Oakland Vacation Rentals & NearbyHoliday Homes

There are a lot of vacation rentals in Oakland. If you plan on staying in the Oakland area, consider making a reservation for a few nights at one of these properties as these have been rated the top Vacation Rentals in Oakland:

• The Brown House - A luxurious UChicago Campus stay
• Cozy 2BR South Loop Condo with Optional Parking and Gym Near McCormick Place, Public Transit & City Hotspots
• Spacious Bronzeville Apartment
• Cozy Woodlawn Retreat 1
• McCormick Place 3BR Luxury Penthouse Duplex with Personal Rooftop and Optional Parking for 8 guests in Chicago South Loop
• New Adorable Unit Located in Historic Greystone
• Modern 3BR in South Loop with Optional Parking and Gym Access Near McCormick Place, Chinatown and Soldier Field
• The Penthouse, Lux stay near Downtown, UofC & Lake
• Hyde Park Modern Private Room - Near Univ of Chicago
• Bridgeport Place - free parking, McCormick Place-Sox Park

There are many large, family vacation homes available in Oakland; however, here are the most popular family rentals listed on our site:

• 5430 Happy Home
• Luxéry Stay Chicago - Themed Units! Close to Downtown, McCormick Place & Wintrust Arena
• Drexel Apartments, Downtown Hyde Park
• Forrestville Ave Large Suite

Yes, there are 78 self-catering vacation homes in Oakland that have hot tubs, swimming pools, and other amenities.

See all vacation rentals in Oakland on NearbyHoliday

There are more than 78 luxury vacation rentals, luxury villas, and vacation homes in or near Oakland. Filter by price to compare the most expensive places to stay on NearbyHoliday.

Yes, there are pet-friendly vacation homes and places to stay available in or near Oakland that you may consider when traveling with your dog.

There are many vacation rentals in Oakland, Chicago. Compare reviews, prices, and amenities to find the right stay.

See all Vacation Rentals in Oakland on NearbyHoliday