Find the best cottages in Woodlawn - We found 101 exact matches
About Woodlawn Cottage Rentals on Vacation Cottage
For travelers seeking a comfortable and luxurious retreat in Woodlawn, Vacation Cottage has you covered. Opt for a cottage rental, lake house retreat, or summer home resort and enjoy the flexibility of a hotel. With over 101 options available in Woodlawn on Vacation Cottage, we can assist you in finding the perfect accommodation.
Elevate your next vacation with a picturesque cottage rental in Woodlawn, offering top-notch amenities such as swimming pools, fitness centers, Wi-Fi, luxury suites, and fully-equipped kitchens. Discover unbeatable deals on outdoor vacation cottages, lake houses, and summer home retreats. Start planning your trip to Woodlawn today and secure your accommodation in minutes on our website.
Whether it's a short-term getaway or a long-term seasonal stay, find the perfect cottage rental, lake house, or summer home for your favorite travel destinations. Compare options with Vacation Cottage and stay close to nature.
Frequently Asked Questions About Woodlawn Rental Cottages
What are the top rated Cottage Rentals in Woodlawn?
There are a lot of options in Woodlawn. If you plan on staying in the Woodlawn area, consider making a reservation for a few nights at one of these properties as these have been rated the top Cottage Rentals in Woodlawn:
- The Hyde Park Haven
- Luxe Loft vibe –4BR/3BA Apt– King Suite-11 minutes from downtown-Families-Groups
- Cozy 3-bedroom condo near University of Chicago
- Book the Great Migration Guest House. Family-sized condo near the Green Line.nn
- Spacious 4-bedroom apartment in fabulous Chicago with WiFi, AC
- Near Lakefront! Minutes from the beach, museum, and 2 golf courses.
- Woodlawn Oasis.10 Minutes to Dining & Downtown
- The Study at the University of Chicago
- Chic 3-bedroom apartment with WiFi, AC in welcoming Chicago
- Eco Stay by UChicago, Lakefront & Hyde Park!
How much does it cost to rent a cottage in Woodlawn?
The average cost for a cottage rental in Woodlawn is $210 per night. Vacation Cottage has a wide list of great cottages near Woodlawn that would suit your needs. There are single and multiple rooms for solo trips or family vacations.
Are there any cottages in Woodlawn that allow pets?
Yes, here are the top cottage rentals in Woodlawn that allow you to bring your pet:
- Modern Apt Near U of Chicago!
- The Brown House - A luxurious UChicago Campus stay
- Best Motel By OYO Chicago I-90
- High-end 2Bdrm Garden Apt. Where Comfort Meets Style
See all pet-friendly vacation rentals in Woodlawn on Vacation Cottage
Do you have any rental cottages in Woodlawn that are suitable for families?
Most of our listed cottages are suitable for families. Check out the complete list of cottages in Woodlawn to find one that works for you.
Are there quality cottages in Woodlawn that have indoor swimming pools?
As of 2025, the data from Vacation Cottage shows that there are Over 101 private swimming pools or cottages with indoor pools in the Woodlawn area along with other great amenities.
Do any cottages in Woodlawn have hot tubs?
About 101 cottages in Woodlawn boast of premium hot tubs. Some of the popular places to stay with hot tubs include:
See all holiday vacation rentals in Woodlawn on Vacation CottageAre there luxury cottages in Woodlawn?
Yes, there are luxury cottages in Woodlawn. Find more luxury, lakefront, winter, & last-minute cottage rentals near Woodlawn.
