Vacation rentals in Middletown

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!

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.

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.

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.

Sweet Bay Overlook

Take it easy at this unique home overlooking the Chesapeake Bay. You will enjoy watching the amazing sunsets on the bluff as the eagles, ospreys and boats drift by. Our little house was built in the 1960’s by a brick mason who was very good at his trade. In recent years, the home had fallen into disrepair, but a talented Amish craftsman purchased the house and renovated it from top to bottom. The Sweet Bay that you see today reflects his incredible attention to detail and quality.

Cozy and private annex

Conveniently located in Newark, this cozy and private one bedroom mother in-law suite is attached to the main house. The unit is comfortable for 2 people. It has a private entrance, TV, full bathroom and a kitchenette with almost all the amenities of home. Perfect for business professional on- the- go or getaway. 15 min away from University of Delaware, Christiana Mall and many local restaurants and bars. Host lives on site full-time. ***Must be 25+ years and older to book ****

Countryside-Stable House-Open Studio-Perfect 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

Country Getaway to Villa Roadstown Art Studio Loft

Feel welcomed as you relax at a rustic and tranquil getaway in the historic hamlet of Roadstown in rural South Jersey with its nature preserves and waterways set among farmlands and fields. Be at home in a renovated art studio adjacent to the Obediah Robbins House c.1769. Your comfort needs are met with a well equipped kitchenette, lounge, workspace, and rain shower bath. Retire upstairs to a loft room complete with cozy reading corner and a comfy queen bed.

The Bohemia Charmer

Take it easy at this unique and tranquil getaway. In the Hack's Point Community, on the shores of the Bohemia River, this home will give you plenty of opportunities to relax, no matter the season. This home has the closest proximity to the community beach and pier, and it also exudes historic charm with a stunning 2-story fireplace, hardwood & stone flooring, and built-ins. ***There is no guest access to the pier for storage or day-use of boats***

3 Bed/1.5 Bath + 2MI - University of Delaware

✨ Cozy Home Near the University of Delaware Welcome to your home away from home in Newark, DE! This cozy retreat is ideally located within walking distance from the University of Delaware, making it perfect for visiting students, families, and alumni. Nestled in a vibrant neighborhood, you'll find yourself surrounded by an abundance of shopping options, great golf courses, top-notch restaurants, and inviting coffee shops.

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.

Green Sanctuary-Pvt Apt for Quiet Rest

Green Sanctuary is the second floor apartment B in a two unit apartment building. It is a bright cheerful one bedroom unit with a large covered balcony located on the grounds of the famous Egyptian house. The apartment is comfortable for 2 people but will accommodate 4 with the living room couch converting to a bed. The property is conveniently located with plenty of off street parking.