Kent Island holiday lettings

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Holiday rentals with weekly discounts – Kent Island

Showing deals for:29 Jan - 5 Feb

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Why visit Kent Island

  • Stunning Beaches: Kent Island boasts beautiful sandy shores, perfect for sunbathing and relaxation at Kent Island Beach.
  • Outdoor Adventures: Enjoy a variety of activities such as hiking, fishing, and boating amidst picturesque landscapes.
  • Rich History: Explore historic houses and sites that reflect the area's cultural heritage and charm.
  • Family-Friendly Atmosphere: The island offers a welcoming environment for families to enjoy recreational activities and local attractions.
  • Delicious Seafood: Indulge in fresh seafood at local eateries, showcasing the island’s culinary delights.

Popular types of accommodation around Kent Island

Kent Island, Maryland, is a charming destination for your next getaway, offering a range of delightful vacation rentals including private homes, cottages, and apartments. Explore the picturesque waterfront, indulge in fresh seafood, and visit local attractions such as historic sites and nature trails. With an inviting atmosphere and stunning views, Kent Island is the perfect spot to relax and enjoy memorable experiences. Discover your ideal rental property and start planning your escape today.

  • Houses: The top choice for visitors seeking space and comfort, offering a home-away-from-home experience.
  • Cottages: Charming and quaint, these properties provide a cozy retreat with a touch of rustic charm.
  • Apartments: Ideal for those wanting convenience, these self-contained units offer flexibility and easy access to local amenities.
  • Condos: These modern accommodations often feature shared facilities, perfect for a laid-back holiday vibe.
  • Cabins: Nestled in nature, cabins offer a serene escape with a unique outdoor ambiance.**

Top attractions near Kent Island

Kent Island, Maryland, offers a delightful blend of outdoor adventures and cultural experiences perfect for family vacations. Visitors can explore scenic urban parks, enjoy the picturesque marina, and delve into the area's rich history at historic houses. With its beautiful beaches and stunning landscapes, Kent Island is an ideal destination for those seeking relaxation and recreation amid charming surroundings.

  • Sandy Point State Park: A stunning national park offering scenic views, diverse wildlife, and ample outdoor activities such as hiking and picnicking, perfect for adventure lovers.
  • Sandy Point Beach: A lovely beach with soft sands and gentle waves, ideal for sunbathing, swimming, and enjoying a relaxing day by the water.
  • Maryland State House: A historic civic building rich in culture, showcasing remarkable architecture and significant American history, making it a must-visit for history enthusiasts.

Things to do recommended for couples

Looking to create unforgettable memories on Kent Island? Enjoy a romantic dinner at a waterfront restaurant, take a leisurely bike ride along scenic trails, or indulge in a sunset cruise on the Chesapeake Bay, soaking in the stunning views together.

Things to do recommended for families

Families can explore the scenic beauty of Kent Island by visiting the Chesapeake Bay Maritime Museum, where kids can learn about local maritime history. A delightful day can also be spent at Sandy Point State Park, offering sandy beaches and picnic areas perfect for family enjoyment.

Things to do recommended for groups

Groups visiting Kent Island can enjoy a delightful seafood feast at local restaurants, embark on a scenic kayak tour of the Chesapeake Bay, and unwind at picturesque parks like Terrapin Nature Park, perfect for leisurely strolls and picnics.

*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 planning your trip—whether you're travelling with a group, with family, bringing along pets, or seeking extended stays—be sure to refine your search based on your essential preferences. Here are some helpful booking tips for Vrbo.

  • Traveling to Kent Island with a group: Think about how many bedrooms you require, along with amenities like a fully-equipped kitchen or outdoor areas for group gatherings. Thankfully, you can easily filter for all these options and more on Vrbo.
  • Traveling to Kent Island with young kids: Travelling with young children can be quite demanding. It's essential to prioritise their comfort and safety, as well as provide suitable amenities, like a private swimming pool. Additionally, it's wise to think about how close you are to family-friendly attractions.
  • Taking your pets with you to Kent Island: For many, a family holiday isn't truly complete without their furry companion by their side. If this resonates with you, take a look at Vrbo properties that welcome pets. Most pet-friendly accommodations come equipped with feeding bowls and beds to ensure that everyone feels comfortable and at home.
  • Planning for a long term stay visiting Kent Island: If you're in search of holiday rentals with offers for stays of a month or more, you've come to the right place. 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 Kent Island

Kent Island, Maryland, offers a delightful blend of natural beauty and historical charm. Visitors can bask in the sun at Kent Island Beach, enjoying stunning views and a relaxing atmosphere. The island's family-friendly vibe invites exploration of its picturesque scenery and rich heritage. With friendly locals and a tranquil pace of life, Kent Island is the perfect destination for those seeking both adventure and leisure on their holiday.

  • Annapolis: Situated a mere 14km from Kent Island, Annapolis is a vibrant city renowned for its rich maritime heritage and charming streets. Visitors are drawn to its family-friendly atmosphere, outdoor adventures, and urban experiences. Explore the historic district, home to the United States Naval Academy, and take leisurely strolls along the picturesque waterfront. The city boasts excellent shopping centres and malls, offering a variety of local boutiques and eateries. Notable attractions include the beautiful Chesapeake Bay and serene beaches, making Annapolis a delightful blend of culture and nature.
  • Stevensville: Just 5km from Kent Island, Stevensville is a quaint town that offers a captivating outdoor experience and stunning scenery. Known for its beautiful beaches and recreational areas, it is an ideal spot for families and nature lovers alike. Visitors can enjoy leisurely walks along the boardwalk and partake in various outdoor activities. The proximity to the Chesapeake Bay and nearby state parks provides ample opportunities for exploration and relaxation. With local attractions centred around education and nature, Stevensville is perfect for those looking to unwind in a serene setting.
  • Chester: Also located 5km from Kent Island, Chester shares a similar charm with Stevensville, offering a scenic backdrop for outdoor enthusiasts. This small town is perfect for leisurely explorations along the boardwalk and access to recreational areas. Chester’s proximity to the bay and local beaches makes it an excellent choice for water-related activities. Visitors can enjoy the natural beauty of the nearby national state park, providing a perfect blend of relaxation and adventure. It’s an inviting destination for anyone looking to soak up the sun and enjoy the great outdoors.

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 iconCalendar Monthtemperature iconTemperaturerain iconPrecipitationmostly cloudy iconCloudinessoccupation rate iconOccupancyprice iconPricing
January35.6°F (2.0°C)Light RainMostly SunnyLowSlightly Low
February37.9°F (3.3°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 (17.9°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 (5.3°C)Light RainMostly SunnyLowAverage

Booking with Vrbo is a breeze

Are you hoping to save on your next holiday? Consider being flexible with your travel dates, as prices can vary significantly. Additionally, booking an extended stay often leads to substantial savings. To discover the perfect Vrbo property that fits your budget, utilise our filters to sort by price, location, and type of holiday rental.

Vrbo Trips: Planning as easy as it gets

Vrbo's Trip Board offers a user-friendly platform for planning your trips, allowing you to easily start new journeys, continue from where you last stopped, or manage your travel arrangements. You can view your saved or booked properties neatly organised into categories: Potential, Upcoming, or Current Trips. To begin exploring Trip Boards, please visit: https://www.vrbo.com/en-gb/trips.

**Based on Vrbo properties bookings.

Explore the waterfront setting in Kent Island

Enjoy the history and other features of Kent Island. Well known for its island views, boating and cycling, this relaxing city won't disappoint. Many rental homes come with outdoor spaces, separate dining areas and full kitchens, perfect if you want to enjoy some home-cooked meals.

Activities and attractions in Kent Island

Do you want to discover attractions to visit in the area? Venture out of your holiday home and check out everything that Kent Island has to offer. Here are some of the most popular attractions to see, all within 30 miles (48.2 km) of the city centre:

  • Queenstown Harbor Golf (9.4 mi / 15.1 km)
  • Bay Hills Golf Club (11 mi / 17.7 km)
  • St. Michaels Winery (12.2 mi / 19.7 km)
  • Maryland Renaissance Festival (14.6 mi / 23.5 km)
  • Thanksgiving Farm Wines (16.7 mi / 26.8 km)
  • Chesapeake Beach Water Park (20.3 mi / 32.6 km)

Exploring the natural features in Kent Island

Whether you're an adventurous traveller or just want to spend some time taking in the scenery, Kent Island is a great place to spend some time outside. Here are some of the area’s most stunning features, all within 30 miles (48.2 km) of the city centre:

  • Northern Chesapeake Bay (2.1 mi / 3.4 km)
  • Sandy Point Beach (6.3 mi / 10.1 km)
  • Bay Ridge Beach (6.9 mi / 11.1 km)
  • Eastern Neck National Wildlife Refuge (8.6 mi / 13.9 km)
  • Maryland Quiet Waters Park (9.1 mi / 14.6 km)
  • Fort Smallwood Park (16.5 mi / 26.6 km)

Frequently asked questions

What is the best area to stay in Kent Island when booking a holiday rental?
One of the more sought-after areas for a Kent Island holiday home is Chester. When you lock in your holiday rental with Vrbo, you'll have the entire place to yourself. This means you don't have to share it with anyone apart from your group.
What is the most popular type of holiday rental accommodation in Kent Island?
Houses are the most popular style of holiday rental in Kent Island, according to our data. Even if you have something else in mind, Vrbo has holiday homes in many sizes and shapes. Filter our options to find your perfect match.
How much does it cost to rent a holiday rental in Kent Island?
The average price for a holiday home in Kent Island is based on several factors, such as property type, season and length of stay. Whether you prefer a villa with space for extended family or a cosy condo perfect for just you and the kids, just enter your travel dates to see stays with unbeatable value.
How much does it cost to rent a beach house in Kent Island?
When you travel and the size and style of the property will help determine the cost of your beachside stay. Type in your Kent Island travel dates to view your options on Vrbo. Can't live without a private pool? Use the filters to pick the features and amenities you want in your beach house.
What are popular rental amenities in Kent Island?
The most popular rental amenities people search for in Kent Island include an ocean view, a water view and an electric car charging station. Whether you're on the road with family, buddies or even pets, Vrbo holiday properties feature the best amenities for ultimate relaxation with the people that matter most.
Can I find two-bedroom holiday rentals in Kent Island?
Take off with your besties and enjoy total privacy and comfort in one of the three two-bedroom holiday properties Kent Island has to offer.
Are there holiday rentals with WiFi in Kent Island?
Kent Island has 23 holiday rentals with WiFi, so you'll be able to stay connected during your holiday. Simply check the "WiFi" box in our search filter for a list of properties with this feature. From streaming TV shows with the family to checking emails, these Vrbo homes will keep you online.
How old do you have to be to rent a holiday rental in Kent Island?
The minimum age allowed can vary across properties on Vrbo, so be sure to look at the rules of the holiday rental in Kent Island you want. But normally, it's 16, 18 or 21.
How long can I rent a holiday rental in Kent Island for?
The length of time you can rent a holiday rental in Kent Island differs according to the property. Simply enter your selected travel dates to look at a list of options offering extended stays. With tons of creature comforts such as air conditioning and full kitchens, as well as some offering weekly or monthly discounts, you're sure to discover somewhere just right to call your home away from home in Kent Island.

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