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Chestertown Hotels

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Jul 3 - Jul 4
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Jul 4 - Jul 5
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Jul 4 - Jul 6
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Jul 11 - Jul 13

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Top 10 trending Chestertown hotels

Red Roof Inn & Suites Chestertown
1 bedroom, desk, laptop workspace, blackout drapes

Red Roof Inn & Suites Chestertown

2.0 star property
7.4 out of 10, Good, (370)
"Was a decent place to stay for the price. "
The price is P3,853
P4,277 total
includes taxes & fees
Jul 9 - Jul 10
Red Roof Inn & Suites Chestertown
Comfort Inn & Suites Chestertown
Lobby

Comfort Inn & Suites Chestertown

2.5 star property
8.6 out of 10, Excellent, (775)
"Comfortable room, friendly staff. "
The price is P6,318
P7,013 total
includes taxes & fees
Aug 3 - Aug 4
Comfort 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 P7,453
P8,273 total
includes taxes & fees
Jul 8 - Jul 9
The Lodge at Great Oak Landing
Driftwood Inn
Lobby

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 P3,577
P3,971 total
includes taxes & fees
Jul 14 - Jul 15
Driftwood Inn
Quality Inn
Property amenity

Quality Inn

2.5 star property
7.6 out of 10, Good, (1000)
"2nd time staying here no major issues "
The price is P5,638
P6,258 total
includes taxes & fees
Jul 7 - Jul 8
Quality Inn
Relax Inn Smyrna
1 bedroom, premium bedding, down comforters, individually furnished

Relax Inn Smyrna

2.0 star property
7.8 out of 10, Good, (81)
"The owner/staff were so sweet and helpful "
The price is P5,582
P6,209 total
includes taxes & fees
Jul 14 - Jul 15
Relax Inn Smyrna
Hampton Inn Middletown
Indoor pool

Hampton Inn Middletown

2.5 star property
8.8 out of 10, Excellent, (809)
"Front desk service was exceptional!!"
The price is P6,709
P7,447 total
includes taxes & fees
Aug 3 - Aug 4
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, (586)
"I would like to share, the staff at the hotel was very pleasant, it felt like a home away from home, and I also enjoyed the breakfast that was offered. "
The price is P7,831
P8,692 total
includes taxes & fees
Jul 6 - Jul 7
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, (247)
"Nice place to stay"
The price is P7,493
P8,317 total
includes taxes & fees
Jul 27 - Jul 28
Fairfield Inn & Suites by Marriott Middletown
Quality Inn
In-room safe, iron/ironing board, free WiFi, bed sheets

Quality Inn

2.5 star property
7.8 out of 10, Good, (782)
"full breakfast, comfortable bed and nice pillows"
The price is P5,456
P6,056 total
includes taxes & fees
Aug 3 - Aug 4
Quality Inn
Vandiver Inn
Terrace/patio

Vandiver Inn

3.5 star property
9.4 out of 10, Exceptional, (500)
"The staff is amazing! Helpful. Friendly. "
Vandiver Inn
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, (914)
"Nice, clean, friendly "
The price is P2,969
P3,325 total
includes taxes & fees
Jul 16 - Jul 17
Super 8 by Wyndham Havre De Grace Aberdeen Area
Hilton Garden Inn Kent Island Marina
Terrace/patio

Hilton Garden Inn Kent Island Marina

3.0 star property
9.0 out of 10, Wonderful, (950)
"Great stay. We have stayed multiple times throughout the years and the quality has always been excellent."
The price is P8,576
P9,519 total
includes taxes & fees
Jul 20 - Jul 21
Hilton Garden Inn Kent Island Marina
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, (864)
"Good location - clean hotel."
The price is P6,704
P7,442 total
includes taxes & fees
Jul 21 - Jul 22
Holiday Inn Express Annapolis East-Kent Island by IHG
Best Western Kent Narrows Inn
In-room safe, individually decorated, individually furnished, desk

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 P7,122
P7,906 total
includes taxes & fees
Jul 24 - Jul 25
Best Western Kent Narrows Inn
Hyatt Place Kent Narrows & Marina
Terrace/patio

Hyatt Place Kent Narrows & Marina

3.0 star property
9.4 out of 10, Exceptional, (571)
"Great place to stay. "
The price is P11,211
P12,444 total
includes taxes & fees
Jul 8 - Jul 9
Hyatt Place Kent Narrows & Marina
Inn at Huntingfield Creek
Lake

Inn at Huntingfield Creek

3.5 star property
10.0 out of 10, Exceptional, (51)
"A quiet and relaxing stay on a beautiful property! We were met by 2 lovely and extremely well mannered labs. The chocolate lab even joined us on a walk to the dock. We stayed in a cabin and spent time on our deck listening to the birds. My Merlin Bird ID app picked up 30 different bird species! The pool was refreshing and we took advantage of that on 2 hot days. Breakfast was delicious and plentiful. We just wish our trip had been longer. "
Inn at Huntingfield Creek
Mariners Motel
Outdoor pool

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 P8,746
P9,709 total
includes taxes & fees
Jul 15 - Jul 16
Mariners Motel
Home2 Suites by Hilton Baltimore / Aberdeen, MD
Exterior

Home2 Suites by Hilton Baltimore / Aberdeen, MD

3.0 star property
8.6 out of 10, Excellent, (311)
"Friendly and helpful staff!"
The price is P6,326
P7,085 total
includes taxes & fees
Jul 28 - Jul 29
Home2 Suites by Hilton Baltimore / Aberdeen, MD
Super 8 by Wyndham Aberdeen MD
Exterior

Super 8 by Wyndham Aberdeen MD

2.0 star property
6.8 out of 10, (812)
"Staff is great & rooms always good "
The price is P3,161
P3,540 total
includes taxes & fees
Jul 14 - Jul 15
Super 8 by Wyndham 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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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 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.

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 40 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.