Vacation rentals in Oakwood Hills, IL

45 available vacation rental offers

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Best vacation rentals and Airbnb offers in Oakwood Hills, IL

The Main Event Game House on the Huntley Square! - Oakwood Hills, IL
10 ★ 21 reviews

The Main Event Game House on the Huntley Square!

Holiday Home, Oakwood Hills

The Main Event Game House on the Huntley Square! is a holiday home in Oakwood Hills, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for exploring…

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About The Main Event Game House on the Huntley Square!

The Main Event Game House on the Huntley Square! is a holiday home in Oakwood Hills, 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 $1,923.

From$275/night
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KING bed | Crystal Lake | McHenry | Cary | COZY - Oakwood Hills, IL
10 ★ 13 reviews

KING bed | Crystal Lake | McHenry | Cary | COZY

Holiday Home, Oakwood Hills

KING bed · Crystal Lake · McHenry · Cary · COZY is a holiday home in Oakwood Hills, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area,…

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About KING bed | Crystal Lake | McHenry | Cary | COZY

KING bed · Crystal Lake · McHenry · Cary · COZY is a holiday home in Oakwood Hills, 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, Sep 26 - Sat, Oct 3 · 7 nights · total from $1,107.

From$158/night
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Chain O' Lakes life...serene bay w/ private beach access. Kayaks & Boats welcome - Oakwood Hills, IL
10 ★ 13 reviews

Chain O' Lakes life...serene bay w/ private beach access. Kayaks & Boats welcome

Holiday Home, Oakwood Hills

Chain O' Lakes life...serene bay w/ private beach access. Kayaks & Boats welcome is a holiday home in Oakwood Hills, with pet-friendly space, easy beach access, and kitchen access. This…

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About Chain O' Lakes life...serene bay w/ private beach access. Kayaks & Boats welcome

Chain O' Lakes life...serene bay w/ private beach access. Kayaks & Boats welcome is a holiday home in Oakwood Hills, 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, Sep 26 - Sat, Oct 3 · 7 nights · total from $2,071.

From$296/night
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McHenry Oasis 3BR Entire Home Dogs OK Extra-Large Fenced Yard Near Lake Geneva - Oakwood Hills, IL
10 ★ 11 reviews

McHenry Oasis 3BR Entire Home Dogs OK Extra-Large Fenced Yard Near Lake Geneva

Holiday Home, Oakwood Hills

McHenry Oasis 3BR Entire Home Dogs OK Extra-Large Fenced Yard Near Lake Geneva is a holiday home in Oakwood Hills, with pet-friendly space, kitchen access, and room for a group. This stay…

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About McHenry Oasis 3BR Entire Home Dogs OK Extra-Large Fenced Yard Near Lake Geneva

McHenry Oasis 3BR Entire Home Dogs OK Extra-Large Fenced Yard Near Lake Geneva is a holiday home in Oakwood Hills, 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, Sep 26 - Sat, Oct 3 · 7 nights · total from $1,807.

From$258/night
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Family-friendly vacation rentals in Oakwood Hills, IL

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

Waterfront Fox Lake Vacation Rental w/ Fire Pit! - Oakwood Hills, IL
10 ★ 13 reviews

Waterfront Fox Lake Vacation Rental w/ Fire Pit!

Cottage, Oakwood Hills

Waterfront Fox Lake Vacation Rental w/ Fire Pit! is a cottage in Oakwood Hills, with pet-friendly space, easy beach access, and parking. This stay gives travelers a comfortable base for…

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About Waterfront Fox Lake Vacation Rental w/ Fire Pit!

Waterfront Fox Lake Vacation Rental w/ Fire Pit! is a cottage in Oakwood Hills, with pet-friendly space, easy beach access, 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, pet friendly, pets friendly, kitchen, and with kitchen.

Sat, Sep 26 - Sat, Oct 3 · 7 nights · total from $3,139.

From$448/night
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Breathtaking Lakefront Cozy Home - Oakwood Hills, IL
10 ★ 9 reviews

Breathtaking Lakefront Cozy Home

Holiday Home, Oakwood Hills

Breathtaking Lakefront Cozy Home is a holiday home in Oakwood Hills, with kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and…

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About Breathtaking Lakefront Cozy Home

Breathtaking Lakefront Cozy Home is a holiday home in Oakwood Hills, 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 kids friendly.

Sat, Sep 26 - Sat, Oct 3 · 7 nights · total from $2,363.

From$338/night
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Lakefront, Newly Renovated, Tranquil Getaway, Free Water Sports - Oakwood Hills, IL
9.6 ★ 20 reviews

Lakefront, Newly Renovated, Tranquil Getaway, Free Water Sports

Cottage, Oakwood Hills

Lakefront, Newly Renovated, Tranquil Getaway, Free Water Sports is a cottage in Oakwood Hills, with parking and kitchen access. This stay gives travelers a comfortable base for exploring…

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About Lakefront, Newly Renovated, Tranquil Getaway, Free Water Sports

Lakefront, Newly Renovated, Tranquil Getaway, Free Water Sports is a cottage in Oakwood Hills, 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 $2,739.

From$391/night
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Lakefront Bliss: Your Ultimate Vacation Haven Surrounded by Nature - Oakwood Hills, IL
8 ★ 2 reviews

Lakefront Bliss: Your Ultimate Vacation Haven Surrounded by Nature

Cottage, Oakwood Hills

Lakefront Bliss: Your Ultimate Vacation Haven Surrounded by Nature is a cottage in Oakwood Hills, with parking and kitchen access. This stay gives travelers a comfortable base for exploring…

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About Lakefront Bliss: Your Ultimate Vacation Haven Surrounded by Nature

Lakefront Bliss: Your Ultimate Vacation Haven Surrounded by Nature is a cottage in Oakwood Hills, 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 $2,397.

From$342/night
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Pet-friendly vacation rentals in Oakwood Hills, IL

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

This is a VACATION spot with a million dollar view! - Oakwood Hills, IL
9.8 ★ 25 reviews

This is a VACATION spot with a million dollar view!

Holiday Home, Oakwood Hills

This is a VACATION spot with a million dollar view! is a holiday home in Oakwood Hills, with pet-friendly space, parking, and kitchen access. This stay gives travelers a comfortable base…

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About This is a VACATION spot with a million dollar view!

This is a VACATION spot with a million dollar view! is a holiday home in Oakwood Hills, 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 $3,346.

From$478/night
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Waterfront Channel 3Bed 4Bath with Hot Tub Gazebo and Pet Friendly - Oakwood Hills, IL
9.6 ★ 10 reviews

Waterfront Channel 3Bed 4Bath with Hot Tub Gazebo and Pet Friendly

Holiday Home, Oakwood Hills

Waterfront Channel 3Bed 4Bath with Hot Tub Gazebo and Pet Friendly is a holiday home in Oakwood Hills, with pet-friendly space, easy beach access, and kitchen access. This stay gives…

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About Waterfront Channel 3Bed 4Bath with Hot Tub Gazebo and Pet Friendly

Waterfront Channel 3Bed 4Bath with Hot Tub Gazebo and Pet Friendly is a holiday home in Oakwood Hills, 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, hot tub, pet friendly, pets friendly, and kitchen.

Sat, Sep 26 - Sat, Oct 3 · 7 nights · total from $2,713.

From$388/night
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Spacious 4-bedroom townhome in amazing Round Lake Beach with AC, WiFi - Oakwood Hills, IL
8.6 ★ 4 reviews

Spacious 4-bedroom townhome in amazing Round Lake Beach with AC, WiFi

Holiday Home, Oakwood Hills

Spacious 4-bedroom townhome in amazing Round Lake Beach with AC, WiFi is a holiday home in Oakwood Hills, with pet-friendly space, easy beach access, and parking. This stay gives travelers…

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About Spacious 4-bedroom townhome in amazing Round Lake Beach with AC, WiFi

Spacious 4-bedroom townhome in amazing Round Lake Beach with AC, WiFi is a holiday home in Oakwood Hills, with pet-friendly space, easy beach access, 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, pet friendly, pets friendly, kitchen, and with kitchen.

Sat, Sep 26 - Sat, Oct 3 · 7 nights · total from $2,276.

From$325/night
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Waterfront Fox Lake Vacation Rental w/ Fire Pit! - Oakwood Hills, IL

Waterfront Fox Lake Vacation Rental w/ Fire Pit!

Holiday Home, Oakwood Hills

Waterfront Fox Lake Vacation Rental w/ Fire Pit! is a holiday home in Oakwood Hills, with pet-friendly space, easy beach access, and parking. This stay gives travelers a comfortable base…

Read more

About Waterfront Fox Lake Vacation Rental w/ Fire Pit!

Waterfront Fox Lake Vacation Rental w/ Fire Pit! is a holiday home in Oakwood Hills, with pet-friendly space, easy beach access, 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, free wifi, pet friendly, pets friendly, and parking.

Sat, Sep 26 - Sat, Oct 3 · 7 nights · total from $3,341.

From$383/night
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Vacation rentals with parking in Oakwood Hills, IL

Find vacation rentals that make arriving by car easier.

4 Acres of private lakefront - Fox Chain Of Lakes - 1 hour from Chicago - Oakwood Hills, IL
10 ★ 62 reviews

4 Acres of private lakefront - Fox Chain Of Lakes - 1 hour from Chicago

Holiday Home, Oakwood Hills

4 Acres of private lakefront - Fox Chain Of Lakes - 1 hour from Chicago is a holiday home in Oakwood Hills, with parking and kitchen access. This stay gives travelers a comfortable base for…

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About 4 Acres of private lakefront - Fox Chain Of Lakes - 1 hour from Chicago

4 Acres of private lakefront - Fox Chain Of Lakes - 1 hour from Chicago is a holiday home in Oakwood Hills, 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 $4,149.

From$593/night
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Relax and recharge! Charming lake view house in quaint Wonder Lake, IL! - Oakwood Hills, IL
10 ★ 4 reviews

Relax and recharge! Charming lake view house in quaint Wonder Lake, IL!

Holiday Home, Oakwood Hills

Relax and recharge! Charming lake view house in quaint Wonder Lake, IL! is a holiday home in Oakwood Hills, with parking, kitchen access, and a quieter setting. This stay gives travelers a…

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About Relax and recharge! Charming lake view house in quaint Wonder Lake, IL!

Relax and recharge! Charming lake view house in quaint Wonder Lake, IL! is a holiday home in Oakwood Hills, 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 wifi, kitchen, with kitchen, parking, and free parking.

Sat, Sep 26 - Sat, Oct 3 · 7 nights · total from $2,162.

From$309/night
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Stunning views and amazing sunsets at the lake! - Oakwood Hills, IL
9.8 ★ 59 reviews

Stunning views and amazing sunsets at the lake!

Holiday Home, Oakwood Hills

Stunning views and amazing sunsets at the lake! is a holiday home in Oakwood Hills, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area,…

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About Stunning views and amazing sunsets at the lake!

Stunning views and amazing sunsets at the lake! is a holiday home in Oakwood Hills, 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: kitchen, with kitchen, parking, free parking, and washer.

Sat, Sep 26 - Sat, Oct 3 · 7 nights · total from $3,066.

From$438/night
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Hensley’s Cornerstone Lakehouse - Oakwood Hills, IL
9.2 ★ 17 reviews

Hensley’s Cornerstone Lakehouse

Holiday Home, Oakwood Hills

Hensley’s Cornerstone Lakehouse is a holiday home in Oakwood Hills, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between…

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About Hensley’s Cornerstone Lakehouse

Hensley’s Cornerstone Lakehouse is a holiday home in Oakwood Hills, 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: kitchen, with kitchen, gym, parking, and free parking.

Sat, Sep 26 - Sat, Oct 3 · 7 nights · total from $3,084.

From$441/night
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Vacation rentals with a kitchen in Oakwood Hills, IL

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

Beautiful Riverhaus Setting - Oakwood Hills, IL
10 ★ 6 reviews

Beautiful Riverhaus Setting

Holiday Home, Oakwood Hills

Beautiful Riverhaus Setting is a holiday home in Oakwood Hills, with kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and…

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About Beautiful Riverhaus Setting

Beautiful Riverhaus Setting is a holiday home in Oakwood Hills, 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 kids friendly.

Sat, Sep 26 - Sat, Oct 3 · 7 nights · total from $3,751.

From$536/night
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Riverfront Oasis with Fun + Relaxation for All, McHenry - Oakwood Hills, IL
10 ★ 3 reviews

Riverfront Oasis with Fun + Relaxation for All, McHenry

Holiday Home, Oakwood Hills

Riverfront Oasis with Fun + Relaxation for All, McHenry is a holiday home in Oakwood Hills, with parking, kitchen access, and a quieter setting. This stay gives travelers a comfortable base…

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About Riverfront Oasis with Fun + Relaxation for All, McHenry

Riverfront Oasis with Fun + Relaxation for All, McHenry is a holiday home in Oakwood Hills, 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, parking, and free parking.

Sat, Sep 26 - Sat, Oct 3 · 7 nights · total from $5,062.

From$723/night
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Dana Guest House - Oakwood Hills, IL

Dana Guest House

Guest House, Oakwood Hills

Dana Guest House is a guest house in Oakwood Hills, 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 Dana Guest House

Dana Guest House is a guest house in Oakwood Hills, 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 wifi, kitchen, with kitchen, parking, and paid parking.

Sat, Sep 26 - Sat, Oct 3 · 7 nights · total from $674.

From$84/night
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Dana Guest House - Oakwood Hills, IL

Dana Guest House

B & B, Oakwood Hills

Dana Guest House is a b & b in Oakwood Hills, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending…

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About Dana Guest House

Dana Guest House is a b & b in Oakwood Hills, 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 wifi, kitchen, with kitchen, parking, and free parking.

Sat, Sep 26 - Sat, Oct 3 · 7 nights · total from $674.

From$84/night
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Top-rated vacation rentals in Oakwood Hills, IL

Explore guest-loved stays with strong review signals.

Home on Fox River: Modern Decor Style! - Oakwood Hills, IL
10 ★ 6 reviews

Home on Fox River: Modern Decor Style!

Holiday Home, Oakwood Hills

Home on Fox River: Modern Decor Style! is a holiday home in Oakwood Hills, with easy beach access, parking, and kitchen access. This stay gives travelers a comfortable base for exploring…

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About Home on Fox River: Modern Decor Style!

Home on Fox River: Modern Decor Style! is a holiday home in Oakwood Hills, 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, beachfront, and beach front.

Sat, Sep 26 - Sat, Oct 3 · 7 nights · total from $7,361.

From$1,052/night
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Home on Fox River: Modern Decor Style! - Oakwood Hills, IL
10 ★ 2 reviews

Home on Fox River: Modern Decor Style!

Cottage, Oakwood Hills

Home on Fox River: Modern Decor Style! is a cottage in Oakwood Hills, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between…

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About Home on Fox River: Modern Decor Style!

Home on Fox River: Modern Decor Style! is a cottage in Oakwood Hills, 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 $7,787.

From$1,006/night
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Majestic Meadows: Beautiful Spacious Home on 25 acres w/ Hot Tub - Sleeps 16+ - Oakwood Hills, IL
10 ★ 1 reviews

Majestic Meadows: Beautiful Spacious Home on 25 acres w/ Hot Tub - Sleeps 16+

Holiday Home, Oakwood Hills

Majestic Meadows: Beautiful Spacious Home on 25 acres w/ Hot Tub - Sleeps 16+ is a holiday home in Oakwood Hills, with pet-friendly space and room for a group. This stay gives travelers a…

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About Majestic Meadows: Beautiful Spacious Home on 25 acres w/ Hot Tub - Sleeps 16+

Majestic Meadows: Beautiful Spacious Home on 25 acres w/ Hot Tub - Sleeps 16+ is a holiday home in Oakwood Hills, 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, pet friendly, pets friendly, and washer.

Sat, Sep 26 - Sat, Oct 3 · 7 nights · total from $6,535.

From$934/night
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Cobblewood Manor on the Lake - Oakwood Hills, IL
10 ★ 1 reviews

Cobblewood Manor on the Lake

Holiday Home, Oakwood Hills

Cobblewood Manor on the Lake is a holiday home in Oakwood Hills, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between…

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About Cobblewood Manor on the Lake

Cobblewood Manor on the Lake is a holiday home in Oakwood Hills, 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: kitchen, with kitchen, parking, free parking, and fireplace.

Sat, Sep 26 - Sat, Oct 3 · 7 nights · total from $6,915.

From$988/night
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