Lake house holiday rentals in Middletown

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Top-rated lakehouse rentals in Middletown

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Guest favourite

Home in Elkton

Breathtaking Waterfront - Christmas on the Water!

2027 Christmas is still available. Now booking for summer 2027. Serenity House in an incredible 4-bed 2-bath waterfront home - The ultimate getaway! Pool/Spa are Seasonal **open mid May through Sept only** Pool and hot tub are **closed Oct - May** We do not have a separate stand alone hot tub. Featuring a fixed boat dock and a floating dock, you can easily bring your boat (up to 21 feet with/ docking fee) Enjoy a variety of water sports, including the provided kayaks (4) and paddle boards (2)

4.95 out of 5 average rating, 20 reviews

Guest favourite

A wooden pier extends from the sandy shore towards a home surrounded by tall trees, with warm light glowing from large windows. The sky displays soft pink and blue hues as the day transitions to evening.

Home in Chestertown

Waterfront Paradise w/ Pier - kayak to Chestertown

Escape to our private paradise where you can enjoy breathtaking sunsets from our pier, catch your own fish/crabs, sit around the fire pit by our 200+ foot private beach while gazing at countless stars, try our outdoor sauna w/panoramic view. It's a destination you can enjoy all year. Our home is located a short bike ride to Historic Chestertown, or you can take one of our kayaks in while you enjoy the Chester River. Bedroom 1: king bed+daybed w/trundle Bedroom 2: Queen Bedroom 3: Queen & bunkbed

4.91 out of 5 average rating, 67 reviews

Top Guest favourite

A serene pond reflects the surrounding greenery, with a fountain spraying water at its center. Two swans glide gracefully across the water. In the background, a gazebo is nestled among the trees, alongside a newly constructed house, enhancing the tranquil setting.

Home in Holtwood

Swan Lake

Swan Lake is located in Southern Lancaster County. The house is situated on 12.5 Acres with a pond and gazebo. This is a secluded family destination in Amish country but close to numerous amenities. You will enjoy beautiful views of the pond from all floors and decks. Numerous hiking trails and the Susquehanna River are within minutes. Working Amish farms surround this property and yet you are within 30 Minutes of Lancaster City. PLEASE NOTE WE REQUIRE RENTERS TO BE A MIN Of 25 YRS OLD

4.99 out of 5 average rating, 180 reviews

Guest favourite

An outdoor fire pit is surrounded by six wooden lounge chairs, arranged on a gravel patio. Lush green grass and trees provide a natural backdrop, while tranquil river views are visible beyond the fire pit, reflecting the soft colors of the sky.

Home in Millington

Anchors Away

Anchors Away beckons as your tranquil waterfront escape! Inside, the cozy gas fireplace awaits. Savor a coffee bar experience and utilize the well-appointed kitchen. Unwind in the screened-in porch with a book and river views. Outdoors, the dock invites relaxation by the water. Gather around the wood fire pit for memorable nights under the stars. Enjoy Kayaks, fishing poles and family games! Anchors Away promises an unforgettable riverside retreat. We look forward to hosting you!

4.93 out of 5 average rating, 45 reviews

Guest favourite

An open living space features high wooden ceilings with exposed beams and large windows allowing natural light to fill the area. A cozy seating arrangement surrounds a central coffee table, while a dining table sits nearby. A large television is mounted on a wall above a brick fireplace.

Home in Abingdon

East Baker Bungalow

Welcome to our home away from home on Bush River! Relax and unwind overlooking the beautiful water where you can bring your own boat. Whether you're here for the weekend to escape the hustle and bustle or bringing all your family and friends for a week on the water, we have something for everyone! Bring your own Boat, kayak or even fishing off your own private pier. Only 40 minutes from Baltimore's airport, 15 minutes to Ripken Stadium and super close to shops and grocery stores!

4.84 out of 5 average rating, 44 reviews

Guest favourite

The back exterior of the vacation home features a spacious lawn with a stone path leading to a large patio area. An umbrella-shaded dining table sits alongside comfortable outdoor seating. A staircase provides access to the upper deck, revealing expansive views.

Home in Aberdeen

Waterfront Family Vacation Home

Relax and unwind in this completely remodeled waterfront vacation home, perfect for family and friends. It boasts four spacious bedrooms, three full bathrooms, a cozy den, a sunroom, a large patio, and an expansive outdoor space. It provides a stunning view of the Bush River and sunsets, with direct access to the water. Immerse yourself in nature’s beauty with kayaks, paddle boards, a fire pit, and outdoor grills/furniture. Perfect place to stay for sports tournaments, too!

4.87 out of 5 average rating, 89 reviews

Guest favourite

A cozy outdoor seating area is set up on a grassy lawn, facing the water. Adirondack chairs and a low sofa surround a fire pit, creating a welcoming space for relaxation. A private dock extends into the Chester River, offering scenic views of the water.

Home in Chestertown

River front cottage with private dock & water fun

Private cottage on the banks of the Chester River. Sleeps 8-14. Private dock with plenty of water activities. This property offers relaxation and serenity as soon as you pull in! Located right on the water with spectacular views of the Chester River, the house is renovated in a cozy, casual farmhouse style. While you will love the house you will spend your days outside enjoying life on the river thanks to your private access to the water and lots of water fun!

4.96 out of 5 average rating, 105 reviews

Top Guest favourite

Home in Lynch

Bamboo Sands Beach Getaway

Where luxury meets coastal by the bay. A perfect spot to make memories, enjoy the views from the house or the hot tub.... Welcome to Bamboo Sands Villa & Captain’s Quarters, A peaceful retreat on a sandy area of the Chesapeake Bay where families can RELAX & reconnect. Here, serenity and fun flow as easily as the coastal breeze. Enjoy sandy beaches without the crowds, the sounds of waves on the bay without the oceanfront price tag, a coastal luxury getaway...

4.96 out of 5 average rating, 27 reviews

Guest favourite

Home in Salem

Beachfront Sunsets on the Water at Oakwood Beach

You’ll instantly relax when you arrive at this private beachfront home on the beautiful Delaware River (2020 River of the year!). This hidden gem is off the beaten path, making it perfect for you to escape the hustle and bustle of your busy day-to-day. You’ll love the amazing sunsets and water fun — walk out the back door directly onto the large deck and sandy beach. Message us for information about the local wineries and distilleries or for kayaking!

4.94 out of 5 average rating, 144 reviews

Top Guest favourite

An aerial view captures a sprawling countryside landscape, featuring a dairy barn with a blue roof and a silo. The main house is visible beside the barn, surrounded by open fields and scattered trees. The horizon showcases a calm body of water in the distance.

Home in Worton

Farm House w/ Water Access (near Chestertown)

The perfect setting for family and friends (up to eight people) to gather and get away to relax. Situated on 140 acres adjacent to Still Pond Creek in Worton, there's room for everyone to spread out -- enjoy the fresh air, outdoor activities and relax in solitude watching abundant wildlife (birds, deer, rabbits, groundhogs, and more!). Chestertown is just 8 miles away with a year round farmer's market, local shopping, art galleries and more.

4.99 out of 5 average rating, 78 reviews

Top Guest favourite

A spacious living area is highlighted by large windows offering views of the sunset. Comfortable seating includes a sectional sofa and a pair of chairs, positioned around a decorative rug. A flat-screen television and an electric fireplace complete the welcoming ambiance.

Home in Charlestown

Catching Sunsets on the Bay

Come and enjoy this brand new home, built for making memories on the Chesapeake Bay! Our spacious 3 bedroom, 2.5 bath is perfect for your next getaway. Our cozy, yet modern home is within feet of the Northeast River where you can take in the beautiful views, go kayaking, swimming or boating, or take a 12 minute drive to the new Great Wolf Lodge! Our home is perfect for couples or families as we have games, toys, and a pack n play if needed!

4.99 out of 5 average rating, 84 reviews

Top Guest favourite

Home in Perryville

Chesapeake Waterfront Vacation Rental with Dock

Relax at this peaceful waterfront vacation rental on the upper Chesapeake. 2 King beds, a Queen, a large Bunk bed, and a Day bed: 5 BRs, 2 Bath with spacious deck. 100 foot dock (has water and electric) with lots of room for water activities and fun in the sun. Tie off your boat or jet skis. 2 kayaks provided. Very clean and comfy. Linens and Kitchen amenities provided. All four 2nd floor bedrooms have smart TVs as does the living room.

4.94 out of 5 average rating, 35 reviews