The Gap Cottage Rentals & Holiday Homes
Find the best cottages in The Gap - We found 1 exact matches
- Chicago
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- Bridgeport
- 0.78 mi to center
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Kitchen
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Air Conditioner
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Child Friendly
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TV
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Kitchen
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Air Conditioner
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Child Friendly
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TV
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Parking
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Kitchen
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Air Conditioner
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Internet
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Parking
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Kitchen
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Air Conditioner
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Internet
- Chicago
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- Grand Boulevard
- 0.46 mi to center
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Parking
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Air Conditioner
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Internet
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Pet Friendly
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Parking
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Air Conditioner
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Internet
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Pet Friendly
- Chicago
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- Bronzeville
- 0.42 mi to center
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Parking
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Ocean View
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Balcony/Terrace
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View
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Parking
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Ocean View
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Balcony/Terrace
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View
- Chicago
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- Grand Boulevard
- 0.64 mi to center
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Parking
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Air Conditioner
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Internet
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Child Friendly
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Parking
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Air Conditioner
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Internet
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Child Friendly
- Chicago
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- South Loop
- 0.49 mi to center
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Balcony/Terrace
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Kitchen
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Air Conditioner
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Internet
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Balcony/Terrace
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Kitchen
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Air Conditioner
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Internet
- Chicago
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- Bridgeport
- 0.63 mi to center
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Parking
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Internet
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Pet Friendly
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Child Friendly
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Parking
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Internet
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Pet Friendly
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Child Friendly
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Parking
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Balcony/Terrace
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Kitchen
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Air Conditioner
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Parking
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Balcony/Terrace
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Kitchen
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Air Conditioner
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Air Conditioner
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Internet
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Child Friendly
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Bedding/Linens
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Air Conditioner
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Internet
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Child Friendly
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Bedding/Linens
- Chicago
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- Armour Square
- 0.77 mi to center
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Parking
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Kitchen
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Internet
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Child Friendly
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Parking
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Kitchen
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Internet
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Child Friendly
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Balcony/Terrace
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Kitchen
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Air Conditioner
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Internet
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Balcony/Terrace
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Kitchen
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Air Conditioner
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Internet
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Parking
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Balcony/Terrace
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Kitchen
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Air Conditioner
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Parking
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Balcony/Terrace
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Kitchen
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Air Conditioner
- Chicago
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- North Kenwood
- 0.10 mi to center
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Parking
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Balcony/Terrace
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Kitchen
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Air Conditioner
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Parking
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Balcony/Terrace
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Kitchen
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Air Conditioner
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Spa
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Ocean View
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Balcony/Terrace
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View
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Spa
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Ocean View
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Balcony/Terrace
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View
- Chicago
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- South Loop
- 0.68 mi to center
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Balcony/Terrace
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Kitchen
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Air Conditioner
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Internet
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Balcony/Terrace
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Kitchen
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Air Conditioner
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Internet
- Chicago
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- Prairie District
- 0.14 mi to center
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Parking
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Balcony/Terrace
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Kitchen
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Air Conditioner
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Parking
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Balcony/Terrace
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Kitchen
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Air Conditioner
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Parking
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Balcony/Terrace
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Kitchen
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Air Conditioner
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Parking
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Balcony/Terrace
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Kitchen
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Air Conditioner
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Kitchen
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Air Conditioner
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Internet
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Child Friendly
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Kitchen
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Air Conditioner
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Internet
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Child Friendly
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Kitchen
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Air Conditioner
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Internet
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Child Friendly
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Kitchen
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Air Conditioner
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Internet
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Child Friendly
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Parking
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Kitchen
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Air Conditioner
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Internet
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Parking
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Kitchen
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Air Conditioner
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Internet
- Chicago
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- Printers Row
- 0.21 mi to center
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Balcony/Terrace
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Kitchen
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Air Conditioner
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Internet
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Balcony/Terrace
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Kitchen
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Air Conditioner
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Internet
- Chicago
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- Bridgeport
- 0.46 mi to center
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Parking
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Balcony/Terrace
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Kitchen
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Air Conditioner
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Parking
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Balcony/Terrace
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Kitchen
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Air Conditioner
- Chicago
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- Printers Row
- 0.13 mi to center
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Parking
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Balcony/Terrace
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Kitchen
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Air Conditioner
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Parking
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Balcony/Terrace
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Kitchen
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Air Conditioner
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Kitchen
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Air Conditioner
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Internet
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Child Friendly
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Kitchen
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Air Conditioner
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Internet
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Child Friendly
About The Gap Cottage Rentals on Grayling Cabins
Searching for cottages to rent near The Gap? Grayling Cabins 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 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. Grayling Cabins’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? Grayling Cabins’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.
Grayling Cabins boasts of 1 holiday cottages and places to stay in The Gap. The site provides unique Airbnb, VRBO, Grayling Cabins-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:
- Vibrant 3BR Pilsen Stay Free Parking Near Downtown
- Toca Bella ~ 7mins to Downtown
- MICH AVE #5|Safe DTown Grant Park, Museums 2bd/2ba
- Luxury Modern home minutes from Downtown Chicago
- 4 #1S - 4 Bedroom/1.5 Bath Condo near McCormick Place, Wintrust Arena
- Family Friendly 2-Bedroom w/Kitchen & Laundry
- Gorgeous historic mansion on UChicago campus. Renovation with original detail.
- 1 #33 - 4 Bedroom/2 Bath Condo near McCormick Place, Wintrust Arena, Chinatown
- Penthouse, Lux stay near Downtown, McComick & Lake
- The Landmark; a comfy suite near McCormick Place
How much does it cost to rent a cottage in The Gap?
The average cost for a cottage rental in The Gap is $153 per night. Graylingcabins 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:
- Urban Cottage
- Vibrant 3BR Pilsen Stay Free Parking Near Downtown
- Luxurious Stay at Modern Apartment with Self Check-in Mins Frm Downtown
- Hyde Park Duplex
- Toca Bella ~ 7mins to Downtown
See all pet-friendly vacation rentals in The Gap on Graylingcabins
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 Graylingcabins shows that there are Over 1 private swimming pools or cottages with indoor pools in the The Gap area along with other great amenities.