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Chester vacation rentals

We found 215 vacation rentals — enter your dates for availability

Immerse yourself in Chester's enchanting atmosphere, where picturesque landscapes and inviting vibes create the perfect backdrop for your next getaway. This charming destination offers a wealth of outdoor adventures, family-friendly attractions, and rich cultural experiences, all within close proximity to stunning spots like the Chesapeake Bay Bridge and Sandy Point State Park. With diverse accommodations ranging from cozy cottages to modern apartments, you'll find comfort and convenience, ensuring a memorable home-like experience for your group.

Holiday rentals with weekly discounts - Chester

Showing deals for:Jan 8 - Jan 15

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Interior
10 out of 10, Exceptional, (47 reviews)
Exceptional
(47 reviews)

Sunset Lodge on the Bay

Rock Hall

9% off
Price is $1,153
$8,069 for 7 nights
All fees included
Sunset Lodge on the Bay

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Find the best place to stay - Chester

Marina
Premier Host
Chesapeake Houseboat Getaway on Kent Island, Maryland
Sleeps 6 · 2 bedrooms · 1 bathroom
10.0 out of 10, Exceptional, 67 reviews
Chesapeake Houseboat Getaway on Kent Island, Maryland

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Find out more about Chester

Why visit Chester

  • Outdoor Adventures: Enjoy a variety of activities in Chester's beautiful parks and marinas, perfect for nature enthusiasts.
  • Scenic Beauty: Experience the picturesque landscapes and inviting vibes of Shore Maryland, ideal for relaxation.
  • Family-Friendly Atmosphere: Chester offers a welcoming environment, making it great for families with children.
  • Cultural Immersion: Explore historic sites and local charm along Academy Street for a taste of Chester's rich history.
  • Diverse Accommodations: Choose from cozy cottages to modern apartments for a comfortable and memorable stay.

Popular types of accommodation in Chester

Discover the charm of Chester with our diverse selection of vacation rentals. Whether you're looking for houses, cozy cottages, or modern apartments, we have the perfect fit for your getaway. Enjoy the comfort of air conditioning in your home rental while exploring everything this beautiful area has to offer. Choose from an array of Chester vacation rentals to make your stay unforgettable.

  • Houses: The top choice for visitors to Chester, these homes offer spacious living and the comforts of home, ideal for families or groups.
  • Cottages: A charming and cozy option, cottages provide a quaint atmosphere perfect for a relaxing getaway.
  • Apartments: Convenient and versatile, apartments are a popular pick for those seeking a home base during their stay.
  • Condos: These modern accommodations often feature amenities like pools and gyms, making them a desirable choice.
  • House Boats: For a unique experience, house boats offer a fun way to enjoy the water while staying in Chester.**

Top attractions near Chester

Chester, Maryland, offers a perfect blend of outdoor adventures and scenic beauty, making it an ideal spot for beach vacations. Visitors can explore a variety of attractions such as urban parks, marinas, and historic houses. Whether you're seeking a family-friendly experience, cultural immersion, or simply want to enjoy the great outdoors, Chester has something for everyone to enjoy during their stay.

  • Chesapeake Bay Bridge: A modern marvel spanning the Chesapeake Bay, this bridge offers stunning views of the water and surrounding landscapes. Experience the bustling energy as you cross, connecting you to the Eastern Shore.
  • Sandy Point State Park: A beautiful national park perfect for outdoor enthusiasts, featuring sandy beaches, hiking trails, and picnic spots. Enjoy adventurous activities like kayaking and fishing while soaking in scenic views of the bay.
  • Annapolis City Dock: A historic dock that serves as a vibrant gathering place, lined with shops and restaurants. Take in the charming scenery and explore the rich maritime history of Annapolis.

Things to do recommended for couples

Chester, Maryland, offers a charming escape for couples. Enjoy a scenic sunset at the Chester River, indulge in a romantic dinner at a waterfront restaurant, or take a leisurely bike ride along the picturesque trails. Don’t forget to explore local artisan shops for unique souvenirs.

Things to do recommended for families

Families visiting Chester, Maryland can enjoy a fun day at the Chesapeake Bay Environmental Center, where kids can explore nature trails and learn about local wildlife. Don't miss a boat tour on the bay for a thrilling adventure together.

Things to do recommended for groups

Groups visiting Chester, Maryland can enjoy a relaxing day at the Chester River, partake in local seafood dining experiences, and explore nearby parks for outdoor activities like hiking and picnicking. Don't miss the chance to visit the historic sites in nearby Kent Island.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

What do I need to keep in mind when booking a vacation in Chester

If you're traveling with a group, family, or pets, or if you're planning an extended stay, be sure to apply the appropriate filters to meet your needs. Here are some helpful tips for booking on Vrbo.

  • Traveling to Chester with a group: Think about how many bedrooms you require, along with features like a full kitchen or outdoor areas for group gatherings. The good news is that you can easily filter for these options and many more on Vrbo.
  • Traveling to Chester with young kids: Traveling with young kids can be tough. It's important to prioritize their comfort and safety, along with suitable amenities like a private swimming pool. Additionally, think about how close you are to attractions that are great for families.
  • Taking your pets with you to Chester: For many, a family vacation isn't truly fulfilling without their furry companion by their side. If that resonates with you, explore Vrbo listings that welcome pets. Most pet-friendly properties offer amenities like feeding bowls and beds to ensure that everyone feels comfortable and at home.
  • Planning for a long term stay visiting Chester: If you're seeking vacation rentals with special offers for stays of a month or more, you've come to the right spot. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. Don't forget to include options like a parking space, a well-equipped kitchen, or a private pool in your search as well.

Where to stay near Chester

Chester, Maryland, offers a delightful mix of outdoor adventures and scenic beauty, perfect for a relaxing getaway. Explore the charming Academy Street, unwind at Chester Country Park, or indulge in upscale experiences at nearby rustic retreats. With its family-friendly atmosphere and friendly locals, you’ll enjoy sunny days by the beach and historical sites that enrich your visit. Discover the inviting vibes of Shore Maryland and make the most of your vacation in this picturesque region.

  • Stevensville: Located a mere mile from Chester, Stevensville offers a delightful escape for nature lovers and beachgoers. With its picturesque scenery and outdoor recreational opportunities, visitors can enjoy the local beaches and the serene environment of nearby state parks. The town features a charming boardwalk, perfect for leisurely strolls, and various educational venues that provide insight into the area's natural beauty. Don't miss the breathtaking views of the bay, where you can soak in the sun or engage in water activities.
  • Annapolis: Just 11 miles away from Chester, Annapolis is a vibrant city rich in history and culture. Known as the sailing capital of the U.S., it provides families with a blend of outdoor adventures and urban experiences. Explore the historic Annapolis Academy or take a leisurely day at the beach along the Chesapeake Bay. The city is also home to bustling shopping centers and malls, offering everything from unique local boutiques to major retailers. A visit to Annapolis promises a delightful mix of education, shopping, and family-friendly activities.
  • Kent Narrows: Situated 3 miles from Chester, Kent Narrows is a quaint village that beckons families and beach enthusiasts alike. The area boasts a lively boardwalk and a variety of shopping options, making it a great spot for a fun-filled day out. Visitors can enjoy the scenic views of the bay and beach while exploring the charming esplanade. Kent Narrows is perfect for those looking to unwind by the water while also providing ample opportunities for exploration and relaxation in a family-friendly atmosphere.

Best time to go to Chester

If you're planning a trip to Chester, it's a good idea to check both the weather and property rates. The warmest month is July. Peak season runs from June to August, while off-peak times, like January to March tend to have fewer bookings and better deals.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January35.1°F (1.7°C)Light RainMostly SunnyModerately LowSlightly Low
February37.4°F (3.0°C)Light RainMostly SunnyModerately LowSlightly Low
March43.9°F (6.6°C)Light RainMostly SunnyModerately LowSlightly Low
April54.1°F (12.3°C)Light RainMostly SunnyAverageAverage
May63.5°F (17.5°C)Light RainMostly SunnyAverageAverage
June72.3°F (22.4°C)Light RainMostly SunnyModerately HighSlightly High
July77.9°F (25.5°C)Light RainMostly SunnyModerately HighSlightly High
August76.3°F (24.6°C)Light RainMostly SunnyModerately HighSlightly High
September70.5°F (21.4°C)Light RainMostly SunnyAverageAverage
October60.3°F (15.7°C)Light RainMostly SunnyAverageAverage
November48.7°F (9.3°C)Light RainMostly SunnyAverageAverage
December41.0°F (5.0°C)Light RainMostly SunnyAverageAverage

Booking with Vrbo is simple

Looking to save on your next vacation? Consider being flexible with your travel dates, as prices can fluctuate. Additionally, extending your stay can often result in significant savings. To discover the ideal Vrbo property that fits your budget, take advantage of our filters to refine your search by price, location, and type of vacation rental.

Vrbo Trips: Planning as easy as it gets

Vrbo’s Trip Board provides a convenient place for you to plan new trips, manage ongoing arrangements, and review your reservations. Your saved or booked properties are neatly categorized into Potential, Upcoming, or Current Trips for easy access. To check out the Trip Boards, simply visit: https://www.vrbo.com/trips.

**Based on Vrbo properties bookings.

Explore the waterfront setting in Chester

The island views and other outdoor surroundings create an inviting atmosphere in Chester. Renowned for its boating, biking and seafood restaurants, this city welcomes all visitors. With a vacation rental, you get a home away from home. Many rentals offer full kitchens and outdoor grills for some home cooking.

Activities and attractions in Chester

Are you hoping to find things to do in the area? Venture out of your vacation home and check out everything that makes Chester a one-of-a-kind vacation spot. Here are some of the major attractions to put on your list, all within 30 miles (48.2 km) of the city center:

  • Queenstown Harbor Golf (6.6 mi / 10.6 km)
  • Bay Hills Golf Club (11.3 mi / 18.1 km)
  • St. Michaels Winery (13.9 mi / 22.4 km)
  • Maryland Renaissance Festival (16.2 mi / 26 km)
  • Paul Reed Smith Guitars (1.6 mi / 2.6 km)
  • U.S. Naval Academy Golf Club (9.5 mi / 15.3 km)

Exploring the natural landscape of Chester

Whether you're an active traveler or just want to spend some time taking in the scenery, Chester is a great place to get outside. These are a few of the area's most stunning sights, all within 30 miles (48.2 km) of the city center:

  • Northern Chesapeake Bay (3.1 mi / 5 km)
  • Eastern Neck National Wildlife Refuge (5.2 mi / 8.4 km)
  • Sandy Point Beach (6.2 mi / 10 km)
  • Bay Ridge Beach (9.2 mi / 14.8 km)
  • Maryland Quiet Waters Park (11.4 mi / 18.3 km)
  • Fort Smallwood Park (15.9 mi / 25.5 km)

Traveling to and around Chester

Fly into Easton, MD (ESN-Easton - Newnam), the closest airport, located 16.6 mi (26.7 km) from the city center. If you can't find a flight that works for your travel itinerary, you could book a flight to Baltimore Washington Intl. Airport (BWI), which is 24.8 mi (39.9 km) away.

Frequently asked questions

How much does it cost to rent a vacation home in Chester?
Prices for vacation rentals in Chester vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're traveling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in Chester to more spacious homes. To get the best value, book early and take advantage of Vrbo's free rewards program.
Are there any discounts for Chester vacation house rentals?
You can find great discounts on house rentals in Chester on Vrbo, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for Last minute bookings, and Early bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
What is the most popular type of vacation rental accomodation in Chester?
In Chester, vacation houses and apartments are both popular types of accommodations, with several of each available in the area. The vacation houses typically offer spacious layouts, multiple bedrooms, fully equipped kitchens, and outdoor spaces such as decks or patios—ideal for families or groups looking to enjoy the nearby Chesapeake Bay. Apartments, often located in quieter neighborhoods, provide a more compact option with amenities like kitchenettes, comfortable living areas, and easy access to local attractions.
Are there any family house rentals in Chester?
In Chester, Maryland, there are some family-friendly vacation rentals available, making it a suitable destination for families seeking a getaway. The area boasts homes with spacious living areas, full kitchens for preparing meals together, and outdoor spaces where children can play safely. Many properties come equipped with modern amenities like Wi-Fi and air conditioning, ensuring a comfortable stay.

Visitors can explore nearby attractions such as the Chester River and the scenic waterfront, great for family outings or picnics. Additionally, the proximity to local parks provides further opportunities for outdoor activities.
Can I find long-stay vacation rentals in Chester?
A long-stay vacation rental in Chester is the best way to experience local living. Plus, you can make the most of long-stay discounts. For month-long stays, save an average of 19%, and for week-long bookings you can save an average of 10%.* Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
Are there pet-friendly house rentals in Chester?
In Chester, Maryland, there are several pet-friendly house rentals available for travelers. Many of these accommodations offer a range of amenities, including spacious backyards, fully equipped kitchens, and comfortable living areas, making them suitable for families and groups.

The area is known for its proximity to beautiful waterfront parks and nature trails, providing ample opportunities for outdoor activities with pets. Nearby, travelers can enjoy the scenic views and walking paths along the Chester River, superb for leisurely strolls with furry companions. Additionally, local pet-friendly cafes and shops enhance the experience for those traveling with pets, ensuring that both guests and their animals feel welcome during their stay.
Are there any remote work vacation rentals in Chester?
In Chester, Maryland, there are several remote work vacation rentals available that cater to traveling professionals. Many of these properties provide essential amenities such as free Wi-Fi, dedicated workspace with desks and chairs, and even printing facilities, making it convenient for guests to manage their work remotely. The charming town offers a peaceful setting, ideal for productivity while still enjoying the comforts of home. Additionally, the location is close to various points of interest, including parks and waterfront areas, providing a nice balance between work and leisure. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Chester vacation rentals with parking?
Vrbo offers a wide selection of vacation rentals in Chester with parking available—perfect for families or travelers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details on Vrbo and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
What are popular rental amenities in Chester?
In Chester, popular vacation rental amenities include fully equipped kitchens, allowing guests to prepare their own meals while enjoying the comforts of home. Many rentals also feature coffee and tea makers, superb for starting the day with a warm beverage. Decks or patios are common, providing outdoor spaces for relaxation and taking in the serene surroundings. Onsite parking is typically available, making it convenient for travelers with vehicles. Additionally, many properties offer desks, suiting those who may need to work during their stay.
How early should I book a Chester vacation rental?
Book your Chester vacation rental at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
What are the top attractions in Chester, Maryland, United States of America?
In Chester, Maryland, visitors can enjoy a variety of attractions that highlight the area's natural beauty and local culture. The Chester River offers opportunities for boating, fishing, and kayaking, superb for outdoor enthusiasts looking to explore the waterways. The nearby Sandy Point State Park is a popular destination, featuring sandy beaches, picnic areas, and scenic trails that provide stunning views of the Chesapeake Bay.

For those interested in history, the local historic sites, such as the Kent Island Historical Society, offer insights into the region's past. The charming waterfront area features local shops and restaurants, where visitors can savor fresh seafood and regional cuisine.
Can I change or cancel my Chester home rental booking on Vrbo?
To find Chester vacation rentals with free cancellation, just use Vrbo's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Vrbo rentals give you the privacy of having the entire place to yourself, and for extra flexibility, some travelers can choose to pay over time with Affirm. Whether you're adjusting your plans or looking for flexible payment options, Vrbo makes it easy to book with confidence.
Why should I join Vrbo as a host?
Joining Vrbo as a host opens the door to a global community of travelers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Vrbo makes it easy to list, manage, and succeed. Whether it's a cozy cabin or a beach condo, you can turn your space into a standout destination, become a host and let Vrbo handle the heavy lifting to help you thrive.

Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.
Are all fees included in the Chester vacation rental prices shown on Vrbo?
Vrbo provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
What is VrboCare™ and how does it work?
Vrbo's mission is to help guests relax, reconnect, and enjoy precious time together. With VrboCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable.

If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
What can I expect from Vrbo customer service and VrboCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, VrboCare™ is here to support you every step of the way. For urgent situations like last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to help resolve problems quickly and effectively.

Vrbo also offers support via live chat through our Help Center, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
Can I plan a group trip on Vrbo?
Vrbo's Trip Planner makes organizing group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favorites, and build the perfect itinerary together.

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