Holiday rentals in Middletown

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Top-rated holiday rentals in Middletown

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Guest favourite

Barn in Ronks

5 out of 5 average rating, 155 reviews

The Carriage House: Beautiful Farmland Views.

The Carriage House is the second floor of our cedar stables that was turned into an apartment years ago. It was completely redone this spring and professionally decorated to make it a cozy + luxe retreat with views to die for. While we no longer use the stables to house animals we still keep a few head of cattle + sheep in the pasture for your enjoyment. The wall of windows along the back of the apartment offer you the most stunning views of the surrounding farmland and an unforgettable sunrise.

Guest favourite

Guest suite in Smyrna

4.82 out of 5 average rating, 119 reviews

King's Landing, Simple & Unique

Our charming home, built circa 1800's, updated with addition's in the 1930's and brought into the 21st century, totally revamped and modernized, 2020. Located within walking distance of downtown Historical Smyrna, where charming pubs and stores await you. Enter your quarters, through the 'Milk Room', pass your private full bath, by the spiral staircase to your spacious private bedroom suite, nestled below a cathedral ceiling on the second floor. Oh, Dover Downs and Wesley college are close by

Guest favourite

Tiny home in Wilmington

4.97 out of 5 average rating, 321 reviews

Unbelievably Charming Tiny Home

Completely private stand alone tiny house, comfortable for 1-4 people. Guaranteed the absolute coziest place to stay in Trolley Square. Unusual amenities include: - *Homemade ice cream* - Loaded pantry and fridge - Yoga mats, blocks, & YogaGlo subscription - King size lofted bed Downtown Trolley and Brandywine Park are less than a minute walk. Right next to restaurants, Acme, several coffee shops, bus stop, and bars. Close to many attractions including Longwood Gardens and Winterthur.

Guest favourite

Rental unit in Havre de Grace

5 out of 5 average rating, 115 reviews

Retro Downtown One Bedroom at JoRetro

Indulge in a nostalgic retreat at our renovated mid-century modern apartments in downtown Havre de Grace, situated above JoRetro. Choose from four meticulously decorated units, each inspired by an iconic Pyrex design. Relax on the queen-size bed, with luxury linens, and enjoy retro and vintage items, including Butterprint Pyrex pieces. Explore a variety of restaurants and unique shops, all within walking distance. Don't miss the opportunity to visit the historic Lighthouse and museums.

Guest favourite

Guest house in Quarryville

4.99 out of 5 average rating, 280 reviews

The Olde Wash House on Camargo

Come and relax in our newly remodeled, cozy, cottage style home with it's own private entrance, surrounded by working Amish farms, just outside of town. A short 15 minute drive to Historic Strasburg, Sight and Sound Theater, Antique Shopping, Tangor Outlets and more! Hiking Trails close by include Enola Grade Trail, Pinnacle Point, Muddy Run Park, and Sickman's Mill. If golfing is your desire, Tanglewood Golf Club is just 10 minutes away. We hope you enjoy your stay!

Guest favourite

Rental unit in Frederica

4.96 out of 5 average rating, 270 reviews

Smokefree Lakeside Relaxation

Quiet smoke free lakefront Carriage House studio over garage with separate entrance. Mini Fridge, microwave, dishes. Use of fire pits, canoe, SUP, dock. Lake is fishable and swimmable. Flatscreen HDTV with Premium Channels. WiFi to use with your own device or use my laptop in unit. 45 min from beach. 20 minutes to Dover. 4 parks with walking paths within 10 miles. Close to Dover Air Force Base but not in flight path. Well behaved social pets with responsible owners are welcome!

Guest favourite

Guest suite in Chestertown

4.99 out of 5 average rating, 202 reviews

Beautiful Waterfront Chestertown Getaway

Lovely three room waterfront apartment/guest suite conveniently located minutes from historic Chestertown and Washington College. Beautiful water views, full kitchen, wooded lot, quiet neighborhood, bird watching, biking, running, kayaking. Friendly pets (comfortable with people and our medium rescue dog) are welcome. We donate 5% of proceeds to Kent Attainable Housing, the Animal Care Shelter of Kent County or ShoreRivers conservation—your choice. Make it your home away from home.

Guest favourite

Place to stay in Airville

4.96 out of 5 average rating, 100 reviews

Waterfront Log Cabin with Hot Tub

Situated on the water's edge of Muddy Creek, this newly renovated log cabin offers a unique, luxury getaway for those seeking a stay immersed in all that nature has to offer. While relaxing on the spacious outdoor deck, you will be treated with a panoramic view of Muddy Creek complete with an occasional sighting of the neighborhood eagle. Perfectly set up for a romantic getaway for two, The Log Cabin on Muddy Creek was created to provide a space for couples to rest and reconnect.

Guest favourite

Cottage in North East

4.97 out of 5 average rating, 477 reviews

Persimmon Pastures

A quiet country setting in North East MD..located on a 7 acre horse farm with easy access to I95. Enjoy all the serenity of the country yet close to the shopping, marinas, and within 50 mile access to Baltimore, Wilmington and Philadelphia. The property is also within 30 minutes of Fair Hill Natural Resources Area with 5,500+acres and 80+ miles of trails for hiking, biking, and beautiful scenery. Pets are allowed. A pet (dog/cat) fee of $5/night/pet will be requested.

Guest favourite

Cottage in North East

4.94 out of 5 average rating, 301 reviews

Cottage Just Off North East's Main Street

Our cozy cottage is located just off Main Street in North East, an easy walk to restaurants, shops and pubs. The cathedral ceilings and exposed rafters create an unexpectedly dramatic space you will find warm and inviting. The relaxing back deck looks down toward a creek that flows through the neighboring property. Our cottage is the perfect place to stay when you're on the road for work, or a romantic weekend (or mid-week) getaway.

Guest favourite

Guest house in Wilmington

4.85 out of 5 average rating, 395 reviews

Beautiful Modern Fully Equipped Private Guesthouse

Beautiful and modern brand new private apartment. This space is brand new and fully sanitized at all moments. Completely separate space with private entrance, patio, bathroom and kitchenette. Enjoy Netflix on our extra large living room tv or a glass of wine from our honor bar! Location is excellent in a beautiful safe neighborhood with convenient access to I-95, downtown Wilmington and shopping centers.

Guest favourite

Cottage in Coatesville

5 out of 5 average rating, 222 reviews

Charming cottage on 50 acre Chester County farm

Frog Hollow Cottage is a newly renovated getaway located in the heart of the Chester County’s rolling farmland and equestrian community. Overlooking beautiful pastures, the cottage was formerly the large painting studio of Delaware Valley artist Peter Sculthorpe. The studio has been re-imagined as a peaceful retreat for families, friends and couples.