Vacation rentals in Middletown

Find and book unique accommodations on Airbnb

Top-rated vacation rentals in Middletown

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

0 of 0 items showing

1 of 3 pages

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

May 5 – 12

G$14,321 GYD 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

Feb 6 – 13

G$27,279 GYD per night

Guest favorite

Apartment in Dover

4.9 out of 5 average rating, 156 reviews

Apartment A Woodbrook Cottage 5G WiFi

Beautifully cottage style décor apartment with bright and sunny windows. Newly remodeled rooms and bathroom Large kitchen and Living Room New queen bed with covered mattress 5G WiFi and Smart TV with Netflix Very clean and neat Front door has smart lock BBQ grill, fire pit and outside seating area No loud music and noises please due to adjacent apt. I do have a whole house listing Apartment has private entrance and back door and is separated from adjacent apt with locked door from both sides

Apr 10 – 17

G$22,287 GYD 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

G$23,367 GYD 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 21 – 28

G$13,486 GYD 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

G$29,086 GYD 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 22 – 29

G$23,057 GYD 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.

Aug 19 – 26

G$20,321 GYD per night

Guest favorite

Guest suite in Bear

4.88 out of 5 average rating, 195 reviews

Luxurious apartment/studio with private entrance

Private luxurious apartment/Studio with Bose surrounding music system, at the back of a new construction (guest suite). Everything is private, nothing is shared, private washer/ dryer (2 in one), private entrance, private bathroom kitchen and private patio. Safe place (working smoke and carbon monoxide detectors) with all amenities brand new. Close to University of Delaware ,Christiana Hospital and Christiana Mall.

Nov 29 – Dec 6

G$23,844 GYD 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.

Jan 22 – 29

G$19,959 GYD 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!

Jan 4 – 11

G$17,734 GYD 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.

May 3 – 10

G$27,099 GYD per night