Oakland Cottage Rentals & Holiday Homes
Find the best cottages in Oakland - We found 1 exact matches
About Oakland Luxury Rental on Weekend Getaways
Searching for cottages to rent near Oakland? Weekend Getaways features more than 1 cottages that are perfect for your next trip. Discover luxury cottage rentals that are a few miles away from the lake or beach. These cottage rentals in Oakland have hot baths, are kid-friendly & family-friendly, and are near top local attraction spots, to give guests the best travel experience they could ever wish for. Weekend Getaways’s cottage listings come in all shapes and sizes for large groups, friends, or couples in Oakland.
Are you planning to travel to the lakeside, beach, or mountain area? Weekend Getaways’s cottage rentals offers a wide selection, giving you direct access to the owners of these cottage rentals, and offering you the best opportunity to find a good price.
Weekend Getaways boasts of 1 holiday cottages and places to stay in Oakland. The site provides unique Airbnb, VRBO, Weekend Getaways-style cottages to fit your trip or get away with your friends and family. This can be a weekend getaway, spring break, summer vacation, or annual holiday -- all fitting within your budget.
Frequently Asked Questions About Oakland Cottage Rentals
What are the top rated Cottage Rentals in Oakland?
There are a lot of options 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 Cottage Rentals in Oakland:
- 4 #1S - 4 Bedroom/1.5 Bath Condo near McCormick Place, Wintrust Arena
- Penthouse, Lux stay near Downtown, McComick & Lake
- Gorgeous historic mansion on UChicago campus. Renovation with original detail.
- 1 #33 - 4 Bedroom/2 Bath Condo near McCormick Place, Wintrust Arena, Chinatown
- Chic 2-Bedroom Townhouse with Rooftop, Free Parking, in Downtown Chicago!
- Large historic home minutes from downtown Chicago and the lakefront.
- Modern Apt Near U of Chicago!
- The Landmark; a comfy suite near McCormick Place
- Gather, relax, enjoy— in chic luxury home near Lake Michigan & McCormick Center
- Luxéry Stay "Hollywood" Downtown/McCormick/WinTrust Area
How much does it cost to rent a cottage in Oakland?
The average cost for a cottage rental in Oakland is $153 per night. Weekendgetaways has a wide list of great cottages near Oakland that would suit your needs. There are single and multiple rooms for solo trips or family vacations.
Are there any cottages in Oakland that allow pets?
Yes, here are the top cottage rentals in Oakland that allow you to bring your pet:
- Urban Cottage
- 4 #1S - 4 Bedroom/1.5 Bath Condo near McCormick Place, Wintrust Arena
- Luxurious Stay at Modern Apartment with Self Check-in Mins Frm Downtown
- Mccormick Place Guest House
- Penthouse, Lux stay near Downtown, McComick & Lake
See all pet-friendly vacation rentals in Oakland on Weekendgetaways
Do you have any rental cottages in Oakland that are suitable for families?
Most of our listed cottages are suitable for families. Check out the complete list of cottages in Oakland to find one that works for you.
Are there quality cottages in Oakland that have indoor swimming pools?
As of 2026, the data from Weekendgetaways shows that there are Over 1 private swimming pools or cottages with indoor pools in the Oakland area along with other great amenities.
