Holiday rentals in Middletown

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Top-rated holiday rentals in Middletown

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Top guest favourite

Flat in Chesapeake City

5 out of 5 average rating, 19 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!

Guest favourite

Townhouse in Middletown

5 out of 5 average rating, 25 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 favourite

Flat in Bear

4.92 out of 5 average rating, 37 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 favourite

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.

Top guest favourite

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.

Guest favourite

Flat in New Castle

4.96 out of 5 average rating, 125 reviews

Private Suburban luxury Apt/Free parking/Near Mall

*Peaceful location*Quiet Suburban Area*Clean & Comfortable * Personal entrance with privacy**5 minutes from Christiana Mall*Free parking next to the entrance with large driveway*Private deck with gazebo/Park views and walking trail* Near I-95 and Rt-1 and all major highways**Convenient & affordable for 1 night or more. *Queen bed/full kitchen/Large TV/Quality appliances *Remodeled/located in cul-de-sac/Free Wi-Fi and YouTube TV-Lower level unit/no smoking or vaping

Superhost

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 favourite

Guest house 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 favourite

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.

Top guest favourite

Cottage in North East

4.95 out of 5 average rating, 360 reviews

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.

Top guest favourite

Loft in Wilmington

5 out of 5 average rating, 37 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.

Guest favourite

Home in Clayton

5 out of 5 average rating, 28 reviews

The Little Gem Cottage/ EV charging station

Little Gem Cottage is the perfect place for a couples getaway! Come enjoy this peaceful countryside setting. We are only minutes from Delaware State University and some of Delaware’s major attractions like Dover Air Base and Dover Motor Speedway This property has it’s own Level 2 multi port EV charging station!