Middletown Holiday Rentals from €455: Search Short-Term Rentals

Q: What are some of the best holiday rentals that Middletown has to offer?

Beachfront Sunsets on the Water at Oakwood Beach : This holiday home rental outside of Middletown is located on the beach, and has a fireplace, a patio and a BBQ to put you at ease in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and a selection of games.

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Holiday Rentals in Middletown

On the beach, sun-loungers, beach towels

"You're messaging ChatGPT, an AI We have no words to describe the perfect experience that John's cabin on the Delaware River provided us. John was a patient and generous host. From the beginning of the process, he was available for any questions, and even agreed to change our arrival date due to an unexpected issue with one of our friends. The house was very clean, delicately and beautifully decorated, and filled with everything one could possibly imagine needing on a vacation. When we arrived, a...

"Celebrated my wife’s special birthday and our family from NY, CT, TX, PA and MD all stayed for the weekend. 12 of us. Plenty of space to all gather together or gather in smaller groups. Game room, pool and hot tub were probably the two favorite places to hang out. Oh and you can’t forget the view overlooking the Bohemia River. Beautiful house. "

"Good location in downtown Wilmington that works well for a small group looking for a good alternative to nearby Riverfront hotels. "

"The house had plenty of space and location was great!"

"it being off season,very quiet. the people in the surrounding neighborhood were very friendly, we had a great time, ash and christine were awsome host. we will deffinately go back again!"

"We had a great two days here! House has everything you need. We really enjoyed the hot tub! We were lucky the weather was so warm and we could just sit outside all day looking at the water and end the day with gorgeous sunsets. We would definitely come back!"

"Property was clean and close to everything in Chesapeake City"

Beach nearby, sun-loungers, beach towels

"We had a great time at the house with friends from our apartment building and neighborhood for the long Thanksgiving weekend. Debbie and Bob had everything we needed to cook with, the porch overlooking the Bay was amazing, and the living room, TV room and dining room were all used frequently. We also played games, and had a nice fire in the portable fire pit outside. Weather got coooold but the house was always warm and cozy. It was a really fun stay. The bedrooms were great, too. They've taken...

"Easy to locate & use street parking. The neighborhood seemed a bit rough, most neighbors were welcoming. 3 large bedrooms rare find at this pricepoint. The bed were fine but springs poked a bit. were poking and not super comfy. "

"The house is cute and clean small house perfect for 9. Comfortable clean linens were provided. Easy to get to. Close to food and easy to get to University of Delaware. Host was easy to get in touch with. The only thing was no TV at all but we enjoyed our time."

"This home was amazing. Nicely decorated for the holiday. Labels on kitchen cavinets. Host was easy to communicate with. Fast responses. doors made it easy to find things (huge kitchen). "

"Decided to try something different, and luckily found the Dockside Doghouse. Very comfortable, incredibly relaxing."

"Porch is filled with cobwebs. Steps inside need a lot of improvement. Inside was very clean, if dated. However I was pleased with the updated shower, refrigerator, kitchen. No tv made the down time lonely. Netflix did not work, nor did dvd player. For me I needed a much more closer bathroom on the second floor. Getting up 3 times a night to use bathroom & navigating those poorly constructed stairs was scary. I did not want to stay in the single bed right by front door. SUZANNE was very...

"Great!"

"The coziest house we have ever stayed at ! The host went above and beyond to have everything we could need! Would definitely recommend ! "

"Cute, up-to-date house, peaceful location, beautiful views. Well supplied kitchen, including sharp knives! Excellent communication with owner – prompt and helpful. Fast internet. Could use more bathroom surface areas; a few more hooks to hang clothes and towels; and an additional umbrella or two outside for shade. My mom, sister, and I thoroughly enjoyed our stay."

"We enjoyed our Thanksgiving get away at this very cute waterfront cottage. Our stay was a extremely relaxing and enjoyable time. 😊👌👍"

"Place was great !"

"The house and location on Still Pond Maryland was great!! House was clean and tiddy. Caught perch, catfish and bass off their dock!! Area is beautiful and quiet! "

"we had a short stay but wished it was longer, the views from the house and peacefulness of the location were incredible"

includes taxes & fees

23 Jan - 24 Jan

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Other types of properties in Middletown you may be interested in

"The property is well kept and the staff was helpful. Fresh coffee 24/7. Breakfast was sub-par."

includes taxes & fees

9 Feb - 10 Feb

"Nothing"

includes taxes & fees

2 Feb - 3 Feb

"The hotel and staff are outstanding!"

includes taxes & fees

9 Feb - 10 Feb

Find out more about Middletown

Everything you need to know about Middletown holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Middletown holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Middletown holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Middletown holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Middletown. If you’re looking for a little peace, consider booking during the quieter months, such as . For more hustle and bustle, you may prefer to visit in .

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Middletown holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Middletown holiday rentals we have selected for you start as low as €455 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Middletown rentals

At Expedia, we put the best Middletown holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Middletown rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Middletown holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Middletown. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Recent reviews of Middletown properties

Baymont by Wyndham Newark at University of Delaware

5/5 Excellent

Excellent

"The people were very friendly, my room was clean and smelled very nice. The only complaint I have is the pillows were not comfortable, other than that everything was wonderful. I would definitely stay again when I go back to Delaware. "

A verified traveller stayed at Baymont by Wyndham Newark at University of Delaware

Posted 2 days ago

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All accommodation types in Middletown

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Frequently asked questions

Can I find a holiday rental in Middletown?

Yes, there are holiday rentals in Middletown close to Frightland, or you can select a more secluded option if you're looking for a relaxing stay. Our travellers say Middletown has a good selection of restaurants. Make sure you have time to check out the festivals and churches during your trip.

What are some of the best holiday rentals that Middletown has to offer?

Beachfront Sunsets on the Water at Oakwood Beach: This holiday home rental outside of Middletown is located on the beach, and has a fireplace, a patio and a BBQ to put you at ease in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and a selection of games.

How many holiday rentals are there in Middletown?

With 5 Expedia holiday rentals, you're guaranteed to find just the right place for your Middletown stay.

What can I see and do in Middletown?

Enjoy the outdoors at Rothwell Estates Park and Mapleton Square, or simply take in cultural attractions like The Everett Annex and Everett Theatre. While here, Frightland and Dutch Country Farmers Market are other places worth a visit.

What are holiday rentals like in Middletown?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Middletown. Holiday rentals feature extras such as kitchens and laundry facilities to help you enjoy your stay. If you're concerned about a clean environment, holiday rentals can offer a sense of safety away from shared hotel lifts and busy lobbies while still allowing you to travel. You'll also find more space in a holiday rental than in a standard hotel, which makes a holiday rental an attractive choice for family trips.

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Holiday Rentals in Middletown

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Holiday Rentals in Middletown

Beachfront Sunsets on the Water at Oakwood Beach

Beachfront Sunsets on the Water at Oakwood Beach

Stunning waterfront villa with indoor pool and kids swing set and play area.

Stunning waterfront villa with indoor pool and kids swing set and play area.

Wilmington Comfort 4 Min to Riverfront fenced yard

Wilmington Comfort 4 Min to Riverfront fenced yard

Spacious Single Family Home Near Water, Recreational Areas/Parks, and Shopping..

Spacious Single Family Home Near Water, Recreational Areas/Parks, and Shopping..

Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay

Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay

Waterfront Cabin With Spectacular Sunsets Overlooking The Chesapeake Bay

Waterfront Cabin With Spectacular Sunsets Overlooking The Chesapeake Bay

Historic Chesapeake City Stay

Historic Chesapeake City Stay

Historic Waterfront Home with Chesapeake Bay View. Sleeps 9. Close to the Beach

Historic Waterfront Home with Chesapeake Bay View. Sleeps 9. Close to the Beach

Super cute 3 bedroom remodeled townhouse near downtown Wilmington

Super cute 3 bedroom remodeled townhouse near downtown Wilmington

Trendy Cozy Cottage Clean Bright Three bed, Two bath Patio

Trendy Cozy Cottage Clean Bright Three bed, Two bath Patio

Chesapeake City Quiet Overlook

Chesapeake City Quiet Overlook

Fully Equipped Docked Houseboat at Log Pond Marina in Havre de Grace, MD.

Fully Equipped Docked Houseboat at Log Pond Marina in Havre de Grace, MD.

Cozy home with fenced in yard-Dog Friendly . 2 block walk to historic downtown!

Cozy home with fenced in yard-Dog Friendly . 2 block walk to historic downtown!

350 Acre Waterfront Farm; High Speed Internet, Pool, Pickleball & Private Dock

350 Acre Waterfront Farm; High Speed Internet, Pool, Pickleball & Private Dock

A cottage on the shore of the Delaware River

A cottage on the shore of the Delaware River

Waterfront house with amazing views. Top of the Chesapeake

Waterfront house with amazing views. Top of the Chesapeake

Amazing Waterfront Views at Sailor's Sunrise Cottage on the Upper Chesapeake Bay

Amazing Waterfront Views at Sailor's Sunrise Cottage on the Upper Chesapeake Bay

Private Carriage House Retreat on a 33 Acre Historic Working Estate

Private Carriage House Retreat on a 33 Acre Historic Working Estate

Waterfront Home & Dock, sleeps 10 Max. Eastern shore, Betterton Chestertown MD.

Waterfront Home & Dock, sleeps 10 Max. Eastern shore, Betterton Chestertown MD.

5-bedroom vacation home 5 minutes from historic Charlestown

5-bedroom vacation home 5 minutes from historic Charlestown

Other types of properties in Middletown you may be interested in

Fairfield Inn & Suites by Marriott Middletown

Fairfield Inn & Suites by Marriott Middletown

Hampton Inn Middletown

Hampton Inn Middletown

Holiday Inn Express And Suites Middletown, an IHG Hotel

Holiday Inn Express And Suites Middletown, an IHG Hotel

Find out more about Middletown

Find out more about Middletown

Recent reviews of Middletown properties

Recent reviews of Middletown properties

Baymont by Wyndham Newark at University of Delaware

Explore a world of travel with Expedia

Explore a world of travel with Expedia

Frequently asked questions