Vacation rentals in Middletown, DE

Best vacation rentals and Airbnb offers in Middletown, DE

Luxury private apartment studio .

Apartment, Middletown

Luxury private apartment studio . is a apartment in Middletown, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between…

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About Luxury private apartment studio .

Luxury private apartment studio . is a apartment in Middletown, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, kitchen, with kitchen, parking, and free parking.

Sat, Oct 10 - Sat, Oct 17 · 7 nights · total from $838.

From$120/night

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Whispering Oak Mansion

Homestay, Middletown

Whispering Oak Mansion is a homestay in Middletown, with parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with…

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About Whispering Oak Mansion

Whispering Oak Mansion is a homestay in Middletown, with parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free breakfast, free wifi, parking, paid parking, and ac.

Sat, Oct 10 - Sat, Oct 17 · 7 nights · total from $1,194.

From$148/night

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Casino House One B/R Condo

Holiday Home, Middletown

Casino House One B/R Condo is a holiday home in Middletown, with pet-friendly space. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and…

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About Casino House One B/R Condo

Casino House One B/R Condo is a holiday home in Middletown, with pet-friendly space. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, non smoking, adult only, pets::not allowed, and pets not allowed.

Sat, Oct 10 - Sat, Oct 17 · 7 nights · total from $1,089.

From$156/night

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

Holiday Home, Middletown

Spacious and luxurious 3 bed/1.5 bath townhome with free parking, sleeps 6 is a holiday home in Middletown, with parking, kitchen access, and room for a group. This stay gives travelers a…

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About 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 is a holiday home in Middletown, with parking, kitchen access, and room for a group. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: kitchen, with kitchen, parking, free parking, and washer.

Sat, Oct 10 - Sat, Oct 17 · 7 nights · total from $1,206.

From$172/night

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Family-friendly vacation rentals in Middletown, DE

Plan a trip with stays that give families more room to spread out.

The Keithley House

Holiday Home, Middletown

The Keithley House is a holiday home in Middletown, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and…

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About The Keithley House

The Keithley House is a holiday home in Middletown, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, kitchen, with kitchen, kids friendly, and kids friendly videos or books.

Sat, Oct 10 - Sat, Oct 17 · 7 nights · total from $1,848.

From$264/night

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Be persuaded to experience this vintage cottage by the Sassa

Cottage, Middletown

Be persuaded to experience this vintage cottage by the Sassa is a cottage in Middletown, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the…

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About Be persuaded to experience this vintage cottage by the Sassa

Be persuaded to experience this vintage cottage by the Sassa is a cottage in Middletown, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, free wifi, kitchen, with kitchen, and parking.

Sat, Oct 10 - Sat, Oct 17 · 7 nights · total from $2,296.

From$328/night

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Countryside Cottage in Sassafras

Holiday Home, Middletown

Countryside Cottage in Sassafras is a holiday home in Middletown, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between…

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About Countryside Cottage in Sassafras

Countryside Cottage in Sassafras is a holiday home in Middletown, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, kitchen, with kitchen, parking, and free parking.

Sat, Oct 10 - Sat, Oct 17 · 7 nights · total from $4,064.

From$581/night

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Bella Vista Holiday Family Gatherings in Coastal Maryland!

Holiday Home, Middletown

Bella Vista Holiday Family Gatherings in Coastal Maryland! is a holiday home in Middletown, with pool access and room for a group. This stay gives travelers a comfortable base for exploring…

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About Bella Vista Holiday Family Gatherings in Coastal Maryland!

Bella Vista Holiday Family Gatherings in Coastal Maryland! is a holiday home in Middletown, with pool access and room for a group. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: pool, hot tub, and free wifi.

Sat, Oct 10 - Sat, Oct 17 · 7 nights · total from $8,269.

From$1,181/night

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Pet-friendly vacation rentals in Middletown, DE

Bring your pet along with stays that welcome four-legged travelers.

Cozy Oasis Waterfront Retreat on the Chesapeake's Elk River.

Apartment, Middletown

Cozy Oasis Waterfront Retreat on the Chesapeake's Elk River. is a apartment in Middletown, with pet-friendly space, easy beach access, and kitchen access. This stay gives travelers a…

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About Cozy Oasis Waterfront Retreat on the Chesapeake's Elk River.

Cozy Oasis Waterfront Retreat on the Chesapeake's Elk River. is a apartment in Middletown, with pet-friendly space, easy beach access, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, free wifi, pet friendly, pets friendly, and kitchen.

Sat, Oct 10 - Sat, Oct 17 · 7 nights · total from $2,050.

From$293/night

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Charming 2-bedroom cabin close to Fair Hill on horse farm

Cabin, Middletown

Charming 2-bedroom cabin close to Fair Hill on horse farm is a cabin in Middletown, with pet-friendly space and room for a group. This stay gives travelers a comfortable base for exploring…

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About Charming 2-bedroom cabin close to Fair Hill on horse farm

Charming 2-bedroom cabin close to Fair Hill on horse farm is a cabin in Middletown, with pet-friendly space and room for a group. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, hot tub, free wifi, pet friendly, and pets friendly.

Sat, Oct 10 - Sat, Oct 17 · 7 nights · total from $2,597.

From$371/night

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House casino

Holiday Home, Middletown

House casino is a holiday home in Middletown, with pet-friendly space. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with…

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About House casino

House casino is a holiday home in Middletown, with pet-friendly space. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pet friendly, pets friendly, non smoking, and non smoking::all.

Sat, Oct 10 - Sat, Oct 17 · 7 nights · total from $2,869.

From$410/night

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Private retreat with pool! Close to North East! Minutes to local wedding venue!

Holiday Home, Middletown

Private retreat with pool! Close to North East! Minutes to local wedding venue! is a holiday home in Middletown, with pet-friendly space, pool access, and a quieter setting. This stay gives…

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About Private retreat with pool! Close to North East! Minutes to local wedding venue!

Private retreat with pool! Close to North East! Minutes to local wedding venue! is a holiday home in Middletown, with pet-friendly space, pool access, and a quieter setting. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pool, free wifi, pet friendly, and pets friendly.

Sat, Oct 10 - Sat, Oct 17 · 7 nights · total from $5,304.

From$758/night

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