Holiday rentals in Middletown

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.

Private Guest Suite

Our suite features a 3-speed ceiling fan with dimmable overhead lighting, a kitchenette, a bidet toilet, an office nook, and more. While this space is most comfortable for 2 people, up to 2 additional people may be added to your reservation for a fee and we will provide an air mattress. Please note: our home shares a small mud room-style entrance with the guest suite, however the suite has a lock and is private with its own bedroom, bathroom, and kitchenette. We look forward to hosting you!

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.

Casa Domino: A Peaceful Waterfront Retreat

Welcome to your fully furnished home-away-from-home in the heart of Historic Fort DuPont, Delaware — where history, nature, and comfort converge in one beautifully curated townhouse. With water views from nearly every room and serene outdoor living spaces, this 2-bedroom, 2.5-bath getaway is designed to help you slow down, reconnect, and settle in without compromising on convenience. Centrally located to Wilmington, Newark and Middletown; everything you need is less than 25 minutes away.

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 University 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, quaint and walkable neighborhood. If you are looking for privacy, serenity and charm, this is the place! Guests describe our studio as immaculately clean, private and calming. Reach out to us.

Countryside-Stablehouse-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

Conowingo Creek Casual

Kick back and relax in this handicap accessible, clean and stylish country charm efficiency apartment, complete with two outdoor seating spaces, walking paths and beautiful scenery located in rural southern Lancaster County. The area is surrounded by country and Amish charm with nearby hiking trails, while a 30 minute drive will have you in downtown historic Lancaster City where you can stroll, shop and on Tuesday, Friday and Saturday visit the historic Central Market.

The Lighthouse

Centrally located in northern Delaware with easy on/off access to 95 and 495. Newer construction, built in 2018. One large bedroom with KING size bed, 1.5 bath, private entrance, living room and full eat in kitchen. Work station area. Twin size pull out in living room. Free WiFi and large smart TVs in living room and bedroom. Deck off of the kitchen and upstairs deck off of the bedroom. Laundry located in bedroom upstairs. NO CLEANING FEE

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.

Quarry Landing • River Views in Historic Town

Enjoy easy access to everything from this perfectly located home. Quarry Landing is a turn-of-the-century Duplex filled with charm and beauty. Located on High Street in the quaint small town of Historic Port Deposit, (Maryland), perfect for couples or families. Great location in a safe neighborhood, short walk to local eateries, waterfront promenade, playground, fishing pier, dog park, and much more.

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.

Blue Tranquility-Pvt Apt for Quiet Rest

Blue Tranquility is the first floor apartment (apartment A) in a two unit apartment building. It is a cozy one bedroom unit with a large covered porch located on the grounds of the famous Egyptian house. The unit 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.