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Welcome to The Landing at Kent Island, featuring 5 bedrooms and lots of space to gather together.
You will have a private pool, cozy fire-pit, and panoramic water views (you’ll might even see egrets, ospreys, herons, and eagles). 
Designed to feel like a hotel but with the space and comfort of a home. Plus fun touches like a vintage record player, kids playroom, and a “car bar” for entertaining. 
The Landing is ready to welcome you! We put our heart and soul into this house and are so grateful to our guests. 
Enjoy the Island life!
GATHER 
🛋️ Great Room: Featuring soaring wooden cathedral ceilings and 270’ water views, this is our favorite spot in the house. With three distinct zones (dining area, seating area, and playroom), this is the heart of the house. The seating area features an oversized sectional, vintage record player, electric fireplace and 65’ flatscreen tv. The Chesapeake Bay themed kids playroom has lots for the kids to explore. 
🛋️ Living Room: The stylish living room is located next to the entry hall and features the comfiest sofa and two swivel chairs as well as a TV and a board game cabinet. 
🛋️ Unplug Zone: Our third living area features 4 arm chairs surrounding a round coffee table making it the perfect gathering spot for conversation and games. Facing a decorative (non-working) fireplace with a pairing by local artist, Kim Hovell. 
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EAT 
🍽️ The Kitchen is ready for your group with everything from a waffle maker to baking sheets and dishes. Dishwasher, oven, microwave, and full-sized fridge (and the sink has a view of the water!) 
🍽️ Two indoor dining areas include the kitchen dining room that seats 8 and the Great Room dining area that seats 10 and features great water views. 
☕️ Our signature “But First, Coffee” bar is in the kitchen. With logo mugs, a French press, and both keurig and Nespresso pods, you will be able to enjoy a peaceful hot cup of coffee anytime. 
————- 
SLEEP 
🛌 Primary Suite (Bedroom 1): The primary suite is a serene retreat, with a king bed, complete with panoramic water views, a spacious dual vanity bathroom with a soaking tub and separate shower, an in-room coffee bar, TV, closet, and a private office nook.
🛌 Bedroom 2: Featuring a queen bed, direct water views, closet, TV, closet, and vintage themes decor. Next to a full bath in the hall. 
🛌 Bedroom 3 (Kids bunk room): Ahoy Mateys! This pirate themed bunk room features two sets of bunk beds (sleeps 4) and plenty of pirate decor to entertain the wee ones! 
🛌 Bedroom 4: This bedroom features a queen bed, California coastal decor, front yard views, TV, en-suite full bath, and a closet. 
🛌 The Landing Lounge (Bedroom 5): This room is off the entry hall and features the “The Landing” logo wall. It has a day bed that opens up to a queen sleeper. The room can be left as a lounge or for sleeping privacy has a barn door on one side and black-out drapes on the other side. This room is next to a half bath. You access the full bath upstairs (shared full bath with Bedroom 2 and kids room).
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OUTDOORS 
💦 Pool: Our gorgeous private pool has water views, is fully fenced when open for the season (open April to October), and is surrounded by loungers, swivel chairs, and umbrellas. We want you to feel like you are at your own resort!
🦀 Outdoor Dining: Our outdoor table seats 10 people and is a great place for crab feasts. We also have a bistro table for 2 and our “car bar” which is great for setting up your spread or for letting the kids set up a lemonade stand. 
🔥 Firepit: Our propane firepit sits on sand and has 8 Polywood Adirondack chairs surround it along with solar lights. From s’mores in the evening to a great place for a quiet coffee in the morning, it’s one of our favorite places. 
💧Waterfront: The Landing sits on Chews Creek which feeds into the Chesapeake Bay. Swimming is not recommended in the creek. You ma see our beautiful wildlife including eagles, herons, osprey, and egrets. 
🌊 Beach: The Landing is a 10 minute walk to the community beach. Here you can enjoy Chesapeake bay sunsets and put your feet in the sand. The backyard shed is fully stocked with beach chairs and lawn games. 
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KENT ISLAND 
You are within minutes of wineries, seafood restaurants, marinas, parks, art galleries, hiking trails, and boutique shops. There are also conviences like Target, grocery stores, and Starbucks nearby. Golf, boat rentals, and wedding venues are all nearby, making this a versatile destination for family vacations, celebrations, or peaceful retreats by the water.
- Host sunset cocktails at the “car bar” 
- Dine on local crab and oysters at nearby seafood restaurants 
- Explore Kent Island’s scenic biking and hiking trails 
- Browse local shops and art galleries in nearby Stevensville 
- Play golf at Queenstown Harbor Golf Links 
Places of Interest
- Chesapeake Bay Bridge – iconic gateway to the Eastern Shore 
- Love Point Vineyards & Winery – scenic waterfront tastings 
- Kent Narrows – restaurants, marinas, and nightlife on the water 
- Matapeake Beach – family-friendly swimming and trails 
- Chesapeake Bay Environmental Center – nature and kayaking adventures 
- Annapolis, St. Michaels, Easton, and Oxford 
THINGS TO KNOW
You may access the entire home and yard with the exception of the garage and the two locked closets upstairs. 
Our neighbor, Kim, is lovely and will be available to assist you during your stay. 
Primary guest must be 25+ and be present for the duration of the stay. 
The Landing is located in a quiet residential neighborhood. The onsite caretaker is the next-door neighbor. 
Please note that part of Island life is having well water. As a result, bottled water is recommended for drinking / cooking. 
No smoking anywhere on property (inside or outside). 
Swim in pool, beach, and waterfront at your own risk, no lifeguard, owner and manager assume no liability.

NEW - Waterfront Kent Island | Pool | Firepit | Kid-Friendly

We stayed at Jenna’s beautiful place for annual Thanksgiving get together, it was me and my family, my two sisters and their families. We spent 4 nights. This was a dream come true for all of us as the place was gorgeous and beautifully maintained, it looked like a lot of thought and love went into preparing this home for guests. We all loved everything about Jenna’s place in Kent Island. However, the most important and impressive thing is that what a great host Jenna is. From the time I booked, she was constantly in touch, she gave clear directions and we found the place to exceed our expectations. She was not there but we felt her presence because everything had a personal touch to it. We are already planning to go again in summer. Lovely home and a super host!! Jenna.

Thanksgiving Stay

A real gem on Kent Island!!!
Don't discount the # of reviews. This place is a new vacation rental and it is worth your look. 
We really loved our stay. Jenna has done a great job with the place. It's warm and inviting. Great for gathering and rest. Love the floor plan and the way she's appointed the place. This is a really quality vacation rental. 
Jenna was an absolutely fabulous host! 
She made it a great rental experience.

A Real Gem on Kent Island

Our Christmas stay at The Landing was absolutely wonderful. We traveled with our oldest daughter and son-in-law, our grandson, and our youngest son who had just graduated college, and it was the perfect place for our family to relax and reconnect. Coming from our busy lifestyle in Washington, DC, The Landing felt like a true retreat.
Some of our fondest memories were simply slowing down, enjoying the peaceful setting, and being together in such a beautiful home. The Landing is stunning, and the renovations were clearly done with great care and style—comfortable, elegant, and thoughtfully designed.
This home provided the perfect backdrop for a memorable holiday, and we are so grateful for the experience. We would absolutely return and highly recommend The Landing to anyone looking for a relaxing and special getaway.

Christmas Stay

We absolutely enjoyed the property. It has everything we needed for a family vacation.

They thought of everything

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