Lake house vacation rentals in Middletown

Find and book unique lake houses on Airbnb

Top-rated lake house rentals in Middletown

Guests agree: these lake houses are highly rated for location, cleanliness, and more.

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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, 306 reviews

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

Enjoy your vacation in this Stylish Coastal-Country 3+ Bedroom Home w/Sauna & 3 acres of outdoor living! Perfect for Families & Wedding Groups. We are 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 Parties & 14 max guests. Book Today!

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, 163 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

Four light blue Adirondack chairs are arranged on a grassy area overlooking a calm body of water. A small side table is positioned between the chairs. The sky displays a gradient of soft colors as the sun sets, reflecting beautifully on the water's surface.

Home in Chester

4.95 out of 5 average rating, 57 reviews

The Fitz Inn

Arrive by boat or car to our cozy 1 BD/1BA private 500 sq ft cottage! Enjoy wineries, restaurants, bars & waterfront activities & return to the peaceful Fitz Inn. Sip coffee at sunrise & wine at sunset on Cox Creek (Benton's Pleasure area). Ideal for 2 guests, but can accommodate 4. Listing has AIRBNB exemption from hosting animals, including service & emotional support ones (please see property description for more details). No smoking. Flexible reschedule option with $100 administrative fee.

Guest favourite

A spacious dining area features a large rectangular table surrounded by metal chairs. Natural light flows in through the windows, illuminating the room. A decorative globe and an open shelving unit are present, adding character to the space. The flooring is a light wood, contributing to a warm atmosphere.

Home in Havre de Grace

4.92 out of 5 average rating, 12 reviews

Comfortable and quiet 3-bedroom-walk to downtown

This charming 3-bedroom, 2-bathroom home in historic Havre de Grace is the perfect mix of perfect location and relaxing getaway. Easily stroll to shopping, restaurants and nightlife in downtown Havre de Grace, or take a kayak down to the Susquehanna River. Three private bedrooms feature a king bed, queen bed, and twin bed. One bathroom has a tub-shower combo and the other has a stand-up shower. Kitchen has all major appliances and gadgets. Parking is free and plentiful. It doesn't get better!

Superhost

A two-story home with a wraparound porch is displayed, elevated on stilts. The exterior is clad in light-colored siding, complemented by a dark shingled roof. Surrounding greenery is visible, along with gravel parking beneath the structure. Soft evening light illuminates the windows, creating a welcoming atmosphere.

Home in Port Deposit

4.89 out of 5 average rating, 54 reviews

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

Guest favourite

Home in Elkton

4.94 out of 5 average rating, 16 reviews

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

Guest favourite

Home in Salem

4.96 out of 5 average rating, 118 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!

Superhost

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, 227 reviews

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.

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

4.98 out of 5 average rating, 60 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 waterfront view is presented at sunset, with calm waters reflecting warm hues of orange and pink. Silhouettes of boats are anchored along wooden docks, and gentle ripples add a touch of tranquility to the scene.

Home in Earleville

4.92 out of 5 average rating, 176 reviews

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.

Guest favourite

An expansive deck with a wooden dining table is surrounded by several chairs. Lush greenery provides a natural backdrop, and a winding path leads down toward the waterfront, offering a view of the serene Chester River.

Home in Millington

4.95 out of 5 average rating, 39 reviews

Lark's Nest on the Chester River

Escape to this stylish, private, waterfront home. Fish or kayak off a private dock on the Chester River and enjoy the views and dine alfresco on the oversized deck. Centrally located just 20 minutes from all of the events, eateries, shops and galleries in Historic Chestertown. Perfect, family and pet-friendly home for Washington College students, parents and alumni. Book today for your family reunion, wedding parties, or romantic get-away!

Guest favourite

A single-story home is framed by tall trees, providing shade and greenery. A front porch with a railing is visible, along with a gravel pathway lined with colorful flowers. A storage shed stands in the background, contributing to the outdoor appeal.

Home in North East

4.82 out of 5 average rating, 11 reviews

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.