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

Top guest favorite

A welcoming living area features exposed wooden beams and hardwood flooring. A gray sofa and patterned armchair provide comfortable seating options. Light streams through large windows, illuminating a circular area rug. A coastal-themed artwork and a leafy plant add character to the space.

Home in Chesapeake City

5 out of 5 average rating, 11 reviews

Modish Cottage w/Bar Shed Charm!

Welcome to your perfect getaway in the heart of historic Chesapeake City! Just steps away from local restaurants, nightlife, boutique shops and scenic canal views, you'll love exploring all this waterfront town has to offer. Inside, a stylish retreat for relaxing. But the real gem...the back yard. Kick back with a drink at the bar shed, grill a meal, and gather around the fire pit to relax under the stars. Don't forget your bike (for the bike trail) or kayak for the more adventurous at heart!

Top guest favorite

A spacious living area is shown, featuring a well-equipped kitchen, dining space for four, and a cozy seating area. Light green chairs provide a pop of color, while a large mirror reflects the room's dimensions. Soft natural light filters in from the window.

Guest suite in Newark

4.97 out of 5 average rating, 161 reviews

Charming Fully Equipped Private Guest Suite Studio

Relax in a stylish guest suite studio in a quiet, safe neighborhood. Its private entrance and parking for 2 vehicles makes the cozy space all the better. Enjoy the full kitchen, work space, high speed internet (1200mbps), 50” TV, full bathroom, and more. Perfect for the business professional on-the-go, or getaway. Take a stroll through White Clay Creek Park with your furry friend. Just a short 5 minute drive from Main St.'s restaurants, local bars, and UD. Only 10 minutes from Christiana Mall.

Top guest favorite

An updated kitchen features modern appliances, including a stainless steel refrigerator and microwave. Quartz countertops are complemented by stylish cabinetry. Above, track lighting enhances the workspace, while a striped rug adds texture to the laminated flooring.

Townhouse in Middletown

5 out of 5 average rating, 34 reviews

Luxury Townhome w/free parking

Welcome to this luxurious, updated and stylish home that is centrally located, yet tucked away in a peaceful area with inside & outside dining. This 2 bed/1.5 bath home is has beautiful lighting, laminated floors, high ceilings, large rooms w/king bed & comfortable sofa for reading or relaxing in the master bedroom. The second room has 2 full beds. The kitchen is updated with all the necessary appliances and utensils that even a chef would enjoy and flows into the classy living/dining area.

Top guest favorite

A comfortable living area is furnished with a light-colored couch and a wooden coffee table. A wall-mounted television is positioned near the window, which is adorned with dark curtains. Soft lighting is provided by a lamp, creating a cozy ambiance.

Guest suite in Newark

4.96 out of 5 average rating, 51 reviews

The Parent Pad - an Interlude for UD Parents

Whether you’re traveling for a campus visit or returning for Parents weekend, or just passing through I provide a convenient, comfortable resting place between events. Perfect for Grandparents coming in for a graduation, or parents supporting their student during finals week. The Parent Pad is a perfect distance from the raucous of the college life, yet close enough for convenience to UD Stadium and sports complex. A safe place for students during holidays when Dorm cleaning occurs, too.

Guest favorite

The screened-in deck features a comfortable seating arrangement with two armchairs and a sofa, all surrounding a central coffee table. A large, decorative plant adds a touch of nature, while panoramic views of the surrounding greenery are visible through the screens.

Home in Galena

4.94 out of 5 average rating, 49 reviews

Connection Pointe•River views•Quiet•Peaceful

Connection Pointe is a great getaway for your family vacation or to reconnect with friends, you will be sure to enjoy this beautiful property that sits right along the Sassafras River, it is quiet and peaceful with amazing views from the house and the screened in deck. Come enjoy the sounds of nature as you take time to relax and refocus! There is no boat access to the river from the property. There is a fairly steep bank going down to the river, so please be mindful of this with children.

Guest favorite

A two-story house is set amidst lush greenery, featuring a garage and a sloped roof. The structure is flanked by trees and bushes, offering a sense of privacy. A paved driveway leads up to the garage, enhancing accessibility.

Apartment in Smyrna

4.96 out of 5 average rating, 27 reviews

Horse Haven

Equestrian decor flavors this cozy second floor apartment. You will find a brand new walk-in shower, coffee bar, carpet, furniture, freshly-painted walls and fast fios internet. We technically live just outside of the town limits yet are only two miles from Route 1, which gives you quick access to Wilmington and Dover. Ten acres of woods and pastures surround our bucolic property. Our eventual goal is to host traveling nurses and military as we are close to several hospitals and DAFB.

Top guest favorite

An open studio space showcases natural light flowing through large windows. A cozy seating area includes a sofa, pull-out couch, and a coffee table. A kitchenette with appliances is visible alongside a small dining area, all framed by wooden accents and warm flooring.

Guest suite in Newark

4.99 out of 5 average rating, 226 reviews

Spacious, light filled studio 2 blocks from UDel

DISCOUNT FOR 30+ DAYS. Our quiet, private studio is located in the historic Old Newark neighborhood, next to the Univ of Delaware, a few minutes' walk to downtown. Newark is a college town with restaurants, history museum, library and small stores. The studio is in a quiet, residential, friendly and walk-able 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.

Guest favorite

An open layout showcases a dining area with a light-colored table set for six, adjacent to a cozy living space featuring a neutral-toned sofa and armchairs. A horse-themed artwork is displayed on the wall, while soft curtains frame the windows allowing natural light in.

Guesthouse in Elkton

4.91 out of 5 average rating, 159 reviews

Countryside-Stable House-Open Studio-Quiet for 2

Get out of the city and stay here. 3+ acre historic Fair Hill horse farm and 590 sq. ft. stable house! Minutes from trails, wineries, orchards, golfing, and scenic small towns! Highlights - Newly renovated! - No checkout chores! - Traditional farmhouse sink - Dine in the garden - Roku TV: Netflix, Hulu - Stables: 6 stalls & 2 paddocks available Lowlights - Two narrow interior doorways - Kitchen minus a conventional oven. A mini-oven/air fryer, microwave, & hotplate provided

Guest favorite

A light-colored sectional sofa is positioned in the living area, complemented by two decorative pillows. Soft yellow curtains frame the windows, allowing natural light to enter. A wooden table is visible beside the sofa, and a wall-mounted television is placed opposite, adding to the cozy atmosphere.

Camper/RV in Hartly

4.86 out of 5 average rating, 35 reviews

Cozy Camper Escape Near Dover

Escape to a cozy camper in Hartly, DE! This stylish retreat sleeps 3 with a queen sized bed with memory foam mattress, and pull-out sofa. Enjoy amenities like AC, a fridge, freezer, 3-burner gas stove, oven, and instant hot water. A space heater is provided for chilly nights. Just 20 minutes from Dover attractions like Dover Motor Speedway and Delaware State University, it’s perfect for a peaceful getaway or event-filled stay. Book today for comfort and convenience!

Superhost

A game room lounge features a green-felt pool table positioned near large glass doors. A circular, patterned rug anchors a round dining table with metal chairs. The walls are painted in a calming blue hue, and natural light floods the space through the doors.

Guest suite in Smyrna

4.63 out of 5 average rating, 16 reviews

Private Guest Suite Close To Dover Downs/DSU

Cozy guest suite in Smyrna, DE, perfect for solo travelers or couples seeking a relaxing getaway. Unwind in the comfortable living room with a TV, challenge friends to games in the dedicated game room lounge, and enjoy a restful sleep in the well-appointed bedroom. The suite also includes a private bathroom for your convenience. Located in a peaceful neighborhood, you'll be close to local attractions while enjoying the tranquility of the area.

Top guest favorite

A welcoming porch features white adirondack chairs and a small blue table. A lantern and a decorative container are placed nearby, with the house's yellow exterior and orange shutters providing a cheerful backdrop. The view includes trees and street activity.

Cottage in Chesapeake City

5 out of 5 average rating, 98 reviews

Bohemia Bungalow

Experience this charming 1940's cottage nestled on bustling Bohemia Avenue in the heart of picturesque Chesapeake City. Enjoy porch-sitting "on the Avenue", or visit numerous local eclectic shops, restaurants, a brew pub, and even a yoga studio, all only steps away. Marvel at massive cargo ships navigating the C&D Canal, just a 2-minute walk from your doorstep. Private off street parking for 2 cars.

Top guest favorite

A private porch is depicted with wooden decking and sleek black railings. Two wooden chairs and a round table are arranged for outdoor seating. Lush greenery is visible along one side, providing a touch of nature, while a glimpse of neighboring homes is seen in the background.

Loft in Wilmington

5 out of 5 average rating, 54 reviews

Tilton Park Loft Studio

A unique tiny home like experience that has everything you need for a enjoyable trip. You have a loft queen bed or a premium queen pull out sofa by American Leather to choose from. Both can be utilized if needed. Perfect for a weekend getaway or short work trip! Nespresso coffee machine, mini fridge stocked with bottle & sparkling water.