Vacation rentals in Orland, IN

55 available vacation rental offers

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Best vacation rentals and Airbnb offers in Orland, IN

Peaceful Retreat on Gilead Lake w/ Grill! - Orland, IN
10 ★ 5 reviews

Peaceful Retreat on Gilead Lake w/ Grill!

Holiday Home, Orland

Peaceful Retreat on Gilead Lake w/ Grill! is a holiday home in Orland, with pet-friendly space, easy beach access, and kitchen access. This stay gives travelers a comfortable base for…

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About Peaceful Retreat on Gilead Lake w/ Grill!

Peaceful Retreat on Gilead Lake w/ Grill! is a holiday home in Orland, 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, pet friendly, pets friendly, kitchen, and with kitchen.

Sat, Sep 26 - Sat, Oct 3 · 7 nights · total from $1,942.

From$277/night
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Cozy lake front cabin with WiFi, AC in awesome Angola - Orland, IN
10 ★ 3 reviews

Cozy lake front cabin with WiFi, AC in awesome Angola

Cabin, Orland

Cozy lake front cabin with WiFi, AC in awesome Angola is a cabin in Orland, with parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and…

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About Cozy lake front cabin with WiFi, AC in awesome Angola

Cozy lake front cabin with WiFi, AC in awesome Angola is a cabin in Orland, 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, parking, free parking, ac, and air conditioning.

Sat, Sep 26 - Sat, Oct 3 · 7 nights · total from $1,198.

From$171/night
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3-bedroom cabin located in Steuben County home of 101 lakes! - Orland, IN
10 ★ 1 reviews

3-bedroom cabin located in Steuben County home of 101 lakes!

Cabin, Orland

3-bedroom cabin located in Steuben County home of 101 lakes! is a cabin in Orland, with parking and room for a group. This stay gives travelers a comfortable base for exploring the area,…

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About 3-bedroom cabin located in Steuben County home of 101 lakes!

3-bedroom cabin located in Steuben County home of 101 lakes! is a cabin in Orland, with parking 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, parking, free parking, fireplace, and washer.

Sat, Sep 26 - Sat, Oct 3 · 7 nights · total from $2,078.

From$297/night
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Start planning your fall get-away!!! Peaceful and relaxing at the lake! - Orland, IN
9.8 ★ 57 reviews

Start planning your fall get-away!!! Peaceful and relaxing at the lake!

Holiday Home, Orland

Start planning your fall get-away!!! Peaceful and relaxing at the lake! is a holiday home in Orland, with parking, kitchen access, and a quieter setting. This stay gives travelers a…

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About Start planning your fall get-away!!! Peaceful and relaxing at the lake!

Start planning your fall get-away!!! Peaceful and relaxing at the lake! is a holiday home in Orland, with parking, 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, kitchen, with kitchen, and parking.

Sat, Sep 26 - Sat, Oct 3 · 7 nights · total from $1,671.

From$239/night
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Family-friendly vacation rentals in Orland, IN

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

Family-friendly Comfortable Lakefront Cottage on beautiful Lake George - Orland, IN
10 ★ 31 reviews

Family-friendly Comfortable Lakefront Cottage on beautiful Lake George

Cottage, Orland

Family-friendly Comfortable Lakefront Cottage on beautiful Lake George is a cottage in Orland, with parking, kitchen access, and room for a group. This stay gives travelers a comfortable…

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About Family-friendly Comfortable Lakefront Cottage on beautiful Lake George

Family-friendly Comfortable Lakefront Cottage on beautiful Lake George is a cottage 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: hot tub, kitchen, with kitchen, parking, and free parking.

Sat, Sep 26 - Sat, Oct 3 · 7 nights · total from $1,929.

From$276/night
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Peaceful lake retreat - Orland, IN
10 ★ 12 reviews

Peaceful lake retreat

Cottage, Orland

Peaceful lake retreat is a cottage in Orland, with parking, kitchen access, and a quieter setting. This stay gives travelers a comfortable base for exploring the area, relaxing between…

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About Peaceful lake retreat

Peaceful lake retreat is a cottage in Orland, with parking, 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, kitchen, with kitchen, and parking.

Sat, Sep 26 - Sat, Oct 3 · 7 nights · total from $1,685.

From$241/night
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2 miles from the Indiana Rails train station, 12 miles from Pokagon State Park - Orland, IN
10 ★ 7 reviews

2 miles from the Indiana Rails train station, 12 miles from Pokagon State Park

Cottage, Orland

2 miles from the Indiana Rails train station, 12 miles from Pokagon State Park is a cottage in Orland, with parking and kitchen access. This stay gives travelers a comfortable base for…

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About 2 miles from the Indiana Rails train station, 12 miles from Pokagon State Park

2 miles from the Indiana Rails train station, 12 miles from Pokagon State Park is a cottage 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, kitchen, with kitchen, kids friendly, and kids friendly videos or books.

Sat, Sep 26 - Sat, Oct 3 · 7 nights · total from $1,255.

From$179/night
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Chillaxin ~ Beautiful Lakefront Home on Coldwater Lake - Orland, IN
9.8 ★ 62 reviews

Chillaxin ~ Beautiful Lakefront Home on Coldwater Lake

Cottage, Orland

Chillaxin ~ Beautiful Lakefront Home on Coldwater Lake is a cottage in Orland, with kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between…

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About Chillaxin ~ Beautiful Lakefront Home on Coldwater Lake

Chillaxin ~ Beautiful Lakefront Home on Coldwater Lake 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: free cancellation, free wifi, kitchen, with kitchen, and gym.

Sat, Sep 26 - Sat, Oct 3 · 7 nights · total from $1,941.

From$277/night
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Pet-friendly vacation rentals in Orland, IN

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

Charming Lakefront Cottage on Coldwater Lake - Orland, IN
10 ★ 3 reviews

Charming Lakefront Cottage on Coldwater Lake

Cottage, Orland

Charming Lakefront Cottage on Coldwater Lake is a cottage in Orland, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for exploring the area,…

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About Charming Lakefront Cottage on Coldwater Lake

Charming Lakefront Cottage on Coldwater Lake 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, free wifi, pet friendly, pets friendly, and kitchen.

Sat, Sep 26 - Sat, Oct 3 · 7 nights · total from $1,691.

From$242/night
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Lake Life Vacation on James 2! - Orland, IN
10 ★ 1 reviews

Lake Life Vacation on James 2!

Holiday Home, Orland

Lake Life Vacation on James 2! is a holiday home in Orland, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings,…

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About Lake Life Vacation on James 2!

Lake Life Vacation on James 2! is a holiday home 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, kitchen, with kitchen, parking, and free parking.

Sat, Sep 26 - Sat, Oct 3 · 7 nights · total from $2,958.

From$423/night
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Charming lake front 3-bedroom cottage in Coldwater, Michigan - Orland, IN
9 ★ 2 reviews

Charming lake front 3-bedroom cottage in Coldwater, Michigan

Cottage, Orland

Charming lake front 3-bedroom cottage in Coldwater, Michigan is a cottage in Orland, with pet-friendly space, kitchen access, and room for a group. This stay gives travelers a comfortable…

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About Charming lake front 3-bedroom cottage in Coldwater, Michigan

Charming lake front 3-bedroom cottage in Coldwater, Michigan is a cottage 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, pet friendly, pets friendly, kitchen, and with kitchen.

Sat, Sep 26 - Sat, Oct 3 · 7 nights · total from $2,199.

From$314/night
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Peaceful Retreat on Gilead Lake w/ Grill! - Orland, IN

Peaceful Retreat on Gilead Lake w/ Grill!

Cottage, Orland

Peaceful Retreat on Gilead Lake w/ Grill! is a cottage in Orland, with pet-friendly space, kitchen access, and a quieter setting. This stay gives travelers a comfortable base for exploring…

Read more

About Peaceful Retreat on Gilead Lake w/ Grill!

Peaceful Retreat on Gilead Lake w/ Grill! is a cottage 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, Sep 26 - Sat, Oct 3 · 7 nights · total from $2,105.

From$258/night
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Vacation rentals with parking in Orland, IN

Find vacation rentals that make arriving by car easier.

'Tis Our Cottage: Modern Lakefront clean lake quiet & relaxing Just off toll Rd - Orland, IN
10 ★ 8 reviews

'Tis Our Cottage: Modern Lakefront clean lake quiet & relaxing Just off toll Rd

Holiday Home, Orland

'Tis Our Cottage: Modern Lakefront clean lake quiet & relaxing Just off toll Rd is a holiday home in Orland, with easy beach access, parking, and kitchen access. This stay gives travelers a…

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About 'Tis Our Cottage: Modern Lakefront clean lake quiet & relaxing Just off toll Rd

'Tis Our Cottage: Modern Lakefront clean lake quiet & relaxing Just off toll Rd is a holiday home in Orland, with easy beach access, 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: kitchen, with kitchen, beachfront, beach front, and parking.

Sat, Sep 26 - Sat, Oct 3 · 7 nights · total from $2,262.

From$323/night
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LAKEFRONT RETREAT with private dock, Relax, play & gather with family & friends. - Orland, IN
10 ★ 7 reviews

LAKEFRONT RETREAT with private dock, Relax, play & gather with family & friends.

Holiday Home, Orland

LAKEFRONT RETREAT with private dock, Relax, play & gather with family & friends. is a holiday home in Orland, with parking, kitchen access, and room for a group. This stay gives travelers a…

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About LAKEFRONT RETREAT with private dock, Relax, play & gather with family & friends.

LAKEFRONT RETREAT with private dock, Relax, play & gather with family & friends. is a holiday home 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, kitchen, with kitchen, parking, and free parking.

Sat, Sep 26 - Sat, Oct 3 · 7 nights · total from $2,549.

From$364/night
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Lakefront Retreat on Big Otter - Orland, IN
10 ★ 1 reviews

Lakefront Retreat on Big Otter

Holiday Home, Orland

Lakefront Retreat on Big Otter is a holiday home in Orland, with parking, kitchen access, and a quieter setting. This stay gives travelers a comfortable base for exploring the area,…

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About Lakefront Retreat on Big Otter

Lakefront Retreat on Big Otter is a holiday home in Orland, with parking, 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, kitchen, with kitchen, kids friendly, and kids friendly videos or books.

Sat, Sep 26 - Sat, Oct 3 · 7 nights · total from $2,712.

From$387/night
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Stunning home with huge game room plenty of space for relaxing and fun.Sleeps 14 - Orland, IN
9.4 ★ 19 reviews

Stunning home with huge game room plenty of space for relaxing and fun.Sleeps 14

Holiday Home, Orland

Stunning home with huge game room plenty of space for relaxing and fun.Sleeps 14 is a holiday home in Orland, with parking, kitchen access, and room for a group. This stay gives travelers a…

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About Stunning home with huge game room plenty of space for relaxing and fun.Sleeps 14

Stunning home with huge game room plenty of space for relaxing and fun.Sleeps 14 is a holiday home 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, kitchen, with kitchen, parking, and free parking.

Sat, Sep 26 - Sat, Oct 3 · 7 nights · total from $2,195.

From$314/night
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Vacation rentals with a kitchen in Orland, IN

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

Crooked Lake, Angola Indiana Large Waterfront Home-Opening 6/12-6/19 2026 - Orland, IN
10 ★ 62 reviews

Crooked Lake, Angola Indiana Large Waterfront Home-Opening 6/12-6/19 2026

Holiday Home, Orland

Crooked Lake, Angola Indiana Large Waterfront Home-Opening 6/12-6/19 2026 is a holiday home in Orland, with easy beach access and kitchen access. This stay gives travelers a comfortable…

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About Crooked Lake, Angola Indiana Large Waterfront Home-Opening 6/12-6/19 2026

Crooked Lake, Angola Indiana Large Waterfront Home-Opening 6/12-6/19 2026 is a holiday home in Orland, with 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 wifi, kitchen, with kitchen, kids friendly, and kids friendly videos or books.

Sat, Sep 26 - Sat, Oct 3 · 7 nights · total from $3,710.

From$530/night
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Large Family Lakehouse on Crooked Lake, Angola, IN-Beautiful Views Outdoor Oasis - Orland, IN
10 ★ 20 reviews

Large Family Lakehouse on Crooked Lake, Angola, IN-Beautiful Views Outdoor Oasis

Holiday Home, Orland

Large Family Lakehouse on Crooked Lake, Angola, IN-Beautiful Views Outdoor Oasis is a holiday home in Orland, with parking, kitchen access, and room for a group. This stay gives travelers a…

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About Large Family Lakehouse on Crooked Lake, Angola, IN-Beautiful Views Outdoor Oasis

Large Family Lakehouse on Crooked Lake, Angola, IN-Beautiful Views Outdoor Oasis is a holiday home 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 wifi, kitchen, with kitchen, parking, and free parking.

Sat, Sep 26 - Sat, Oct 3 · 7 nights · total from $3,535.

From$505/night
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Lake James Waterfront Cottage with a Beach - Sleeps 14! - Orland, IN
10 ★ 3 reviews

Lake James Waterfront Cottage with a Beach - Sleeps 14!

Holiday Home, Orland

Lake James Waterfront Cottage with a Beach - Sleeps 14! is a holiday home in Orland, with easy beach access, parking, and kitchen access. This stay gives travelers a comfortable base for…

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About Lake James Waterfront Cottage with a Beach - Sleeps 14!

Lake James Waterfront Cottage with a Beach - Sleeps 14! is a holiday home in Orland, with easy beach access, 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, Sep 26 - Sat, Oct 3 · 7 nights · total from $3,080.

From$440/night
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Game Room & Outdoor Fun - Gilead Lake Getaway! - Orland, IN
9.2 ★ 5 reviews

Game Room & Outdoor Fun - Gilead Lake Getaway!

Holiday Home, Orland

Game Room & Outdoor Fun - Gilead Lake Getaway! is a holiday home in Orland, with pet-friendly space, parking, and kitchen access. This stay gives travelers a comfortable base for exploring…

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About Game Room & Outdoor Fun - Gilead Lake Getaway!

Game Room & Outdoor Fun - Gilead Lake Getaway! is a holiday home 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, Sep 26 - Sat, Oct 3 · 7 nights · total from $3,203.

From$458/night
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Top-rated vacation rentals in Orland, IN

Explore guest-loved stays with strong review signals.

Beautiful Lake James Lake House- Angola, Indiana - Orland, IN
10 ★ 85 reviews

Beautiful Lake James Lake House- Angola, Indiana

Cottage, Orland

Beautiful Lake James Lake House- Angola, Indiana is a cottage in Orland, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About Beautiful Lake James Lake House- Angola, Indiana

Beautiful Lake James Lake House- Angola, Indiana is a cottage 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, kitchen, with kitchen, parking, and free parking.

Sat, Sep 26 - Sat, Oct 3 · 7 nights · total from $3,913.

From$559/night
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Rose Lake, Cottage with Pontoon, Coldwater, Michigan (aka Lake of the Woods) - Orland, IN
10 ★ 47 reviews

Rose Lake, Cottage with Pontoon, Coldwater, Michigan (aka Lake of the Woods)

Cottage, Orland

Rose Lake, Cottage with Pontoon, Coldwater, Michigan (aka Lake of the Woods) is a cottage in Orland, with parking and kitchen access. This stay gives travelers a comfortable base for…

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About Rose Lake, Cottage with Pontoon, Coldwater, Michigan (aka Lake of the Woods)

Rose Lake, Cottage with Pontoon, Coldwater, Michigan (aka Lake of the Woods) is a cottage 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, free wifi, kitchen, with kitchen, and parking.

Sat, Sep 26 - Sat, Oct 3 · 7 nights · total from $3,442.

From$492/night
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Spacious lakefront home. Bring family and friends! Summer dates filling fast! - Orland, IN
10 ★ 42 reviews

Spacious lakefront home. Bring family and friends! Summer dates filling fast!

Cottage, Orland

Spacious lakefront home. Bring family and friends! Summer dates filling fast! is a cottage in Orland, with kitchen access and room for a group. This stay gives travelers a comfortable base…

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About Spacious lakefront home. Bring family and friends! Summer dates filling fast!

Spacious lakefront home. Bring family and friends! Summer dates filling fast! 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, free wifi, kitchen, with kitchen, and kids friendly.

Sat, Sep 26 - Sat, Oct 3 · 7 nights · total from $3,614.

From$516/night
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Coldwater Lake - Perfect for Large Gatherings - Orland, IN
10 ★ 30 reviews

Coldwater Lake - Perfect for Large Gatherings

Holiday Home, Orland

Coldwater Lake - Perfect for Large Gatherings is a holiday home in Orland, with pet-friendly space. This stay gives travelers a comfortable base for exploring the area, relaxing between…

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About Coldwater Lake - Perfect for Large Gatherings

Coldwater Lake - Perfect for Large Gatherings is a holiday home 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: hot tub, free wifi, pet friendly, and pets friendly.

Sat, Sep 26 - Sat, Oct 3 · 7 nights · total from $3,076.

From$439/night
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