Vacation rentals in Winthrop Harbor, IL

40 available vacation rental offers

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Best vacation rentals and Airbnb offers in Winthrop Harbor, IL

Always a Great Idea To Unwind, Kitchen, Pets Allowed, Private Parking - Winthrop Harbor, IL

Always a Great Idea To Unwind, Kitchen, Pets Allowed, Private Parking

Apartment, Winthrop Harbor

Always a Great Idea To Unwind, Kitchen, Pets Allowed, Private Parking is a apartment in Winthrop Harbor, with pet-friendly space, parking, and kitchen access. This stay gives travelers a…

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About Always a Great Idea To Unwind, Kitchen, Pets Allowed, Private Parking

Always a Great Idea To Unwind, Kitchen, Pets Allowed, Private Parking is a apartment in Winthrop Harbor, with pet-friendly space, 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, hot tub, free wifi, pet friendly, and pets friendly.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $896.

From$128/night
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Enjoy a Hassle-Free Stay, Parking, Kitchen, Pet-Friendly Property - Winthrop Harbor, IL

Enjoy a Hassle-Free Stay, Parking, Kitchen, Pet-Friendly Property

Apartment, Winthrop Harbor

Enjoy a Hassle-Free Stay, Parking, Kitchen, Pet-Friendly Property is a apartment in Winthrop Harbor, with pet-friendly space, parking, and kitchen access. This stay gives travelers a…

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About Enjoy a Hassle-Free Stay, Parking, Kitchen, Pet-Friendly Property

Enjoy a Hassle-Free Stay, Parking, Kitchen, Pet-Friendly Property is a apartment in Winthrop Harbor, with pet-friendly space, 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, hot tub, free wifi, pet friendly, and pets friendly.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $896.

From$128/night
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Waukegan History Museum Tour! Private Parking, Near O'Plaine Park - Winthrop Harbor, IL

Waukegan History Museum Tour! Private Parking, Near O'Plaine Park

Apartment, Winthrop Harbor

Waukegan History Museum Tour! Private Parking, Near O'Plaine Park is a apartment in Winthrop Harbor, with pet-friendly space and parking. This stay gives travelers a comfortable base for…

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About Waukegan History Museum Tour! Private Parking, Near O'Plaine Park

Waukegan History Museum Tour! Private Parking, Near O'Plaine Park is a apartment in Winthrop Harbor, with pet-friendly space and 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 cancellation, hot tub, free wifi, pet friendly, and pets friendly.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $896.

From$128/night
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2-bedroom house in peaceful Waukegan with WiFi, AC - Winthrop Harbor, IL

2-bedroom house in peaceful Waukegan with WiFi, AC

Holiday Home, Winthrop Harbor

2-bedroom house in peaceful Waukegan with WiFi, AC is a holiday home in Winthrop Harbor, with parking, kitchen access, and room for a group. This stay gives travelers a comfortable base for…

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About 2-bedroom house in peaceful Waukegan with WiFi, AC

2-bedroom house in peaceful Waukegan with WiFi, AC is a holiday home in Winthrop Harbor, 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 ac.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $914.

From$131/night
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Vacation rentals with parking in Winthrop Harbor, IL

Find vacation rentals that make arriving by car easier.

Tiny Home Retreat with hot tub - Winthrop Harbor, IL

Tiny Home Retreat with hot tub

Cabin, Winthrop Harbor

Tiny Home Retreat with hot tub is a cabin in Winthrop Harbor, with parking and a quieter setting. This stay gives travelers a comfortable base for exploring the area, relaxing between…

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About Tiny Home Retreat with hot tub

Tiny Home Retreat with hot tub is a cabin in Winthrop Harbor, with parking 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: hot tub, parking, free parking, and fireplace.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,726.

From$247/night
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*King bed/3bds house Near Naval Base & 6Flags* - Winthrop Harbor, IL

*King bed/3bds house Near Naval Base & 6Flags*

Apartment, Winthrop Harbor

*King bed/3bds house Near Naval Base & 6Flags* is a apartment in Winthrop Harbor, with parking. This stay gives travelers a comfortable base for exploring the area, relaxing between…

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About *King bed/3bds house Near Naval Base & 6Flags*

*King bed/3bds house Near Naval Base & 6Flags* is a apartment in Winthrop Harbor, 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 cancellation, free wifi, parking, paid parking, and ac.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,386.

From$269/night
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Spacious 3BR Apartment Near Navy Base Six Flags and Casino. - Winthrop Harbor, IL

Spacious 3BR Apartment Near Navy Base Six Flags and Casino.

Apartment, Winthrop Harbor

Spacious 3BR Apartment Near Navy Base Six Flags and Casino. is a apartment in Winthrop Harbor, with parking, kitchen access, and room for a group. This stay gives travelers a comfortable…

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About Spacious 3BR Apartment Near Navy Base Six Flags and Casino.

Spacious 3BR Apartment Near Navy Base Six Flags and Casino. is a apartment in Winthrop Harbor, 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: free cancellation, kitchen, with kitchen, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,105.

From$301/night
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Spacious 4 Bed Retreat W/ back Porch and large Primary, Near Navy Base! - Winthrop Harbor, IL

Spacious 4 Bed Retreat W/ back Porch and large Primary, Near Navy Base!

Holiday Home, Winthrop Harbor

Spacious 4 Bed Retreat W/ back Porch and large Primary, Near Navy Base! is a holiday home in Winthrop Harbor, with pet-friendly space, parking, and kitchen access. This stay gives travelers…

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About Spacious 4 Bed Retreat W/ back Porch and large Primary, Near Navy Base!

Spacious 4 Bed Retreat W/ back Porch and large Primary, Near Navy Base! is a holiday home in Winthrop Harbor, with pet-friendly space, 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, pet friendly, pets friendly, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,874.

From$411/night
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Pet-friendly vacation rentals in Winthrop Harbor, IL

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

Ray Bradbury Experience Museum Tour! Kitchen, Pets Allowed - Winthrop Harbor, IL

Ray Bradbury Experience Museum Tour! Kitchen, Pets Allowed

Apartment, Winthrop Harbor

Ray Bradbury Experience Museum Tour! Kitchen, Pets Allowed is a apartment in Winthrop Harbor, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for…

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About Ray Bradbury Experience Museum Tour! Kitchen, Pets Allowed

Ray Bradbury Experience Museum Tour! Kitchen, Pets Allowed is a apartment in Winthrop Harbor, with pet-friendly space 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, hot tub, free wifi, pet friendly, and pets friendly.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,274.

From$182/night
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Get Ready for Blissful Getaway! 2 Convenient Units, Full Kitchen, Pets Allowed! - Winthrop Harbor, IL

Get Ready for Blissful Getaway! 2 Convenient Units, Full Kitchen, Pets Allowed!

Apartment, Winthrop Harbor

Get Ready for Blissful Getaway! 2 Convenient Units, Full Kitchen, Pets Allowed! is a apartment in Winthrop Harbor, with pet-friendly space and kitchen access. This stay gives travelers a…

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About Get Ready for Blissful Getaway! 2 Convenient Units, Full Kitchen, Pets Allowed!

Get Ready for Blissful Getaway! 2 Convenient Units, Full Kitchen, Pets Allowed! is a apartment in Winthrop Harbor, with pet-friendly space 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, hot tub, free wifi, pet friendly, and pets friendly.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,744.

From$249/night
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Beautiful Updated Home near Great Lakes Naval Base - Winthrop Harbor, IL

Beautiful Updated Home near Great Lakes Naval Base

Holiday Home, Winthrop Harbor

Beautiful Updated Home near Great Lakes Naval Base is a holiday home in Winthrop Harbor, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for…

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About Beautiful Updated Home near Great Lakes Naval Base

Beautiful Updated Home near Great Lakes Naval Base is a holiday home in Winthrop Harbor, with pet-friendly space 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, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,909.

From$273/night
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Cute 3-bedroom house near Naval base & Six Flags - Winthrop Harbor, IL

Cute 3-bedroom house near Naval base & Six Flags

Holiday Home, Winthrop Harbor

Cute 3-bedroom house near Naval base & Six Flags is a holiday home in Winthrop Harbor, with pet-friendly space, kitchen access, and room for a group. This stay gives travelers a comfortable…

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About Cute 3-bedroom house near Naval base & Six Flags

Cute 3-bedroom house near Naval base & Six Flags is a holiday home in Winthrop Harbor, with pet-friendly space, 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: free cancellation, hot tub, pet friendly, pets friendly, and kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,142.

From$306/night
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Vacation rentals with a kitchen in Winthrop Harbor, IL

Compare stays with kitchen access for longer trips and easier meals.

Your Home Away From Home! 2 Relaxing Units, Pet-friendly Property, Full Kitchen! - Winthrop Harbor, IL

Your Home Away From Home! 2 Relaxing Units, Pet-friendly Property, Full Kitchen!

Apartment, Winthrop Harbor

Your Home Away From Home! 2 Relaxing Units, Pet-friendly Property, Full Kitchen! is a apartment in Winthrop Harbor, with pet-friendly space, kitchen access, and a quieter setting. This stay…

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About Your Home Away From Home! 2 Relaxing Units, Pet-friendly Property, Full Kitchen!

Your Home Away From Home! 2 Relaxing Units, Pet-friendly Property, Full Kitchen! is a apartment in Winthrop Harbor, with pet-friendly space, kitchen 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, hot tub, free wifi, pet friendly, and pets friendly.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,780.

From$254/night
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☆Spacious 3bdr near 6 Flags-Naval Base-Casino☆ - Winthrop Harbor, IL

☆Spacious 3bdr near 6 Flags-Naval Base-Casino☆

Holiday Home, Winthrop Harbor

☆Spacious 3bdr near 6 Flags-Naval Base-Casino☆ is a holiday home in Winthrop Harbor, with kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About ☆Spacious 3bdr near 6 Flags-Naval Base-Casino☆

☆Spacious 3bdr near 6 Flags-Naval Base-Casino☆ is a holiday home in Winthrop Harbor, with 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 wifi, kitchen, with kitchen, and gym.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,086.

From$298/night
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Enjoy a Hassle-Free & Suiting Stay! 2 Relaxing Units with Kitchen, Pet-friendly! - Winthrop Harbor, IL

Enjoy a Hassle-Free & Suiting Stay! 2 Relaxing Units with Kitchen, Pet-friendly!

Apartment, Winthrop Harbor

Enjoy a Hassle-Free & Suiting Stay! 2 Relaxing Units with Kitchen, Pet-friendly! is a apartment in Winthrop Harbor, with pet-friendly space, kitchen access, and a quieter setting. This stay…

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About Enjoy a Hassle-Free & Suiting Stay! 2 Relaxing Units with Kitchen, Pet-friendly!

Enjoy a Hassle-Free & Suiting Stay! 2 Relaxing Units with Kitchen, Pet-friendly! is a apartment in Winthrop Harbor, with pet-friendly space, kitchen 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, hot tub, free wifi, pet friendly, and pets friendly.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,548.

From$364/night
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Spacious New 5 Bed Family Retreat Near Naval Base! - Winthrop Harbor, IL

Spacious New 5 Bed Family Retreat Near Naval Base!

Holiday Home, Winthrop Harbor

Spacious New 5 Bed Family Retreat Near Naval Base! is a holiday home in Winthrop Harbor, with pet-friendly space, parking, and kitchen access. This stay gives travelers a comfortable base…

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About Spacious New 5 Bed Family Retreat Near Naval Base!

Spacious New 5 Bed Family Retreat Near Naval Base! is a holiday home in Winthrop Harbor, with pet-friendly space, 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, pet friendly, pets friendly, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $3,262.

From$466/night
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Family-friendly vacation rentals in Winthrop Harbor, IL

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

Perfect family spot near Great Lakes Naval Base! - Winthrop Harbor, IL

Perfect family spot near Great Lakes Naval Base!

Apartment, Winthrop Harbor

Perfect family spot near Great Lakes Naval Base! is a apartment in Winthrop Harbor, with pet-friendly space, kitchen access, and room for a group. This stay gives travelers a comfortable…

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About Perfect family spot near Great Lakes Naval Base!

Perfect family spot near Great Lakes Naval Base! is a apartment in Winthrop Harbor, with pet-friendly space, 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: free cancellation, free wifi, pet friendly, pets friendly, and kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,850.

From$264/night
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Cozy Family spot near Great Lake Lakes Naval Base! - Winthrop Harbor, IL

Cozy Family spot near Great Lake Lakes Naval Base!

Apartment, Winthrop Harbor

Cozy Family spot near Great Lake Lakes Naval Base! is a apartment in Winthrop Harbor, with pet-friendly space, kitchen access, and room for a group. This stay gives travelers a comfortable…

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About Cozy Family spot near Great Lake Lakes Naval Base!

Cozy Family spot near Great Lake Lakes Naval Base! is a apartment in Winthrop Harbor, with pet-friendly space, 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: free cancellation, free wifi, pet friendly, pets friendly, and kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,923.

From$275/night
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Charming Family home near Great Lakes Naval Base! - Winthrop Harbor, IL

Charming Family home near Great Lakes Naval Base!

Holiday Home, Winthrop Harbor

Charming Family home near Great Lakes Naval Base! is a holiday home in Winthrop Harbor, with pet-friendly space, kitchen access, and room for a group. This stay gives travelers a…

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About Charming Family home near Great Lakes Naval Base!

Charming Family home near Great Lakes Naval Base! is a holiday home in Winthrop Harbor, with pet-friendly space, 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: free cancellation, free wifi, pet friendly, pets friendly, and kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,962.

From$280/night
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Family&Friends Relax Here 3BR/2BA Near Naval Base - Winthrop Harbor, IL

Family&Friends Relax Here 3BR/2BA Near Naval Base

Holiday Home, Winthrop Harbor

Family&Friends Relax Here 3BR/2BA Near Naval Base is a holiday home in Winthrop Harbor, with parking, kitchen access, and room for a group. This stay gives travelers a comfortable base for…

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About Family&Friends Relax Here 3BR/2BA Near Naval Base

Family&Friends Relax Here 3BR/2BA Near Naval Base is a holiday home in Winthrop Harbor, 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: free wifi, kitchen, with kitchen, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,041.

From$292/night
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