Holiday rentals in Middletown

The Pearl: A hip & cozy canal-side apartment

The Pearl is located in the heart of historic Chesapeake City; just steps from all the boutiques, restaurants & nightlife with a lovely view of the C&D Canal. It's cozy, but functional with 2 workspaces, 2 bedrooms & all the amenities you'd want in your home away! We provide a Nespresso machine & excellent coffee, snacks, sparkling water, full kitchen,etc. It's got a 70s vibe, an eclectic combo of euro/scan/boho hip! It's not your usual Victorian spot. Come stay with us, you won't regret it!

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.

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.

Idyllic carriage house private 2 car garage W/D

This is a one-of-a-kind space perched on a hill along a peaceful stretch of country-like road, surrounded by lush green space. Enjoy the convenience of your own private 2-car garage with an interior walk-up to the spacious 825 sq ft apartment above. The property also features a handicapped ramp at the front for easy access. Inside, you’ll find a washer and dryer, EV charger, dual-head walk-in shower, and a fully equipped kitchen for all your needs. Ideal for comfort and privacy.

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

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.

free parking and best location apartment

Enjoy easy access to everything from this perfectly located home base, near to trolley square and little Italy, enjoy the restaurant, parks and more, this is a really nice and safe neighborhood. The apartment has own parking, the apartment has own been completely renovated, new kitchen cabinets, appliances, new furniture. This apartment has two “Alexa” devices to control lights and music.

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.

Private entrance King Suite

Forget your worries in this spacious and serene space. Brand new private room on historic waterfront Chesapeake City Farm. You will have a private entrance to your roomy king suite, complete with luxurious bathroom, kitchenette efficiency, and coffee bar. You will have access to the Bohemia River, and a 200 acre horse farm, where wildlife abounds and the views are spectacular.

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.