Vacation rentals in Orland, IL

Best Vacation rentals and Airbnb offers in Orland, IL

Copper & Oak House - Pickleball, Hot Tub, Trails

Cabin, Orland

Copper & Oak House - Pickleball, Hot Tub, Trails is a cabin in Orland, with pet-friendly space. This stay gives travelers a comfortable base for exploring the area, relaxing between…

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About Copper & Oak House - Pickleball, Hot Tub, Trails

Copper & Oak House - Pickleball, Hot Tub, Trails is a cabin in Orland, 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, hot tub, free wifi, pet friendly, and pets friendly.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,391.

From$152/night

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Located behind a tree filled garden near our horse barn and Farm Sanctuary.

Cabin, Orland

Located behind a tree filled garden near our horse barn and Farm Sanctuary. is a cabin in Orland, with kitchen access. This stay gives travelers a comfortable base for exploring the area,…

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About Located behind a tree filled garden near our horse barn and Farm Sanctuary.

Located behind a tree filled garden near our horse barn and Farm Sanctuary. is a cabin in Orland, 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 cancellation, hot tub, free wifi, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,372.

From$160/night

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White Lantern Cabin: Pickleball & Hot tub

Cabin, Orland

White Lantern Cabin: Pickleball & Hot tub is a cabin in Orland, with pet-friendly space. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and…

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About White Lantern Cabin: Pickleball & Hot tub

White Lantern Cabin: Pickleball & Hot tub is a cabin in Orland, 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, hot tub, free wifi, pet friendly, and pets friendly.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,478.

From$163/night

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Airport House of Hocking Hills A Perfect Pet Friendly Getaway Clean&Comfortable

Holiday Home, Orland

Airport House of Hocking Hills A Perfect Pet Friendly Getaway Clean&Comfortable is a holiday home in Orland, with pet-friendly space and kitchen access. This stay gives travelers a…

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About Airport House of Hocking Hills A Perfect Pet Friendly Getaway Clean&Comfortable

Airport House of Hocking Hills A Perfect Pet Friendly Getaway Clean&Comfortable is a holiday home in Orland, 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 $1,642.

From$177/night

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Browse Vacation Rentals with a Pool in Orland, IL

Add a pool to the search when you want an easy place to cool off between outings.

A-Frame #16 - Hosted by The Chalets

Cabin, Orland

A-Frame #16 - Hosted by The Chalets is a cabin in Orland, with pet-friendly space and pool access. This stay gives travelers a comfortable base for exploring the area, relaxing between…

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About A-Frame #16 - Hosted by The Chalets

A-Frame #16 - Hosted by The Chalets is a cabin in Orland, with pet-friendly space and pool access. 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, pet friendly, and pets friendly.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,896.

From$201/night

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A-Frame #02 - Hosted by The Chalets

Cabin, Orland

A-Frame #02 - Hosted by The Chalets is a cabin in Orland, with pet-friendly space and pool access. This stay gives travelers a comfortable base for exploring the area, relaxing between…

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About A-Frame #02 - Hosted by The Chalets

A-Frame #02 - Hosted by The Chalets is a cabin in Orland, with pet-friendly space and pool access. 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, pet friendly, and pets friendly.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,896.

From$203/night

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A-Frame #06 - Hosted by The Chalets

Cabin, Orland

A-Frame #06 - Hosted by The Chalets is a cabin in Orland, with pet-friendly space and pool access. This stay gives travelers a comfortable base for exploring the area, relaxing between…

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About A-Frame #06 - Hosted by The Chalets

A-Frame #06 - Hosted by The Chalets is a cabin in Orland, with pet-friendly space and pool access. 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, pet friendly, and pets friendly.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,909.

From$205/night

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A-Frame #14 - Hosted by The Chalets

Cabin, Orland

A-Frame #14 - Hosted by The Chalets is a cabin in Orland, with pet-friendly space and pool access. This stay gives travelers a comfortable base for exploring the area, relaxing between…

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About A-Frame #14 - Hosted by The Chalets

A-Frame #14 - Hosted by The Chalets is a cabin in Orland, with pet-friendly space and pool access. 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, pet friendly, and pets friendly.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,937.

From$206/night

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Best Orland, IL vacation rentals with parking

Find vacation rentals that make arriving by car easier.

Cozy Amish Log Cabin, Near Caves, Grill, Fire Pit, DirecTV, High-Speed WiFi!

Cabin, Orland

Cozy Amish Log Cabin, Near Caves, Grill, Fire Pit, DirecTV, High-Speed WiFi! is a cabin in Orland, with parking and kitchen access. This stay gives travelers a comfortable base for…

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About Cozy Amish Log Cabin, Near Caves, Grill, Fire Pit, DirecTV, High-Speed WiFi!

Cozy Amish Log Cabin, Near Caves, Grill, Fire Pit, DirecTV, High-Speed WiFi! is a cabin in Orland, 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, hot tub, kitchen, with kitchen, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $798.

From$89/night

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Hocking Hills Half Stoned Cabin in the Woods

Cabin, Orland

Hocking Hills Half Stoned Cabin in the Woods is a cabin in Orland, with pet-friendly space, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the area,…

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About Hocking Hills Half Stoned Cabin in the Woods

Hocking Hills Half Stoned Cabin in the Woods is a cabin in Orland, 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 $1,870.

From$194/night

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Russell Cabin in Hocking Hills

Cabin, Orland

Russell Cabin in Hocking Hills is a cabin in Orland, 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 Russell Cabin in Hocking Hills

Russell Cabin in Hocking Hills is a cabin in Orland, 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: hot tub, kitchen, with kitchen, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,841.

From$196/night

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Modern Tiny Cabin + Hot Tub | Fire Pit in the Hocking Hills!

Cabin, Orland

Modern Tiny Cabin + Hot Tub · Fire Pit in the Hocking Hills! is a cabin in Orland, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area,…

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About Modern Tiny Cabin + Hot Tub | Fire Pit in the Hocking Hills!

Modern Tiny Cabin + Hot Tub · Fire Pit in the Hocking Hills! is a cabin in Orland, 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: hot tub, kitchen, with kitchen, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,371.

From$274/night

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Best Pet-Friendly Vacation Rentals in Orland, IL

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

1 Bedroom,1 Bath, Porch, Fire Pit, Grill, Beautiful Wooded Location, Wi-Fi also!

Cabin, Orland

1 Bedroom,1 Bath, Porch, Fire Pit, Grill, Beautiful Wooded Location, Wi-Fi also! is a cabin in Orland, with parking, kitchen access, and room for a group. This stay gives travelers a…

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About 1 Bedroom,1 Bath, Porch, Fire Pit, Grill, Beautiful Wooded Location, Wi-Fi also!

1 Bedroom,1 Bath, Porch, Fire Pit, Grill, Beautiful Wooded Location, Wi-Fi also! is a cabin in Orland, 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, hot tub, kitchen, with kitchen, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $798.

From$89/night

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Near Caves; HOT TUB!, WiFi; Deck, Grill, Fire Pit, Pets OK, Wooded Location

Cabin, Orland

Near Caves; HOT TUB!, WiFi; Deck, Grill, Fire Pit, Pets OK, Wooded Location is a cabin in Orland, with pet-friendly space, outdoor space, and kitchen access. This stay gives travelers a…

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About Near Caves; HOT TUB!, WiFi; Deck, Grill, Fire Pit, Pets OK, Wooded Location

Near Caves; HOT TUB!, WiFi; Deck, Grill, Fire Pit, Pets OK, Wooded Location is a cabin in Orland, with pet-friendly space, outdoor 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, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,174.

From$134/night

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Nature-Quiet Retreat • Firepit + BBQ • PetFriendly

Holiday Home, Orland

Nature-Quiet Retreat · Firepit + BBQ · PetFriendly is a holiday home in Orland, with pet-friendly space, kitchen access, and a quieter setting. This stay gives travelers a comfortable base…

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About Nature-Quiet Retreat • Firepit + BBQ • PetFriendly

Nature-Quiet Retreat · Firepit + BBQ · PetFriendly is a holiday home in Orland, 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, free wifi, pet friendly, pets friendly, and kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,606.

From$169/night

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Quiet and modern 3-bedroom cabin near Ash Cave!

Cabin, Orland

Quiet and modern 3-bedroom cabin near Ash Cave! is a cabin in Orland, with pet-friendly space, kitchen access, and room for a group. This stay gives travelers a comfortable base for…

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About Quiet and modern 3-bedroom cabin near Ash Cave!

Quiet and modern 3-bedroom cabin near Ash Cave! is a cabin in Orland, 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 $1,814.

From$210/night

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Best Orland, IL vacation rentals with a kitchen

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

Hocking Hills Cottage with beautiful pond

Cottage, Orland

Hocking Hills Cottage with beautiful pond is a cottage in Orland, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About Hocking Hills Cottage with beautiful pond

Hocking Hills Cottage with beautiful pond is a cottage in Orland, 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, pet friendly, pets friendly, and kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,823.

From$190/night

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Lazy Lane Cabins - Wren's Nest

Cabin, Orland

Lazy Lane Cabins - Wren's Nest is a cabin in Orland, with kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time…

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About Lazy Lane Cabins - Wren's Nest

Lazy Lane Cabins - Wren's Nest is a cabin in Orland, 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 cancellation, hot tub, free wifi, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,796.

From$203/night

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Grey Pines | Private Hot Tub · Dog-Friendly · Couples Cabin · Hocking Hills

Holiday Home, Orland

Grey Pines · Private Hot Tub · Dog-Friendly · Couples Cabin · Hocking Hills is a holiday home in Orland, with pet-friendly space and kitchen access. This stay gives travelers a comfortable…

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About Grey Pines | Private Hot Tub · Dog-Friendly · Couples Cabin · Hocking Hills

Grey Pines · Private Hot Tub · Dog-Friendly · Couples Cabin · Hocking Hills is a holiday home in Orland, 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: hot tub, pet friendly, pets friendly, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,825.

From$213/night

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Dogwood Cabin near Ash Cave

Cabin, Orland

Dogwood Cabin near Ash Cave is a cabin in Orland, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings,…

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About Dogwood Cabin near Ash Cave

Dogwood Cabin near Ash Cave is a cabin in Orland, 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: hot tub, kitchen, with kitchen, and fireplace.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,971.

From$224/night

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Our Favorite Family-Friendly Vacation Rentals in Orland, IL

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

The Blue Cove

Cottage, Orland

The Blue Cove is a cottage in Orland, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending…

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About The Blue Cove

The Blue Cove is a cottage in Orland, 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, pet friendly, pets friendly, and kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $860.

From$104/night

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Blackswan Cottage, Hocking Hills | Ohio University

Holiday Home, Orland

Blackswan Cottage, Hocking Hills · Ohio University is a holiday home in Orland, with kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between…

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About Blackswan Cottage, Hocking Hills | Ohio University

Blackswan Cottage, Hocking Hills · Ohio University is a holiday home in Orland, 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 cancellation, kitchen, with kitchen, ac, and air conditioning.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,422.

From$149/night

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Two bedroom cabin with hot tub and sunset views

Cottage, Orland

Two bedroom cabin with hot tub and sunset views is a cottage in Orland, with kitchen access and room for a group. This stay gives travelers a comfortable base for exploring the area,…

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About Two bedroom cabin with hot tub and sunset views

Two bedroom cabin with hot tub and sunset views is a cottage in Orland, with 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, free wifi, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,570.

From$179/night

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Luna Cottage Tiny House Shipping Container

Cottage, Orland

Luna Cottage Tiny House Shipping Container is a cottage in Orland, with kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and…

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About Luna Cottage Tiny House Shipping Container

Luna Cottage Tiny House Shipping Container is a cottage in Orland, 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: hot tub, free wifi, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,182.

From$257/night

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