Lake house holiday 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

Home in Stevensville

4.93 out of 5 average rating, 289 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

Home in North East

4.97 out of 5 average rating, 62 reviews

Boho River Cottage

A Chesapeake Bay getaway located on the North East River. The renovated cottage sleeps 4 people with secluded backyard gardens. The cottage includes water access, kayaks, bikes, and a SUP board. Explore the town of NE to shop and dine in the region's top restaurants. Minutes from Elk Neck State Park which offers hiking, fishing, bird watching, and mountain biking. Visit the lighthouse, Havre de Grace, Hollywood Casino, or relax & catch a sunset with a cool breeze coming off the North East River.

Top guest favourite

Home in Holtwood

4.99 out of 5 average rating, 156 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

Home in Port Deposit

4.9 out of 5 average rating, 48 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

Top guest favourite

Home in Millington

5 out of 5 average rating, 32 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!

Top guest favourite

Home in Charlestown

4.99 out of 5 average rating, 69 reviews

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.

Guest favourite

Home in Salem

4.96 out of 5 average rating, 109 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 backdoor directly onto the large deck and sandy beach. Message us for information about the local wineries and distilleries or for kayaking!

Guest favourite

Home in Bridgeton

4.95 out of 5 average rating, 217 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.

Top guest favourite

Home in Worton

4.99 out of 5 average rating, 73 reviews

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.

Guest favourite

Home in Charlestown

4.98 out of 5 average rating, 55 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

Home in Earleville

4.92 out of 5 average rating, 172 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

Home in Millington

4.94 out of 5 average rating, 35 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!