Middletown Vacation Rentals

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Our top choices for Middletown vacation rentals

Heated Pool • Private Backyard • Home Theater

Heated Pool • Private Backyard • Home Theater
2.0 star property
Middletown
$457 nightly
The price is $487
Dec 16 - Dec 17
Total with taxes and fees
Heated Pool • Private Backyard • Home Theater

Country Get Away 1 Bedroom Apartment

Country Get Away 1 Bedroom Apartment
Elkton
9.8 out of 10, Exceptional, (40)
"Absolutely love the accommodations. First impression when entering room was so fresh and clean."
United States
Beverly M.
$105 nightly
The price is $111
Dec 17 - Dec 18
Total with taxes and fees
Country Get Away 1 Bedroom Apartment

Guest Suite for up to 2 in a Victorian on the Chester River

Guest Suite for up to 2 in a Victorian on the Chester River
Millington
9.6 out of 10, Exceptional, (19)
"So pleased with all aspects of my stay. Clean, Comfortable, Quiet, Amenities all beyond expectation."
United States
Cynthia C.
$118 nightly
The price is $125
Dec 15 - Dec 16
Total with taxes and fees
Guest Suite for up to 2 in a Victorian on the Chester River

Summer Rustic Camping with AC and King Bed

Summer Rustic Camping with AC and King Bed
Elkton
9.6 out of 10, Exceptional, (5)
"The owners were very attentive to our needs, and everything was exactly as advertised. We came up for a horse show in Maryland and the convenience to the grounds was exceptional, and everything was wonderful from the privacy to the beauty of the property."
United States
Rees L.
$162 nightly
The price is $163
Jan 7 - Jan 8, 2026
Total with taxes and fees
Summer Rustic Camping with AC and King Bed

The Loft at Gilpin Place*King Bed*Trolley Square! by RedAwning

The Loft at Gilpin Place*King Bed*Trolley Square! by RedAwning
2.0 star property
Trolley Square
8.0 out of 10, Very Good, (1)
"I'm local to Wilmington and stayed here with my husband while our bathroom was being renovated. The apartment is adorable and in a great location, Trolley Square. Walkable to restaurants and bars. Parking can be tough, but it's a safe neighborhood, so to park a block away isn't a problem. This would be a good place to stay for someone who needed to be in Wilmington for business (there's a desk in the living room, and the wifi seemed reliable) or a couple coming here for an event or to check out...
United States
Bridget E.
$281 nightly
The price is $305
Dec 14 - Dec 15
Total with taxes and fees
The Loft at Gilpin Place*King Bed*Trolley Square! by RedAwning

Cozy studio in charming Elkton with AC and WiFi included. 3 miles from Fair Hill

Cozy studio in charming Elkton with AC and WiFi included. 3 miles from Fair Hill
2.0 star property
Elkton
9.8 out of 10, Exceptional, (7)
"Great stay. Everything you need, quiet and clean. "
United States
Melissa J.
$152 nightly
The price is $161
Dec 12 - Dec 13
Total with taxes and fees
Cozy studio in charming Elkton with AC and WiFi included. 3 miles from Fair Hill

Historic Chesapeake City Stay

Historic Chesapeake City Stay
Chesapeake City
9.0 out of 10, Wonderful, (19)
"This place was very cute and clean, also convenient to Shaefers Marina. It was a perfect place for us to spend a weekend on the bay. "
United States
Benay N.
$263 nightly
The price is $279
Dec 12 - Dec 13
Total with taxes and fees
Historic Chesapeake City Stay

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

Hello, welcome to our COMFY 2 BEDROOM apartment located in Wilmington Delaware.
Wilmington
8.8 out of 10, Excellent, (13)
"Very quiet place with comfortable bed. Great overnight stay!"
United States
Rhonda Y.
$169 nightly
The price is $173
Dec 12 - Dec 13
Total with taxes and fees
Hello, welcome to our COMFY 2 BEDROOM apartment located in Wilmington Delaware.

Trolley Teacup Charming Cozy Studio 1 Bedroom Apts by RedAwning

Trolley Teacup Charming Cozy Studio 1 Bedroom Apts by RedAwning
3.0 star property
Trolley Square
6.0 out of 10, (1)
"Be aware that there is on street parking that requires a permit from the city of Wilmington. Red Awni ng worked with me to resolve the issue but it took some time and a few texts to make it work.The on street parking placed me a block and half from the propery. No cost but need proof of renting the space. The GPS sent you down a one way street that does not bring by the front of the property. This was a problem finding the property after dark. No climate control of the rental unit. The bed was...
United States
Clifford
$266 nightly
The price is $280
Dec 14 - Dec 15
Total with taxes and fees
Trolley Teacup Charming Cozy Studio 1 Bedroom Apts by RedAwning

Amazing Modern house with a full kitchen and parking

Amazing Modern house with a full kitchen and parking
Smyrna
9.8 out of 10, Exceptional, (8)
"The house is a beautiful place to stay. The location was ideal for going to attractions and stores. "
United States
Laurie S.
$343 nightly
The price is $351
Dec 12 - Dec 13
Total with taxes and fees
Amazing Modern house with a full kitchen and parking

Family-Friendly 4BR Home in Elkton - AC, High-Speed WiFi & Relaxing Vibes

Family-Friendly 4BR Home in Elkton - AC, High-Speed WiFi & Relaxing Vibes
Elkton
10.0 out of 10, Exceptional, (1)
"The house was clean and a nice place. The kitchen was nice. "
United States
Anthony C.
$321 nightly
The price is $340
Dec 12 - Dec 13
Total with taxes and fees
Family-Friendly 4BR Home in Elkton - AC, High-Speed WiFi & Relaxing Vibes

Private townhouse near downtown and state park

Private townhouse near downtown and state park
Downtown Wilmington
9.4 out of 10, Exceptional, (11)
"Great little spot in a perfect location for us"
United States
j m.
$274 nightly
The price is $281
Dec 15 - Dec 16
Total with taxes and fees
Private townhouse near downtown and state park

Room #2 in Elkton, MD – Easy Access to I-95

Room #2 in Elkton, MD – Easy Access to I-95
2.0 star property
Elkton
$101 nightly
The price is $107
Dec 18 - Dec 19
Total with taxes and fees
Room #2 in Elkton, MD – Easy Access to I-95

Cozy 2-bedroom apartment close to Canal Bike Trail in wonderful Chesapeake City

Cozy 2-bedroom apartment close to Canal Bike Trail in wonderful Chesapeake City
2.0 star property
Chesapeake City
9.4 out of 10, Exceptional, (3)
"House clean ac work great on hot weekends. Great bike path near by and nice restaurants by and the river was great on bike . Not to far from Dover for race I would stay again "
United States
Wayne
$316 nightly
The price is $335
Dec 12 - Dec 13
Total with taxes and fees
Cozy 2-bedroom apartment close to Canal Bike Trail in wonderful Chesapeake City

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

Quarry Landing - Center of Town & River View - 3 Bedroom
Port Deposit
10.0 out of 10, Exceptional, (11)
"Was a great stay would definitely stay again "
United States
jerel p.
$216 nightly
The price is $229
Jan 5 - Jan 6, 2026
Total with taxes and fees
Quarry Landing - Center of Town & River View - 3 Bedroom

Cozy loft above ink shop

Cozy loft above ink shop
Bear
9.6 out of 10, Exceptional, (5)
$103 nightly
The price is $107
Dec 17 - Dec 18
Total with taxes and fees
Cozy loft above ink shop

Charming 3-bedroom house with WiFi, AC in peaceful Elk Neck

Charming 3-bedroom house with WiFi, AC in peaceful Elk Neck
Elkton
8.0 out of 10, Very Good, (10)
"Nice and quiet place to stay"
United States
Gary M.
$268 nightly
The price is $284
Dec 15 - Dec 16
Total with taxes and fees
Charming 3-bedroom house with WiFi, AC in peaceful Elk Neck

A Cool Place to Stay in Wilmington DE

A Cool Place to Stay in Wilmington DE
Wilmington
$150 nightly
The price is $155
Dec 12 - Dec 13
Total with taxes and fees
A Cool Place to Stay in Wilmington DE

New Construction townhome close to everything downtown w/transparent pricing

New Construction townhome close to everything downtown w/transparent pricing
Hilltop
9.8 out of 10, Exceptional, (22)
"Very nice and clean. We do work on Fire Apparatus in the area and this will be my go to spot when in the area."
United States
Peter F.
$176 nightly
The price is $182
Dec 17 - Dec 18
Total with taxes and fees
New Construction townhome close to everything downtown w/transparent pricing

Thunder Hill Retreat - Spacious/Deck/Hot tub

Thunder Hill Retreat - Spacious/Deck/Hot tub
Lincoln University
10.0 out of 10, Exceptional, (16)
"Our stay was perfect! We had a wonderful time with family celebrating our daughter's UD graduation."
United States
Heidi Z.
$386 nightly
The price is $427
Dec 15 - Dec 16
Total with taxes and fees
Thunder Hill Retreat - Spacious/Deck/Hot tub
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 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 $111 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?

Upper Chesapeake Bay 5 bedroom, 3 bath, Hot Tub, Waterfront: This vacation home rental near Middletown is located on a river and has a patio, a garden, and a barbecue grill 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 you can cook with friends or family. You can relax into your vacation with a selection of games and a hot tub.

How many vacation rentals are there in Middletown?

With 6 Expedia vacation rentals, you're sure 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 Historic District and Middletown Town Hall 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.