Tree House Rentals in Oakland
Apartment
- Chicago
- ·
- Near South Side
- 0.27 mi to center
10.0Exceptional
(1 Review)
3 Bedrooms
2 Baths
6 Guests
1500 ft²
Balcony/Terrace
Kitchen
Air Conditioner
Internet
US $435/Night
7 Nights - US $3,047
Apartment
10.0Exceptional
(5 Reviews)
3 Bedrooms
2 Baths
6 Guests
1496.18 ft²
Parking- Air Conditioner
- Internet
Child Friendly
US $686/Night
7 Nights - US $4,800
House
- Chicago
- ·
- Bronzeville
- 0.16 mi to center
8.2Excellent
(104 Reviews)
1 Bedroom
1 Bath
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $176/Night
7 Nights - US $1,233
New
Apartment
- Chicago
- ·
- Washington Park
- 0.66 mi to center
10.0Exceptional
(1 Review)
3 Bedrooms
1 Bath
3 Guests
1600 ft²
- Balcony/Terrace
- Kitchen
- Air Conditioner
- Internet
US $162/Night
7 Nights - US $1,137
Apartment
- Chicago
- ·
- Near South Side
- 0.34 mi to center
10.0Exceptional
(4 Reviews)
2 Bedrooms
2 Baths
8 Guests
8611.13 ft²
EV Charge Station- Parking
- Air Conditioner
- Internet
US $437/Night
7 Nights - US $3,061
Condo
9.2Exceptional
(17 Reviews)
3 Bedrooms
1 Bath
6 Guests
1000 ft²
- Parking
- Kitchen
- Air Conditioner
- Internet
US $354/Night
7 Nights - US $2,475
New
Apartment
9.0Exceptional
(7 Reviews)
2 Bedrooms
2 Baths
9 Guests
1000 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $371/Night
7 Nights - US $2,597
New
House
4 Bedrooms
4 Baths
7 Guests
4500 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $984/Night
7 Nights - US $6,891
New
Condo
- Chicago
- ·
- South Loop
- 0.28 mi to center
3 Bedrooms
3 Baths
6 Guests
Hot Tub- Parking
Pool
Ocean View
US $471/Night
7 Nights - US $3,300
Luxury Tree House Rentals in Oakland
Over 1084+ Luxury Tree House Rentals in or Near Oakland
Hotel
8.9Fabulous
(209 Reviews)
4 Baths
349.83 ft²
- EV Charge Station
- Parking
- Balcony/Terrace
- Air Conditioner
US $2,333/Night
7 Nights - US $16,331
Hotel
- Chicago
- ·
- Near South Side
- 0.34 mi to center
3 Baths
1101.51 ft²
- EV Charge Station
- Parking
- Balcony/Terrace
- Air Conditioner
US $2,250/Night
7 Nights - US $15,750
New
House
5 Bedrooms
3 Baths
12 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $2,202/Night
7 Nights - US $15,413
Apartment
- Chicago
- ·
- Near South Side
- 0.34 mi to center
5 Bedrooms
4 Baths
12 Guests
2303.48 ft²
- EV Charge Station
- Parking
- Air Conditioner
- Internet
US $2,198/Night
7 Nights - US $15,383
Apartment
- Chicago
- ·
- Near South Side
- 0.34 mi to center
5 Bedrooms
3 Baths
12 Guests
1851.39 ft²
- EV Charge Station
- Parking
- Air Conditioner
- Internet
US $2,119/Night
7 Nights - US $14,833
House
- Chicago
- ·
- Bridgeport
- 0.68 mi to center
8.8Fabulous
(7 Reviews)
7 Bedrooms
5 Baths
16 Guests
4499.31 ft²
- Parking
View- Air Conditioner
- Internet
US $1,785/Night
7 Nights - US $12,497
House
5 Bedrooms
4 Baths
12 Guests
4004.17 ft²
- Parking
- Air Conditioner
- Internet
- Child Friendly
US $1,539/Night
7 Nights - US $10,771
Hotel
- Chicago
- ·
- Near South Side
- 0.37 mi to center
8.2Excellent
(825 Reviews)
13 Baths
423.11 ft²
Breakfast- Parking
- Balcony/Terrace
- Air Conditioner
US $1,495/Night
7 Nights - US $10,465
Apartment
- Chicago
- ·
- Near South Side
- 0.34 mi to center
9.6Exceptional
(11 Reviews)
3 Bedrooms
2 Baths
8 Guests
2368.06 ft²
- EV Charge Station
- Parking
- Air Conditioner
- Internet
US $1,466/Night
7 Nights - US $10,262
Top-Rated Treehouses with a Pool in Oakland
Over 50+ Top-Rated Private Treehouses with a Pool in or Near Oakland
New
House
- Chicago
- ·
- Bronzeville
- 0.38 mi to center
9.6Exceptional
(5 Reviews)
3 Bedrooms
1 Bath
6 Guests
1500 ft²
Private Pool- Parking
- Pool
- Balcony/Terrace
US $399/Night
7 Nights - US $2,793
Hotel
- Chicago
- ·
- Near South Side
- 0.41 mi to center
9.2Exceptional
(874 Reviews)
1 Bath
- Breakfast
- Parking
- Pool
- Balcony/Terrace
US $363/Night
7 Nights - US $2,539
Hotel
- Chicago
- ·
- Near South Side
- 0.40 mi to center
9.0Exceptional
(1005 Reviews)
1 Bath
- Breakfast
- Parking
- Pool
- Balcony/Terrace
US $200/Night
7 Nights - US $1,400
Hotel
- Chicago
- ·
- Near South Side
- 0.40 mi to center
8.6Fabulous
(1005 Reviews)
1 Bath
- Breakfast
- Parking
- Pool
- Balcony/Terrace
US $208/Night
7 Nights - US $1,458
Hotel
- Chicago
- ·
- Near South Side
- 0.40 mi to center
8.6Fabulous
(284 Reviews)
1 Bath
301.39 ft²
- Private Pool
Oceanfront- Parking
- Pool
US $291/Night
7 Nights - US $2,035
Hotel
- Chicago
- ·
- Near South Side
- 0.40 mi to center
8.5Fabulous
(750 Reviews)
1 Bath
333.68 ft²
- Private Pool
- Parking
- Pool
- Balcony/Terrace
US $229/Night
7 Nights - US $1,604
Hotel
8.3Excellent
(360 Reviews)
5 Baths
363.82 ft²
- Private Pool
- Oceanfront
- Pool
- Ocean View
US $198/Night
7 Nights - US $1,384
House
- Chicago
- ·
- Grand Boulevard
- 0.32 mi to center
8.3Excellent
(12 Reviews)
6 Bedrooms
5 Baths
15 Guests
3196.88 ft²
- Parking
- Pool
- Balcony/Terrace
- View
US $657/Night
7 Nights - US $4,597
Hotel
- Chicago
- ·
- Near South Side
- 0.40 mi to center
7.7Very Good
(348 Reviews)
1 Bath
333.68 ft²
- Private Pool
- Parking
- Pool
- Balcony/Terrace
US $162/Night
7 Nights - US $1,133
Pet-Friendly Treehouses in Oakland
Over 331+ Pet-Friendly Private Treehouses in or Near Oakland
New
Apartment
- Chicago
- ·
- Washington Park
- 0.39 mi to center
3 Bedrooms
2 Baths
8 Guests
- Air Conditioner
- Internet
Pet Friendly- Child Friendly
US $323/Night
7 Nights - US $2,261
Apartment
- Chicago
- ·
- Near South Side
- 0.34 mi to center
10.0Exceptional
(3 Reviews)
2 Bedrooms
2 Baths
8 Guests
796.53 ft²
- EV Charge Station
- Parking
- Air Conditioner
- Internet
US $429/Night
7 Nights - US $3,001
Condo
- Chicago
- ·
- Grand Boulevard
- 0.49 mi to center
1 Bedroom
1 Bath
- Kitchen
- Internet
- Pet Friendly
- Child Friendly
US $180/Night
7 Nights - US $1,259
New
House
- Chicago
- ·
- Back of the Yards
- 0.85 mi to center
5 Bedrooms
1 Bath
9 Guests
- Kitchen
- Air Conditioner
- Internet
- Pet Friendly
US $117/Night
7 Nights - US $817
Apartment
- Chicago
- ·
- Near South Side
- 0.34 mi to center
10.0Exceptional
(2 Reviews)
2 Bedrooms
2 Baths
8 Guests
796.53 ft²
- EV Charge Station
- Parking
- Air Conditioner
- Internet
US $817/Night
7 Nights - US $5,722
New
Condo
10.0Exceptional
(12 Reviews)
2 Bedrooms
2 Baths
6 Guests
1000 ft²
- Parking
- Kitchen
- Air Conditioner
- Internet
US $322/Night
7 Nights - US $2,256
Apartment
10.0Exceptional
(3 Reviews)
2 Bedrooms
1 Bath
5 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $263/Night
7 Nights - US $1,844
Apartment
- Chicago
- ·
- Lower West Side
- 1.59 mi to center
10.0Exceptional
(1 Review)
2 Bedrooms
2 Baths
8 Guests
- Air Conditioner
- Internet
- Pet Friendly
- Child Friendly
US $399/Night
7 Nights - US $2,790
Apartment
- Chicago
- ·
- Bronzeville
- 0.39 mi to center
9.8Exceptional
(30 Reviews)
1 Bedroom
1 Bath
4 Guests
750 ft²
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
US $223/Night
7 Nights - US $1,561
Large Private Treehouses in Oakland
Over 130+ Large Treehouses in or Near Oakland for Groups and Families
Apartment
- Chicago
- ·
- Back of the Yards
- 0.61 mi to center
1 Bedroom
1 Bath
16 Guests
- Air Conditioner
- Child Friendly
Security/Safety
US $173/Night
7 Nights - US $1,209
Apartment
- Chicago
- ·
- Near South Side
- 0.34 mi to center
10.0Exceptional
(1 Review)
3 Bedrooms
2 Baths
10 Guests
1194.79 ft²
- EV Charge Station
- Parking
- Air Conditioner
- Internet
US $549/Night
7 Nights - US $3,845
Apartment
- Chicago
- ·
- Armour Square
- 0.77 mi to center
10.0Exceptional
(22 Reviews)
4 Bedrooms
1 Bath
12 Guests
1100 ft²
- Parking
- Kitchen
- Internet
- Child Friendly
US $541/Night
7 Nights - US $3,790
Bed & Breakfast
- Chicago
- ·
- Bridgeport
- 0.22 mi to center
9.2Exceptional
(47 Reviews)
8 Bedrooms
3 Baths
19 Guests
932.87 ft²
- Breakfast
- Parking
- Air Conditioner
- Internet
US $360/Night
7 Nights - US $2,520
House
10.0Exceptional
(20 Reviews)
5 Bedrooms
4 Baths
8 Guests
- Ocean View
- Balcony/Terrace
- View
- Kitchen
US $761/Night
7 Nights - US $5,325
Condo
10.0Exceptional
(16 Reviews)
4 Bedrooms
2 Baths
20 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $570/Night
7 Nights - US $3,993
House
10.0Exceptional
(15 Reviews)
5 Bedrooms
3 Baths
8 Guests
4000 ft²
- Hot Tub
- Parking
- Balcony/Terrace
- Kitchen
US $902/Night
7 Nights - US $6,312
House
10.0Exceptional
(11 Reviews)
5 Bedrooms
2 Baths
10 Guests
3000 ft²
- Parking
- Ocean View
- Balcony/Terrace
- View
US $754/Night
7 Nights - US $5,277
House
10.0Exceptional
(8 Reviews)
4 Bedrooms
4 Baths
10 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
US $698/Night
7 Nights - US $4,886
Wheelchair Accessible Holiday Homes in Oakland
Over 393+ Wheelchair Accessible Treehouses and Holiday Homes in or Near Oakland
New
Condo
- Chicago
- ·
- South Loop
- 0.27 mi to center
2 Bedrooms
2 Baths
4 Guests
- Hot Tub
- Parking
- Pool
- Balcony/Terrace
US $268/Night
7 Nights - US $1,873
House
- Chicago
- ·
- Near South Side
- 0.88 mi to center
10.0Exceptional
(1 Review)
1 Bedroom
2 Baths
8 Guests
1797.57 ft²
- View
- Air Conditioner
- Internet
- Pet Friendly
US $441/Night
7 Nights - US $3,089
Hotel
9.6Exceptional
(1007 Reviews)
1 Bath
- Breakfast
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $344/Night
7 Nights - US $2,406
New
Hotel
- Chicago
- ·
- Near South Side
- 0.48 mi to center
2 Baths
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $346/Night
7 Nights - US $2,423
House
- Chicago
- ·
- Near South Side
- 0.88 mi to center
10.0Exceptional
(1 Review)
1 Bedroom
2 Baths
8 Guests
1797.57 ft²
- Air Conditioner
- Internet
- Pet Friendly
Wheelchair Accessible
US $351/Night
7 Nights - US $2,454
Apartment
- Chicago
- ·
- Near South Side
- 0.39 mi to center
10.0Exceptional
(2 Reviews)
2 Bedrooms
2 Baths
6 Guests
850 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $252/Night
7 Nights - US $1,767
New
Apartment
- Chicago
- ·
- Near South Side
- 0.39 mi to center
8.8Fabulous
(3 Reviews)
2 Bedrooms
1 Bath
6 Guests
900 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $248/Night
7 Nights - US $1,734
Apartment
- Chicago
- ·
- Near South Side
- 0.39 mi to center
8.0Excellent
(7 Reviews)
2 Bedrooms
2 Baths
6 Guests
950 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $222/Night
7 Nights - US $1,554
New
Apartment
- Chicago
- ·
- Near South Side
- 0.39 mi to center
8.0Excellent
(1 Review)
2 Bedrooms
2 Baths
6 Guests
850 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $198/Night
7 Nights - US $1,388
Oakland Treehouses, Airbnb and Holiday Homes Under $200
Over 332+ Oakland Private Treehouses, Airbnb and Holiday Homes Under $200
Apartment
- Chicago
- ·
- Grand Boulevard
- 0.54 mi to center
9.8Exceptional
(104 Reviews)
1 Bedroom
1 Bath
5 Guests
1000 ft²
- Hot Tub
- Parking
- Balcony/Terrace
- Kitchen
US $167/Night
7 Nights - US $1,170
Apartment
- Chicago
- ·
- South Loop
- 0.22 mi to center
10.0Exceptional
(1 Review)
1 Bedroom
1 Bath
2 Guests
441.32 ft²
- Air Conditioner
- Internet
- Pet Friendly
- Child Friendly
US $185/Night
7 Nights - US $1,295
Hotel
9.6Exceptional
(1006 Reviews)
1 Bath
- Breakfast
- Parking
- Kitchen
- Air Conditioner
US $189/Night
7 Nights - US $1,323
Apartment
- Chicago
- ·
- Grand Boulevard
- 0.52 mi to center
9.6Exceptional
(77 Reviews)
2 Bedrooms
1 Bath
8 Guests
1600 ft²
- Oceanfront
- Parking
- Ocean View
- View
US $180/Night
7 Nights - US $1,257
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
Apartment
9.4Exceptional
(6 Reviews)
1 Bedroom
1 Bath
2 Guests
- Balcony/Terrace
- Kitchen
- Air Conditioner
- Internet
US $179/Night
7 Nights - US $1,253
Apartment
- Chicago
- ·
- Bridgeport
- 0.46 mi to center
8.4Excellent
(15 Reviews)
3 Bedrooms
1 Bath
7 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $165/Night
7 Nights - US $1,153
Condo
6.0Good
(1 Review)
2 Bedrooms
2 Baths
3 Guests
- Hot Tub
- Parking
- Balcony/Terrace
- Kitchen
US $130/Night
7 Nights - US $908
Apartment
- Chicago
- ·
- South Loop
- 0.32 mi to center
4.0Average
(2 Reviews)
2 Bedrooms
2 Baths
1 Guest
- Kitchen
- Air Conditioner
- Internet
Laundry
US $149/Night
7 Nights - US $1,040
Instantly Bookable Treehouse Rentals in Oakland
Over 537+ Instantly Bookable Private Treehouses in or Near Oakland
New
Apartment
- Chicago
- ·
- Lower West Side
- 1.5 mi to center
3 Bedrooms
1 Bath
7 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
US $379/Night
7 Nights - US $2,655
Bed & Breakfast
- Chicago
- ·
- Bronzeville
- 0.16 mi to center
2.0Average
(1 Review)
1 Bedroom
1 Bath
2 Guests
237 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $194/Night
7 Nights - US $1,357
Apartment
- Chicago
- ·
- North Kenwood
- 0.10 mi to center
10.0Exceptional
(18 Reviews)
2 Bedrooms
2 Baths
4 Guests
1400 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $355/Night
7 Nights - US $2,487
Apartment
10.0Exceptional
(5 Reviews)
2 Bedrooms
1 Bath
5 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $254/Night
7 Nights - US $1,775
New
Apartment
- Chicago
- ·
- Near South Side
- 0.40 mi to center
10.0Exceptional
(1 Review)
2 Bedrooms
2 Baths
6 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $257/Night
7 Nights - US $1,801
Apartment
- Chicago
- ·
- Bridgeport
- 0.52 mi to center
9.8Exceptional
(7 Reviews)
1 Bedroom
1 Bath
4 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $252/Night
7 Nights - US $1,765
Condo
- Chicago
- ·
- Grand Boulevard
- 0.66 mi to center
9.6Exceptional
(20 Reviews)
1 Bedroom
1 Bath
2 Guests
- Internet
- Child Friendly
Bedding/Linens
Wellness Facilities
US $299/Night
7 Nights - US $2,090
Condo
9.4Exceptional
(15 Reviews)
2 Bedrooms
1 Bath
7 Guests
800 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $295/Night
7 Nights - US $2,062
Apartment
- Chicago
- ·
- Bridgeport
- 0.70 mi to center
9.4Exceptional
(3 Reviews)
1 Bedroom
1 Bath
2 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
US $255/Night
7 Nights - US $1,788
Book a Last Minute Place to Stay in Oakland
About Oakland Treehouse Rentals
Explore more than 1093 treehouses in Oakland. 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 Oakland.
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 Oakland. 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 Oakland offer approximately 725.07 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 Oakland typically ranges around US $432.
Treehouse Rentals offers a secure and convenient platform to compare and book the best treehouses in Oakland. 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 Oakland
| Type | Count |
|---|---|
| Holiday Apartments | 777 |
| Vacation Homes | 131 |
| Villas | 2 |
| Cottages | 1 |
Use these Quick Filters to Find a Vacation Rental in Oakland
★ 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 Oakland.
Weather in Oakland, IL
View the weather forecast for Oakland before booking your Oakland 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 Oakland, IL
Frequently Asked Questions About Oakland?
What are the top treehouse rentals in Oakland?
Looking for a place to stay in Oakland? Explore these highly-rated treehouses for a one-of-a-kind retreat surrounded by nature:
- Luxury Hyde Park Haven- Perfect for families and digital nomads. Pet Friendly.
- 4 #1S - 4 Bedroom/1.5 Bath Condo near McCormick Place, Wintrust Arena
- 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.
- Chic 2-Bedroom Townhouse with Rooftop, Free Parking, in Downtown Chicago!
- Modern Apt Near U of Chicago!
- Bronzeville-Lakefront property, near Sox, McCormick, Museums & Downtown Chicago.
- Spacious 3BR on UChicago Campus & Hospitals Free Street Parking
What are the top-rated treehouses in Oakland for family stays?
Searching for a family-friendly treehouse in Oakland? Discover these top-rated options, each loved by families and groups who have stayed in Oakland:
- Spacious unit in historic gem
- McCormick Place 2BR Oasis with Optional Parking, Patio, Gym for up to 6 guests Near Museum Campus, Grant Park & Soldier Field
- Hyatt Regency McCormick Place Chicago
How many treehouses are available in Oakland?
Treehouse Rentals, as of 2026, features over 1093 unique treehouse, cabins and forest homes in Oakland. Choose from treetop hideaways, eco-friendly lodges, and off-grid properties, with new options added frequently.
By 2026, Treehouse Rentals has curated over 1093 stunning properties in Oakland, sourced from trusted platforms. Plan your nature-inspired getaway now.
For 2026, Treehouse Rentals provides access to over 1093 premier accommodations in Oakland. Find your ideal escape among the treetops today.
Nearby Neighborhood (2)
| Neighborhood | Property Count |
|---|---|
| Bronzeville Vacation Rentals in Chicago, Illinois | 65 |
| North Kenwood Vacation Rentals in Chicago, Illinois | 760 |
People Also Ask
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