Book Holiday Homes in Middletown

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Featured Holiday Homes in Middletown

Chesapeake City Quiet Overlook

Chesapeake City Quiet Overlook

Chesapeake City
Stay at this vacation home in Chesapeake City. Enjoy patios, an in-room coffeemaker, and air conditioning. Popular attractions C and D Canal Museum and Back ...
Chesapeake City Quiet Overlook
New Construction townhome close to everything downtown w/transparent pricing

New Construction townhome close to everything downtown w/transparent pricing

Wilmington
The price is NZ$320 per night from 2 Jan to 3 Jan
NZ$320
includes taxes & fees
2 Jan - 3 Jan 2025
Stay at this vacation home in Wilmington. Enjoy an in-room coffeemaker, in-room fireplaces, and air conditioning. Popular attractions Delaware Theatre Company ...
New Construction townhome close to everything downtown w/transparent pricing
Luxurious and spacious townhome with all necessary amenities awaits your stay.

Luxurious and spacious townhome with all necessary amenities awaits your stay.

Middletown
Stay at this vacation home in Middletown. Enjoy an in-room coffeemaker, in-room fireplaces, and air conditioning. Popular attractions Frog Hollow Golf Club and ...
Luxurious and spacious townhome with all necessary amenities awaits your stay.
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Trendy Cozy Cottage Clean Bright Three bed, Two bath Patio

Trendy Cozy Cottage Clean Bright Three bed, Two bath Patio

Elkton
Book a stay at this family-friendly vacation home in Elkton. Enjoy free WiFi, a garden, and furnished patios. Popular attractions Upper Bay Museum and Milburn ...
Trendy Cozy Cottage Clean Bright Three bed, Two bath Patio
Private townhouse near downtown and state park

Private townhouse near downtown and state park

Wilmington
The price is NZ$616 per night from 26 Dec to 27 Dec
NZ$616
includes taxes & fees
26 Dec - 27 Dec
Stay at this vacation home in Wilmington. Enjoy air conditioning. Popular attractions The Playhouse on Rodney Square and Grand Opera House are located ...
Private townhouse near downtown and state park
Beautiful Brick-Wall House in Historic Newcastle

Beautiful Brick-Wall House in Historic Newcastle

New Castle
Stay at this vacation home in New Castle. Enjoy free WiFi, an in-room coffeemaker, and air conditioning. Popular attractions Christiana Mall and DuPont Environmental ...
Beautiful Brick-Wall House in Historic Newcastle
Beachfront Sunsets on the Water at Oakwood Beach

Beachfront Sunsets on the Water at Oakwood Beach

Salem
Book a stay at this beach vacation home in Salem. Enjoy free WiFi, a beach locale, and a garden. Popular attractions Hickory Island and Fort Delaware State Park ...
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

Perryville
Stay at this vacation home in Perryville. Enjoy free WiFi, a garden, and patios. Popular attractions Concord Point Lighthouse and Havre de Grace Maritime Museum ...
Amazing Waterfront Views at Sailor's Sunrise Cottage on the Upper Chesapeake Bay
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

Betterton
Book a stay at this family-friendly vacation home in Betterton. Enjoy free WiFi, a garden, and tennis courts. Popular attraction Betterton Beach is located ...
Historic Waterfront Home with Chesapeake Bay View. Sleeps 9. Close to the Beach
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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 Holiday Houses

Do you love last minute road trips and late-night food runs and sunrises on the beach? Do words like “schedule” and “calendar” make you shout, “Don’t box me in!”? You might be a little bit of a rebel. But you’re a rebel with a cause: having a smashing holiday. Itinerary? What’s that? Our Middletown vacation homes are the perfect way for you to wing it.

Holiday houses in Middletown let you live life on your own terms. You’ll have so much space, you’ll wish you had more friends and family—but you can always invite over the neighbours. You can often have luxury amenities, but with all the attractions of Middletown in your backyard, budget holiday homes will do just fine, too. That will just leave you more dough to spend on the important things: cocktails, brunch, and local Middletown adventures, obvs.

If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in Middletown with your name on it.

No need to spend big bickies for a holiday beach house the size of Buckingham Palace—unless you’re really in trouble with bae. We’ve got a great selection of Middletown vacation homes with everything you need for a seriously amazing getaway. Throw out that daily planner and hit “reject” on all those meeting invites. You’re off to a place where there are no rules.

Middletown Holiday Homes essential information

Accommodation
129 Holiday Homes
Lowest Price
NZ$148
Highest Price
NZ$616
Popular accommodation
Chesapeake City Quiet Overlook, New Construction townhome close to everything downtown w/transparent pricing , Luxurious and spacious townhome with all necessary amenities awaits your stay., Trendy Cozy Cottage Clean Bright Three bed, Two bath Patio, Private townhouse near downtown and state park, Beautiful Brick-Wall House in Historic Newcastle, Beachfront Sunsets on the Water at Oakwood Beach, Amazing Waterfront Views at Sailor's Sunrise Cottage on the Upper Chesapeake Bay, Historic Waterfront Home with Chesapeake Bay View. Sleeps 9. Close to the Beach

Top trending hotels in Middletown

Fairfield Inn & Suites by Marriott Middletown

Fairfield Inn & Suites by Marriott Middletown

2.5 out of 5
411 MERRIMAC AVENUE, Middletown, DE
Fully refundableReserve now, pay when you stay
The price is NZ$226 per night from 5 Jan to 6 Jan
NZ$226
includes taxes & fees
5 Jan - 6 Jan 2025
Stay at this hotel in Middletown. Enjoy free breakfast, free WiFi, and a 24-hour front desk. Our guests praise the helpful staff in our reviews. Popular attractions ...
Fairfield Inn & Suites by Marriott Middletown
Hampton Inn Middletown

Hampton Inn Middletown

2.5 out of 5
117 Sandhill Dr, Middletown, DE
Fully refundableReserve now, pay when you stay
The price is NZ$199 per night from 20 Jan to 21 Jan
NZ$199
includes taxes & fees
20 Jan - 21 Jan 2025
Stay at this hotel in Middletown. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular attractions ...
Hampton Inn Middletown
Holiday Inn Express And Suites Middletown, an IHG Hotel

Holiday Inn Express And Suites Middletown, an IHG Hotel

2.5 out of 5
315 Auto Park Dr, Middletown, DE
Fully refundable
The price is NZ$198 per night from 1 Jan to 2 Jan
NZ$198
includes taxes & fees
1 Jan - 2 Jan 2025
Stay at this hotel in Middletown. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. ...
Holiday Inn Express And Suites Middletown, an IHG Hotel
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Bally's Dover Casino Resort

Bally's Dover Casino Resort

4 out of 5
1131 N Dupont Hwy, Dover, DE
Fully refundableReserve now, pay when you stay
The price is NZ$148 per night from 24 Dec to 25 Dec
NZ$148
includes taxes & fees
24 Dec - 25 Dec
Stay at this 4-star business-friendly hotel in Dover. Enjoy free WiFi, free parking, and 5 restaurants. Our guests praise the helpful staff and the clean rooms ...
Bally's Dover Casino Resort
Don't see what you're looking for?
See all available properties in Middletown
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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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^Subject to availability and chosen travel dates.