Book hotels in Chestertown online

We found 27 hotels from 132 sites

Star rating
Review Score
$64 — $106
Driftwood Inn
Driftwood Inn
5.4
pleasant,
87 reviews
609 Washington Avenue, Chestertown, MD 21620, United States of America
Comfort Inn & Suites Chestertown
Comfort Inn & Suites Chestertown
7.7
good,
229 reviews
150 Scheeler Road, Chestertown, 21620, United States of America
Brampton Bed and Breakfast Inn
Brampton Bed and Breakfast Inn
0
pleasant,
0 reviews
25227 Chestertown Road, Chestertown, MD 21620, United States of America, Chestertown
John L Stam House
John L Stam House
0
pleasant,
0 reviews
114 Washington Ave, Chestertown, MD 21620, USA, Chestertown
Comfort Suites
Comfort Suites
0
pleasant,
0 reviews
160 Scheeler Rd. , 21620 Chestertown, Chestertown
The Loft at The Remington
The Loft at The Remington
0
pleasant,
0 reviews
6369 Main Street, Chestertown
Pine Tree Motel & Cabins
Pine Tree Motel & Cabins
0
pleasant,
0 reviews
5537 State Route 8, Chestertown
Conways Lake Manor
Conways Lake Manor
0
pleasant,
0 reviews
5381 State Route 8, Chestertown, NY 12817, United States of America, Chestertown
Wren Retweet
Wren Retweet
0
pleasant,
0 reviews
214 North Mill Street, Chestertown, MD 21620, United States of America
Simply Bed & Bread
Simply Bed & Bread
0
pleasant,
0 reviews
208 Mt Vernon Ave, Chestertown, MD 21620, USA, Chestertown
Lodging at The Imperial
Lodging at The Imperial
0
pleasant,
0 reviews
208 High Street, Chestertown
Widows Walk Inn
Widows Walk Inn
0
pleasant,
0 reviews
402 High Street Chestertown, Chestertown
The White Swan Tavern
The White Swan Tavern
0
pleasant,
0 reviews
231 High Street Chestertown Maryland 21620, Chestertown
Tree Tops Retreat ~ 19 Mi to Lake George!
Tree Tops Retreat ~ 19 Mi to Lake George!
0
pleasant,
0 reviews
45 McPhillips Pine Ln, Chestertown
Home2 Suites by Hilton Baltimore/Aberdeen MD
Home2 Suites by Hilton Baltimore/Aberdeen MD
8
good,
0 reviews
20 Newton Road, Aberdeen, MD 21001, United States of America
Remodeled Abingdon House with Spacious Yard!
Remodeled Abingdon House with Spacious Yard!
0
pleasant,
0 reviews
Abingdon, 21009, United States of America
Bay Side Inn & Suites
Bay Side Inn & Suites
5.7
pleasant,
0 reviews
424 S Philadelphia Blvd, Aberdeen, MD 21001, United States of America
Super 8 by Wyndham Aberdeen MD
Super 8 by Wyndham Aberdeen MD
6.1
pleasant,
0 reviews
1008 Beards Hill Road, Aberdeen, MD 21001, United States of America
La Quinta by Wyndham Aberdeen-APG
La Quinta by Wyndham Aberdeen-APG
8.5
very good,
511 reviews
793 West Bel Air Avenue , Aberdeen, MD 21001, United States of America
Hampton Inn & Suites By Hilton Baltimore/Aberdeen, Md
Hampton Inn & Suites By Hilton Baltimore/Aberdeen, Md
8.7
very good,
161 reviews
795 West Bel Air Avenue , Aberdeen, MD 21001, United States of America
Comfort Inn & Suites Aberdeen
Comfort Inn & Suites Aberdeen
8
good,
0 reviews
980 Hospitality Way, Aberdeen, 21001, United States of America
Days Inn by Wyndham Aberdeen
Days Inn by Wyndham Aberdeen
7
pleasant,
657 reviews
783 West Belair Avenue, Aberdeen, MD 21001, United States of America
Hilton Garden Inn Aberdeen
Hilton Garden Inn Aberdeen
8
good,
86 reviews
1050 Beards Hill Road, Aberdeen, MD 21001, United States of America
Red Roof Inn Aberdeen
Red Roof Inn Aberdeen
5.7
pleasant,
425 reviews
988 Hospitality Way, Aberdeen, MD 21001, United States of America
Travelodge by Wyndham Aberdeen
Travelodge by Wyndham Aberdeen
5.9
pleasant,
283 reviews
820 West Bel Air Avenue, Aberdeen, MD 21001, United States of America
Holiday Inn Express Aberdeen-Chesapeake House, an IHG Hotel
Holiday Inn Express Aberdeen-Chesapeake House, an IHG Hotel
8.3
very good,
0 reviews
1007 Beards Hill Road, Aberdeen, MD 21001, United States of America
Fairfield by Marriott Inn & Suites Aberdeen
Fairfield by Marriott Inn & Suites Aberdeen
8.9
very good,
103 reviews
907 Barnett Lane, Aberdeen, 21001, United States of America

A total of 27 hotels found in Chestertown. Select the perfect accommodation for your stay and enjoy a seamless booking experience. Booking Chestertown hotels online has never been easier.


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Frequently asked questions

If you are planning to book hotel accommodation in Chestertown and are looking for the ultimate in comfort, Sagamore Pendry Baltimore, Four Seasons Baltimore, and Ulysses, an Ash Hotel are among the top choices. These luxury options provide impeccable service, spacious rooms, and upscale amenities such as fine dining, spas, and stunning waterfront views. If you’re searching online for where to book hotels in Chestertown, these choices frequently appear at the top of every trusted website to book hotels.
Yes, many hotels in Chestertown, United States of America, offer free Wi-Fi as a standard amenity. For example, 134 Prince - Luxury Boutique Hotel, Brampton 1860, Roost Baltimore, The Study at Johns Hopkins, and others make it easy to stay connected during your trip. As a frequent traveler, I recommend checking online platforms when you book hotels online in Chestertown to ensure free Wi-Fi is included along with other amenities such as complimentary parking or airport shuttle services. Using the cheapest website to book hotels can help you compare and filter these features.
Absolutely! Chestertown is very welcoming to travelers with pets and offers around 70 pet-friendly hotels, including Roost Baltimore, The Study at Johns Hopkins, Graduate by Hilton Annapolis, Sagamore Pendry Baltimore, and Four Seasons Baltimore. When using an online website to book hotels in Chestertown, make sure to apply the pet-friendly filter to find the perfect match for you and your furry companion. For many travelers, the ability to book hotels online in Chestertown with ease and find the cheapest deals for you and your pet is a top priority.
Yes, there are vacation rentals available near Chestertown. One of the best options is Wren Retweet, ideal for those seeking a home-like experience with easy access to nature and outdoor activities. If you’re unsure where to book hotels or vacation rentals in Chestertown, many online platforms allow you to compare hotels and rentals side by side. For those looking for both flexibility and the cheapest rates, websites to book hotels in Chestertown often include vacation rental listings alongside hotel options.
There are 43 hotels in Chestertown with on-site dining facilities for guests who prefer convenience and excellent cuisine. Top picks include Roost Baltimore, The Study at Johns Hopkins, Capital Hotel Annapolis, Graduate by Hilton Annapolis, Sagamore Pendry Baltimore, Four Seasons Baltimore, and Hotel Revival Baltimore. When you book hotels online in Chestertown using an online platform, filter for amenities such as on-site dining to enhance your stay. This is particularly useful if you want to find the cheapest deals on hotels with premium facilities in Chestertown.

Choose the right hotel in Chestertown

How to Book Hotels Online in Chestertown: A Traveler’s Guide Chestertown, located in the United States of America, is a charming destination with colonial history, scenic waterfronts, and welcoming local culture. When looking to book hotels online in Chestertown, it’s important to factor in not only the price but also the amenities and location that will make your trip more enjoyable. As a tourist, my key advice is to start your search on the top website to book hotels in Chestertown that provides plenty of filtering options. These sites let you compare rates, check for the cheapest deals, and see real guest reviews for each hotel. Some features to prioritize when booking hotels online in Chestertown: - Free Wi-Fi: Most modern travelers need reliable internet; hotels such as the Four Seasons Baltimore, Ulysses, an Ash Hotel, and Sagamore Pendry Baltimore are excellent choices. - Pet-friendly options: Traveling with pets? Select from hotels like Roost Baltimore or The Study at Johns Hopkins, which welcome your furry friends. - On-site dining: Eliminate the need to search for restaurants late at night by choosing from 43 hotels in Chestertown with on-site dining, including Capital Hotel Annapolis and Hotel Revival Baltimore. - Free parking and cancellation: Convenience and flexibility are essential; many local hotels provide these features. - Vacation rentals: For a quieter experience, the Wren Retweet rental lets you enjoy outdoor activities and the region's natural beauty outside the city. When using online platforms, don’t forget to: 1. Check several websites to compare where to book hotels for the best offers and policies. 2. Consider the hotel’s proximity to historic attractions like the Chester River, colonial-era architecture, or local markets for a more immersive experience. 3. Always read the hotel’s most recent reviews and ratings before completing your booking. Choosing the Cheapest and Best Website to Book Hotels in Chestertown For those on a tighter budget or seeking the best value, Chestertown offers a range of options to help you find the cheapest rates without compromising on comfort. The key is to use a reputable online platform—your go-to website to book hotels in Chestertown should have clear policies and a robust customer support team, especially if you are booking from abroad and using US dollars as your travel currency. Whether you’re planning a family holiday, a solo business trip, or a romantic getaway, Chestertown’s hospitality scene can cater to all needs—ranging from upscale, luxury properties to more affordable, practical stays. To make the process smooth, use this checklist: - Start your search in advance and keep an eye out for seasonal discounts or package deals. - Filter specifically by free amenities (Wi-Fi, parking, shuttle service) to trim extra costs. - Compare the cheapest available room across several sites for the exact same hotel before booking. - Confirm the hotel’s flexibility with cancellations or changes, in case your travel plans shift. When booking online for your Chestertown stay, remember to: 1. Check if the hotel you’re considering is included in lists of the best luxury or pet-friendly hotels, such as Sagamore Pendry Baltimore or Graduate by Hilton Annapolis. 2. Make sure the hotel’s location aligns with your sightseeing agenda, like being close to the city’s colonial downtown or riverside. 3. Take advantage of on-site dining whenever possible; it saves both time and additional expenses, allowing you to focus more on experiencing the city’s charm and hospitality. A thoughtful approach to book hotels online in Chestertown ensures that you enjoy the best of this historic American town’s warmth, heritage, and local flavor.

Chestertown hotels information

Number of reviews339
Accommodation4 hotels

Cheapest hotels in Chestertown

Searching for the cheapest hotels in Chestertown, United States of America? I always recommend travelers compare options on several sites to find where to book hotels at the lowest rates. Chestertown offers a surprising range of budget accommodations; booking in advance increases your chances to secure the best deals. If you are unsure about the website to book cheapest hotels, try verified platforms like Booking.com or Hostelworld. As a frequent visitor to Chestertown, my tip is to check reviews and flexible cancellation options—sometimes prices drop closer to your stay! Using incognito mode when searching can reveal cheaper prices. For travelers who want to save more, look for cheapest hotels just outside the city center and use local transport.

Find hotels in different neighborhoods of Chestertown

When you book hotels in Chestertown, it’s important to consider the distinct characteristics of each district. Downtown Chestertown offers charming boutique options close to historic landmarks and the scenic Chester River, perfect if you want to experience authentic local vibes. If you prefer a quieter scene, try booking hotels in the outskirts, where you can enjoy peaceful surroundings and easy access to nature trails. A local tip: book hotels online in Chestertown well in advance during college events or festivals, as rooms can fill quickly. For convenience, use an official website to book hotels in Chestertown, which often has exclusive rates and detailed descriptions of each neighborhood’s atmosphere and amenities, making your selection easier.

Popular attractions in Chestertown

Chestertown, United States of America, is famous for its historic charm and vibrant cultural scene. Explore the beautiful Washington College campus and take a stroll along the scenic Chester River. The historic district is perfect for those seeking authentic architecture and unique shops. For art lovers, the RiverArts Gallery is a must-see. Curious where to book hotels in Chestertown? Consider staying near High Street to enjoy easy access to local cafes and boutiques. Don’t miss the Chestertown Farmers’ Market and the yearly Tea Party Festival for a true local experience.