Photo by Michelle Gonzalez

Middletown Holiday Rentals

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Holiday Rentals in Middletown

1 bedroom, WiFi, bed sheets
Oaxaca, a private room with private entrance
9.0 out of 10, Wonderful, (8)
"Ms Laura is such a great hostess. The room is so comfy and clean. We hope to stay again.. :)"
The price is NZ$187
per night
2 Jun - 3 Jun
Oaxaca, a private room with private entrance
Beach nearby, sun-loungers
Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay
9.8 out of 10, Exceptional, (36)
"Waterview cottage is comfortable and very clean. The accommodations look new and we had good sleep. The kitchen has most of the necessary equipment for meal preparation. A baking sheet pan is needed. WiFi and Roku TV was excellent. The primary bedroom bed was so tall/high my wife could not get in or out of it. That necessitated sleeping in the 2 twins. Plus, one of the twins was missing the top mini mattress. The view is mostly of the neighborhood street, nearby homes and their roofs and a small...
Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay
Pool
Historic Chesapeake City Stay
8.0 out of 10, Very good, (1)
"The place overall is very simple and nice. The bed was a little uncomfortable And decided to not stay the extra night and come home and use my own bed. Overall, very clean very nice."
The price is NZ$386
per night
29 May - 30 May
Historic Chesapeake City Stay
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Pool
350 Acre Waterfront Farm; High Speed Internet, Pool, Pickleball & Private Dock
10.0 out of 10, Exceptional, (52)
"Beautiful and huge property. Paddling in the river was great!"
350 Acre Waterfront Farm; High Speed Internet, Pool, Pickleball & Private Dock
Property grounds
Fully Equipped Docked Houseboat at Log Pond Marina in Havre de Grace, MD.
9.2 out of 10, Wonderful, (10)
"This was my second time to the houseboat and it was wonderful! It is conveniently located and many small shops, restaurants, brewery/bars are walking distance, and a short drive to wineries. Also a park right across from the marina."
Fully Equipped Docked Houseboat at Log Pond Marina in Havre de Grace, MD.
Property grounds
Two bedroom luxury apartment! Amenities included!
The price is NZ$463
per night
29 May - 30 May
Two bedroom luxury apartment! Amenities included!
Property grounds
Waterfront Home with Private Dock, Eastern shore, Betterton Chestertown MD.
9.8 out of 10, Exceptional, (80)
"House was fine. Odd they did not provide sheets. Was difficult for folks who came from far away. But the house was lovely and we enjoyed our time there!!"
Waterfront Home with Private Dock, Eastern shore, Betterton Chestertown MD.
Fridge, microwave, oven, stovetop
WORLD’S BEST SUNSETS ON UPPER CHESAPEAKE BAY -CRYSTAL BEACH MANOR, EARLEVILLE,MD
10.0 out of 10, Exceptional, (19)
"Was very warm and cozy home and right on the water with beach you can easily access"
WORLD’S BEST SUNSETS ON UPPER CHESAPEAKE BAY -CRYSTAL BEACH MANOR, EARLEVILLE,MD
Property grounds
Entire place with private parking
7.8 out of 10, Good, (6)
"Overall great location, space and with secure parking."
The price is NZ$234
per night
30 May - 31 May
Entire place with private parking
Exterior
House on 3 acres near Fair Hill Nature Park. Close to Pa, and De.
9.8 out of 10, Exceptional, (85)
"Such a comfortable place to stay! Fully stocked kitchen, big rooms with comfortable beds and linens. Everything is clean and the appliances are new. Sweet welcome gift of pastries and water. Quiet neighborhood. Easy to access and property host was very responsive."
House on 3 acres near Fair Hill Nature Park. Close to Pa, and De.
Private kitchen
Private townhouse near downtown and state park
10.0 out of 10, Exceptional, (4)
"Property was extremely clean!"
The price is NZ$562
per night
10 Jun - 11 Jun
Private townhouse near downtown and state park
Property grounds
Waterfront Cabin With Spectacular Sunsets Overlooking The Chesapeake Bay
10.0 out of 10, Exceptional, (65)
"We had a great get-away for a few days with our friends. The cabin was in a quiet neighborhood with amazing views. We especially enjoyed using the fire pit while sitting in the comfortable Adirondack chairs overlooking the Chesapeake Bay. The owners were friendly and great to work with. Highly recommend!"
Waterfront Cabin With Spectacular Sunsets Overlooking The Chesapeake Bay
Property grounds
Beachfront Sunsets on the Water at Oakwood Beach
10.0 out of 10, Exceptional, (19)
"The location was great for us because it was relatively close to Newark, DE and Philadelphia. Water views were great from so much of the house and owners had thought of every possible touch to make people feel at home. There were plenty of outlets, chargers, TVs, tables & chairs, hooks in bathrooms, nightlights, etc. The fridge was free of all sorts of open condiments that are probably supposed to be helpful for guests but that drive my husband crazy as they've taken up half the fridge in the...
Beachfront Sunsets on the Water at Oakwood Beach
Property grounds
Quarry Landing - Center of Town & River View - 3 Bedroom
10.0 out of 10, Exceptional, (5)
"What a beautiful home. The host was attentive to the small details in the house, and my friend and I greatly enjoyed our stay."
The price is NZ$498
per night
24 Jun - 25 Jun
Quarry Landing - Center of Town & River View - 3 Bedroom
Fridge, microwave, oven, stovetop
Trendy Cozy Cottage Clean Bright Three bed, Two bath Patio
9.8 out of 10, Exceptional, (27)
"This location was perfect for our stay during a bass tournament on the upper bay. boa parking was great and very secure compared to hotels. SAhelly was very accomadating"
Trendy Cozy Cottage Clean Bright Three bed, Two bath Patio
Pool
Riverfront Retreat: Panoramic water views with Hot Tub. Sleeps 16.
9.6 out of 10, Exceptional, (154)
"The property was beautiful and just as described. The property managers were quick to respond and very helpful. We truly enjoyed our stay."
Riverfront Retreat: Panoramic water views with Hot Tub. Sleeps 16.
Property grounds
Cozy home with fenced in yard-Pet Friendly. 2 block walk to historic downtown!
9.6 out of 10, Exceptional, (43)
"This cozy home was perfect for me and my dog for an extended stay! We loved walking in HdG every day and went on several hikes throughout the area. The kitchen was well-appointed and I found everything I needed and then some! Suzanne left a bottle of wine for me, and she was responsive and made herself available for any issues/questions. I loved my time here and look forward to visiting again. Thank you for sharing your home with me!"
Cozy home with fenced in yard-Pet Friendly. 2 block walk to historic downtown!
Interior
Historic home in the heart of Main Street- walkable to shops and restaurants
10.0 out of 10, Exceptional, (7)
"Way to make us feel welcome. From the accommodations to the amenities this property is a vrbo treasure. The owners exceeded our expectations in every way."
Historic home in the heart of Main Street- walkable to shops and restaurants
Interior
Hidden Gem! - Downtown
Hidden Gem! - Downtown
Fridge, microwave, oven, stovetop
Lark's Nest on the Chester River. Spacious, waterfront home with private dock.
10.0 out of 10, Exceptional, (3)
"Lark’s Nest was a cute little place! Very clean! The view from the patio was stunning, and if you’re a bird lover you will be in your glory! Bring your binoculars and sit on the deck and wait! House was well equipped with most everything you would need! Host was very quick to write back when asked a question! First time in this area and hopefully be back again in the future!"
Lark's Nest on the Chester River. Spacious, waterfront home with private dock.
Don't see what you're looking for?
See all available properties in Middletown
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.

Other types of properties in Middletown you may be interested in

Lobby
Fairfield Inn & Suites by Marriott Middletown
2.5 star property
9.2 out of 10, Wonderful, (106)
"This hotel is fairly new and in good condition. Large room. Not overly crowded. Satisfied with this hotel."
The price is NZ$199
per night
23 Jun - 24 Jun
Fairfield Inn & Suites by Marriott Middletown
Exterior
Holiday Inn Express And Suites Middletown, an IHG Hotel
2.5 star property
9.2 out of 10, Wonderful, (440)
"The staff was very nice and accommodating. I needed a shower chair and they were able to provide it without a hassle. The rooms were clean and up to date. "
The price is NZ$226
per night
2 Jun - 3 Jun
Holiday Inn Express And Suites Middletown, an IHG Hotel
Indoor pool
Hampton Inn Middletown
2.5 star property
8.8 out of 10, Excellent, (678)
"Great"
The price is NZ$229
per night
4 Jun - 5 Jun
Hampton Inn Middletown
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.

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Middletown holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Middletown. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Middletown. Seeing all the best attractions is bound to make you fall in love with Middletown. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Middletown short-term rentals, that won’t be hard to do.

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?

Oaxaca, a private room with private entrance: This holiday home rental outside of Middletown is located in the city centre, and offers a garden, air conditioning and laundry facilities to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a fridge, a microwave and a coffee maker.

How many holiday rentals are there in Middletown?

With 3 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 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.

Recent reviews of Middletown properties
Expedia verified reviews