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 favorite

Home in Stevensville

4.93 out of 5 average rating, 283 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 favorite

Home in Edgewater

4.97 out of 5 average rating, 188 reviews

Annapolis Area Waterside Retreat

This Rhode River home is your perfect getaway to the Annapolis area - whether you’re looking to get away to a unique home overlooking incredible sunsets, a fun weekend with friends along the water, a family trip to the Chesapeake, or a private work retreat away from the bustle of the city, this home has it all. The house is a short drive from DC or Baltimore and unlike any Airbnb this side of the Chesapeake - it is on a 3 acre marina just minutes from Annapolis but private and away from it all!

Top guest favorite

Home in Holtwood

4.99 out of 5 average rating, 153 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 favorite

Home in Riviera Beach

4.95 out of 5 average rating, 143 reviews

Waterfront Cheerful 5 home

Welcome to this brand-new relaxing home with an 80ft pier by the water for your getaway. It is perfect for vacations, retreats, meetings, family reunion and business travelers’. Create memories and beautiful experiences while enjoying the beautiful 5 Bedrooms, 3 Bathroom .one bed on the first floor and four beds on the second floor. House has a large custom kitchen. It is located 11 miles from BWI airport,11.8 miles from downtown Baltimore,17 miles Naval academy and 40 miles to the DC .

Top guest favorite

Home in Millington

5 out of 5 average rating, 28 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 favorite

Home in Edgewater

4.98 out of 5 average rating, 127 reviews

Luxury Modern Home on Water+Hotub- Annapolis 25min

Waterside mid-century modern home, perfectly appointed. Join with colleagues, family, and friends. Paddleboard, roast marshmallows, watch fireworks, take a hot tub or team building. Our "Flight Deck" is perfect for meetings and retreats. Breathtaking, peaceful grounds with an abundance of space. Approximately 2800 SF sits on a 3/4 acre property - perfect for lawn games and zip lining. 20x20 furnished deck + dock Mayo Beach and Beverly Triton 1 mile away. Within an hour of the DMV

Guest favorite

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 favorite

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 favorite

Home in Earleville

4.92 out of 5 average rating, 170 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 favorite

Home in Millington

4.94 out of 5 average rating, 33 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 favorite

Home in Annapolis

4.97 out of 5 average rating, 152 reviews

Cozy Annapolis Cottage.

Stay in the heart of Annapolis! 1 Gig Internet speeds. 220v outlet for EV charging (bring your own cable).Walk to downtown, the Naval Academy and Navy Stadium. Meticulously kept home and newly renovated. Professional cleaning team with every turnover of the house. Stay in the comforts of your own home and experience all that Annapolis has to offer. Art throughout home by local artist Amy Holt Cline.

Guest favorite

Home in Bridgeton

4.96 out of 5 average rating, 214 reviews

WATERFRONT w/ Hot Tub & Fire Pit | 4 Bedrooms

Our favorite place to escape from the daily grind, The Foxtail is an 1860s colonial home that was thoughtfully and carefully renovated to preserve the original character and introduce modern conveniences. A special place to be at any time of year, enjoy sightings of eagles and other animals, tuning in to nature's soundtrack, and of course, looking out over the oh-so-beautiful Cohansey River.