Middletown Holiday Rentals from €453: Search Short-Term Rentals

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

Waterfront house with amazing views. Top of the Chesapeake : This holiday home rental outside of Middletown is located on the beach, and has a fireplace, a balcony and a BBQ to put you at ease in your new surroundings. It has 3 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.

Check Middletown holiday rental availability

Holiday Rentals in Middletown

"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!"

On the beach, sun-loungers, beach towels

"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."

"This house exceeded our expectations! From the pictures, we knew it would be beautiful, but once we got there it seemed so much bigger and brighter than what the pictures show. Its so light and airy and was perfect for what we came for. It was VERY clean, each bedroom came with towels and makeup wipes. You can tell the hosts put a lot of thought into this home. We went in the fall, but was still such a wonderful time walking along the quiet beach and having drinks on the patio. Would highly...

"Very quaint and cute cottage really enjoyed sleeping on the porch , The sound of the waves because it was windy was so soothing. I felt We were on a sailboat."

"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."

"We really enjoyed the property. The location was within walking distance to the downtown area providing many food and shopping options. We were in MD for a lacrosse tournament which was minutes away from the house. The house was recently renovated, clean and bright. We had more than enough space for our group of 8."

includes taxes & fees

2 Dec - 3 Dec

"Couple little things were annoying. Overall a place/property we love. This was our third visit and plan for another."

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

includes taxes & fees

27 Nov - 28 Nov

Beach nearby, sun-loungers, beach towels

"This house had the most amazing views and was clean and tidy. It was perfect for us and the dogs. The yard was clean and mowed and provided plenty of room for frisbee play which is part of my german shepherd's job. The kitchen was very adequate for our needs! As expected, the upstairs bedrooms were "historic" and the staircase was steep also "historic". The showers were perfect. We had a great visit and would love to come back here!"

"This home was absolutely magnificent! Location and scenery were wonderful. Just so much to keep our attention and kept us in awe. This was a family trip with siblings and soooo many wonderful memories were made. We are older now and it means more than ever before. Thank you to our host Jane who kept in touch and was so very attentive. Most gracious. We are already talking about going back. Cannot say enough it thank you from the bottom of our hearts.♥️"

"The house was perfect for our stay. We were in town for a family event and needed a place for 8 adults and 4 children and this was perfect. Lots of space to spread out with a great rec room that kept both kids and adults entertained during down time. The neighborhood was beautiful and had easy access to area restaurants and shopping. Close to many area attractions. It was the perfect location to have close proximity to points of interest and then return to at end of day to a relaxing...

"We enjoyed our stay. Condo was comfortable and very clean. It provided convenient access for our weekend plans in Kennedyville and Chestertown."

"Great value, was a great jumping point for our group, who was here for a wedding"

"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 ! "

"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!"

"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! "

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Other types of properties in Middletown you may be interested in

"Love the restaurant "

includes taxes & fees

1 Dec - 2 Dec

"Lovely attentive front of house staff. Room v clean. Breakfast wasnt great but included in room rate"

includes taxes & fees

23 Dec - 24 Dec

"All nice"

includes taxes & fees

1 Dec - 2 Dec

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 €453 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

4/5 Good

"Nice stay"

A verified traveller stayed at Days Inn by Wyndham Newark Wilmington

Posted 10 hours ago

Staybridge Suites Wilmington Downtown, an IHG Hotel

5/5 Excellent

"This hotel was excellent. The customer service was top notch, the room was spacious, and the morning breakfast was full of excellent, delicious options. Would absolutely stay here again!"

A verified traveller stayed at Staybridge Suites Wilmington Downtown, an IHG Hotel

Posted 4 days ago

Comfort Inn & Suites Newark - Wilmington

5/5 Excellent

"I especially liked the complementary breakfast which offered many choices. I liked that you could get coffee anytime. And fresh lemon infused water was available in the lobby. I also appreciated having a microwave, refrigerator and coffeemaker in my room. Extra pillows on the very comfortable bed were a plus, as was the controllable A/C thermostat. The effective blackout curtains & the quiet were wonderful! All in all, a very favorable experience."

A verified traveller stayed at Comfort Inn & Suites Newark - Wilmington

Posted 6 days ago

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All accommodation types in Middletown

B&B in Middletown

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?

Waterfront house with amazing views. Top of the Chesapeake: This holiday home rental outside of Middletown is located on the beach, and has a fireplace, a balcony and a BBQ to put you at ease in your new surroundings. It has 3 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 4 Expedia holiday rentals, you're guaranteed to find just the right place for your Middletown stay.

What can I see and do in Middletown?

Explore the area and family-friendly sights such as Frightland, or get out into nature at a spot like Lums Pond State Park. While here, Dutch Country Farmers Market and Frog Hollow Golf Club 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

Check Middletown holiday rental availability

Holiday Rentals in Middletown

Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay

Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay

Waterfront house with amazing views. Top of the Chesapeake

Waterfront house with amazing views. Top of the Chesapeake

Beachfront Sunsets on the Water at Oakwood Beach

Beachfront Sunsets on the Water at Oakwood Beach

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

Trendy Cozy Cottage Clean Bright Three bed, Two bath Patio

Trendy Cozy Cottage Clean Bright Three bed, Two bath Patio

Historic home in the heart of Main Street- walkable to shops and restaurants

Historic home in the heart of Main Street- walkable to shops and restaurants

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.

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

Chesapeake City Quiet Overlook

Chesapeake City Quiet Overlook

Welcome to Woodview Estates!

Welcome to Woodview Estates!

BEACH WITHOUT THE BUSTLE

BEACH WITHOUT THE BUSTLE

Wilmington Comfort 4 Min to Riverfront fenced yard

Wilmington Comfort 4 Min to Riverfront fenced yard

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-Pet Friendly . 2 block walk to historic downtown!

Cozy home with fenced in yard-Pet 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 Cabin With Spectacular Sunsets Overlooking The Chesapeake Bay

Waterfront Cabin With Spectacular Sunsets Overlooking The 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 8 Max. Eastern shore, Betterton Chestertown MD.

Waterfront Home & Dock, sleeps 8 Max. Eastern shore, Betterton Chestertown MD.

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

Days Inn by Wyndham Newark Wilmington

Explore a world of travel with Expedia

Explore a world of travel with Expedia

Frequently asked questions