Lake house holiday rentals in Middletown

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Top-rated lake house rentals in Middletown

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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

4.91 out of 5 average rating, 58 reviews

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

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

4.99 out of 5 average rating, 166 reviews

Swan Lake

Swan Lake is a newly constructed home in Southern Lancaster County. The house is situated on 12.5 Acres with pond, 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 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

Guest favourite

A clear, inviting saltwater pool is framed by textured ivory paver stones. Lush greenery and ornamental shrubs line the pool area, providing a tranquil atmosphere. The expansive water view extends beyond the pool, under a bright blue sky adorned with fluffy clouds.

Home in Elkton

4.94 out of 5 average rating, 16 reviews

Breathtaking Waterfront w/pool and private dock

Now Booking winter and Summer 2026 the summer is going quick! The incredible 4-bed 2-bath water-facing home is the ultimate getaway Featuring a fixed boat dock and a floating dock, you can easily bring your boat (up to 21 feet with a $125 docking fee) Enjoy a variety of water sports, including the provided kayaks (4) and paddle boards (2) Pool/Spa are Seasonal **open mid May through Sept only** Pool and hot tub are **closed Oct - mid May** We do not have a separate stand alone hot tub

Top guest favourite

A spacious living room features a large sectional sofa, a coffee table, and a TV stand. Natural light enters through multiple windows, illuminating the wood flooring. An open view leads towards the kitchen area, where bar stools are positioned at a counter.

Home in Stevensville

4.93 out of 5 average rating, 341 reviews

❤️Charming Coastal/Country Home w/3 Acres & Sauna!❤️

Relax in this Stylish Coastal-Country Home w/Sauna & 3 acres of outdoor living! Perfect for Families & Wedding Groups! We're conveniently located to many areas/cities: Annapolis- 15 miles Baltimore- 40 Wash. DC- 45 Easton- 30 Enjoy a Self-Check-in to this Beautiful Home that is perfectly situated near all the local Kent Island Restaurants, Shops, Attractions, including Chesapeake Beaches. This is a Non-Smoking House. Also No Pets or Parties & 14 max guests (8 max adults). Book Today!

Guest favourite

Home in Bridgeton

4.86 out of 5 average rating, 66 reviews

Modern Lakefront Getaway | Jersey Shore

Enjoy breathtaking sunrises and sunsets over the lake while sipping your favorite hot beverage. Snuggle up on comfy modern décor in front of the warm crackles of the fireplace. Surprise her with the perfect Romantic Getaway! Treat your family to the perfect Family Adventure! A nature enthusiast’s dream! 360 degree gallery great for bird watching and star gazing. Escape the city and enjoy hiking trails and sip your favorite wine at the nearby winery, all at the Jersey Shore countryside!

Top 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

5 out of 5 average rating, 36 reviews

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!

Guest favourite

An outdoor seating area is presented with two dark wooden adirondack chairs positioned around a stone fire pit. A scenic view of the Susquehanna River and hills is framed by trees, with a soft sunset glow illuminating the sky.

Home in Pequea

4.92 out of 5 average rating, 184 reviews

Charming River view cottage

Take it easy at this unique and tranquil getaway. River view cottage is nestled up on a hillside with beautiful views of the Susquehanna river and Pequea creek. Come relax and enjoy the beauty of the outdoors, the magical sunsets with multiple outdoor seating areas, flower gardens and an outdoor fire pit. The cottage is tucked back in on 5 acres allowing for full privacy. The cottage was built in the 1950s and has a unique, charming character for you and your family/friends to enjoy!

Guest favourite

A lush green yard borders a calm body of water, where a private pier is visible. Flower beds with white and pink blooms add color to the scene. A small boat is moored at the pier, with trees providing shade along the waterfront.

Home in Annapolis

4.97 out of 5 average rating, 90 reviews

Annapolis USNA Waterfront Cottage w/Pier & Firepit

Kick back and relax in this calm, charming newly renovated coastal farmhouse waterfront two-story home with private pier/dock! Gorgeous sunrises! Experience fresh Maryland Crabs & fish caught from your private pier & enjoy the peace, serenity, bay breezes & waterfront green space! Connect to nature and explore Meredith Creek on the Chesapeake Bay by kayak or boat! Super CLEAN & new with water views from dining, living room, kitchen and bedroom! 1.5 miles to the Beach!

Guest favourite

An aerial view of a charming colonial home surrounded by lush greenery and mature trees. A well-maintained lawn with brick pathways leads to the house, which features a gray roof and white siding. The Cohansey River is visible in the background.

Home in Bridgeton

4.96 out of 5 average rating, 233 reviews

WATERFRONT w/ Hot Tub & Fire Pit | 4 Bedrooms

**Relaunching April 15 - secure current rates before they adjust.** Tucked along the banks of the Cohansey River, The Foxtail enters its new chapter this spring. A restored 1860s colonial balancing historic character with modern ease, it has been thoughtfully refined into a more elevated retreat that so many of our guests return to year after year. Reservations secured by April 14 lock in existing pricing while enjoying the full relaunch. Rates adjust April 15.

Guest favourite

Home in Salem

4.95 out of 5 average rating, 128 reviews

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!

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

4.99 out of 5 average rating, 68 reviews

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!

Guest favourite

A serene river view features vibrant orange and pink hues reflected in the calm water at sunset. Silhouetted dock posts and boats create a tranquil atmosphere against the expansive sky, enhancing the peaceful setting of the Elk River.

Home in Elkton

5 out of 5 average rating, 21 reviews

The River House - waterfront

Relax with the whole family at this peaceful home on the Elk River. Enjoy breathtaking sunsets in the backyard overlooking the river. The kids will love running and splashing around in the yard. Outside patio features sectional sofa, Adirondack chairs and a fire pit to enjoy nights on the river. Plenty of restaurants and things to do in the area. Come enjoy the beauty of life on the Chesapeake!