Book Holiday Homes in Middletown

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Featured Holiday Homes in Middletown

Sailor's Sunrise Cottage - Chesapeake Bay

Sailor's Sunrise Cottage - Chesapeake Bay

Perryville MD
When you stay at this vacation home in Perryville, you'll be on the waterfront, within a 10-minute walk of Chesapeake Bay and Northern Chesapeake Bay.
Opens in a new windowSailor's Sunrise Cottage - 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 MD
With a stay at this vacation home in Betterton, you'll be on the waterfront, just a 4-minute walk from Betterton Historic District and 7 minutes by foot from ...
Opens in a new windowHistoric Waterfront Home with Chesapeake Bay View. Sleeps 9. Close to the Beach
Luxurious and spacious townhome with all necessary amenities awaits your stay.

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

Middletown DE
Located in Middletown, this vacation home is within a 5-minute drive of Middletown Historic District and The Everett Annex.
Opens in a new windowLuxurious and spacious townhome with all necessary amenities awaits your stay.
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Sunset River Shack -amazing waterfront view

Sunset River Shack -amazing waterfront view

Elkton MD
Located in Elkton, this vacation home is on the waterfront, within a 10-minute drive of Chesland Park and Brantwood Park.
Opens in a new windowSunset River Shack -amazing waterfront view
Chesapeake Bay House with Dock & Private Beach

Chesapeake Bay House with Dock & Private Beach

Elkton MD
Located in Elkton, this vacation home is on the waterfront, within a 10-minute drive of Chesland Park and Brantwood Park.
Opens in a new windowChesapeake Bay House with Dock & Private Beach
5-bedroom vacation home 5 minutes from historic Charlestown

5-bedroom vacation home 5 minutes from historic Charlestown

Perryville MD
The price is AU$784 per night from 27 May to 28 May
AU$784
27 May - 28 May
includes taxes & fees
Located in Perryville, this vacation home is on the waterfront, within a 5-minute drive of Chestnut Point Estates and Marina and Craft Haven Marina.
Opens in a new window5-bedroom vacation home 5 minutes from historic Charlestown
Beachfront Sunsets on the Water at Oakwood Beach

Beachfront Sunsets on the Water at Oakwood Beach

Salem NJ
Located in Salem, this vacation home is on the waterfront, a 4-minute drive from Salem River Wildlife Management Area and 10 minutes from Salem Medical ...
Opens in a new windowBeachfront Sunsets on the Water at Oakwood Beach
Cozy home w/fenced in yard-Dog Friendly with Pet fee. 2 block walk to downtown!

Cozy home w/fenced in yard-Dog Friendly with Pet fee. 2 block walk to downtown!

Havre De Grace MD
A stay at this vacation home places you in the heart of Havre De Grace, within a 15-minute walk of Lock House Museum and Susquehanna River.
Opens in a new windowCozy home w/fenced in yard-Dog Friendly with Pet fee. 2 block walk to downtown!
Hook Wine & Sinker~sleeps 14 to 16 🚤 includes slip at Inn 🚤water views!!!

Hook Wine & Sinker~sleeps 14 to 16 🚤 includes slip at Inn 🚤water views!!!

Chesapeake City MD
A stay at this vacation home places you in the heart of Chesapeake City, steps from Chesapeake City Bridge and South Chesapeake City Historic District.
Opens in a new windowHook Wine & Sinker~sleeps 14 to 16 🚤 includes slip at Inn 🚤water views!!!
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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
168 Holiday Homes
Lowest Price
AU$130
Highest Price
AU$784
Popular accommodation
Sailor's Sunrise Cottage - Chesapeake Bay, Historic Waterfront Home with Chesapeake Bay View. Sleeps 9. Close to the Beach, Luxurious and spacious townhome with all necessary amenities awaits your stay., Sunset River Shack -amazing waterfront view, Chesapeake Bay House with Dock & Private Beach, 5-bedroom vacation home 5 minutes from historic Charlestown, Beachfront Sunsets on the Water at Oakwood Beach, Cozy home w/fenced in yard-Dog Friendly with Pet fee. 2 block walk to downtown!, Hook Wine & Sinker~sleeps 14 to 16 🚤 includes slip at Inn 🚤water views!!!

Top trending hotels in Middletown

Fairfield Inn & Suites by Marriott Middletown

Fairfield Inn & Suites by Marriott Middletown

3 out of 5
411 MERRIMAC AVENUE Middletown DE
Fully refundableReserve now, pay when you stay
The price is AU$164 per night from 31 May to 1 June
AU$164
31 May - 1 June
includes taxes & fees
Located in Middletown, Fairfield Inn & Suites by Marriott Middletown is within a 5-minute drive of Westown and Middletown Historic District.
Opens in a new windowFairfield Inn & Suites by Marriott Middletown
Holiday Inn Express & Suites Middletown by IHG

Holiday Inn Express & Suites Middletown by IHG

2.5 out of 5
315 Auto Park Dr Middletown DE
Fully refundable
The price is AU$171 per night from 31 May to 1 June
AU$171
31 May - 1 June
includes taxes & fees
Located in Middletown, Holiday Inn Express & Suites Middletown by IHG is within a 5-minute drive of Dutch Country Farmers Market and Frog Hollow Golf Club.
Opens in a new windowHoliday Inn Express & Suites Middletown by IHG
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 AU$205 per night from 28 May to 29 May
AU$205
28 May - 29 May
includes taxes & fees
With a stay at Hampton Inn Middletown in Middletown, you'll be within a 15-minute walk of Westown and Middletown Historic District.
Opens in a new windowHampton Inn Middletown
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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 AU$130 per night from 25 May to 26 May
AU$130
25 May - 26 May
includes taxes & fees
With a stay at Bally's Dover Casino Resort in Dover, you'll be just steps from Dover Downs Casino and 7 minutes by foot from Dover International Speedway.
Opens in a new windowBally's Dover Casino Resort
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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.

**Terms and Conditions apply.
^Subject to availability and chosen travel dates.