The Gap Cottage Rentals & Holiday Homes
Find the best cottages in The Gap - We found 1445 exact matches
About The Gap Luxury Rental on Lakes Resorts
Searching for cottages to rent near The Gap? Lakes Resorts features more than 1445 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 The Gap 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. Lakes Resorts’s cottage listings come in all shapes and sizes for large groups, friends, or couples in The Gap.
Are you planning to travel to the lakeside, beach, or mountain area? Lakes Resorts’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.
Lakes Resorts boasts of 1445 holiday cottages and places to stay in The Gap. The site provides unique Airbnb, VRBO, Lakes Resorts-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 The Gap Cottage Rentals
What are the top rated Cottage Rentals in The Gap?
There are a lot of options in The Gap. If you plan on staying in the The Gap area, consider making a reservation for a few nights at one of these properties as these have been rated the top Cottage Rentals in The Gap:
- Family Friendly 2-Bedroom w/Kitchen & Laundry
- Splendid Corner 3BR in the Loop | City Views
- Chic 2-Bedroom Townhouse with Rooftop, Free Parking, in Downtown Chicago!
- Large historic home minutes from downtown Chicago and the lakefront.
- Gather, relax, enjoy— in chic luxury home near Lake Michigan & McCormick Center
- McCormick South Loop 2BR Suite Near Soldier Field & Museum Campus
- Spacious unit in historic gem
- Lux Apts with Lake Views and Top Amenities
- 2BR South Loop Apt—Walk to Lake, Museums, Aquarium + Pool, Gym, WiFi, & Conv Ct
- Stylish Apartment near Chicago Downtown
How much does it cost to rent a cottage in The Gap?
The average cost for a cottage rental in The Gap is $468 per night. Lakesresorts has a wide list of great cottages near The Gap that would suit your needs. There are single and multiple rooms for solo trips or family vacations.
Are there any cottages in The Gap that allow pets?
Yes, here are the top cottage rentals in The Gap that allow you to bring your pet:
- Vibrant 3BR Pilsen Stay Free Parking Near Downtown
- Luxurious Stay at Modern Apartment with Self Check-in Mins Frm Downtown
- Plymouth Studio Suite with Gym, Rooftop, and Lobby
- 4 #1S - 4 Bedroom/1.5 Bath Condo near McCormick Place, Wintrust Arena
See all pet-friendly vacation rentals in The Gap on Lakesresorts
Do you have any rental cottages in The Gap that are suitable for families?
Most of our listed cottages are suitable for families. Check out the complete list of cottages in The Gap to find one that works for you.
Are there quality cottages in The Gap that have indoor swimming pools?
As of 2026, the data from Lakesresorts shows that there are Over 1445 private swimming pools or cottages with indoor pools in the The Gap area along with other great amenities.
