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Vacation rentals in Middletown

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Quick stats about vacation rentals in Middletown

  • Total vacation rentals

    Explore 20 vacation rentals in Middletown

  • Nightly prices starting at

    Middletown vacation rentals start at R 807 ZAR per night before taxes and fees

  • Verified guest reviews

    Over 310 verified reviews to help you choose

  • Wi-Fi availability

    10 of Middletown vacation rentals include wi-fi 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 vacation rentals in Middletown

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

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Top guest favorite
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
4.98 out of 5 average rating, 701 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.

ValueLocationTV

Top guest favorite
Apartment in Chesapeake City
4.94 out of 5 average rating, 127 reviews

Hygge Haven: A cozy apartment in a canal-side town

Chesapeake City is a historic town located on the C & D Canal; it's not unusual to be greeted by locals as you explore the town. The apartment is a bedroom with sitting area, fully equipped kitchen & bath. It's in the heart of the town & walkable to all the boutiques, restaurants & nightlife! It comes equipped with a Nespresso machine, coffee pods,sparkling water, wifi & tv if you just want to chill. It's steps from the canal for lovely sunrise/sunsets! There are bike/walking paths nearby.

LocationFamilyLong stay

Guest favorite
Home in New Castle
4.94 out of 5 average rating, 16 reviews

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!

LocationAccuracyCheckout

Guest favorite
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
4.98 out of 5 average rating, 60 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.

ValueFamilyAmenities

Top guest favorite
Home in Middletown
5.0 out of 5 average rating, 21 reviews

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!

LocationFamilyCleanliness

Top guest favorite
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
5.0 out of 5 average rating, 20 reviews

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.

FamilyLocationDecor

Top guest favorite
A sailboat glides across the water during sunset, with the sun casting a warm glow over the surface. Silhouetted trees frame the scene, enhancing the serene atmosphere of the evening along the Chesapeake Bay.
Cottage in North East
5.0 out of 5 average rating, 63 reviews

Vintage Waterfront Cottage with Stunning Sunsets

This unique Red Point Cottage offers vintage charm, rustic accents and incredible sunsets overlooking the Chesapeake bay from a 50 ft cliffside waterfront location. Our cottage has two bedrooms, one queen and one king - all bedding is provided and included. We have an open cottage concept with water views from every room. A stone gas fireplace, fully equipped custom kitchen, central air, washer & dryer, WIFI, flat screen TV, stereo, gas grill, fire pit, outside shower and front porch.

LocationFamilyGetting around

Guest favorite
A charming two-story cottage is framed by tall trees and a grassy yard. The light siding contrasts with the darker roof, while the front steps lead to a welcoming door. Clouds fill the sky, and the surrounding greenery complements the tranquil setting.
Home in Galena
4.92 out of 5 average rating, 12 reviews

Hunter's Lodge

Escape to our charming countryside cottage nestled on a picturesque farm on the Eastern Shore and just a stone’s throw from Delaware. Surrounded by rolling fields, this cozy retreat offers the perfect blend of rustic charm and modern comfort. Enjoy morning coffee on the porch, explore nearby towns and outdoor experiences. With easy access to local attractions, you can experience farm life while being close to charming towns and beautiful landscapes. Your serene getaway awaits!

LocationFamilyCleanliness

Top guest favorite
Cottage in Charlestown
4.96 out of 5 average rating, 291 reviews

Long Beach Cottage, Hot Tub, Beachfront

The cottage is waterfront and is a PERFECT spot for a romantic couple's getaway! honeymoon/celebrations Designed with that in mind, a kitchen w/ espresso machine, living room with wood burning fire and a romantic luxurious suite with a king bed & cozy ambiance complete w/ water views and a stunning bathroom that features a double vanity, a large soaking tub, a tile shower with a soothing 3 function rain shower is complete with luxury linens, cozy robes & soft towels...

FamilyLocationPool

Top guest favorite
The exterior of the two-story home is showcased, featuring a gray facade with white trim. A welcoming porch extends along the front, framed by colorful flower beds. Maryland flags are displayed, and a covered area is visible on the side, enhancing the property's charm.
Home in Chesapeake City
5.0 out of 5 average rating, 64 reviews

McReynolds-Woods House -Private 3 Bedroom Home

Enjoy this private home located on the South Side of Historic Chesapeake City C.1870. The property is walking distance to dining, shopping & local attractions. Stroll around town, enjoy the beautiful views or spend time relaxing on the porch. Small dogs allowed (two only under 25 lb.). We have a small fenced yard which is nice for the little ones and there is off-street parking in driveway on side of the house.

LocationFamilyParking

Top guest favorite
A welcoming porch features white adirondack chairs and a small blue table. A lantern and a decorative container are placed nearby, with the house's yellow exterior and orange shutters providing a cheerful backdrop. The view includes trees and street activity.
Cottage in Chesapeake City
5.0 out of 5 average rating, 128 reviews

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.

FamilyLocationCondition

Top guest favorite
A cozy living area features a dark leather sofa with blue accent pillows, complemented by a round coffee table. Colorful wall art adorns the light blue walls, and natural light enters through the window. Two doors lead to separate areas, enhancing accessibility.
Apartment in Newark
4.95 out of 5 average rating, 38 reviews

Cozy and private annex

Cozy and private 1-bedroom in-law suite attached to the main home in Newark. Ideal for 2 guests, featuring a private entrance, full bathroom, TV, and a well-equipped kitchenette. Conveniently located just 15 minutes from the University of Delaware, Christiana Mall, and local dining spots. Perfect for business travelers or a quick getaway. Host lives on-site. Must be 25+ to book.

LocationValueQuiet

Popular amenities for Middletown vacation rentals

KitchenWifiPoolFree parking on premisesAir conditioning

Other great vacation rentals in Middletown

Top guest favorite
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
5.0 out of 5 average rating, 26 reviews

Modish Cottage - Walk to everything!

FamilyLocationQuiet

Top guest favorite
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
5.0 out of 5 average rating, 44 reviews

Wister Loft: Charm & History with Modern Love.

LocationAmenitiesAccuracy

Top guest favorite
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
4.96 out of 5 average rating, 76 reviews

Connection Pointe•River views•Quiet•Peaceful

LocationValueCondition

Top guest favorite
Two individuals are seated on a covered porch, overlooking the marina. Comfortable wooden chairs enhance the space, while vibrant trees provide shade. The view includes boats moored in the water, framed by a clear blue sky.
Home in Chesapeake City
4.96 out of 5 average rating, 71 reviews

The Ferry Slip House

ValueLocationAccess

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
4.77 out of 5 average rating, 62 reviews

Quiet Country Relaxing Farm

LocationFamilyCleanliness

Superhost
A fire pit filled with colorful glass stones is centrally placed on a wooden table. The vibrant sunset casts shades of purple and orange across the sky, reflecting on the calm water of the Elk River. The setting creates a serene and inviting ambiance.
Home in Elkton
4.84 out of 5 average rating, 49 reviews

Waterfront House on the Upper Chesapeake Bay

FamilyValueAir conditioning

Guest favorite
Condo in Newark
4.92 out of 5 average rating, 50 reviews

Quiet condo near Christiana, UD, Wilmington | Desk

LocationFamilyDecor

Guest favorite
An open layout showcases a dining area with a light-colored table set for six, adjacent to a cozy living space featuring a neutral-toned sofa and armchairs. A horse-themed artwork is displayed on the wall, while soft curtains frame the windows allowing natural light in.
Guesthouse in Elkton
4.92 out of 5 average rating, 203 reviews

Countryside-Stablehouse-Cozy for 2-Autumn Getaway!

LocationValueIndoor spaces

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