Book Holiday Homes in Middletown

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Featured Holiday Homes in Middletown

Chesapeake Bay House with Dock & Private Beach

Chesapeake Bay House with Dock & Private Beach

Elkton
Located in Elkton, this vacation home is on the waterfront, within a 15-minute drive of Chesland Park and Chesapeake City Bridge.
Chesapeake Bay House with Dock & Private Beach
Cozy home with fenced in yard-Dog Friendly . 2 block walk to historic downtown!

Cozy home with fenced in yard-Dog Friendly . 2 block walk to historic downtown!

Havre De Grace
A stay at this vacation home places you in the heart of Havre De Grace, within a 15-minute walk of Susquehanna Museum at the Lock House and Susquehanna ...
Cozy home with fenced in yard-Dog Friendly . 2 block walk to historic downtown!
Cozy Farmhouse in Greenville, DE

Cozy Farmhouse in Greenville, DE

Wilmington
With a stay at this vacation home in Wilmington, you'll be within a 15-minute drive of Longwood Gardens and Wilmington Riverwalk.
Cozy Farmhouse in Greenville, DE
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Stay & Play at Our Beautiful Retreat

Stay & Play at Our Beautiful Retreat

Elkton
Located in Elkton, this vacation home is in a rural location, within a 15-minute drive of Milburn Stone Theater and Lower Chrome Serpentine Barrens.
Stay & Play at Our Beautiful Retreat
Lark's Nest on the Chester River. Spacious, waterfront home with private dock.

Lark's Nest on the Chester River. Spacious, waterfront home with private dock.

Millington
Located in Millington, this vacation home is on the waterfront, within a 10-minute drive of Crumpton Auction and Crumpton Park.
Lark's Nest on the Chester River. Spacious, waterfront home with private dock.
Spacious and luxurious 3 bed/1.5 bath townhome with free parking, sleeps 6

Spacious and luxurious 3 bed/1.5 bath townhome with free parking, sleeps 6

Middletown
With a stay at this vacation home in Middletown, you'll be within a 5-minute drive of Middletown Historic District and The Everett Annex.
Spacious and luxurious 3 bed/1.5 bath townhome with free parking, sleeps 6
Walk to Town & River: Charming Home in North East!

Walk to Town & River: Charming Home in North East!

North East
Located in North East, this vacation home is a 2-minute drive from Upper Bay Museum and 5 minutes from Milburn Stone Theater.
Walk to Town & River: Charming Home in North East!
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
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 ...
Historic Waterfront Home with Chesapeake Bay View. Sleeps 9. Close to the Beach
*** NEWLY RENOVATED**** Escape to a Beautiful Getaway on the Chesapeake Bay

*** NEWLY RENOVATED**** Escape to a Beautiful Getaway on the Chesapeake Bay

Perryville
When you stay at this vacation home in Perryville, you'll be on the waterfront, within a 5-minute drive of Chestnut Point Estates and Marina and Craft Haven ...
*** NEWLY RENOVATED**** Escape to a Beautiful Getaway on the Chesapeake Bay
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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
187 Holiday Homes
Lowest Price
AU$131
Highest Price
AU$197
Popular accommodation
Chesapeake Bay House with Dock & Private Beach, Cozy home with fenced in yard-Dog Friendly . 2 block walk to historic downtown!, Cozy Farmhouse in Greenville, DE, Stay & Play at Our Beautiful Retreat, Lark's Nest on the Chester River. Spacious, waterfront home with private dock., Spacious and luxurious 3 bed/1.5 bath townhome with free parking, sleeps 6, Walk to Town & River: Charming Home in North East!, Historic Waterfront Home with Chesapeake Bay View. Sleeps 9. Close to the Beach, *** NEWLY RENOVATED**** Escape to a Beautiful Getaway on the Chesapeake Bay

Top trending hotels in Middletown

Holiday Inn Express And Suites Middletown by IHG

Holiday Inn Express And Suites Middletown by IHG

2.5 out of 5
315 Auto Park Dr, Middletown, DE
Fully refundable
The price is AU$197 per night from 27 Aug to 28 Aug
AU$197
27 Aug - 28 Aug
includes taxes & fees
Located in Middletown, Holiday Inn Express And Suites Middletown by IHG is within a 5-minute drive of Dutch Country Farmers Market and Frog Hollow Golf ...
Holiday Inn Express And Suites Middletown by IHG
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 AU$175 per night from 8 Sept to 9 Sept
AU$175
8 Sept - 9 Sept
includes taxes & fees
Located in Middletown, Fairfield Inn & Suites by Marriott Middletown is within a 5-minute drive of Westown and Middletown Historic District.
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 AU$186 per night from 25 Aug to 26 Aug
AU$186
25 Aug - 26 Aug
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.
Hampton Inn Middletown
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Pleasant Hill Motel

Pleasant Hill Motel

2.5 out of 5
3155 Dupont Pkwy, Middletown, DE
Fully refundableReserve now, pay when you stay
The price is AU$131 per night from 14 Sept to 15 Sept
AU$131
14 Sept - 15 Sept
includes taxes & fees
With a stay at Pleasant Hill Motel in Middletown, you'll be within a 5-minute drive of Appoquinimink Friends Meeting House and Historic Houses of Odessa.
Pleasant Hill Motel
Don't see what you're looking for?
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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.