Kent Island vacation rentals

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Welcome to Kent Island, a picturesque paradise where scenic waterfront views blend seamlessly with outdoor adventures and rich local history. This charming destination invites families and groups to explore its beautiful parks, marinas, and sandy beaches, perfect for hiking, boating, and creating unforgettable memories. With a variety of cozy cottages and modern apartments to choose from, you can enjoy the comforts of home while immersing yourself in the island’s enchanting atmosphere.

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Find out more about Kent Island

Why visit Kent Island

  • Outdoor Adventures: Kent Island offers a range of activities like hiking, biking, and water sports, perfect for nature lovers.
  • Scenic Beaches: Enjoy the beautiful coastline and relax on the sandy shores, ideal for family outings and picnics.
  • Rich History: Explore nearby historic towns with charming homes and local culture that reflect the island's heritage.
  • Family-Friendly Attractions: Kent Island features numerous parks and recreational spots that cater to visitors of all ages.
  • Diverse Accommodations: Choose from a variety of vacation rentals, from cozy cottages to spacious homes, for a comfortable stay.

Popular types of accommodation around Kent Island

Discover the perfect getaway on Kent Island with a variety of vacation rentals to suit your needs. Whether you're looking for houses, cozy cottages, or convenient apartments, we have options for everyone. From charming single-family homes to pet-friendly rentals near Kent Narrows, you'll find the ideal base for your adventure. Explore, relax, and create unforgettable memories in this beautiful destination.

  • Houses: The top choice among travelers, offering spacious and comfortable accommodations for families or groups.
  • Cottages: A charming option, perfect for a cozy getaway with a touch of rustic charm.
  • Apartments: A convenient choice for those seeking a home-like atmosphere with easy access to local attractions.
  • Condos: Ideal for vacationers wanting upscale amenities and stunning views.
  • Cabins: A delightful retreat for nature enthusiasts, providing a tranquil escape in the woods.**

Top attractions near Kent Island

Kent Island, Maryland, offers a perfect blend of outdoor activities for families, couples, and solo travelers. Visitors can enjoy urban parks, scenic beaches, and nearby national and state parks. With a variety of attractions catering to those seeking adventure, culture, and family-friendly experiences, Kent Island is an ideal destination for a memorable vacation. Be sure to explore the local points of interest to enhance your visit.

  • U.S. Naval Academy: Located 9 miles from Kent Island, this historic academy offers breathtaking architecture and rich maritime history, making it a must-visit for history buffs and those interested in military traditions.
  • Chesapeake Bay Bridge: Just 6 miles away, this impressive modern bridge connects the Eastern and Western shores, providing stunning views of the bay and a unique urban experience.
  • Sandy Point State Park: Situated 7 miles from Kent Island, this national park is perfect for outdoor enthusiasts, offering scenic trails, picnic areas, and adventurous activities along the beautiful waterfront.

Things to do recommended for couples

For a romantic getaway on Kent Island, visit St. Michaels Winery for a delightful wine tasting, or set sail with Annapolis Sailing School for an adventurous day on the water. Don’t miss a captivating performance at the Ballet Theater of Maryland to complete your memorable experience.

Things to do recommended for families

Your family will have a blast at the Navy-Marine Corps Memorial Stadium, just 10 miles away, soaking in the sports atmosphere. For more fun, visit the Annapolis Bowl, 13 miles away, for an arcade adventure, or catch a game at Alumni Hall, only 9 miles from Kent Island.

Things to do recommended for groups

Explore the craftsmanship at Paul Reed Smith Guitars, only 4 miles from Kent Island. For shopping and entertainment, visit Queenstown Premium Outlets, located 10 miles away. If your group enjoys sports, the Queenstown Harbor Golf Club, 9 miles away, offers a fantastic outdoor golfing experience.

*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 around Kent Island

When traveling with a group, family, or pets, or if you're seeking extended stays, be sure to prioritize your filters accordingly. Here are some helpful booking tips for Vrbo.

  • Traveling to Kent Island with a group: Think about how many bedrooms you require, along with features like a full kitchen or outdoor space for group gatherings. The good news is that you can easily filter for these options and many more on Vrbo.
  • Traveling to Kent Island with young kids: Traveling with young children can be quite a challenge. It's important to prioritize their comfort and safety, along with suitable amenities like a private swimming pool. Additionally, it's worthwhile to think about how close you are to family-friendly attractions.
  • Taking your pets with you to Kent Island: For many, a family vacation isn't truly a family vacation without their furry companion by their side. If that resonates with you, explore Vrbo listings that welcome pets. Many of these pet-friendly accommodations offer feeding bowls and cozy beds to ensure everyone feels comfortable and at home.
  • Planning for a long term stay visiting Kent Island: If you're in search of vacation rentals that offer discounts for month-long stays, you've come to the right spot. By using the appropriate filters, you can effortlessly locate and save on monthly accommodations. 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 Kent Island

Kent Island, the largest island in Maryland, offers a peaceful getaway perfect for outdoor adventures and family vacations. With its beautiful coastline and charming homes, visitors can relish in a relaxing atmosphere while exploring nearby towns rich in history and friendly locals. Whether you're seeking a romantic retreat or a rustic experience, Kent Island provides a unique blend of sunny weather and scenic views that will make your stay unforgettable.

  • Annapolis: Located a mere 9 miles from Kent Island, Annapolis is the charming capital of Maryland and a hub for family-friendly activities and urban exploration. Visitors can enjoy a variety of attractions, from educational landmarks such as the United States Naval Academy to shopping experiences at local malls and unique boutiques. The city is also renowned for its waterfront, where you can take leisurely strolls along the scenic beach and enjoy picturesque views of the lake. Whether you’re exploring the historic district or indulging in local cuisine, Annapolis provides a vibrant city experience that caters to all ages.
  • Northern Chesapeake Bay: Just 1 mile away, Northern Chesapeake Bay is a picturesque retreat known for its stunning outdoor scenery and romantic settings. This area is perfect for those who appreciate nature, offering a range of recreational activities from kayaking in tranquil waters to golfing at scenic courses. Visitors can explore the beautiful beaches, visit notable monuments, or cross the impressive modern bridge that connects various waterfront attractions. It’s an ideal spot for couples looking to enjoy a peaceful getaway or families seeking outdoor adventures.
  • Stevensville: A short 3 miles from Kent Island, Stevensville is a delightful city that invites visitors to immerse themselves in outdoor activities and family fun. The area boasts a vibrant recreational scene, including well-maintained parks and a charming boardwalk perfect for leisurely walks. Shop at local centers or explore nearby beaches and the stunning national state park, which offers hiking trails and breathtaking views. With its inviting atmosphere and numerous attractions, Stevensville is a great destination for those looking to experience the beauty of Maryland’s coastline.

Best time to go to Kent Island

If you're planning a trip to Kent Island, 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 November to January tend to have fewer bookings and better deals.

Calendar MonthTemperaturePrecipitationCloudinessOccupancyPricing
January35.6°F (2.0°C)Light RainMostly SunnyLowSlightly Low
February37.9°F (3.3000000000000003°C)Light RainMostly SunnyAverageSlightly Low
March44.6°F (7.0°C)Light RainMostly SunnyAverageSlightly Low
April55.0°F (12.8°C)Light RainMostly SunnyAverageAverage
May64.2°F (17.900000000000002°C)Light RainMostly SunnyAverageAverage
June73.0°F (22.8°C)Light RainMostly SunnyHighSlightly High
July78.4°F (25.8°C)Light RainMostly SunnyHighSlightly High
August76.8°F (24.9°C)Light RainMostly SunnyHighSlightly High
September70.7°F (21.5°C)Light RainMostly SunnyAverageAverage
October60.4°F (15.8°C)Light RainMostly SunnyAverageAverage
November48.7°F (9.3°C)Light RainMostly SunnyLowAverage
December41.5°F (5.300000000000001°C)Light RainMostly SunnyLowAverage

Booking with Vrbo is simple

Are you hoping to save money on your upcoming trip? Being flexible with your travel dates can make a difference, as prices often fluctuate. Additionally, consider booking a longer stay to take advantage of substantial savings. To discover a Vrbo property that suits your budget, utilize our filters to narrow down options by price, location, and type of vacation rental. We're here to help you find the perfect getaway.

Vrbo Trips: Effortless planning

Vrbo’s Trip Board offers a user-friendly platform where you can effortlessly plan new trips, resume your previous work, or manage your travel arrangements. You can easily access your saved or booked properties, organized into categories like Potential, Upcoming, or Current Trips. To begin using Trip Boards, simply visit: https://www.vrbo.com/trips.

**Based on Vrbo properties bookings.

Frequently Asked Questions

What are the best cities to stay in a vacation rental in Kent Island?

Kent Island offers a selection of vacation rentals primarily located in Chester, providing a comfortable base for various trip types. Vrbo helps you find a whole place to yourself, offering more space, privacy, and room to settle in comfortably. Chester is the central hub for vacation rentals in Kent Island, catering to different guest needs. Here are some top picks for your stay:

  • Best for families: Chester — You will find several family-friendly vacation rentals in Chester, many of which are houses. The city is close to Love Point State Park, about 2 miles away, offering outdoor space for children to explore.
  • Best for groups: Chester — With many large group vacation rentals available, Chester provides spacious houses ideal for gatherings. These properties often feature multiple bedrooms and common areas, perfect for friends or extended family.
  • Best for a relaxed getaway: Chester — For those seeking a quieter coastal experience, Chester offers a selection of houses, some with ocean views and balconies, providing a peaceful retreat. You can enjoy local shopping and dining options, or visit nearby Ferry Park, about 6 miles away.

What are the most popular vacation rentals in Kent Island?

Houses are the most popular type of vacation rentals in Kent Island, with several options available, predominantly in Chester. These homes are favored by guests seeking ample space and privacy, making them ideal for families and groups. Vacation rentals in Kent Island offer a comfortable and private setting, allowing guests to enjoy their stay with room to spread out and relax.

What amenities do vacation rentals in Kent Island usually offer?

Vacation rentals in Kent Island typically offer a range of amenities designed for a comfortable and convenient stay. You will often find fully equipped kitchens, making it easy to prepare meals, along with outdoor spaces like balconies for enjoying the fresh air. Many properties also include parking, laundry facilities, and barbecue grills. For entertainment and relaxation, some vacation rentals in Kent Island feature hot tubs, fireplaces, and games for children. Other common amenities include dining tables, separate living rooms, and even kayaks for water activities.

Are there family-friendly vacation rentals in Kent Island?

Yes, Kent Island offers several family-friendly vacation rentals, primarily houses located in Chester. These properties are designed to accommodate families, providing amenities that make traveling with children easier and more enjoyable. You can find vacation rentals in Kent Island that include travel cribs, books and games for children, and outdoor play areas. Many also feature fully equipped kitchens with dishwashers and microwaves, along with laundry facilities, ensuring a comfortable and convenient stay for the whole family.

Are there pet-friendly vacation rentals in Kent Island?

Yes, you can find pet-friendly vacation rentals in Kent Island, with a selection of houses available in Chester. These properties welcome your furry companions, allowing them to join in on your vacation adventures. When searching for vacation rentals in Kent Island, look for listings that specify pets are permitted, ensuring a comfortable stay for every member of your family.

What are the best cities for group vacation rentals in Kent Island?

Chester is an excellent choice for group vacation rentals in Kent Island, offering several houses well-suited for larger parties. These spacious properties provide ample room for everyone to gather and relax, making them ideal for family reunions or friends' getaways. Vacation rentals in Kent Island for groups often come with multiple bedrooms, large dining areas, and fully equipped kitchens. Many also include convenient parking for several cars, ensuring a smooth arrival and comfortable stay for your entire group.

What are the best luxury vacation rentals in Kent Island?

Kent Island features a selection of luxury vacation rentals, with several high-end houses available in Chester. These properties offer enhanced comfort and amenities for a more indulgent stay. You can find luxury vacation rentals in Kent Island that boast ocean views, private balconies, and hot tubs for ultimate relaxation. Some also include cozy fireplaces, adding to the upscale experience.

Are there any budget-friendly vacation rentals in Kent Island?

Yes, Kent Island offers some budget-friendly vacation rental options, including a house in Chester that provides great value. While the average nightly rate for houses is around $641, you can find options starting from approximately $477 per night. These vacation rentals in Kent Island often come with essential amenities like fully equipped kitchens, laundry facilities, and parking, helping you save on dining out and other expenses during your trip.

Are there any vacation rentals in Kent Island with a hot tub?

Yes, you can find vacation rentals in Kent Island that feature a hot tub, with a selection of houses available in Chester. These properties offer a relaxing amenity, perfect for unwinding after a day of exploring. Many of these vacation rentals in Kent Island also include a fireplace, creating a cozy atmosphere for your getaway.

Are there any short-term vacation rentals in Kent Island for a weekend getaway?

Yes, Kent Island offers short-term vacation rentals perfect for a weekend getaway, primarily in Chester. You will find houses and apartments that provide a comfortable and convenient base for a two or three-night trip. These vacation rentals in Kent Island are well-suited for quick escapes, offering easy access to local attractions like Love Point State Park, which is about 2 miles away, and the Chesapeake Bay Bridge, about 13 miles away.

How much does a Kent Island vacation rental cost?

The average nightly cost for a house in Kent Island is approximately $641, with options starting from around $477 per night. Prices for vacation rentals in Kent Island can vary based on factors such as the size of the property, its specific location within Chester, and the time of year you plan to visit. For instance, rates may be higher during peak travel months like July and August compared to quieter periods in January or February.

What are some top things to do while staying in a Kent Island vacation rental?

While staying in a vacation rental in Kent Island, you have several engaging activities to enjoy before returning to your comfortable home away from home. You can take a scenic walk across the Chesapeake Bay Bridge, an event typically held on the first Sunday of May, which is about a 13-mile drive from Chester. Explore Historic Stevensville, Kent Island's charming downtown area with restored 19th-century buildings, offering shopping and dining, located a short drive from typical rental cities. For nature lovers, Terrapin Park, about 3 miles from Chester, provides beautiful views of the Chesapeake Bay and the Bay Bridge, with trails for walking and biking. You can also visit Love Point State Park, approximately 2 miles from Chester, for more outdoor recreation.

Are all fees included in the Kent Island 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.

Are there any discounts for Kent Island vacation house rentals?

You can find great discounts on house rentals in Kent Island 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 discounted rates.

Are there any last-minute vacation rentals near Kent Island?

Vrbo makes it simple to find last-minute vacation rentals near Kent Island that blend comfort, style, and great value. Vrbo offers plenty of options for guests ready to pack up and go. Families and groups will find these deals especially appealing. Many spacious homes, complete with full kitchens, private pools, and multiple bedrooms, often become available when hosts want to fill open dates on their calendars. Finding these stays is easy. Just enter your destination and travel dates, then use Vrbo's "Last Minute" or "Discounts" filter to uncover great offers. You'll see reduced rates in the listings where available. Vrbo's last-minute rentals are a smart way to save while you explore. Whether you're planning a quick trip or a weekend getaway with friends, your last-minute escape is waiting.

Can I change or cancel my Kent Island home rental booking on Vrbo?

To find Kent Island 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.

Can I find long-stay vacation rentals in Kent Island?

A long-stay vacation rental in Kent Island 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 travel 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.

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.

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.

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.

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 house, 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.

Will I have to share my Kent Island vacation rental with the host or other guests?

No. When you book a stay in Kent Island through Vrbo, you are booking an entire home. Under Vrbo's Shared Spaces Policy, we maintain high standards for our hosts and homes, ensuring that all listings are private rental spaces. You will never have to share your Kent Island vacation rental's interior living spaces with a host or strangers, allowing your group to enjoy your trip in total privacy.

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