chestertown

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

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Open Photo by Assya A

Best guest reviews of Chestertown

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. Red Roof Inn & Suites Chestertown and The Lodge at Great Oak Landing 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.

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 43 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.