Vacation rentals in Middletown

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Top-rated vacation rentals in Middletown

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Top guest favorite

A calm scene captures the reflection of a brightly lit building along the water's edge at dusk. The surrounding architecture features a mix of traditional and charming homes, with soft clouds above and a tranquil water surface mirroring the lights.

Apartment in Chesapeake City

5 out of 5 average rating, 20 reviews

The Pearl: a 70s vibe, hip/cozy

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!

Top guest favorite

An exterior view of the cottage showcases a welcoming wooden deck with ramps, facilitating accessibility. A glass door leads inside while a white chair and barbecue grill are present nearby. Lush greenery and a horse fence frame the scene, enhancing the country setting.

Cottage in North East

4.98 out of 5 average rating, 568 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 the day of your arrival.

Guest favorite

An updated kitchen stovetop is showcased with a glass lid resting on a burner. A metallic kettle sits nearby, reflecting light from the overhead source. The countertop features modern appliances and utensils, contributing to a functional cooking space.

Townhouse in Middletown

5 out of 5 average rating, 26 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.

Guest favorite

A spacious community lounge area is highlighted by a high ceiling with wooden beams and large windows offering natural light. Comfortable seating arrangements, including armchairs and a modern coffee table, surround a stone fireplace. Decorative artwork adorns the wall, and the space flows into an entertainment area.

Apartment in Bear

4.92 out of 5 average rating, 38 reviews

Welcome 2 CasaCozy! 1164 sq ft, 2 Bed/2 Bath

Welcome to casa cozy! This 2 BR & 2 Bath, 1,164 sq ft apt is close to the Christiana Mall, University of Delaware, Christiana Hospital, restaurants, shops, parks & more. Enjoy the comfy bedrooms with dedicated bathrooms, fully equipped kitchen, cozy living & dining rooms. Both beds are Queens. Your TV has Prime Video, Roku + more. High speed Verizon WiFi. 24-hour guarded gate access, full gym, park, business center, outdoor pool and tennis courts. Note: This apartment is on the 3rd floor.

Guest favorite

A corner of a bathroom features a jetted tub beside a window offering views of the surrounding trees and water. Soft white towels are neatly arranged on the tiled ledge, and a simple vase holds decorative dried grasses.

Home in Galena

4.93 out of 5 average rating, 40 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.

Superhost

A neatly arranged coffee station is displayed on a marble-top console table. Items include a coffee maker, a glass carafe, a basket with assorted tea bags, and a variety of single-serve coffee pods arranged in a circular holder.

Home in Smyrna

4.76 out of 5 average rating, 37 reviews

Entire house sleeps 8 with parking, Wi-fi, kitchen

Welcome to our home! Located in the heart of DE, in front of Smyrna rest stop on exit 119 on route 1, making it convenient to explore North or South: Dover Airforce 16 miles away, Ballys Dover casino is 11 miles away, DE Turf complex 29 miles away, Harrington Casino 36 miles away, Smyrna downtown 3 miles away full of shops and restaurants, Middletown downtown 11 miles away, Bay health hospital 13 miles away, Neumorus Children Hospital 38 miles away, Wilmington River front 35 miles away.

Top guest favorite

A modern shower area features smooth, large gray tiles with subtle variations in color. A built-in niche holds two bottles of shower products. Natural light filters in through a small window, enhancing the serene environment.

Guest suite in Newark

4.98 out of 5 average rating, 131 reviews

Charming Fully Equipped Private Guestsuite

Relax in a stylish guesthouse 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.

Superhost

A serene landscape captures the early sunrise over a foggy field, with a gentle reflection on the calm water of a pond. A white fence outlines the area, and trees are shrouded in mist, creating a tranquil atmosphere.

Farm stay in Townsend

4.68 out of 5 average rating, 41 reviews

NBR Farms Guest House

Serene Farm Getaway. Escape to a peaceful retreat on a private estate. Immerse yourself in the tranquility of nature as you explore the sprawling grounds, featuring picturesque apple orchards and peaceful fishing ponds. Enjoy 3-bedroom guest house. Relax and unwind in the rejuvenating hot tub or indulge in a luxurious soak in the Jacuzzi. This serene farm getaway offers the perfect retreat. Bring your furry friend along to enjoy the scenic surroundings together

Guest favorite

An outdoor patio features a shaded table and chairs under a large red umbrella. The landscape includes open grassy areas, with trees in the background. A pathway leads from the patio toward the lush greenery, connecting to other buildings in the distance.

Guesthouse in Dover

4.88 out of 5 average rating, 120 reviews

Country Guest House

Relax with the whole family at this peaceful place to stay on the farm. You will see horses, cows, goats, chickens & ducks. Family friendly. Animals roam the property & are safe to pet. You will hear many farm noises such as roosters crowing, cows mooing & more. This home is located in the country & a min of 5 miles from stores and shopping. Full kitchen, 1 full bathroom & 1 queen bed included. Upon request Queen Air Mattress or Twin Bed can be provided.

Top guest favorite

The spacious lower-level guest suite features an open living area with hardwood flooring. A dining table with wooden chairs is visible, alongside an exercise treadmill. Bright artwork adorns the walls, and the layout includes designated zones for dining and relaxation.

Guest suite in Newark

5 out of 5 average rating, 21 reviews

Charming Retreat Near U of Del with Nature Views

Cozy, Private Retreat in Newark, DE Relax in our beautifully renovated lower-level guest suite with a private entrance and peaceful wooded views. Just 2 miles from the University of Delaware, 6 miles from Christiana Hospital, and 8.5 miles from Christiana Mall, it’s ideal for UD families, medical professionals, business travelers, and couples. Whether for a short or medium stay, enjoy all the comforts and convenience you need for a relaxing getaway.

Guest favorite

Guest suite in Bear

4.88 out of 5 average rating, 222 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.

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, 38 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.