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Kent Island vacation rentals

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Vacation rentals with weekly discounts - Kent Island

Showing deals for:Oct 17 - Oct 24
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Find out more about Kent Island

Why visit Kent Island

  1. Stunning waterfront views: Enjoy picturesque scenery and stunning sunsets along Kent Island's beautiful coastline.
  2. Outdoor adventures: Engage in various activities like kayaking, fishing, and hiking in urban parks and along scenic trails.
  3. Rich cultural experiences: Discover historic houses and vibrant art scenes that reflect the island's unique heritage.
  4. Family-friendly atmosphere: Kent Island offers a welcoming environment with parks and beaches perfect for family outings.
  5. Charming accommodations: Choose from private vacation homes, cozy cottages, and comfortable apartments for a memorable stay.

Popular types of accommodation around Kent Island

If you’re exploring vacation rentals in Kent Island, you’re in for a treat! Our most popular accommodations include houses, charming cottages, and comfortable apartments. Whether you’re seeking ideal house rentals for a family getaway or a cozy Annapolis apartment for a romantic retreat, we have the perfect options to ensure your stay is memorable and enjoyable.

  • Houses: The top choice for visitors in Kent Island, these homes offer spacious accommodations perfect for families or groups seeking a home-like atmosphere.
  • Cottages: Quaint and charming, cottages provide a cozy retreat for couples and small families wanting a peaceful getaway.
  • Apartments: Ideal for travelers seeking convenience, apartments offer modern amenities and easy access to local attractions.
  • Condos: Offering a blend of comfort and luxury, condos are a popular choice for those wanting resort-style living.
  • Cabins: Nestled in nature, cabins provide a rustic experience for those looking to escape into the great outdoors.**

Top attractions near Kent Island

Kent Island, Maryland, is perfect for outdoor, family, and romantic getaways. Visitors can explore a variety of attractions, including urban parks, beautiful beaches, and historic houses that offer rich cultural experiences. Whether you're seeking adventure or relaxation, Kent Island caters to travelers of all kinds, making it an ideal destination for your next vacation.

  1. U.S. Naval Academy: A historic institution located 9 miles from Kent Island, the U.S. Naval Academy offers stunning architecture and rich maritime heritage, perfect for history buffs and those interested in military tradition.
  2. Chesapeake Bay Bridge: This modern marvel, just 6 miles away, connects the Eastern Shore to the Western Shore, providing breathtaking views of the bay and a vibrant atmosphere that captures the essence of coastal life.
  3. Sandy Point State Park: Located 7 miles from Kent Island, this national state park is an outdoor lover's paradise, featuring scenic trails, sandy beaches, and opportunities for adventure, such as hiking and kayaking.

Things to do recommended for couples

For a romantic getaway on Kent Island, explore St. Michaels Winery for a delightful tasting experience, sail the waters with Annapolis Sailing School for adventure, or enjoy a captivating performance at the Ballet Theater of Maryland. Each offers unique vibes for couples to cherish together.

Things to do recommended for families

Your family will love visiting the Navy-Marine Corps Memorial Stadium for an exciting sports experience, just 10 miles from Kent Island. For some arcade fun, head to the Annapolis Bowl, located 13 miles away, where adventure awaits for everyone. Don’t miss Alumni Hall, only 9 miles away, for more sports excitement!

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

When planning your trip—whether with a group, family, pets, or for an extended stay—it's important to set the right priorities in your search. 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, as well as features like a full kitchen or outdoor area for group gatherings. Luckily, you can easily filter for these options and much more on Vrbo.
  • Traveling to Kent Island with young kids: Traveling with young children can be demanding. It's important to prioritize their comfort and safety, along with 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 families, a vacation wouldn't feel complete without their furry companion along for the adventure. If you can relate, consider exploring Vrbo listings that welcome pets. Many of these pet-friendly homes come equipped with feeding bowls and cozy beds, ensuring that every member of your family feels comfortable and at home.
  • Planning for a long term stay visiting Kent Island: If you're in search of vacation rentals offering discounts 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 rental options. Don't forget to include features like a parking space, a well-equipped kitchen, or a private pool in your search criteria as well.

Where to stay near Kent Island

Discover the charm of Kent Island, Maryland, where sunny weather and stunning waterfront views create the perfect backdrop for outdoor adventures and romantic getaways. Explore the idyllic island's family-friendly atmosphere, rich history, and vibrant art scene. Nearby, you'll find welcoming neighborhoods boasting beautiful homes and inviting parks, making Kent Island an excellent destination for relaxation and exploration. Embrace the Shore Thing and create unforgettable memories in this picturesque setting.

  • Annapolis: Annapolis, located 9 miles from Kent Island, is a charming city known for its rich history and vibrant waterfront. As the state capital of Maryland, it offers a blend of cultural experiences and outdoor activities. Visitors can explore the United States Naval Academy, stroll along the picturesque waterfront, or indulge in shopping at local boutiques. With its historic architecture and lively atmosphere, Annapolis is perfect for families and those seeking an urban adventure.
  • Northern Chesapeake Bay: Just 1 mile from Kent Island, Northern Chesapeake Bay is a nature lover's paradise. This area is renowned for its stunning water views and outdoor recreational opportunities, making it ideal for couples and adventure seekers. Enjoy activities such as kayaking, fishing, or simply relaxing on the beach. The scenic beauty of the region, highlighted by its iconic bridges and monuments, creates a romantic backdrop for any getaway.
  • Stevensville: Located 3 miles from Kent Island, Stevensville is a delightful city that offers a perfect blend of outdoor fun and family-friendly activities. Visitors can explore the local recreational areas, shop at the nearby shopping centers, or enjoy a leisurely stroll along the boardwalk. With attractions like beautiful beaches and the nearby national state park, Stevensville provides plenty of opportunities for scenic adventures and relaxation amidst nature.

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

Looking to save on your next vacation? Consider being flexible with your travel dates, as prices can fluctuate significantly. Moreover, extending your stay can often result in substantial 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.

Unlock savings with One Key

Reserve an eligible Vrbo for your group getaway and earn OneKeyCash™ on your booking. Being the planner comes with its perks! When you join our travel rewards program, One Key, you’ll gain immediate access to member discounts and the ability to earn and redeem OneKeyCash™ on qualifying reservations. Sign up today and begin enjoying your savings!

Vrbo Trips: Planning as easy as it gets

Vrbo's cutting-edge Trip Board offers you a convenient way to plan your travels, pick up from where you last left off, or manage your itinerary. You can easily access properties you've saved or booked in the sections for Potential, Upcoming, or Current Trips. To explore Trip Boards, simply visit: https://www.vrbo.com/en-ca/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 biking, 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 find top things to see and do while you're in the area? Although it can be tempting to stay in your comfortable vacation rental, you'll want to check out everything that makes Kent Island a fun place to get away. Here are some of the major attractions to see, all within 30 miles (48.2 km) of the city center:

  • 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 looking for exciting outdoor activities or just want to appreciate the scenery, Kent Island is a great place to get outside. Here are some of the area’s most stunning sights, all within 30 miles (48.2 km) of the city center:

  • 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 most popular type of vacation rental accommodation in Kent Island?
Villas are the most popular kind of vacation rental in Kent Island, according to our data. Even if you have a different idea about what you'd like, Vrbo has vacation homes in loads of sizes and shapes. Filter our options to find your perfect Kent Island pad.
How much does it cost to rent a vacation rental in Kent Island?
Property type, length of stay and time of year are some of the conditions that can influence the price of a vacation home. Simply add your travel dates to find your ideal fit. From homey country cottages to expansive luxury villas, all Vrbo vacation rentals provide amazing 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 determine the cost of your beachside escape. Type in your Kent Island travel dates to view your options on Vrbo. Looking for basics like WiFi, or perks like a private pool? Use our filters to pick the features and amenities you need.
What are popular rental amenities in Kent Island?
Some of the most popular rental amenities people search for in Kent Island are a barbecue grill, a sauna and an ocean view. Whether you're on the road with your besties, family or even pets, Vrbo vacation rentals come with the best amenities for beginning new traditions with the people closest to you.
Can I find two-bedroom vacation rentals in Kent Island?
Gather your family and enjoy peace, privacy and comfort in one of the three two-bedroom vacation rentals Kent Island has to offer.
Are there vacation rentals with WiFi in Kent Island?
You can pick from 26 vacation rentals with WiFi in Kent Island. If you'd like to disconnect from daily life on your escape, but still want to be connected to the internet, these getaways are for you. Narrow your search by applying the WiFi filter on Vrbo.
How old do you have to be to rent a vacation rental in Kent Island?
The minimum age is usually 16, 18 or 21. It can differ across properties on Vrbo, so look at the rules of your chosen Kent Island stay before booking your stay.
How long can I rent a vacation rental in Kent Island for?
The amount of time you can rent a Kent Island vacation home for differs depending on the property. Simply tap in your preferred travel dates to browse available options that offer extended stays. They have all you require to make your extended trip more comfortable and enjoyable, such as kitchens and backyards. Some vacation homes might also offer discounted weekly or monthly prices, so you can stick around for longer for less.
Does Vrbo offer discounts for vacation homes in Kent Island?
In Kent Island, you'll find some incredible discounts and bargains for weekly and monthly discounts on vacation rentals, as well as newly listed homes on Vrbo. Whether it's a mini escape or a couple of weeks away, we've got a variety of options that'll suit your style.

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