Vacation rentals in Middletown

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Top-rated vacation rentals in Middletown

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Guest favorite

Barn in Ronks

5.0 out of 5 average rating, 139 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.

Feb 10 – 17

R2,796 ZAR per night

Guest favorite

Guest suite in Dover

4.92 out of 5 average rating, 137 reviews

💖 Edi’s Suite *Privacy & Comfort Away From Home*

THIS IS A SMOKE-FREE PROPERTY w/ a Spacious apartment connected to my home. Large bedroom w/ queen sized bed, queen sized air mattress, living room, dinning nook, kitchenette & bathroom. Just off of the Rt. 1 exit, it's 5 miles from Dover Downs & DSU, 3 miles from Wesley College, minutes from Dover AFB, & 15 min (13.5 mi) via DE-1 S to DE Turf Sport Complex. Rehoboth Beach is 53 min (42.9 mi) via DE-1 S. Bethany Beach is 1 h 7 min (54.0 mi) via DE-1 S Dewey Beach is 53 min (43.2 mi) via DE-1 S

Jun 9 – 16

R1,479 ZAR per night

Guest favorite

Guest suite in New Castle

4.91 out of 5 average rating, 147 reviews

Private Cozy Suburban Master Suite & Sport Room

Must see! Private entrance & parking! Forget your worries in this spacious, exclusive and serene space. Your stay is in an apartment style finished basement almost the size of the house foundation! A Queen size master bedroom, a day bed with two twin beds, a treadmill, a full-size pool table, massage chair, 4 TV’s, Netflix, heated fireplace, living room, fridge, kitchen area. Microwave, iron & more! A short walk to the Kirkwood field and many local shops. Just 10 minutes from Mall & Hospital

Jan 24 – 31

R2,488 ZAR per night

Guest favorite

Guest suite in Newark

4.99 out of 5 average rating, 170 reviews

Spacious, light filled studio 2 blocks from UDel

Our quiet, private studio is located in the historic Old Newark neighborhood, next to the Univ of Delaware, only a few minutes' walk to the center of downtown Newark. Newark is a thriving college town with restaurants, history museum, library, small stores erc. The studio is in a quiet, friendly, safe, historic and walkable neighborhood. If you are looking for privacy and serenity in this charming town, this is the place! Guests describe our studio as immaculately clean, private and calming.

May 5 – 10

R2,142 ZAR per night

Guest favorite

Home in Rising Sun

4.95 out of 5 average rating, 239 reviews

Home Away from Home in Rising Sun, MD

PLEASE READ: Children under 12 years of age are not suitable for this home. Check in:3-8pm can be flexible to fit your schedule.Check out: 11am This home has a living room, kitchen and dining area, two bedrooms and a full bath. No pets! THE THIRD BEDROOM is a master suite that can be added for an ADDITIONAL CHARGE. It includes a living area, queen bed, bathroom and kitchenette. Ask for more details. This home is very comfy and has a history room from family collectibles dating back to 1854.

Nov 12 – 19

R2,650 ZAR per night

Guest favorite

Apartment in Frederica

4.97 out of 5 average rating, 258 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!

Sep 9 – 16

R1,239 ZAR per night

Guest favorite

Guest suite in Chestertown

4.99 out of 5 average rating, 191 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.

Oct 1 – 8

R2,666 ZAR per night

Guest favorite

Cottage in North East

4.97 out of 5 average rating, 439 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.

Mar 19 – 26

R2,113 ZAR per night

Guest favorite

Cottage in North East

4.94 out of 5 average rating, 280 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.

Dec 29 – Jan 5

R1,874 ZAR per night

Guest favorite

Guesthouse in Wilmington

4.84 out of 5 average rating, 366 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.

Dec 19 – 26

R1,829 ZAR per night

Guest favorite

Loft in Wilmington

4.97 out of 5 average rating, 125 reviews

NYC Style Loft in Wilmington, DE.

Third floor loft with private entrance in a historic neighborhood. Conveniently located off I-95. Close to Trolley Square, Wilmington’s Business district St.Frances hospital, and less than 25 minutes to Philadelphia Airport. This is one the best deal in the city and has everything you need for an enjoyable stay!

Oct 31 – Nov 7

R1,625 ZAR per night

Guest favorite

Apartment in Chesapeake City

4.93 out of 5 average rating, 142 reviews

Bohemia Vista CC Horse Farm Apartment

Comfortable and private, 10 minutes from Chesapeake City This private apartment comes with a basic kitchen, private bedroom with king sized bed, common area twin bed, sitting area, bath with a jacuzzi tub, and expansive views of farmland and horses. Private entrance and use of private laundry room included.

Dec 26 – Jan 2

R2,497 ZAR per night