Lake house vacation rentals in Middletown

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

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

Riverside Retreat: Port Deposit w Boat Slip

Step into our historic haven nestled in Port Deposit! Experience riverside tranquility in this charming Airbnb, boasting quaint decor and modern comforts. Just an 8-minute drive to Great Wolf Lodge and Hollywood Casino, a short 20-minute drive to Susquehanna State Park. Explore the town's rich heritage, stroll along the Susquehanna River, or unwind on the private deck overlooking the water. Walking distance to local attractions, and access to the Tomes landing dock. Boat slip available to rent

Waterfront Winter on the river 2025/26 available!

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

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!

The Cooper House in Charlestown, MD

If you are looking for breathtaking views, great local dining, and a chance to relax with family and friends, then the look no further. The Cooper House in Charlestown, Maryland is a new waterfront property offering 3 individual suites or, for larger parties, the entire house with 4 bedrooms. Each suite has a private entrance, wi-fi, tv, individual climate control, and parking. Unwind on the two-tiered porch or sit by the cozy outdoor fire pit. The property owner lives on site.

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!