Old Mansions - Vacation Rentals in Oakwood Hills

Newly Remodeled 2BR 2BA Home ★ Close to Barrington From US $189
         

10.0 (32 Reviews)
Apartment
  • Air Conditioner
  • TV
  • Balcony/Terrace
Riverfront Cottage From US $200
         

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10.0 (1 Review)
House
  • Air Conditioner
  • Parking
  • Balcony/Terrace
The Adorable "Blue Breeze"! From US $170
         

10.0 (21 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Little Fox Cottage - A Cozy Riverview Getaway From US $221
         

10.0 (17 Reviews)
Cottage
  • Air Conditioner
  • Parking
  • TV
In-ground pool, private! In town location near it all. Updated, Clean! From US $284
         

10.0 (4 Reviews)
House
  • Air Conditioner
  • Pet Friendly
  • Security/Safety

Luxury Places to Stay in Oakwood Hills

Over 63+ Luxury Places to Stay in or Near Oakwood Hills
HUGE Crystal Lake 7 Acre Ranch w/Pool & Hot Tub From US $1,070
         

9.2 (42 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Riverfront Oasis with Fun + Relaxation for All, McHenry From US $535
         

Lake In The Hills FHS Rental From US $494
         

New
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Lake In The Hills FHS Rental From US $494
         

New
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Hensley’s Cornerstone Lakehouse From US $431
         

9.2 (17 Reviews)
House
  • Air Conditioner
  • Parking
  • TV
Spacious Family & Pet-Friendly Getaway in Lake in the Hills From US $392
         

9.0 (4 Reviews)
House
  • Air Conditioner
  • Pet Friendly
  • Security/Safety
Stylish Home for 12~Games Room~Pet Friendly From US $383
         

10.0 (2 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Modern Lux Escape: 3BR & Gameroom From US $367
         

New
House
  • Air Conditioner
  • Pet Friendly
  • Security/Safety

Top-Rated Vacation Rentals with a Pool in Oakwood Hills

Over 12+ Top-Rated Vacation Rentals with a Pool in or Near Oakwood Hills
Horse Country Quonset Home From US $137
         

10.0 (41 Reviews)
House
  • Air Conditioner
  • Parking
  • Pool
Hampton Inn McHenry From US $115
         

9.0 (878 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool
Country Inn & Suites by Radisson, Crystal Lake, IL From US $111
         

Hampton Inn McHenry From US $110
         

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8.7 (224 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool
Holiday Inn Chicago Nw Crystal Lk Conv Ctr by IHG From US $123
         

Country Inn & Suites by Radisson, Crystal Lake, IL From US $144
         

Holiday Inn Chicago Nw Crystal Lk Conv Ctr by IHG From US $113
         

Comfort Inn Crystal Lake - Algonquin From US $108
         

8.0 (980 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool

Pet-Friendly Vacation Rentals in Oakwood Hills

Over 17+ Pet-Friendly Vacation Rentals in or Near Oakwood Hills
Fenced Yard: Fox River Grove Home, Dogs Welcome From US $271
         

9.6 (19 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Super 8 by Wyndham Crystal Lake From US $72
         

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6.4 (123 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pet Friendly
Beautiful lake house tucked away in quiet neighborhood From US $106
         

9.4 (20 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Modern 4BD Home in Lake Hills Pet friendly From US $315
         

8.0 (1 Review)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Riverfront Cottage/sauna/nkayaks/dock/firepit From US $237
         

9.8 (7 Reviews)
Cottage
  • Air Conditioner
  • Parking
  • Pet Friendly
*Cozy home near downtown and fox river* From US $180
         

9.6 (18 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Relaxing Riverfront Home with Pier From US $242
         

9.8 (15 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly

Large Vacation Homes & Villas in Oakwood Hills

Over 6+ Large Vacation Homes & Villas in or Near Oakwood Hills
Spacious 5BR Family-Friendly Oasis w/ Hot Tub From US $571
         

Wheelchair Accessible Vacation Homes in Oakwood Hills

Over 2+ Wheelchair Accessible Vacation Homes in or Near Oakwood Hills
Super 8 by Wyndham McHenry Fox Lake Area From US $81
         

5.4 (119 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Wheelchair Accessible
Super 8 by Wyndham McHenry/Fox Lake Area From US $71
         

6.2 (487 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • TV

Oakwood Hills Varoom and Airbnb Places to Stay Under $200

Over 17+ Oakwood Hills Varoom and Airbnb Places to Stay Under $200
Lakehouse Getaway From US $175
         

8.0 (4 Reviews)
Cottage
  • Air Conditioner
  • Parking
  • TV
Newly Remodeled 2BR 2BA Home - Close to Barrington From US $181
         

9.5 (2 Reviews)
House
  • Security/Safety
  • Child Friendly
  • Internet
Super 8 by Wyndham Crystal Lake From US $86
         

6.6 (548 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • TV
Spacious 3 Bedroom
New
From US $169
         

New
House
  • Air Conditioner
  • Parking
  • TV
KING bed | Crystal Lake | McHenry | Cary | COZY From US $185
         

10.0 (10 Reviews)
House
  • Air Conditioner
  • Parking
  • TV
The Acorn @ Oaks on The Fox From US $169
         

10.0 (1 Review)
House
  • Air Conditioner
  • Parking
  • TV
2 BR remodeled home near Cary/Crystal Lake/McHenry From US $192
         

Instantly Bookable Vacation Homes in Oakwood Hills

Over 7+ Instantly Bookable Vacation Homes in or Near Oakwood Hills
Cozy 3 bedroom river cottage w/indoor fireplace From US $286
         

9.8 (24 Reviews)
Cottage
  • Air Conditioner
  • Parking
  • TV
Riverfront Home Oasis with Sauna and Rooftop Deck From US $374
         

Spacious 3 Bedroom
New
From US $299
         

New
House
  • Air Conditioner
  • Parking
  • TV
Romantic Lake Cottage for Two. With Patio and Firepit. From US $225
         

10.0 (2 Reviews)
Cottage
  • Balcony/Terrace
  • Security/Safety
  • Barbecue/Outdoor Cooking
Oaks On The Fox From US $211
         

New
House
  • Air Conditioner
  • Security/Safety
  • Bedding/Linens

About Oakwood Hills Vacation Rentals

With more than 72 Oakwood Hills vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Old Mansions and other short-term private accommodations, have top-notch amenities with the best value, providing you with comfort and luxury at the same time. Get more value and more room when you stay at a rental property in Oakwood Hills.

Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With Old Mansions Oakwood Hills, you have the flexibility of comparing different options of various deals with a single click. Looking for a rental by owner with the best swimming pools, hot tubs, allows pets, or even those with huge master suite bedrooms and have large screen televisions? You can find vacation rentals by owner, and other popular Airbnb-style properties in Oakwood Hills. Places to stay near Oakwood Hills are 717.3 ft² on average, with prices averaging $274 a night.

Old Mansions makes it easy and safe to find and compare vacation rentals in Oakwood Hills with prices often at a 30-40% discount versus the price of a hotel. Just search for your destination and secure your reservation today.

Top Rental Accommodation Types in Oakwood Hills

Type Count
Vacation Homes 43
Hotels with Suites 14
Cottages 8
Holiday Apartments 5
Others 1

Use these Quick Filters to Find a Vacation Rental in Oakwood Hills

Pro Tip: Old Mansions makes it easy to compare the best listings on Old Mansions homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Old Mansions homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals availability, eco-friendly properties, property type, cancellation policies, prices, and several different options. All these make it easier to find the perfect accommodation for your next vacation in Oakwood Hills.

Weather in Oakwood Hills

View the weather forecast for Oakwood Hills before booking your Oakwood Hills Vacation Rentals to confirm your best time to go.

December - February
High 60°F       Low 26°F
March - May
High 77°F       Low 40°F
June - August
High 91°F       Low 64°F
September - November
High 84°F       Low 38°F