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Kent Island holiday lettings

We found 1,038 holiday rentals — enter your dates for availability

Holiday rentals with weekly discounts - Kent Island

Showing deals for:10 Oct - 17 Oct
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Why visit Kent Island

  • Stunning waterfront: Enjoy picturesque views and serene beaches that showcase the island's natural beauty.
  • Outdoor activities: Engage in kayaking, hiking, and exploring nearby national and state parks for adventure.
  • Rich history: Immerse yourself in the island’s cultural heritage and historical sites.
  • Charming accommodations: Choose from delightful holiday rentals, including cottages and modern apartments.
  • Friendly local atmosphere: Experience the welcoming vibe of nearby towns, perfect for relaxation and exploration.

Popular types of accommodation around Kent Island

Planning a getaway to Kent Island? The excitement begins with selecting your perfect accommodation. Explore a variety of options, including houses, charming cottages, and modern apartments. With an array of Kent Island area rentals available, you're sure to find the ideal holiday rental that suits your needs. Discover your home away from home and make the most of your stay on this beautiful island.

  • Houses: The top choice for visitors to Kent Island, offering spacious and comfortable settings ideal for families or groups.
  • Cottages: A delightful option for a quaint and homely experience, perfect for a romantic getaway or a peaceful retreat.
  • Apartments: Convenient and well-equipped, ideal for those seeking a self-catering option with easy access to local attractions.
  • Condos: A popular choice providing modern amenities and often stunning views, great for a relaxing stay.
  • Cabins: An enchanting selection for those wanting to immerse themselves in nature while enjoying a rustic charm.**

Top attractions near Kent Island

Kent Island offers a delightful escape for families, couples, and outdoor enthusiasts alike. With its stunning parks, beautiful beaches, and nearby national and state parks, visitors can enjoy a variety of activities that showcase the region's natural beauty and cultural experiences. Whether you're seeking adventure or a relaxing retreat, Kent Island has something for everyone to explore and enjoy during your holiday.

  • U.S. Naval Academy: A prestigious institution with rich history and stunning architecture, offering guided tours that provide insight into naval traditions and the training of future officers.
  • Chesapeake Bay Bridge: An iconic engineering marvel that connects the Eastern Shore to the mainland, perfect for a scenic drive with impressive views of the bay and the city skyline.
  • Sandy Point State Park: A beautiful national park ideal for outdoor enthusiasts, featuring sandy beaches, hiking trails, and picnic areas, all set against a backdrop of picturesque scenery.

Things to do recommended for couples

For a romantic getaway on Kent Island, indulge in wine tasting at St. Michaels Winery, embark on an adventurous sailing trip with Annapolis Sailing School, or enjoy an enchanting performance at the Ballet Theater of Maryland. Each experience promises to create lasting memories together.

Things to do recommended for families

Your family will love visiting the Navy-Marine Corps Memorial Stadium, a vibrant sports venue just 6.2km from Kent Island. For some arcade fun, head to the Annapolis Bowl, 8.1km away, or catch a game at Alumni Hall, only 5.6km from your base.

Things to do recommended for groups

Groups visiting Kent Island can explore the Paul Reed Smith Guitars store for an authentic musical experience, shop at the Queenstown Premium Outlets for a blend of business and entertainment, or enjoy a round of golf at the picturesque Queenstown Harbor Golf Club, perfect for sports enthusiasts.

Booking with Vrbo is a breeze

Are you seeking to make your next getaway more affordable? Being flexible with your travel dates can lead to considerable savings, as prices often fluctuate. Additionally, booking a longer stay can yield even greater discounts. To discover a Vrbo property that suits your budget, utilise our filters to sort by price, location, and type of holiday rental.

Where to stay near Kent Island

Kent Island, Maryland, offers a delightful blend of outdoor adventures and tranquil escapes, perfect for families and couples alike. Explore the stunning waterfront, indulge in kayaking, and immerse yourself in the island’s rich history. Nearby towns exude a friendly atmosphere, making it easy to relax and enjoy the local culture. Whether you're seeking a romantic getaway or a family-friendly holiday, Kent Island presents an idyllic destination for all types of travellers.

  • Annapolis: Annapolis, located a mere 5.6km from Kent Island, is a charming city renowned for its rich maritime history and vibrant cultural scene. Visitors can immerse themselves in family-friendly activities, explore educational institutions, and indulge in retail therapy at local shopping centres. The city is dotted with iconic landmarks such as the United States Naval Academy, stunning waterfront views, and nearby beaches and lakes, making it an excellent destination for outdoor enthusiasts and city explorers alike.
  • Northern Chesapeake Bay: Just 621m from Kent Island, Northern Chesapeake Bay is a breathtaking locale that offers a picturesque escape into nature. This region is perfect for those seeking outdoor adventures and romantic getaways, with its scenic vistas and tranquil waters. Visitors can enjoy recreational activities, including golf and leisurely strolls along the beach. The area is also home to significant landmarks such as monuments and bridges, providing ample opportunities for exploration and photography against stunning backdrops.
  • Stevensville: Located 1.9km away from Kent Island, Stevensville is a delightful city that boasts a perfect balance of outdoor fun and family-oriented attractions. The city features various recreational areas, shopping centres, and a charming boardwalk that invites leisurely walks. Highlights include captivating beaches and the nearby national state park, which offers hiking trails and wildlife spotting opportunities. Stevensville is ideal for those looking to enjoy scenic views while engaging in family-friendly activities.

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.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
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

What do I need to keep in mind when booking a vacation around Kent Island

If you're travelling with a group, family, pets, or planning a longer stay, it's important to filter your options according to your specific needs. Here are some helpful Vrbo booking tips to guide you.

  • Traveling to Kent Island with a group: Think about how many bedrooms you'll require, along with features like a fully equipped kitchen or outdoor areas for group gatherings. Thankfully, you can easily filter for these options and much more on Vrbo.
  • Traveling to Kent Island with young kids: Travelling with young children can present its challenges. It's important to prioritise their comfort and safety, as well as to look for suitable amenities, like a private swimming pool. Additionally, it would be wise to think about your closeness to attractions that are friendly for families.
  • Taking your pets with you to Kent Island: For many, a family holiday feels incomplete without their furry companion by their side. If this resonates with you, take a look at Vrbo properties that welcome pets. Most of these pet-friendly accommodations offer feeding bowls and beds, ensuring 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 great 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 accommodations. Don't forget to include features like a parking space, a well-equipped kitchen, or a private pool in your search criteria as well.

Vrbo Trips: Planning as easy as it gets

Vrbo's unique Trip Board offers you a convenient way to plan your next adventures, pick up from where you last left off, or easily view and organise your travel arrangements. You can now access the properties you've previously saved or booked under Potential, Upcoming, or Current Trips. To explore Trip Boards, simply 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:

  • U.S. Naval Academy Golf Club (8.3 mi / 13.4 km)
  • Queenstown Harbor Golf Links (9.3 mi / 15 km)
  • Queenstown Harbor Golf Club (9.3 mi / 15 km)
  • St. Michaels Winery (12.2 mi / 19.7 km)
  • Maryland Renaissance Festival (14.6 mi / 23.5 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:

  • Chesapeake Bay Environmental Center (5.4 mi / 8.8 km)
  • Sandy Point Beach (6.3 mi / 10.1 km)
  • Bay Ridge Beach (6.9 mi / 11.1 km)
  • Carrs Beach (7.7 mi / 12.4 km)
  • Eastern Neck National Wildlife Refuge (8.6 mi / 13.9 km)
  • Maryland Quiet Waters Park (9.1 mi / 14.6 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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