Tree House Rentals in The Gap
House
4 Bedrooms
5 Baths
10 Guests
Fireplace/Heating
Air Conditioner
Internet
Child Friendly
US $906/Night
7 Nights - US $6,340
Apartment
10.0Exceptional
(4 Reviews)
13 Bedrooms
12 Baths
32 Guests
1435.19 ft²
Private Pool
Hot Tub- Fireplace/Heating
Pool
US $1,582/Night
7 Nights - US $11,076
House
- Chicago
- ·
- Bronzeville
- 0.16 mi to center
8.6Fabulous
(89 Reviews)
1 Bedroom
1 Bath
- Fireplace/Heating
Balcony/Terrace
Kitchen
Parking
US $190/Night
7 Nights - US $1,331
New
Apartment
1 Bedroom
1 Bath
2 Guests
500 ft²
- Fireplace/Heating
- Kitchen
- Air Conditioner
- Internet
US $474/Night
7 Nights - US $3,318
Apartment
- Chicago
- ·
- Near South Side
- 0.34 mi to center
10.0Exceptional
(4 Reviews)
2 Bedrooms
2 Baths
8 Guests
8611.13 ft²
- Fireplace/Heating
Pet Friendly- Parking
- Air Conditioner
US $443/Night
7 Nights - US $3,103
New
Apartment
1 Bedroom
1 Bath
2 Guests
500 ft²
- Fireplace/Heating
- Kitchen
- Air Conditioner
- Internet
US $434/Night
7 Nights - US $3,037
Apartment
- Chicago
- ·
- Bridgeport
- 0.64 mi to center
2 Bedrooms
1 Bath
3 Guests
- Fireplace/Heating
- Pet Friendly
- Kitchen
- Air Conditioner
US $223/Night
7 Nights - US $1,558
New
Apartment
- Chicago
- ·
- Bronzeville
- 0.52 mi to center
3 Bedrooms
2 Baths
5 Guests
- Fireplace/Heating
- Air Conditioner
- Internet
- Child Friendly
US $149/Night
7 Nights - US $1,043
New
Hotel
- Chicago
- ·
- Near South Side
- 0.54 mi to center
2 Baths
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
Unlock the Best Price
Luxury Tree House Rentals in The Gap
Over 1455+ Luxury Tree House Rentals in or Near The Gap
New
Hotel
- Chicago
- ·
- Near South Side
- 0.48 mi to center
3 Baths
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
Unlock the Best Price
New
Apartment
2 Bedrooms
2 Baths
8 Guests
1205.56 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Parking
US $6,350/Night
7 Nights - US $44,450
Condo
10.0Exceptional
(3 Reviews)
10 Bedrooms
9 Baths
16 Guests
3337 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $3,563/Night
7 Nights - US $24,944
Condo
9 Bedrooms
5 Baths
16 Guests
2831 ft²
- Fireplace/Heating
- Kitchen
- Air Conditioner
- Internet
US $2,931/Night
7 Nights - US $20,514
Apartment
- Chicago
- ·
- South Loop
- 0.39 mi to center
8.8Fabulous
(4 Reviews)
2 Bedrooms
2 Baths
13 Guests
1001.04 ft²
- Fireplace/Heating
- Parking
- Air Conditioner
- Internet
US $2,671/Night
7 Nights - US $18,695
Apartment
10.0Exceptional
(1 Review)
5 Bedrooms
6 Baths
16 Guests
3165 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $2,656/Night
7 Nights - US $18,592
Hotel
9.1Exceptional
(220 Reviews)
4 Baths
349.83 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Parking
US $2,333/Night
7 Nights - US $16,331
New
Hotel
- Chicago
- ·
- Near South Side
- 0.34 mi to center
5 Baths
1575.84 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Parking
US $2,250/Night
7 Nights - US $15,750
Apartment
- Chicago
- ·
- Printers Row
- 0.12 mi to center
5 Bedrooms
5 Baths
14 Guests
2368 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $2,218/Night
7 Nights - US $15,526
Top-Rated Treehouses with a Pool in The Gap
Over 164+ Top-Rated Private Treehouses with a Pool in or Near The Gap
Apartment
10.0Exceptional
(1 Review)
3 Bedrooms
3 Baths
6 Guests
1086 ft²
- Fireplace/Heating
- Pool
- Kitchen
- Parking
US $717/Night
7 Nights - US $5,017
Apartment
9.8Exceptional
(4 Reviews)
2 Bedrooms
2 Baths
5 Guests
882.64 ft²
- Fireplace/Heating
- Pool
- Air Conditioner
- Internet
US $767/Night
7 Nights - US $5,366
House
- Chicago
- ·
- Bronzeville
- 0.38 mi to center
9.4Exceptional
(3 Reviews)
3 Bedrooms
1 Bath
6 Guests
1500 ft²
- Private Pool
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $338/Night
7 Nights - US $2,366
Apartment
9.2Exceptional
(1174 Reviews)
1 Bedroom
1 Bath
2 Guests
- Fireplace/Heating
- Pool
- Balcony/Terrace
- Pet Friendly
US $358/Night
7 Nights - US $2,504
Hotel
- Chicago
- ·
- Near South Side
- 0.41 mi to center
9.2Exceptional
(849 Reviews)
1 Bath
- Fireplace/Heating
- Pool
- Balcony/Terrace
Breakfast
US $199/Night
7 Nights - US $1,390
Apartment
9.2Exceptional
(5 Reviews)
2 Bedrooms
2 Baths
5 Guests
882.64 ft²
- Fireplace/Heating
- Pool
- Air Conditioner
- Internet
US $312/Night
7 Nights - US $2,182
Hotel
- Chicago
- ·
- Near South Side
- 0.40 mi to center
9.0Exceptional
(1008 Reviews)
1 Bath
- Pool
- Balcony/Terrace
- Breakfast
- Kitchen
US $190/Night
7 Nights - US $1,329
Hotel
- Chicago
- ·
- South Loop
- 0.59 mi to center
8.8Fabulous
(2020 Reviews)
1 Bath
- Pool
- Balcony/Terrace
- Breakfast
- Kitchen
US $174/Night
7 Nights - US $1,221
Hotel
8.7Fabulous
(1896 Reviews)
8 Baths
862.91 ft²
- Private Pool
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $246/Night
7 Nights - US $1,720
Pet-Friendly Treehouses in The Gap
Over 569+ Pet-Friendly Private Treehouses in or Near The Gap
Condo
- Chicago
- ·
- South Loop
- 0.68 mi to center
10.0Exceptional
(13 Reviews)
2 Bedrooms
2 Baths
5 Guests
689 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $604/Night
7 Nights - US $4,230
Apartment
- Chicago
- ·
- Near South Side
- 0.34 mi to center
10.0Exceptional
(3 Reviews)
6 Bedrooms
4 Baths
12 Guests
1851.39 ft²
- Fireplace/Heating
- Pet Friendly
- Parking
- Air Conditioner
US $1,136/Night
7 Nights - US $7,951
Apartment
9.6Exceptional
(442 Reviews)
1 Bedroom
1 Bath
2 Guests
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $186/Night
7 Nights - US $1,302
Condo
- Chicago
- ·
- South Loop
- 0.39 mi to center
10.0Exceptional
(12 Reviews)
2 Bedrooms
3 Baths
6 Guests
1000 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $618/Night
7 Nights - US $4,323
Apartment
- Chicago
- ·
- Near South Side
- 0.34 mi to center
10.0Exceptional
(3 Reviews)
2 Bedrooms
2 Baths
8 Guests
796.53 ft²
- Fireplace/Heating
- Pet Friendly
- Parking
- Air Conditioner
US $434/Night
7 Nights - US $3,041
Apartment
- Chicago
- ·
- Printers Row
- 0.13 mi to center
10.0Exceptional
(11 Reviews)
2 Bedrooms
2 Baths
7 Guests
1109 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $747/Night
7 Nights - US $5,229
Apartment
10.0Exceptional
(3 Reviews)
1 Bedroom
1 Bath
12 Guests
969 ft²
- Fireplace/Heating
- Pet Friendly
- Kitchen
- Parking
US $426/Night
7 Nights - US $2,980
Apartment
10.0Exceptional
(1 Review)
1 Bedroom
1 Bath
2 Guests
583 ft²
- Fireplace/Heating
- Pet Friendly
- Kitchen
- Air Conditioner
US $310/Night
7 Nights - US $2,170
Apartment
9.8Exceptional
(75 Reviews)
2 Bedrooms
2 Baths
6 Guests
1200 ft²
- Fireplace/Heating
- Pet Friendly
- Kitchen
- Air Conditioner
US $598/Night
7 Nights - US $4,185
Large Private Treehouses in The Gap
Over 178+ Large Treehouses in or Near The Gap for Groups and Families
Apartment
- Chicago
- ·
- South Loop
- 0.39 mi to center
9.0Exceptional
(26 Reviews)
2 Bedrooms
2 Baths
13 Guests
1000 ft²
- Fireplace/Heating
- Kitchen
- Air Conditioner
- Internet
US $331/Night
7 Nights - US $2,317
Apartment
- Chicago
- ·
- Near South Side
- 0.71 mi to center
10.0Exceptional
(2 Reviews)
4 Bedrooms
3 Baths
10 Guests
1937.5 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Parking
US $772/Night
7 Nights - US $5,404
Apartment
3 Bedrooms
1 Bath
10 Guests
- Fireplace/Heating
- Pet Friendly
- Kitchen
- Parking
US $309/Night
7 Nights - US $2,163
Apartment
- Chicago
- ·
- Back of the Yards
- 0.61 mi to center
1 Bedroom
1 Bath
16 Guests
- Air Conditioner
- Child Friendly
Security/Safety
US $167/Night
7 Nights - US $1,171
Apartment
- Chicago
- ·
- Near South Side
- 0.34 mi to center
10.0Exceptional
(1 Review)
6 Bedrooms
3 Baths
12 Guests
2723.27 ft²
- Fireplace/Heating
- Pet Friendly
- Parking
- Air Conditioner
US $1,181/Night
7 Nights - US $8,267
Apartment
- Chicago
- ·
- Armour Square
- 0.77 mi to center
10.0Exceptional
(22 Reviews)
4 Bedrooms
1 Bath
11 Guests
1100 ft²
- Kitchen
- Parking
- Internet
- Child Friendly
US $447/Night
7 Nights - US $3,131
House
10.0Exceptional
(19 Reviews)
5 Bedrooms
4 Baths
8 Guests
- Fireplace/Heating
Ocean View- Balcony/Terrace
View
US $725/Night
7 Nights - US $5,078
Condo
10.0Exceptional
(16 Reviews)
4 Bedrooms
2 Baths
20 Guests
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $516/Night
7 Nights - US $3,613
House
10.0Exceptional
(12 Reviews)
5 Bedrooms
3 Baths
8 Guests
4000 ft²
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $692/Night
7 Nights - US $4,841
Wheelchair Accessible Holiday Homes in The Gap
Over 654+ Wheelchair Accessible Treehouses and Holiday Homes in or Near The Gap
New
Hotel
- Chicago
- ·
- South Loop
- 0.55 mi to center
2 Baths
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $1,318/Night
7 Nights - US $9,224
House
- Chicago
- ·
- Near South Side
- 0.88 mi to center
10.0Exceptional
(1 Review)
1 Bedroom
2 Baths
8 Guests
1797.57 ft²
- Fireplace/Heating
- View
- Pet Friendly
- Air Conditioner
US $441/Night
7 Nights - US $3,089
Hotel
9.6Exceptional
(1259 Reviews)
1 Bath
- Breakfast
- Kitchen
- Parking
- Air Conditioner
US $248/Night
7 Nights - US $1,739
New
Hotel
2 Baths
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $1,108/Night
7 Nights - US $7,757
House
- Chicago
- ·
- Near South Side
- 0.88 mi to center
10.0Exceptional
(1 Review)
1 Bedroom
2 Baths
8 Guests
1797.57 ft²
- Fireplace/Heating
- Pet Friendly
- Air Conditioner
- Internet
US $351/Night
7 Nights - US $2,454
New
Hotel
- Chicago
- ·
- Near South Side
- 0.45 mi to center
4 Baths
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $985/Night
7 Nights - US $6,895
New
Hotel
- Chicago
- ·
- Near South Side
- 0.47 mi to center
3 Baths
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $985/Night
7 Nights - US $6,893
New
Hotel
- Chicago
- ·
- South Loop
- 0.54 mi to center
2 Baths
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $740/Night
7 Nights - US $5,178
New
Hotel
- Chicago
- ·
- Printers Row
- 0.14 mi to center
2 Baths
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $668/Night
7 Nights - US $4,676
The Gap Treehouses, Airbnb and Holiday Homes Under $200
Over 407+ The Gap Private Treehouses, Airbnb and Holiday Homes Under $200
Apartment
10.0Exceptional
(2 Reviews)
1 Bedroom
1 Bath
2 Guests
400 ft²
- Hot Tub
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $193/Night
7 Nights - US $1,352
Apartment
- Chicago
- ·
- Grand Boulevard
- 0.60 mi to center
10.0Exceptional
(1 Review)
2 Bedrooms
1 Bath
5 Guests
9687.52 ft²
- Air Conditioner
- Internet
- Child Friendly
US $180/Night
7 Nights - US $1,260
House
- Chicago
- ·
- Bronzeville
- 0.35 mi to center
7.8Very Good
(60 Reviews)
1 Bedroom
1 Bath
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $120/Night
7 Nights - US $840
Apartment
- Chicago
- ·
- Heart of Chicago
- 0.16 mi to center
10.0Exceptional
(1 Review)
1 Bedroom
1 Bath
4 Guests
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $175/Night
7 Nights - US $1,224
Apartment
- Chicago
- ·
- East Hyde Park
- 0.14 mi to center
10.0Exceptional
(1 Review)
1 Bedroom
1 Bath
2 Guests
495.14 ft²
- Ocean View
- View
- Air Conditioner
- Internet
US $54/Night
7 Nights - US $378
Apartment
- Chicago
- ·
- Grand Boulevard
- 0.54 mi to center
9.8Exceptional
(102 Reviews)
1 Bedroom
1 Bath
5 Guests
1000 ft²
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $138/Night
7 Nights - US $966
Apartment
- Chicago
- ·
- Grand Boulevard
- 0.52 mi to center
9.6Exceptional
(76 Reviews)
2 Bedrooms
1 Bath
8 Guests
1600 ft²
- Fireplace/Heating
- Ocean View
- View
- Kitchen
US $174/Night
7 Nights - US $1,215
Apartment
9.6Exceptional
(4 Reviews)
1 Bedroom
1 Bath
2 Guests
- Fireplace/Heating
- Air Conditioner
- Child Friendly
Laundry
US $171/Night
7 Nights - US $1,195
House
- Chicago
- ·
- Heart of Chicago
- 0.11 mi to center
9.0Exceptional
(11 Reviews)
1 Bedroom
1 Bath
2 Guests
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $188/Night
7 Nights - US $1,317
Instantly Bookable Treehouse Rentals in The Gap
Over 797+ Instantly Bookable Private Treehouses in or Near The Gap
Hotel
- Chicago
- ·
- South Loop
- 0.72 mi to center
2 Baths
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $654/Night
7 Nights - US $4,578
Bed & Breakfast
- Chicago
- ·
- Bronzeville
- 0.16 mi to center
2.0Average
(1 Review)
1 Bedroom
1 Bath
2 Guests
237 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $194/Night
7 Nights - US $1,357
New
Hotel
- Chicago
- ·
- Near South Side
- 0.81 mi to center
2 Baths
800 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $639/Night
7 Nights - US $4,473
New
Hotel
- Chicago
- ·
- Printers Row
- 0.22 mi to center
2 Baths
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $634/Night
7 Nights - US $4,440
New
Hotel
2 Baths
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $632/Night
7 Nights - US $4,426
New
Hotel
- Chicago
- ·
- Printers Row
- 0.10 mi to center
2 Baths
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $627/Night
7 Nights - US $4,388
New
Hotel
- Chicago
- ·
- Near South Side
- 0.48 mi to center
2 Baths
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $458/Night
7 Nights - US $3,203
New
Hotel
- Chicago
- ·
- Near South Side
- 0.42 mi to center
2 Baths
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $389/Night
7 Nights - US $2,720
New
Hotel
- Chicago
- ·
- Near South Side
- 0.48 mi to center
2 Baths
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $373/Night
7 Nights - US $2,608
Book a Last Minute Place to Stay in The Gap
About The Gap Treehouse Rentals
Explore more than 1464 treehouses in The Gap. From luxurious treetop retreats to cozy forest homes, cabins and off-grid properties, each offers premium amenities designed for families, groups, and adventurers. Enjoy exceptional comfort and a one-of-a-kind nature experience with these incredible accommodations. Perfect for tranquil escapes, adventurous retreats, or nature-inspired getaways, these treehouses provide style and comfort in The Gap.
Looking for last-minute deals or the best offers on treehouses, cozy forest homes, cabins and off-grid properties? Treehouse Rentals makes it easy to compare options in The Gap. Choose from spacious family-friendly stays, charming woodland escapes, or luxurious treetop getaways tailored for ultimate relaxation and adventure
Find spacious family-friendly accommodations, cozy forest homes, or luxurious treetop stays—all designed for maximum comfort and convenience during your visit.On average, treehouses in The Gap offer approximately 811.31 ft² of space, giving you and your group plenty of room to relax and enjoy the stunning natural surroundings.
The average nightly rate for treehouses in The Gap typically ranges around US $487.
Treehouse Rentals offers a secure and convenient platform to compare and book the best treehouses in The Gap. Explore a wide range of properties at unbeatable rates, and enjoy a unique stay immersed in nature with us.
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Top Treehouse Accommodation Types in The Gap
| Type | Count |
|---|---|
| Holiday Apartments | 1062 |
| Vacation Homes | 134 |
| Villas | 2 |
| Cottages | 1 |
Use these Quick Filters to Find a Vacation Rental in The Gap
★ Pro Tip: Treehouse Rentals simplifies your search for the best treehouse accommodations from leading vacation rental OTAs like Booking.com and more. Use our Advanced Filter to explore treehouses, cozy cabins, secluded forest homes and off-grid properties. Filter by availability, pricing, cancellation options, and amenities to discover the ideal treehouse getaway in The Gap.
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.
December - February
High 60°F Low 26°F
March - May
High 77°F Low 40°F
June - August
High 91°F Low 64°F
September - November
High 84°F Low 38°F
Other Places to Stay in The Gap, IL
Frequently Asked Questions About The Gap?
What are the top treehouse rentals in The Gap?
Looking for a place to stay in The Gap? Explore these highly-rated treehouses for a one-of-a-kind retreat surrounded by nature:
- Vibrant 3BR Pilsen Stay Free Parking Near Downtown
- 4 #1S - 4 Bedroom/1.5 Bath Condo near McCormick Place, Wintrust Arena
- 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
- 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 treehouses with private pools are available in The Gap?
Find exceptional treehouses with private pools near The Gap on Treehouse Rentals. Relax in serene treetop accommodations with exclusive pool access and picturesque nature views. Whether it's a spacious treehouse or a secluded forest retreat, these properties provide the ideal mix of luxury and adventure.
- Spacious 1 bd sleeps 4 quiet and near Michigan Ave. free gift
- S Loop Studio w Pool Gym Spa nr Grant Park CHI-739
- S Loop 1BR w Pool Gym nr Museum Campus CHI-352
- S Loop 2BR w Pool Gym Spa nr Grant Park CHI-740
What are the top-rated treehouses in The Gap for family stays?
Searching for a family-friendly treehouse in The Gap? Discover these top-rated options, each loved by families and groups who have stayed in The Gap:
- Cozy smoking Suite Downtown McCormick Lakefront
- Spacious 2BR South Loop Suite with Skyline View, Optional Parking and Gym Access Close to McCormick Place, Grant Park, Museum Campus & CTA Lines
- Stylish Apartment near Chicago Downtown
How many treehouses are available in The Gap?
Treehouse Rentals, as of 2026, features over 1464 unique treehouse, cabins and forest homes in The Gap. Choose from treetop hideaways, eco-friendly lodges, and off-grid properties, with new options added frequently.
By 2026, Treehouse Rentals has curated over 1464 stunning properties in The Gap, sourced from trusted platforms. Plan your nature-inspired getaway now.
For 2026, Treehouse Rentals provides access to over 1464 premier accommodations in The Gap. Find your ideal escape among the treetops today.
Nearby Neighborhood (3)
| Neighborhood | Property Count |
|---|---|
| Bronzeville Vacation Rentals in Chicago, Illinois | 74 |
| Douglas Vacation Rentals in Chicago, Illinois | 39 |
| Lake Meadows Vacation Rentals in Chicago, Illinois | 1403 |
People Also Ask
Finding the best prices in The Gap
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