Kent Island holiday homes

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Holiday rentals with weekly discounts – Kent Island

Showing deals for:6 Nov - 13 Nov

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Why visit Kent Island

  • Outdoor adventures: Embrace the island’s natural beauty with beach activities, marinas, and scenic parks perfect for day outings.
  • Historic heritage: Discover the rich history through preserved houses and landmarks that tell the story of Kent Island.
  • Family-friendly charm: Enjoy a welcoming environment with plenty of activities suited for families and groups.
  • Cultural experiences: Immerse in local traditions and community events reflecting the island’s unique character.
  • Relaxed atmosphere: Unwind in a tranquil setting, ideal for a laid-back holiday amidst nature and heritage.

Top attractions near Kent Island

Kent Island offers a delightful blend of outdoor adventures and cultural experiences, ideal for families, groups, and couples. Explore urban parks, marinas, and historic houses that showcase the island's rich heritage and scenic beauty. With plenty of outdoor and beach activities, Kent Island is perfect for a relaxed holiday that combines nature, history, and local charm.

  • Sandy Point Beach: A picturesque beach destination featuring soft sand and stunning views of the Chesapeake Bay, perfect for relaxing in the sun or enjoying a swim.
  • Annapolis Maritime Museum: This engaging museum showcases the rich maritime heritage of the area, offering interactive exhibits and insights into local history and culture.
  • Bay Ridge Beach: A charming beach spot ideal for sunbathing and picnicking, with a friendly community vibe and beautiful scenery along the bay.

Things to do recommended for couples

For a romantic getaway on Kent Island, enjoy a sunset sail on the Chesapeake Bay, explore the charming local shops in historic Stevensville, or indulge in a candlelit dinner at a waterfront restaurant. Don’t miss the scenic views from the Kent Narrows Bridge for a perfect photo opportunity.

Things to do recommended for families

Families can explore the beautiful Chesapeake Bay with kayaking adventures, visit the fun-filled Kent Island Farmers Market, or enjoy a day at the thrilling Terrapin Nature Park, perfect for picnics and nature walks. Don't miss the scenic views while cycling along the picturesque trails.

Things to do recommended for groups

Explore the scenic Chesapeake Bay by taking a group kayak tour, or enjoy a delightful seafood feast at a waterfront restaurant. For a bit of fun, consider a visit to the local escape rooms that challenge your teamwork skills.

*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

Whether you're journeying with friends, as a whānau, bringing your four-legged mates along, or planning an extended stay, be sure to refine your search with the most important filters. Here are some Vrbo booking pointers for you.

  • Traveling to Kent Island with a group: Consider how many bedrooms you'll require, along with features like a fully-equipped kitchen or an outdoor area for group gatherings. Thankfully, you can refine your search on Vrbo to include all of these options and more.
  • Traveling to Kent Island with young kids: Travelling with young children can present its challenges. It's important to prioritise their comfort and safety, along with suitable amenities like a private swimming pool. Additionally, it's wise to think about your closeness to family-friendly attractions.
  • Taking your pets with you to Kent Island: For many, a family holiday isn’t complete without their four-legged mate tagging along. If that sounds like you, then have a look at Vrbo properties that welcome pets. Most pet-friendly properties provide feeding bowls and beds, ensuring everyone feels right at home.
  • Planning for a long term stay visiting Kent Island: If you're in search of holiday 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 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

Kent Island, Maryland, offers a delightful escape for travellers seeking outdoor adventures and stunning scenery. With its beautiful beaches and picturesque views, visitors can bask in the sun while enjoying a relaxing atmosphere. The island is rich in history, making it a perfect destination for those who appreciate both nature and culture. Families will find a welcoming environment, creating lasting memories amidst the tranquil charm of Kent Island living.

  • Annapolis: Nestled 14km away from Kent Island, Annapolis offers a mix of family-friendly, outdoor and city-themed experiences. The city boasts a blend of educational venues and vibrant shopping centres, providing an urban experience with a touch of coastal charm. Visitors can explore local landmarks such as the academy, bay and beach, which highlight the city’s rich maritime history and scenic vistas. Annapolis is perfect for those seeking a balanced holiday of culture, family fun and outdoor exploration.
  • Kent Narrows: A quaint village located 8km from Kent Island, Kent Narrows is ideal for travellers looking to enjoy an outdoor, family and beach-centric holiday. The village features a delightful boardwalk, accessible shopping centres and a spacious shopping mall centre, ensuring plenty of leisure opportunities. Local attractions include a beautiful bay, beach and esplanade that together create a serene coastal retreat perfect for a relaxed day out.
  • St. Michaels: Situated 19km from Kent Island, St. Michaels invites visitors to experience its outdoor, beach and scenic attractions. The city’s charming boardwalk and recreational areas provide ample space for leisurely strolls and family outings. With the allure of a nearby beach and a picturesque bay, St. Michaels offers a refreshing escape where maritime beauty and outdoor adventures blend seamlessly, making it a must-visit destination for holidaymakers seeking a taste of coastal life.

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.

calendar iconCalendar Monthtemperature iconTemperaturerain iconPrecipitationmostly cloudy iconCloudinessoccupation rate iconOccupancyprice iconPricing
January35.6°F (2.0°C)Light RainMostly SunnyLow
February37.9°F (3.3°C)Light RainMostly SunnyAverage
March44.6°F (7.0°C)Light RainMostly SunnyAverage
April55.0°F (12.8°C)Light RainMostly SunnyAverage
May64.2°F (17.9°C)Light RainMostly SunnyAverage
June73.0°F (22.8°C)Light RainMostly SunnyHigh
July78.4°F (25.8°C)Light RainMostly SunnyHigh
August76.8°F (24.9°C)Light RainMostly SunnyHigh
September70.7°F (21.5°C)Light RainMostly SunnyAverage
October60.4°F (15.8°C)Light RainMostly SunnyAverage
November48.7°F (9.3°C)Light RainMostly SunnyLow
December41.5°F (5.3°C)Light RainMostly SunnyLow

Booking with Vrbo is a breeze

If you’re keen to trim costs on your upcoming journey, consider a flexible approach with your travel dates – prices can fluctuate quite a bit. Additionally, opting for a longer stay could lead to even greater savings. To discover a Vrbo property that suits your budget, simply use our filters to sort by price, location, and the type of holiday rental you’re after.

Vrbo Trips: Effortless planning

Here’s a paraphrased version in a reliable and supportive tone of voice, using New Zealand English phrases:Vrbo’s Trip Board provides a dedicated area where you can start planning new adventures, pick up where you left off with your current plans, or review and organise your bookings. Properties that you’ve either saved or booked are neatly categorised into Potential, Upcoming, or Current Trips. For more details and to explore Trip Boards, please visit: https://www.bookabach.co.nz/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)
  • 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)
  • Paul Reed Smith Guitars (3.6 mi / 5.7 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)
  • 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)
  • Maryland Quiet Waters Park (9.1 mi / 14.6 km)
  • Rocky Point Park and Beach (22.1 mi / 35.6 km)

Frequently asked questions

What is the best area to stay in Kent Island when booking a holiday home?
One of the more sought-after areas for a Kent Island holiday home is Chester. When you lock in your holiday home with Bookabach, 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 home accommodation in Kent Island?
Houses are the most popular style of holiday home in Kent Island, according to our data. Even if you have something else in mind, Bookabach 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 home 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 Bookabach. 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 home amenities in Kent Island?
The most popular home 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, Bookabach holiday properties feature the best amenities for ultimate relaxation with the people that matter most.
Can I find two-bedroom holiday homes 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 homes with WiFi in Kent Island?
Kent Island has 23 holiday homes 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 Bookabach homes will keep you online.
How old do you have to be to rent a holiday home in Kent Island?
The minimum age allowed can vary across properties on Bookabach, so be sure to look at the rules of the holiday home in Kent Island you want. But normally, it's 16, 18 or 21.
How long can I rent a holiday home in Kent Island for?
The length of time you can rent a holiday home 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.