Top Rated Activities & Tours in The Gap
The Gap Vacation Rentals, Hotels, & Places to Stay
About The Gap Vacation Rentals
There are more than 1473 places to stay that are available in The Gap. These choices include hotels as well as other short-term private accommodations (including vacation rentals, cabins, condos, RVs, and more), have a wide selection of amenities at great prices, providing you with all the comforts of home or a touch of luxury. We like to help you find more room with Varoom when booking your property in The Gap.
Varoom features many last-minute deals on hotels, resorts and places to stay including many that are nearby. If you need a place for a group or event, be it a hotel or vacation rental (as well as cabins and private luxury villas), let us help. With Varoom's places in The Gap, you have the flexibility of comparing different options from multiple suppliers with a single click. Group deals, private pools, hot tubs, allows pets, or even those with huge master suite bedrooms with open-air showers? You can find vacation rentals and resorts as well as Airbnb-style properties in The Gap. Places to stay near The Gap are 814.74 ft² on average, with prices averaging US $478 a night.
Varoom helps you discover places to stay and suggests things to do to create great travel memories in The Gap. Prices listed are often found to be at a 30-40% discount versus the rack rates. Just search for your destination and secure your perfect place to stay today.
Top Rental Accommodation Types in The Gap
| Type | Count |
|---|---|
| Holiday Apartments | 1072 |
| Vacation Homes | 134 |
| Villas | 2 |
| Cottages | 1 |
Use these Quick Filters to Find a Vacation Rental in The Gap
★ Pro Tip: Varoom is a meta travel and activities site, and as such we combine results from many of the leading travel websites, helping you compare the best places to stay and things to do in each market. Use the filter option to narrow down your selection and let us help you find more room to stay, play, and discover. Create new memories in The Gap today.
Weather in The Gap, IL
View the weather forecast for The Gap before booking your The Gap Vacation Rentals to confirm your best time to go.
Other Places to Stay in The Gap, IL
Frequently Asked Questions About The Gap?
What are the top vacation rentals in The Gap?
We have scoured the web to find you options in The Gap. If you plan on staying near or in the The Gap area, consider one of the following places to stay for a week or more. Weekly stays are a great way to unwind and unplug. These places to stay have all been rated as one of the Top Places to Stay in The Gap:
- Vibrant 3BR Pilsen Stay Free Parking Near Downtown
- Luxury Hyde Park Haven- Perfect for families and digital nomads. Pet Friendly.
- Luxury Modern home minutes from Downtown Chicago
- Gorgeous historic mansion on UChicago campus. Renovation with original detail.
- Penthouse, Lux stay near Downtown, McComick & Lake
- 1 #33 - 4 Bedroom/2 Bath Condo near McCormick Place, Wintrust Arena, Chinatown
- Large historic home minutes from downtown Chicago and the lakefront.
- Dtown Penthouse 3bd VIEWS+Parking +Gym+Pool
- Cozy Downtown MICH AVE #7 | gym+rooftop
- Chic 2-Bedroom Townhouse with Rooftop, Free Parking, in Downtown Chicago!
How many vacation rentals have private pools in The Gap?
We have found 8 places to stay that feature a private swimming pool in or near The Gap. Some of the best places to stay that feature or have access to a swimming pool are:
- Spacious 1 bd sleeps 4 quiet and near Michigan Ave. free gift
- Lux Apts with Lake Views and Top Amenities
- S Loop 1BR w Pool Gym nr Museum Campus CHI-352
- S Loop 2BR w Pool Gym Spa nr Grant Park CHI-740
Which vacation homes in The Gap are best for families?
If you are looking for a place to stay that is family-friendly in The Gap, check out one of the following places as all are highly-rated options and have received excellent reviews for families or groups staying in The Gap:
- Luxury 2BR/2BA Suite near McCormick Place, Lakefront with Parking & Gym
- McCormick Place 2BR Oasis with Optional Parking, Patio, Gym for up to 6 guests Near Museum Campus, Grant Park & Soldier Field
- Villa Dubois Guest House Room 5
How many Varoom vacation rentals are available in The Gap?
Varoom updates its properties nightly to bring you a great selection of places to stay. Currently, the total number of properties listed by Varoom in 2026 is over 1473 in the The Gap area, and still growing every day. When we combine listings from multiple websites and travel providers, Varoom can provide you with a diverse amount of choice of the best places to stay in The Gap.
Nearby Neighborhood (3)
| Neighborhood | Property Count |
|---|---|
| Bronzeville Vacation Rentals in Chicago, Illinois | 71 |
| Douglas Vacation Rentals in Chicago, Illinois | 36 |
| Lake Meadows Vacation Rentals in Chicago, Illinois | 1403 |
