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Holiday rentals in Middletown

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Quick stats about holiday rentals in Middletown

  • Total holiday rentals

    Explore 20 holiday rentals in Middletown

  • Nightly prices starting at

    Middletown holiday rentals start at £37 per night before taxes and fees

  • Verified guest reviews

    Over 310 verified reviews to help you choose

  • Wifi availability

    10 of Middletown holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Middletown rentals

  • 4.8 Average rating

    Middletown stays are highly rated by guests – averaging 4.8 out of 5!

Top-rated holiday rentals in Middletown

Guests agree: these stays are highly rated for location, cleanliness and more.

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Top guest favourite
A spacious living room is presented with natural light streaming through large windows. Minimalist furniture includes a comfortable sofa and two accent chairs. A round coffee table is centrally located on a patterned area rug, complementing the neutral color palette of the room.
Home in Bear

Work crews and families, less than 1 hr to Philly

✔ Spacious open floor plan ✔ Outdoor dining ✔ Quiet neighborhood ✔ 5 beds total with optional twin in 1st-floor bedroom ✔ 30+ day stays welcome ✔ 1 GB Wi-Fi ✔ Dedicated workstations in each bedroom ✔ 5 Smart TVs - Master has a 55"TV ✔ In Unit Laundry ✔ Fully Stocked & Equipped Kitchen ✔ Garage Access for storage ✔ Off street parking for two oversized vehicles ✔ Street Parking ✔ Prime Location: Go to "Neighborhood Highlights" to view nearby hospitals, schools, places to visit, etc.

4.97 out of 5 average rating, 30 reviews
Top guest favourite
A single-story cottage is surrounded by lush greenery and vibrant flower beds. A wooden deck extends around the front, providing access to the home. The well-maintained lawn features a variety of plants and shrubs, enhancing the inviting outdoor space.
Cottage in North East

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.

4.97 out of 5 average rating, 713 reviews
Top guest favourite
Home in New Castle

Elegant Spacious Family Gem • 20 Min to Wilmington

Step into the spacious and elegant 3BR 2.5BA family getaway in the tranquil and friendly New Castle neighborhood. It promises a relaxing retreat with quick access to I‑95 and Route 1, with a short drive from the tax-free Christiana Mall, restaurants, shops, and exciting attractions. The vintage ambiance paired with modern comforts and a rich amenity list will leave you in awe. ✔ 3 Comfortable Bedrooms ✔ 3 Lounge Areas ✔ Full Kitchen ✔ Backyard ✔ Smart TV ✔ Wi-Fi ✔ Parking Learn more below!

4.96 out of 5 average rating, 24 reviews
Guest favourite
An updated kitchen features modern appliances, including a stainless steel refrigerator and microwave. Quartz countertops are complemented by stylish cabinetry. Above, track lighting enhances the workspace, while a striped rug adds texture to the laminated flooring.
Townhouse in Middletown

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.

4.98 out of 5 average rating, 66 reviews
Top guest favourite
Home in Middletown

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!

5.0 out of 5 average rating, 21 reviews
Top guest favourite
The screened-in deck features a comfortable seating arrangement with two armchairs and a sofa, all surrounding a central coffee table. A large, decorative plant adds a touch of nature, while panoramic views of the surrounding greenery are visible through the screens.
Home in Galena

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.

4.96 out of 5 average rating, 79 reviews
Guest favourite
A gravel driveway leads to a white house surrounded by lush green trees. The landscape features a spacious front yard with well-maintained grass and an array of trees providing shade. The sky is partly cloudy, creating a serene outdoor setting.
Home in Galena

Countryside Cottage

The Sassafras Lodge welcomes groups to a quaint country setting in the Sassafras River watershed. The lodge is situated overlooking beautiful farmland to help guests escape life's daily hustle and bustle while still having all of the amenities to be connected to the "real world" Located minutes from several desired travel destinations: St Andrew’s - 15 mins Galena/Georgetown - Sassafras River - 5 Historic Chestertown - 15 Chesapeake City MD - 25 Rock Hall MD - 25 Middletown DE - 10

4.9 out of 5 average rating, 10 reviews
Top guest favourite
A welcoming porch is visible, framed by multiple windows allowing natural light to enter. The light yellow exterior contrasts with vibrant flower pots positioned along the steps. Scenic river views are seen in the background, enhancing the peaceful ambiance of the cottage.
Home in Earleville

Stunning 2BR Cottage w/River views

Cozy Riverside Cottage in Scenic Hacks Point on the Bohemia 2BR | 1.5BA | Steps from the Water | Family-Friendly Escape the everyday and unwind in this charming riverside cottage with views of the Bohemia River. Whether you're looking for a weekend getaway, a week-long family retreat, or a beautiful place to stay while attending a nearby event or wedding, our 2-bedroom, 1.5-bathroom cottage offers the perfect blend of comfort and charm with direct access to the beautiful Bohemia River.

4.96 out of 5 average rating, 23 reviews
Top guest favourite
Flat in Chesapeake City

The Pearl: A hip & cozy canal-side apartment

The Pearl is a 2nd floor apartment 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,full kitchen,etc. It's got a 70s vibe, an eclectic combo of euro/scan/boho hip! Come stay with us, you won't regret it!

4.98 out of 5 average rating, 61 reviews
Top guest favourite
An outdoor patio area is seen, furnished with comfortable seating around a central table. Lush greenery and a view of the C&D Canal can be enjoyed, along with the backdrop of a bridge and a charming house across the water.
Home in Chesapeake City

Canal views/Walk to Shops/Luxury 2Bed/1.5Bath

The Miss Francis Kirk House. Escape to this elegant 2-bed, 1.5-bath luxury home in the heart of Chesapeake City. It offers breathtaking views of the C&D Canal and is the perfect haven for a romantic couples retreat or a sophisticated getaway. As you step inside, this luxury home's warm, inviting atmosphere invites you, to indulge in its array of opulent amenities. The master bedroom is a true sanctuary with a private deck for peaceful mornings or starlit evenings.

5.0 out of 5 average rating, 32 reviews
Superhost
An aerial view showcases the expansive layout of the Delaware City Oasis. The property features a spacious exterior area, highlighted by a large deck and a well-maintained lawn, surrounded by mature trees. Ample parking space is visible along the winding driveway.
Home in Delaware City

Delaware City Oasis|Indoor Heated Pool

Delaware City Oasis, is a premier luxury property that is truly one of its kind in the entire state. The Oasis is a serene and picturesque retreat nestled in the heart of Delaware City, Delaware. This hidden gem offers an escape from the hustle and bustle of everyday life, providing a perfect blend of modern amenities. As you enter the Oasis you are greeted by 5000 sq ft including a Great room with a heated indoor pool making this home prime for entertaining.

4.89 out of 5 average rating, 70 reviews
Top guest favourite
Two vibrant blue adirondack chairs are positioned beside a small, round table, creating an inviting outdoor seating area. In the background, the tranquil waters of the Bohemia River reflect the warm hues of sunset, framed by lush trees and marina boats.
Cottage in Earleville

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***

4.96 out of 5 average rating, 109 reviews

Popular amenities for Middletown holiday rentals

KitchenWifiPoolFree parking on premisesAir conditioning

Other great holiday rentals in Middletown

Top guest favourite
A newly renovated two-story house features a large front porch with white columns, offering ample space for relaxation. Decorative trim adds charm, while neatly arranged greenery and low shrubs border the yard. The driveway provides two off-street parking spaces beside a well-maintained path.
Home in Chesapeake City

Chesapeake City Charm at the Boho House!

5.0 out of 5 average rating, 66 reviews
Superhost
A wide view of a grassy field is complemented by a rainbow arching above the tree line. The lush greenery of the surrounding woods is visible, providing a serene backdrop to the open space.
Farm stay in Galena

Quiet Country Relaxing Farm

4.77 out of 5 average rating, 62 reviews
Top guest favourite
A bridge spans across the water, silhouetted against a vibrant sunset. The sky is filled with hues of purple and orange, reflecting on the water's surface. Along the riverbank, the outline of trees is visible, adding to the scenic backdrop.
Home in Chesapeake City

Breathtaking views!

5.0 out of 5 average rating, 26 reviews
Top guest favourite
A light and airy living area features a comfortable cream-colored sectional sofa and two accent chairs with blue cushions. A large piece of wall art adds a touch of color, while a flat-screen TV is mounted above a dark wood entertainment unit. Natural light floods the space through multiple windows.
Flat in Chesapeake City

Vista 27 Luxury Ches City Apt on Waterfront Farm

4.98 out of 5 average rating, 48 reviews
Top guest favourite
The image showcases a spacious backyard featuring a well-maintained in-ground heated pool, surrounded by lounge chairs. A large two-story house stands in the background, with a landscaped area and patio furniture creating an inviting outdoor setting.
Home in Clayton

The Hidden Gem•Heated pool•Pickleball Court

4.99 out of 5 average rating, 90 reviews
Top guest favourite
Home in Newark

Renovated 4BR/2BA Near UDel for Families/Groups

5.0 out of 5 average rating, 20 reviews
Top guest favourite
A welcoming living area features exposed wooden beams and hardwood flooring. A gray sofa and patterned armchair provide comfortable seating options. Light streams through large windows, illuminating a circular area rug. A coastal-themed artwork and a leafy plant add character to the space.
Home in Chesapeake City

Modish Cottage - Walk to everything!

5.0 out of 5 average rating, 31 reviews
Top guest favourite
The charming exterior of Unicorn Farmhouse features a rustic brick pathway leading to a spacious covered porch. A vibrant peacock stands in the foreground, while decorative ferns hang from the eaves. A whimsical figure in yellow attire is positioned beside the entrance, adding character to the inviting setting.
Home in Chesapeake City

Wister Loft: Charm & History with Modern Love.

5.0 out of 5 average rating, 46 reviews

Frequently Asked Questions

  • What are the best places to stay in Middletown?

    Visitors often stay in neighborhoods close to the town center, where shops, restaurants, and parks are within reach. Some seek out residential areas that are quiet and walkable, providing a local perspective on daily life.

  • What are the best things to do in Middletown with kids?

    Families often explore local parks, playgrounds, and seasonal farm stands that invite hands-on activities. Community centers host children’s programs, while library events, and summer fairs are also frequently suggested.

  • What are some of the best things to do in Middletown?

    Stroll through historic downtown, explore local parks, or join community festivals that celebrate the area’s traditions. Art spaces and farm markets are also often recommended for experiencing Middletown’s local culture.

  • How is the weather in Middletown?

    Middletown has cold winters with temperatures often between 26–41°F (-4–5°C), and warm, humid summers reaching around 87°F (31°C). Spring and fall are milder, with temperatures commonly shifting between 44–67°F (6–20°C).

  • When is the best time to visit Middletown?

    Late spring and early fall are often recommended, with comfortable temperatures and less humidity. Many visitors enjoy outdoor events and harvest markets during these seasons, taking advantage of the mild weather.

  • What are the best places to visit in Middletown?

    Visitors frequently explore historic downtown, local parks, and area nature preserves. Around town, you may also find seasonal markets and arts venues that showcase community talent.

  • What are some hiking trails in Middletown?

    Middletown has walking paths in local parks, nature preserves, and community greenways. Nearby state parks expand the options with trails through woods, meadows, and streams, appealing to various ability levels.

  • What are some family activities we can do in Middletown?

    Families can explore playgrounds, attend library story hours, visit community pools, or take part in local art workshops. Seasonal events, outdoor movies, and interactive farm visits are also frequently enjoyed.

  • What are some of the best day trip ideas from Middletown?

    Many choose to explore historic sites, wildlife refuges, or nearby state parks for outdoor recreation. Regional art centers and farm tours are frequently suggested by locals for a change of scenery.

  • Are there any pet friendly accommodations available in Middletown?

    Some vacation rentals in Middletown allow pets, especially in residential neighborhoods with easy access to parks or walking trails. It is best to check individual property details for specific pet policies before booking.

  • What are some local tips for visiting Middletown?

    Locals suggest exploring the nearby parks and farm markets for seasonal produce. Bringing layers can be helpful, as temperatures shift between day and evening, especially in spring and fall. Middletown has community festivals and a walkable town center.

  • What is Middletown known for?

    Middletown is known for its agricultural heritage, community-centered events, and welcoming neighborhoods. The town has seasonal produce stands, historic sites, and a blend of small-town and modern amenities.

  • What are the best hidden gems to explore in Middletown?

    Explore local art galleries, tucked-away farm stands, or quiet nature paths that wind through preserved green spaces. Community events and homemade bakeries also offer glimpses into traditions cherished by residents.

  • What are the best foods to try in Middletown?

    Local menus highlight crab cakes, sweet corn, and peach desserts, drawing on regional produce. Farm-to-table eateries and classic diners around town are frequently suggested for freshly prepared comfort foods.

  • What should I bring for a trip to Middletown?

    Pack comfortable walking shoes, weather-appropriate clothing, and layers for changing temperatures. A reusable water bottle and seasonal gear—such as hats in summer or a rain jacket in spring—help make the most of your visit.

  • What is the nightlife in Middletown like?

    Middletown has a casual nightlife scene with local pubs, relaxed taverns, and a few venues for live music or trivia nights. Many visitors opt for evening meals at local restaurants and family-friendly spots around town.

  • What are the most popular events or festivals in Middletown?

    Middletown hosts community festivals in late summer and autumn, often featuring parades, live music, and local food. Farmers markets and seasonal fairs are also among the most popular gatherings for residents and visitors.

  • Are there family friendly vacation rentals in Middletown?

    Middletown has a variety of family friendly vacation rentals, often located in quiet neighborhoods close to parks and schools. Some hosts provide amenities like kitchens, outdoor space, or extra beds for groups.

Destinations to explore