
Lake house vacation rentals in Middletown
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Top-rated lake house rentals in Middletown
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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

LAKE HOUSE S. Waterfront, HotTub, 10 guest, 7 beds
Lake House ~ South is a Waterfront Retreat on the Susquehanna River. Dock space available for your boat in front of the house. Just come to escape and relax and enjoy watching the eagles fly by from the hot tub at eye level. The main deck is 960 sq. ft. with plenty of space for everyone, perfect for watching the incredible sunsets. Or come play on the lake. Lake Aldred is an eight mile lake known for water skiing/fishing/kayaking. Eight eagles nest surround the lake with sightings everyday.

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

❤️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!

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!

Bamboo Sands Villa & Captains Lookout
Where luxury meets coastal by the bay. A perfect spot to make memories, enjoy the views from the house or the hot tub, and we offer a WOOD BURNING FIREPLACE! Welcome to Bamboo Sands Villa & Captain’s Quarters, A peaceful retreat on 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...

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!

WATERFRONT w/ Hot Tub & Fire Pit | 4 Bedrooms
Tucked quietly along the banks of the Cohansey River, The Foxtail is our refuge from the world. A lovingly restored 1860s colonial, it brings together timeless charm and modern ease. Surrounded by wild nature and stillness, it's a place to truly tap out, reconnect, and take a deep breath. Whether you're here for a romantic weekend, a cozy family getaway, or a gathering with old friends, this home offers space to stretch out, gather in, and just be.

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!

Cozy 4 BR 3 BA Near Chesapeake City
Peaceful, cozy modern cottage with many amenities in a water-oriented community along the Bohemia River. Just minutes from Chesapeake City and located across the street from the water. Our house is perfect for family vacations, tranquil retreats, girl/guy getaways, weddings, wedding guests. Two queen master BR’s w/private baths on the first floor, second floor has one larger BR w/twins and smaller BR w/daybed +trundle and shared bathroom.

Chesapeake Bay Cottage
This cozy home, just a block away from the Chesapeake Bay, offers the perfect mix of comfort, convenience, and outdoor charm. Tucked into a small, walkable neighborhood, the location is ideal for anyone looking to spend time near the water. Whether you’re planning a fishing weekend, a peaceful solo escape, or an exciting holiday with friends, this space offers the flexibility and ease that make everything feel effortless.

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!
Popular amenities for Middletown lake house rentals
Waterfront lakehouse rentals

Waterfront Retreat

The River House: Family Friendly

Waterfront Oasis w/ Dock, Sunset Views & Arcade

Chesapeake Waterfront Vacation Rental with Dock

⇚Family Getaway⇛| Lakeside + A Nature View |

Mac's Waterfront Wonder

The "Dock House"

Still Pond Creek Headwaters Hideaway
Pet-friendly lake house rentals

River front cottage with private dock & water fun

Waterfront! Private Dock, Boat Tie-Up & Near Town

Entire River Front Home - 4 Bedrooms 4.5 Baths

Waterfront Paradise w/ Pier - kayak to Chestertown

Rogue Wave River Retreat

HOOK WINE & SINKER sleeps 14 w/ Boat Slip and Inn

Boho River Cottage

Backyard Treehouse
Private lake house rentals

Backyard Overlook

Pet-Friendly Dover Retreat w/ Yard & Pool Table!

The Grey Goose by the Chester River

Rockfish Keeper

Comfortable and quiet 3-bedroom-walk to downtown

Beautiful water front house

Rumsey Island Waterfront Retreat

Still Waters River House
Destinations to explore
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- Eastern State Penitentiary




