1027+ Vacation Home Rentals in Oakland |
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Oakland Vacation Rentals & Ski-in/Ski-out Homes

About Oakland Vacation Rentals

Explore over 1027 vacation rentals in Oakland with SunSki Resorts. These accommodations, comprising vacation homes, cottages, cabins, and condos, boast excellent amenities at great value, ensuring comfort and luxury. Enhance your stay with SunSki Resorts in Oakland for more space and value.

In search of last-minute deals or the best bargains on vacation rentals? With SunSki Resorts, you can conveniently compare various options and deals in Oakland. Discover rentals with desirable amenities like swimming pools, hot tubs, and pet-friendly options. Find the ideal vacation rental in Oakland tailored to your preferences. On average, these rentals offer 788.41 ft² of space, and are priced at an average of US $398 per night.

SunSki Resorts simplifies and secures the process of finding and comparing vacation rentals in Oakland at prices typically 30-40% lower than hotels. Discover your perfect vacation rental and book now.

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Top Types of Ski Accommodations in Oakland

Type Count
Holiday Apartments 754
Vacation Homes 108
B&B 18
Villas 2
Cottages 1

Use these Quick Filters to Find a Vacation Rental in Oakland

★ Pro Tip: Discover Your Ideal Vacation Rental in Oakland with SunSki Resorts™. Compare a diverse array of properties, including RBO homes, vacation rentals, cottages, cabins, and more. Utilize our advanced filters to search by location, amenities, and price. Book with confidence and enjoy savings of up to 40-60% compared to a hotel stay. Create unforgettable memories with SunSki Resorts™.

Weather in Oakland, IL

View the weather forecast for Oakland before booking your Oakland 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

Other Places to Stay in Oakland, IL


Mercy Family Health Center 1,053 Properties
41st Street Beach 896 Properties
Cleaverville 57 Properties

Frequently Asked Questions About Oakland?

What are the top vacation rentals in Oakland?

When organizing your trip to Oakland, don't miss the chance to explore the top-rated vacation rentals in the vicinity. With a plethora of options available, you're bound to discover the ideal accommodation for your stay in Oakland. Peruse our collection of highly-rated properties and secure your reservation today.

Which vacation homes or resorts in Oakland are best for families?

Choose SunSki for a wide variety of vacation rentals, including family-friendly homes, ski cabins, cottages, and more in Oakland. Enjoy great views, locations and save money with SunSki Resorts.™

How many SunSkiResorts vacation rentals or resorts are available in Oakland?

Discover the ideal vacation rental in Oakland with SunSki Resorts™. We provide an extensive selection of over 1027 properties, encompassing vacation homes, private villas, cottages, and more. Explore our listings to find the perfect place to stay for your upcoming trip to Oakland.

Nearby Neighborhood (2) 
Neighborhood Property Count
Bronzeville Vacation Rentals in Chicago, Illinois 113
North Kenwood Vacation Rentals in Chicago, Illinois 660

People Also Ask

There are 1027 Oakland, IL Vacation Rentals

Recently Booked Vacation Rentals in Oakland