Photo by Michelle Gonzalez

Middletown Vacation Rentals

Vacation 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 $75
$115 total
includes taxes & fees
May 27 - May 28
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 $120
$237 total
includes taxes & fees
May 27 - May 28
Historic Chesapeake City Stay
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Pool | Outdoor pool
350 Acre Waterfront Farm; High Speed Internet, Pool, Pickleball & Private Dock
10.0 out of 10, Exceptional, (51)
"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 $150
$280 total
includes taxes & fees
May 27 - May 28
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, (18)
"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 $79
$139 total
includes taxes & fees
May 27 - May 28
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.
2 bedrooms, WiFi
Private townhouse near downtown and state park
10.0 out of 10, Exceptional, (4)
"Property was extremely clean!"
The price is $179
$346 total
includes taxes & fees
May 27 - May 28
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 $209
$306 total
includes taxes & fees
Jun 9 - Jun 10
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 | Outdoor pool, a heated 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, (42)
"Suzanne's place was very comfortable and she supplied everything you'd need. It was fun cooking in her kitchen and I was also able to work remotely as well."
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
Private kitchen
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.

Middletown Vacation Rental Travel Info

Number of vacation rentals
2
Popular accommodation
Middletown private vacation homes
Known landmarks
Lums Pond State Park, Frightland and Historic Houses of Odessa
International airport
Philadelphia, PA (PHL-Philadelphia Intl.)

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 $114
$127 total
includes taxes & fees
Jun 2 - Jun 3
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, (439)
"The location was great, the front desk Phil I think was super nice and very pleasant to deal with. He answered all of our questions about the area and was very welcoming."
The price is $110
$122 total
includes taxes & fees
May 30 - May 31
Holiday Inn Express And Suites Middletown, an IHG Hotel
Indoor pool
Hampton Inn Middletown
2.5 star property
8.8 out of 10, Excellent, (677)
"Great"
The price is $121
$135 total
includes taxes & fees
May 30 - May 31
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.

Everything you need to know about Middletown vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Middletown vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Middletown vacation 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 low season months. For more hustle and bustle, you may prefer to visit Middletown in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $75 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Middletown rentals

At Expedia, we put the best Middletown vacation 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 vacation.

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 vacation rental in Middletown?

Yes, you can find vacation rentals in Middletown close to Frightland, or you can choose a secluded option if you're looking for extra privacy while you relax. Our travelers 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 vacation rentals that Middletown has to offer?

Oaxaca, a private room with private entrance: This vacation home rental near Middletown is located in the city center 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 vacation rentals are there in Middletown?

With 3 Expedia vacation rentals, you're sure 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 vacation rentals like in Middletown?

Vacation rentals are private accommodations you can stay in for several days or more in Middletown. Vacation rentals provide amenities such as kitchens and laundry facilities so your stay will be comfortable. If you're concerned about a clean environment, vacation rentals can offer a sense of safety away from shared hotel elevators and lobbies packed with people while still allowing you the excitement and enjoyment of travel. You'll also get more space in a vacation rental than in a standard hotel, which makes a vacation rental a popular choice for family gatherings.

Recent reviews of Middletown properties
Expedia verified reviews

SureStay Plus Hotel by Best Western Brandywine Valley

SureStay Plus Hotel by Best Western Brandywine Valley

5/5 Excellent
"This hotel is really old, tiny bathroom, towels have seen better days. It needs an update. "
A verified traveler from Annapolis stayed at SureStay Plus Hotel by Best Western Brandywine Valley
Posted 1 day ago
SureStay Plus Hotel by Best Western Brandywine Valley