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Middletown Holiday Rentals

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Holiday Rentals in Middletown

Chesapeake Bay House with Dock & Private Beach

Elkton
10.0 out of 10, Exceptional, (177)
"Absolutely love this property! This is my family’s second stay here, we will definitely be coming back. Great hosts, clean house, wonderful location!"
United States
Katie H.
Chesapeake Bay House with Dock & Private Beach

Beachfront Sunsets on the Water at Oakwood Beach

Salem
10.0 out of 10, Exceptional, (43)
"House was well maintained and very clean. Fantastic view."
United States
Paul P.
Beachfront Sunsets on the Water at Oakwood Beach

Hello, welcome to our COMFY 2 BEDROOM apartment located in Wilmington Delaware.

Wilmington
8.6 out of 10, Excellent, (12)
"Was in Wilmington to work a trade show at the Chase Center on the Riverfront. Everything was as described and the communications with the host were great. Only about a 12 minute drive to the venue and lots of restaurants within a 10 minute drive. It’s nothing fancy but for about the same price as a budget hotel room you get a kitchen, two comfy bedrooms and a living room. "
United States
Douglas R.
The price is NZ$308
includes taxes & fees
16 Nov - 17 Nov
Hello, welcome to our COMFY 2 BEDROOM apartment located in Wilmington Delaware.

5-bedroom vacation home 5 minutes from historic Charlestown

Perryville
9.8 out of 10, Exceptional, (146)
"Can’t wait to come back during warmer weather. It was a perfect over night stay. "
United States
Ashlee S.
The price is NZ$1,063
includes taxes & fees
17 Nov - 18 Nov
5-bedroom vacation home 5 minutes from historic Charlestown

Waterfront house with amazing views. Top of the Chesapeake

Perryville
10.0 out of 10, Exceptional, (102)
"Great accommodation overall - would visit again! Calm, great view, perfect spot for a private getaway."
United States
Jörg
Waterfront house with amazing views. Top of the Chesapeake

Charming 2-bedroom house with WiFi, AC in marvelous Wilmington

Wilmington
2.0 out of 10, (2)
"The neighborhood was creepy. Mail was on the doorstep unopened, the owner never communicated the code to get in. I sent a text/email and never got a response. The neighbors were doing drugs. … some sort of sniffing, smoking?!? We felt totally unsafe and went to an Embassy Suites. I would expect a full refund and have contacted my credit card company to enter a complaint. I would never recommend this place to anyone !!!"
United States
marsha k.
The price is NZ$220
includes taxes & fees
13 Nov - 14 Nov
Charming 2-bedroom house with WiFi, AC in marvelous Wilmington

Charming 2-bedroom cabin close to Fair Hill on horse farm

Elkton
9.6 out of 10, Exceptional, (12)
"Good experience"
United States
Thomas Z.
Charming 2-bedroom cabin close to Fair Hill on horse farm

Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay

Earleville
9.8 out of 10, Exceptional, (58)
"Wonderful house in a welcoming, friendly community. "
United States
Benjamin A.
Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay

Charming 2-bedroom cottage with BOAT SLIP, WiFi, and AC

Elkton
9.8 out of 10, Exceptional, (14)
"It was a lovely home and we very much enjoyed our stay. Clean, comfortable beds and great location. "
United States
Deborah M.
Charming 2-bedroom cottage with BOAT SLIP, WiFi, and AC

*** NEWLY RENOVATED**** Escape to a Beautiful Getaway on the Chesapeake Bay

Perryville
9.2 out of 10, Wonderful, (181)
"Perfect spot for a relaxing weekend on the water, even if the kids are playing in a sports tournament."
United States
Donald R.
*** NEWLY RENOVATED**** Escape to a Beautiful Getaway on the Chesapeake Bay

Outrange at Blue Heron Farm. Pet friendly cabin at waterfront farm!

Chestertown
10.0 out of 10, Exceptional, (10)
"Check-in was very easy. House was clean and well supplied with everything we needed. Peaceful and quiet. Mowed and cleared trails to enjoy. "
United States
Carol B.
Outrange at Blue Heron Farm. Pet friendly cabin at waterfront farm!

Two-story condo in luxury townhouse. Free parking.

Downtown Wilmington
9.6 out of 10, Exceptional, (16)
"This is a great place and super conveniently located. We loved all the amenities! Special shout out for the lovely towels! We would definitely stay here again!"
United States
Shelly S.
The price is NZ$636
includes taxes & fees
23 Nov - 24 Nov
Two-story condo in luxury townhouse. Free parking.

Historic Chesapeake City Stay

Chesapeake City
9.0 out of 10, Wonderful, (17)
"Perfect little place for 2. Quiet Very close to Schaefers. "
United States
Karen H.
The price is NZ$493
includes taxes & fees
22 Nov - 23 Nov
Historic Chesapeake City Stay

Tiny Home Tranquil Oasis

Bear
The price is NZ$427
includes taxes & fees
13 Nov - 14 Nov
Tiny Home Tranquil Oasis

Summer Rustic Camping with AC and King Bed

Elkton
9.6 out of 10, Exceptional, (5)
"The dome and surrounding areas looks like it does in the photos, and using the compost toilet, shower, etc were pretty easy even for a camping novice like myself. The farm is beautiful and quiet. Good opportunities for birding too. I never saw or heard the gentlemen who live in the farmhouse, I only saw their cars come and go. I came here for rest and a connection to nature, and that’s what I got. I’d love to come back in the future! I think it would be even nicer later in the spring."
United States
Lady N.
The price is NZ$282
includes taxes & fees
13 Nov - 14 Nov
Summer Rustic Camping with AC and King Bed

Luxury Condo + Free Garage Parking 402

Downtown Wilmington
The price is NZ$366
includes taxes & fees
1 Dec - 2 Dec
Luxury Condo + Free Garage Parking 402

Trendy Cozy Cottage Clean Bright Three bed, Two bath Patio

Elkton
9.8 out of 10, Exceptional, (42)
"We stayed for my Birthday! It was definitely a great place to stay. The house was decorated beyond my expectation. We are planing to book again for Girls Weekend."
United States
Billie W.
Trendy Cozy Cottage Clean Bright Three bed, Two bath Patio

A cottage on the shore of the Delaware River

Salem
9.8 out of 10, Exceptional, (68)
"This small home was perfect for a stay on our road trip. Beautiful views and quiet place to stay."
United States
Taylor A.
A cottage on the shore of the Delaware River

Quarry Landing - Center of Town & River View - 3 Bedroom

Port Deposit
9.8 out of 10, Exceptional, (10)
"Amy has a beautiful home, filled with character and special touches. We absolutely loved our stay and have zero complaints. The location was wonderful and we were extremely comfortable."
United States
Geoff F.
The price is NZ$375
includes taxes & fees
13 Nov - 14 Nov
Quarry Landing - Center of Town & River View - 3 Bedroom

Private townhouse near downtown and state park

Downtown Wilmington
9.4 out of 10, Exceptional, (11)
"Property was extremely clean!"
United States
margaret p.
The price is NZ$501
includes taxes & fees
13 Nov - 14 Nov
Private townhouse near downtown and state park
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Middletown Hotel Reviews

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, 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 NZ$220 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. 

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?

Chesapeake Bay House with Dock & Private 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 5 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You and your friends and family can relax into your holiday with amenities such as a selection of games.

How many holiday rentals are there in Middletown?

With 6 Expedia holiday rentals, you're guaranteed to find just the right place for your Middletown stay.

What can I see and do in Middletown?

Cultural attractions include The Everett Annex and Everett Theatre, whereas Frightland is just one of the family-friendly sights. While here, Middletown Town Hall and Back Creek 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.