Top 24 Hotels In Chester, Maryland 21619

Guests traveling to Chester will appreciate the cozy-like accommodations at Best Western Kent Narrows Inn, with rooms starting at $97.99, creating a welcoming atmosphere. Experience the coziness of Best Western’s fireside seating areas, perfect for chilly evenings or casual conversations.

With downtown Chester only a short drive from Best Western Kent Narrows Inn, guests can enjoy the city’s top destinations while returning to a quieter stay. Take advantage of Chester travel with lodging that delivers exceptional value—book today!

At Holiday Inn Express Annapolis Kent Island an IHG Hotel, travelers visiting Chester can enjoy homely accommodations with rooms from $139.00, creating a warm, inviting space perfect for relaxation. Relax with the premium television channels available in every room, perfect for unwinding after a busy day.

With downtown Chester only a short drive away, guests at Holiday Inn Express Annapolis Kent Island an IHG Hotel can explore the city’s top attractions while enjoying a quieter stay. Experience Chester worry-free with a hotel that offers everything you need—book today!

Unwind at Hilton Garden Inn Kent Island Marina as you travel to Chester, where quality accommodations provide warmth and relaxation, with starting rates beginning at $127.99 per night. Wake up to a freshly prepared breakfast at Hilton Garden Inn, with a range of cooked-to-order dishes designed to start your day right.

With a brief drive into downtown Chester, guests at Hilton Garden Inn Kent Island Marina can explore the city’s best destinations while staying in a quieter, more peaceful area. Find the ideal place to rest in Chester with accommodations that are both stylish and practical—secure now!

Unwind in the peaceful ambiance of Kent Island Resort as you visit Chester, where relaxing accommodations provide comfort, with nightly rates starting at $161.99. Experience a stay that offers more than comfort, with rooms that provide luxurious amenities and elegant surroundings.

Guests staying at Kent Island Resort are only a short drive from downtown Chester, where they can easily explore the city’s most exciting sights. Stay in Chester with a hotel that brings elegance and convenience to your travels—book today!

Experience elegance and comfort at The Inn at Chesapeake Bay Beach Club as you explore Chester, where refined rooms create a relaxing stay, with rates beginning at just $289.99. Experience a new level of opulence in rooms that combine luxury with cutting-edge technology for a truly unique stay.

Guests staying at The Inn at Chesapeake Bay Beach Club will love the convenience of being close to downtown Chester, where a brief drive takes them to the city’s best destinations. Discover how exquisite Chester can be with accommodations that redefine elegance—secure now!

Guests visiting Chester will appreciate the inviting comfort at Quality Inn, with budget-friendly rooms starting at $98.99, creating a clean, welcoming space. Relax with a book from Quality Inn's lending library, featuring a selection of popular novels and local travel guides.

At Quality Inn, a brief drive takes guests into downtown Chester, where the city’s top destinations are easily accessible. Make Chester travel a breeze with a hotel that blends comfort and savings—secure now!

With rooms starting at $75.99, Village Inn offers budget-friendly comfort for travelers visiting Chester, creating a relaxed environment ideal for unwinding. Find comfort and convenience in rooms that deliver essential amenities, perfect for travelers looking for reliability and value.

For a restful stay, Village Inn offers serene surroundings with downtown Chester still close enough for easy access. Plan your Chester trip with savings and extra comfort—reserve your room now!

Experience the serene elegance of Annapolis Waterfront Hotel Autograph Collection near Chester, where quality rooms create a relaxing escape, with budget-friendly nightly rates starting at $399.99. Relish in the personalized attention and bespoke services that are the hallmark of the Autograph Collection's hospitality.

Unwind at Annapolis Waterfront Hotel Autograph Collection, where the calm atmosphere is complemented by easy access to downtown Chester for a day of adventure. Choose a hotel in Chester that creates a travel experience you’ll never forget—book today!

With a welcoming environment, Historic Inns of Annapolis near Chester provides comfortable rooms designed for relaxation, with budget-friendly rates starting at $185.00. Experience a superior level of comfort in rooms that offer luxurious amenities and attentive service, catering to all your needs.

For a quiet stay, Historic Inns of Annapolis offers serene surroundings with the convenience of downtown Chester still a short drive away. Step into a world of comfort and elegance in Chester with a hotel that goes above and beyond—secure now!

With a blend of elegance and charm, Graduate by Hilton Annapolis near Chester provides quality accommodations, with budget-friendly nightly rates beginning at $204.99. Take advantage of Hilton's state-of-the-art fitness centers, equipped to support your wellness journey while away from home.

Guests staying at Graduate by Hilton Annapolis will love the calm environment, with downtown Chester still within reach for easy sightseeing and adventure. Find out how Chester becomes extraordinary with accommodations that make relaxation effortless—lock in today!

Stay at Hilton Garden Inn Annapolis Downtown when visiting Chester, where secure accommodations offer a welcoming experience, with nightly rates starting at an accessible $141.99. Unwind at the end of the day with Hilton Garden Inn's in-room entertainment options, including HDTVs and premium channels.

Travelers seeking both peace and proximity will find Hilton Garden Inn Annapolis Downtown ideal, with downtown Chester still within reach for exploration. Discover how Chester can be a breeze with a hotel that offers exceptional amenities—secure now!

Unwind in opulent surroundings at The Westin Annapolis near Chester, where plush accommodations invite you to relax in comfort, with budget-friendly rates starting at $199.99. Venture on Westin’s architectural tours, highlighting the design and historical significance of the hotel and its surroundings.

A calm retreat awaits at The Westin Annapolis, where guests can rest and still reach downtown Chester with ease. Choose a hotel in Chester that turns your stay into an experience you’ll never forget—book today!

Enjoy a peaceful stay at Residence Inn by Marriott Annapolis on your journey to Chester, where inviting rooms provide comfort, with affordable rates beginning at $179.99 per night. Enjoy a worry-free stay with Residence Inn's comprehensive safety protocols, including regular sanitization and health checks.

Travelers seeking a peaceful getaway will love Residence Inn by Marriott Annapolis, with its serene surroundings and easy access to downtown Chester. Step into your Chester adventure with a hotel that prioritizes comfort and convenience—reserve now!

Fairfield Inn & Suites by Marriott Annapolis offers travelers to Chester a cozy-like option, with quality accommodations designed for relaxation, with rates starting from just $185.99 per night. Discover Fairfield's convenient locations, ideally situated near highways, airports, and popular attractions for easy travel.

Enjoy a restful stay at Fairfield Inn & Suites by Marriott Annapolis, where peaceful surroundings meet easy access to downtown Chester for exploration. Take your Chester experience to new heights with exceptional amenities and great rates—reserve now!

Immerse yourself in the splendor of Inn at Perry Cabin near Chester, where unparalleled service and elegance promise an extraordinary stay, with rates from $412.99. Stay in rooms that offer a glimpse into a world of elegance, with antique furniture, museum-quality art, and uninterrupted sea views.

Escape the rush of downtown Chester and retreat to the calm at Inn at Perry Cabin, where tranquility and easy access combine for the perfect stay. Take advantage of Chester splendor with a hotel that delivers top-notch service and comfort—book today!

At Holiday Inn Express & Suites Annapolis an IHG Hotel, travelers bound for Chester will find budget-conscious comfort with rooms starting at $134.00, creating a clean, inviting space for relaxation. Experience the convenience of Holiday Inn Express's grocery delivery service, bringing fresh ingredients right to your room.

Unwind at Holiday Inn Express & Suites Annapolis an IHG Hotel, where peaceful surroundings offer a relaxing stay and downtown Chester remains nearby for city exploration. Make the most of your Chester adventure with accommodations that prioritize savings—lock in now!

Enjoy a peaceful retreat at Crowne Plaza Annapolis an IHG Hotel as you travel to Chester, where inviting rooms offer a warm environment, with rates beginning at $144.00. Relax with Crowne Plaza's aromatherapy kits, part of the Sleep Advantage® program, designed to enhance your rest and relaxation.

For those who want to enjoy both relaxation and city access, Crowne Plaza Annapolis an IHG Hotel provides the perfect blend, with downtown Chester just a drive away. Unwind in Chester with a hotel that makes comfort feel effortlessly elegant—lock in today!

With a refined atmosphere, DoubleTree by Hilton Hotel Annapolis near Chester offers quality accommodations designed for a peaceful stay, with nightly rates from just $120.47. Discover DoubleTree by Hilton's comfortable rooms and suites, designed with thoughtful amenities to make you feel at home.

With downtown Chester a scenic drive away, guests at DoubleTree by Hilton Hotel Annapolis can enjoy the city's top spots while retreating to a quieter, more serene stay. Enjoy your Chester adventure with a hotel that delivers an impeccable guest experience—book today!

With rates starting at $109.99, Best Western Annapolis is ideal for guests bound for Chester, providing charming accommodations in a warm, inviting setting. Indulge in the luxury of Best Western's premier suites, offering upscale amenities and extra space for a superior stay.

Relax in the peaceful surroundings of Best Western Annapolis, with downtown Chester remaining within reach for a day of city adventure. Choose a hotel that takes your Chester experience to the next level—book now!

For a restful and affordable stay, Red Roof Inn Annapolis offers inviting rooms with rates starting at $79.00, creating a enveloping and comfortable space ideal for travelers bound for Chester. Appreciate the accessibility features at Red Roof Inn, ensuring a comfortable stay for guests with disabilities.

The peaceful atmosphere at Red Roof Inn Annapolis offers guests a quiet retreat, with the convenience of downtown Chester still a short drive away. Plan your Chester adventure wisely and lock in a comfortable room now!

Guests headed to Chester can enjoy affordable comfort at Hampton Inn & Suites Annapolis, with rooms starting at $115.99, providing a alluring space perfect for relaxation. Find solace in the quiet of Hampton's soundproof rooms, allowing for a peaceful retreat from the day's activities.

Travelers staying at Hampton Inn & Suites Annapolis will appreciate the calm atmosphere, while downtown Chester is just a convenient drive away. Choose a hotel that complements your Chester plans with ease and affordability—secure now!

Guests traveling to Chester will find harmonious accommodations at St Michaels Inn, where rooms begin at $129.99, creating a warm, inviting environment ideal for relaxation. Relax in rooms that cater to budget-conscious guests, offering a comfortable and clean environment without unnecessary extras.

For a peaceful retreat, St Michaels Inn offers quiet surroundings, with the added convenience of downtown Chester being nearby. Enjoy Chester without financial worries by choosing a budget-savvy hotel—secure now!

Relax in the inviting surroundings of SpringHill Suites by Marriott Annapolis as you visit Chester, where comfortable accommodations provide a peaceful stay, with rates beginning at $134.99. Enjoy a welcoming atmosphere at SpringHill Suites, where every guest is valued and treated with care.

With a relaxing drive into downtown Chester, guests at SpringHill Suites by Marriott Annapolis can explore the city’s best spots before retreating to the peaceful surroundings of their stay. Stay in Chester with a hotel that brings comfort and convenience to your doorstep—secure now!

At Sonesta ES Suites Annapolis, travelers to Chester can unwind in alluring accommodations designed to provide a sense of relaxation, with inviting rates starting at $143.00 per night. Stay active with Sonesta’s fitness centers, equipped with the latest equipment and various fitness classes to keep you in shape.

A quiet retreat at Sonesta ES Suites Annapolis provides rest and relaxation, with downtown Chester easily accessible for a day of adventure. Get the relaxation you deserve during your Chester trip with inviting accommodations—book today!