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Find hotels in Chestertown, MD from SAR 198

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27 Jun - 28 Jun
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Compare 1,081 hotels, room rates, hotel reviews and availability. Most hotels are fully refundable.

Red Roof Inn & Suites Chestertown
Suite, Multiple Beds, Non Smoking | 1 bedroom, desk, laptop workspace, blackout drapes

Red Roof Inn & Suites Chestertown

2.0 star property
  • Pet friendly
  • Parking included
  • Free WiFi
  • Air conditioning
  • Laundry
  • Housekeeping
7.4 out of 10, Good, (368)
  • cleanliness
    Guests can warm up by the lobby fireplace, explore Chestertown's hidden downtown gems, and experience attentive service from the helpful staff.

What verified guests said

"Was a decent place to stay for the price. "

Red Roof Inn & Suites Chestertown highlights

Red Roof Inn & Suites in Chestertown offers a welcoming base with practical amenities like laundry facilities, WiFi, lobby coffee, and extended parking. Guests consistently felt supported by the staff during their stays.
The price is SAR 257
SAR 285 total
includes taxes & fees
6 Jul - 7 Jul
Red Roof Inn & Suites Chestertown
Comfort Inn & Suites Chestertown
Lobby

Comfort Inn & Suites Chestertown

2.5 star property
  • Pool
  • Breakfast included
  • Pet friendly
  • Parking included
  • Free WiFi
  • Air conditioning
8.6 out of 10, Excellent, (773)
  • cleanliness
    Guests start their day with complimentary coffee in the welcoming lobby, energize with a workout, and unwind by the fireplace near River Arts Chestertown.

What verified guests said

"Comfortable room, friendly staff. "

Comfort Inn & Suites Chestertown highlights

Comfort Inn & Suites in Chestertown offers a warm atmosphere with a lobby fireplace and free full breakfast. Enjoy in-room WiFi, gym access, and a business center to stay productive. The attentive staff consistently earns positive reviews from visitors.
The price is SAR 427
SAR 474 total
includes taxes & fees
24 Jul - 25 Jul
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
  • Pool
  • Parking included
  • Free WiFi
  • Restaurant
  • Air conditioning
  • Gym
7.8 out of 10, Good, (52)
  • cleanliness
    Waterfront relaxation awaits with a private beach, 9-hole golf course, and seasonal outdoor pool where travelers can unwind at their own pace

What verified guests said

"not super fancy but really well done. comfy beds and a first rate chef. plus great for the boating crowd"

The Lodge at Great Oak Landing highlights

The Lodge at Great Oak Landing offers a waterfront stay with a private beach and sun loungers. Enjoy golf, summer drinks at the poolside bar, or evening firepit gatherings. Free in-room WiFi, express check-out, and charcoal grills for outdoor cooking are provided.
The price is SAR 496
SAR 551 total
includes taxes & fees
29 Jun - 30 Jun
The Lodge at Great Oak Landing
Driftwood Inn
Lobby

Driftwood Inn

2.0 star property
  • Pet friendly
  • Parking included
  • Free WiFi
  • Air conditioning
  • Housekeeping
  • 24/7 front desk
5.2 out of 10, (171)
  • cleanliness
    Travelers enjoy relaxation with express check-in, convenient self-parking, and 24-hour front desk assistance.

What verified guests said

"Rooms were clean. Check-in was a breeze, and the housekeeping lady is the best left her a nice tip"

Driftwood Inn highlights

Driftwood Inn creates a relaxing atmosphere where guests connect using in-room WiFi. The property streamlines the travel experience with express check-in/check-out services. Self parking adds convenience, while the 24-hour front desk ensures help is always available.
The price is SAR 238
SAR 264 total
includes taxes & fees
28 Jul - 29 Jul
Driftwood Inn
Quality Inn
Free daily self-serve breakfast

Quality Inn

2.5 star property
  • Pool
  • Breakfast included
  • Parking included
  • Free WiFi
  • Air conditioning
  • Gym
7.6 out of 10, Good, (1000)
  • cleanliness
    Travelers start their day with a self-serve breakfast before checking email at the business center or unwinding by the outdoor pool at this comfortable hotel

What verified guests said

"2nd time staying here no major issues "

Quality Inn highlights

Quality Inn offers a practical stay with in-room WiFi, an outdoor pool, and a business center. Laundry facilities and express check-out add convenience. The staff consistently impresses visitors.
The price is SAR 375
SAR 416 total
includes taxes & fees
29 Jun - 30 Jun
Quality Inn
Relax Inn Smyrna
Reception

Relax Inn Smyrna

2.0 star property
  • Parking included
  • Free WiFi
  • Air conditioning
  • 24/7 front desk
7.8 out of 10, Good, (81)
  • cleanliness
    Travelers find a welcoming retreat near Delaware State University where helpful staff and practical amenities create a hassle-free experience for every guest.

What verified guests said

"The owner/staff were so sweet and helpful "

Relax Inn Smyrna highlights

Relax Inn Smyrna, near Delaware State University, offers a refreshing getaway with practical comforts. Guests enjoy in-room WiFi, free self parking, and consistently praise the attentive staff for enhancing their experience.
The price is SAR 334
SAR 371 total
includes taxes & fees
29 Jun - 30 Jun
Relax Inn Smyrna
Hampton Inn Middletown
Reception

Hampton Inn Middletown

2.5 star property
  • Pool
  • Hot Tub
  • Breakfast included
  • Pet friendly
  • Parking included
  • Free WiFi
8.8 out of 10, Excellent, (806)
  • cleanliness
    Travelers find relaxation in the spa tub and convenience at every turn, from smooth check-in to evening drinks, with numerous dining options to explore

What verified guests said

"Good location. Breakfast was great and plenty of parking. "

Hampton Inn Middletown highlights

Hampton Inn Middletown welcomes guests with free breakfast and access to 20 on-site restaurants. The spa tub offers a perfect place to unwind, while the indoor pool provides refreshing exercise. Free WiFi keeps everyone connected throughout their stay.
The price is SAR 490
SAR 544 total
includes taxes & fees
30 Jun - 1 Jul
Hampton Inn Middletown
Holiday Inn Express And Suites Middletown by IHG
Exterior

Holiday Inn Express And Suites Middletown by IHG

2.5 star property
  • Pool
  • Breakfast included
  • Parking included
  • Free WiFi
  • Air conditioning
  • Gym
9.2 out of 10, Wonderful, (586)
  • cleanliness
    Travelers start their day with a complimentary breakfast buffet before unwinding in the indoor pool or energizing in the 24-hour fitness center

What verified guests said

"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. "

Holiday Inn Express And Suites Middletown by IHG highlights

The Holiday Inn Express And Suites Middletown captures the town's charm. Guests enjoy a free breakfast buffet, a 24-hour gym, and an indoor pool. Attentive staff, convenient laundry facilities, and a business center meet practical needs.
The price is SAR 536
SAR 595 total
includes taxes & fees
2 Jul - 3 Jul
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
  • Pool
  • Breakfast included
  • Pet friendly
  • Free WiFi
  • Air conditioning
  • 24/7 front desk
9.2 out of 10, Wonderful, (245)
  • cleanliness
    Travelers enjoy the indoor pool at this Middletown hotel where the friendly staff ensures a memorable stay and electric car owners can recharge their vehicles

What verified guests said

"Clean, friendly staff on checkin and checkout. "

Fairfield Inn & Suites by Marriott Middletown highlights

Fairfield Inn & Suites by Marriott Middletown welcomes guests with an indoor pool and high-speed WiFi in every room. Visitors praise the helpful staff. Amenities include an electric car charging station and 24/7 front desk service.
The price is SAR 499
SAR 554 total
includes taxes & fees
27 Jul - 28 Jul
Fairfield Inn & Suites by Marriott Middletown
Quality Inn
Suite, 1 Queen Bed, Non Smoking | In-room safe, iron/ironing board, free WiFi, bed sheets

Quality Inn

2.5 star property
  • Pool
  • Breakfast included
  • Parking included
  • Free WiFi
  • Air conditioning
  • Business services
7.8 out of 10, Good, (780)
  • cleanliness
    Travelers start their day with a hearty breakfast buffet before relaxing poolside or venturing out to discover the attractions surrounding this welcoming inn

What verified guests said

"Very well run and clean with comfortable beds."

Quality Inn highlights

Quality Inn offers comfortable accommodations near Chesapeake Bay Environmental Center. Guests enjoy a breakfast buffet and in-room WiFi. The seasonal outdoor pool provides a refreshing break, and RV/bus/truck parking ensures easy arrival for all travelers.
The price is SAR 362
SAR 401 total
includes taxes & fees
6 Jul - 7 Jul
Quality Inn
Vandiver Inn
The Stokes (Standard / 2nd Floor Vandiver Mansion) | Terrace/patio

Vandiver Inn

3.5 star property
  • Breakfast included
  • Pet friendly
  • Parking included
  • Free WiFi
  • Air conditioning
  • Business services
9.4 out of 10, Exceptional, (499)
  • cleanliness
    Travelers relax by the crackling fireplace or wander through lovely gardens at this city-center inn before enjoying a freshly prepared breakfast

What verified guests said

"We alway enjoy our stays at the Vandiver"

Vandiver Inn highlights

Located in the heart of the city, Vandiver Inn offers a warm atmosphere. Guests enjoy a cooked-to-order breakfast, in-room WiFi, and can relax by the fireplace or explore the garden. Previous visitors consistently praise the attentive staff.
Vandiver Inn
Super 8 by Wyndham Havre De Grace Aberdeen Area
Standard Room, 2 Queen Beds | In-room safe, desk, soundproofing, rollaway beds

Super 8 by Wyndham Havre De Grace Aberdeen Area

2.0 star property
  • Breakfast included
  • Parking included
  • Free WiFi
  • Air conditioning
  • Housekeeping
  • 24/7 front desk
6.8 out of 10, (912)
  • cleanliness
    Travelers wake up to bay views before enjoying continental breakfast at this welcoming hotel where staff provide assistance at any hour of the day

What verified guests said

"Nice, clean, friendly "

Super 8 by Wyndham Havre De Grace Aberdeen Area highlights

Super 8 by Wyndham Havre De Grace Aberdeen Area offers bay views and starts mornings with continental breakfast. Guests enjoy in-room WiFi and 24-hour front desk assistance. A vending machine provides snacks, and the staff consistently earns praise from previous visitors.
The price is SAR 198
SAR 221 total
includes taxes & fees
7 Jul - 8 Jul
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
  • Pool
  • Pet friendly
  • Parking included
  • Free WiFi
  • Restaurant
  • Air conditioning
9.0 out of 10, Wonderful, (945)
  • cleanliness
    Waterfront relaxation at this Kent Island retreat: shop on site, swim in the indoor pool, or explore nearby attractions.

What verified guests said

"Very nice place to stay. Will definitely stay there again!"

Hilton Garden Inn Kent Island Marina highlights

The Hilton Garden Inn Kent Island sits right on the waterfront, offering a peaceful getaway with convenient on-site shopping and laundry facilities. Guests can relax in the indoor pool, enjoy the views from the terrace, or connect with WiFi in the public areas.
The price is SAR 571
SAR 633 total
includes taxes & fees
6 Jul - 7 Jul
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
  • Pool
  • Breakfast included
  • Pet friendly
  • Parking included
  • Free WiFi
  • Air conditioning
9.2 out of 10, Wonderful, (858)
  • cleanliness
    Lounge by the seasonal outdoor pool or explore Chesapeake Bay's beauty with hiking and biking trails just steps from this comfy retreat.

What verified guests said

"Good location - clean hotel."

Holiday Inn Express Annapolis East-Kent Island by IHG highlights

Holiday Inn Express Annapolis - Kent Island, by Chesapeake Bay, is perfect for outdoor adventures. Guests relax at the seasonal outdoor pool with sun loungers after hiking or biking. The hotel offers free in-room WiFi, laundry facilities, and a business center.
The price is SAR 416
SAR 462 total
includes taxes & fees
13 Jul - 14 Jul
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
  • Pool
  • Hot Tub
  • Breakfast included
  • Pet friendly
  • Parking included
  • Free WiFi
8.2 out of 10, Very Good, (1000)
  • cleanliness
    Travelers find a peaceful urban escape at this hotel, where they can relax in the spa tub after a busy day or maintain their fitness routine at the gym

What verified guests said

"Second time staying, it’s priced right, great staff, and amazing restaurants right across the street, quiet area right by the bay bridge. "

Best Western Kent Narrows Inn highlights

Located in the city center, Best Western Kent Narrows Inn offers a quiet retreat with a garden and sauna. Guests enjoy continental breakfast, relax in the spa tub or indoor pool, and have free WiFi throughout their stay. Previous visitors appreciate the attentive staff.
The price is SAR 411
SAR 456 total
includes taxes & fees
29 Jun - 30 Jun
Best Western Kent Narrows Inn
Hyatt Place Kent Narrows & Marina
Terrace/patio

Hyatt Place Kent Narrows & Marina

3.0 star property
  • Pool
  • Breakfast included
  • Pet friendly
  • Parking included
  • Free WiFi
  • Restaurant
9.4 out of 10, Exceptional, (566)
  • cleanliness
    Travelers start their day with a hearty breakfast before choosing between an energizing workout at the 24-hour gym or relaxation by the indoor pool

What verified guests said

"Great place to stay. "

Hyatt Place Kent Narrows & Marina highlights

Hyatt Place Kent Narrows & Marina, in the historical district, offers a welcoming retreat with a coffee shop and bar. Guests can use the 24-hour gym or relax on sun loungers by the indoor pool. The hotel provides free self parking, laundry facilities, and attentive staff.
The price is SAR 649
SAR 720 total
includes taxes & fees
7 Jul - 8 Jul
Hyatt Place Kent Narrows & Marina
Inn at Huntingfield Creek
Lake

Inn at Huntingfield Creek

3.5 star property
  • Pool
  • Spa
  • Parking included
  • Free WiFi
  • Air conditioning
  • Business services
10.0 out of 10, Exceptional, (50)
  • cleanliness
    Travelers lounge poolside with natural views at this peaceful retreat, where the spa offers rejuvenating treatments amid beautiful garden surroundings

What verified guests said

"Lovely property with wonderful owners and staff, including three very welcoming dogs. We had a perfect weekend getaway."

Inn at Huntingfield Creek highlights

Inn at Huntingfield Creek combines waterfront tranquility with modern comforts. Guests relax in the garden, enjoy massage treatments at the spa, or browse the library for a good book to complete their peaceful getaway.
Inn at Huntingfield Creek
Mariners Motel
Property grounds

Mariners Motel

2.0 star property
  • Pool
  • Pet friendly
  • Parking included
  • Free WiFi
  • Air conditioning
  • Laundry
9.4 out of 10, Exceptional, (89)
  • cleanliness
    Make memories around the firepit or take to the water for some motor boating fun. Enjoy easy access to self parking and amenities that make your stay feel like home.

What verified guests said

"Very nice old school motel just about on the water in Rock Hall. Perfect if you’re in town for marina stuff. "

Mariners Motel highlights

Nestled near Rock Hall Harbor, Mariners Motel offers a warm atmosphere with a firepit and garden. Take advantage of the seasonal pool, motor boating activities, barbecue grills and laundry facilities while staying connected with in-room WiFi.
The price is SAR 582
SAR 646 total
includes taxes & fees
29 Jun - 30 Jun
Mariners Motel
Home2 Suites by Hilton Baltimore / Aberdeen, MD
Exterior

Home2 Suites by Hilton Baltimore / Aberdeen, MD

3.0 star property
  • Pool
  • Breakfast included
  • Pet friendly
  • Parking included
  • Free WiFi
  • Air conditioning
8.6 out of 10, Excellent, (311)
  • cleanliness
    Travelers find a comfortable retreat with warm hospitality and connectivity at this conveniently located hotel just outside Baltimore

What verified guests said

"Friendly and helpful staff!"

Home2 Suites by Hilton Baltimore / Aberdeen, MD highlights

Home2 Suites by Hilton Baltimore/Aberdeen offers comfort with practical amenities. Start your day with a hearty breakfast, work out in the 24-hour gym, or swim in the indoor pool. Enjoy free WiFi and laundry facilities. Attentive staff are always ready to help.
The price is SAR 424
SAR 475 total
includes taxes & fees
28 Jul - 29 Jul
Home2 Suites by Hilton Baltimore / Aberdeen, MD
Super 8 by Wyndham Aberdeen MD
Exterior

Super 8 by Wyndham Aberdeen MD

2.0 star property
  • Breakfast included
  • Pet friendly
  • Parking included
  • Free WiFi
  • Air conditioning
  • Housekeeping
6.8 out of 10, (809)
  • cleanliness
    Convenience awaits at this shopping district motel where travelers can fuel up for the day with a to-go breakfast before heading out to explore Aberdeen

What verified guests said

"Staff is great & rooms always good "

Super 8 by Wyndham Aberdeen MD highlights

Located in Aberdeen's shopping district, Super 8 by Wyndham offers practical comforts. Guests start their day with a to-go breakfast, enjoy in-room WiFi, and rely on the 24-hour front desk. Vending machines provide quick snack options throughout the stay.
The price is SAR 210
SAR 236 total
includes taxes & fees
7 Jul - 8 Jul
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
Somewhere over the rainbow... Terrific view on the plane back to the North.
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.

What are some of the best vacation rentals that Chestertown has to offer?

Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably: This vacation home rental outside of Chestertown offers a balcony, a garden, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. It has 6 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. See all 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 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 LGBTQ-friendly accommodation 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 other good options for your trip.

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 fitness center and laundry facilities 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 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'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 41 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.