Grand Boulevard holiday homes
We found 98 holiday rentals — enter your dates for availability
Discover a selection of 12 homes, 19 apartments and other holiday rentals in Grand Boulevard that are perfect for your trip. Whether you're travelling with a group or just with your pet, holiday homes have the amenities that you expect for your stay, such as Wi-Fi and cable TV. You're sure to find a property to rent for everyone's needs, including places that are non-smoking or accessible.
Holiday rentals with weekly discounts - Grand Boulevard
Showing deals for:17 Oct - 24 Oct
Image gallery for Gorgeous N. Kenwood/Hyde Park

9.6 out of 10 rating
Exceptional
(5 reviews)
Gorgeous N. Kenwood/Hyde Park
Chicago, IL
7% off
Price is NZ$5,189
NZ$741 per night
includes taxes & fees
Image gallery for Luxury Hyde Park Haven- Perfect for families and digital nomads. Pet Friendly.

9.6 out of 10 rating
Exceptional
(8 reviews)
Luxury Hyde Park Haven- Perfect for families and digital nomads. Pet Friendly.
Chicago, IL
14% off
Price is NZ$6,992
NZ$999 per night
includes taxes & fees
Image gallery for Lux Home in Chicago 7mins Downtown

9.8 out of 10 rating
Exceptional
(21 reviews)
Lux Home in Chicago 7mins Downtown
Chicago, IL
7% off
Price is NZ$8,205
NZ$1,172 per night
includes taxes & fees
Image gallery for Spacious 4 Bedroom (5 queen beds) 2 Bath in the kenwood neighborhood

9.4 out of 10 rating
Exceptional
(41 reviews)
Spacious 4 Bedroom (5 queen beds) 2 Bath in the kenwood neighborhood
Chicago, IL
7% off
Price is NZ$4,722
NZ$675 per night
includes taxes & fees
Find spaces that suit your style
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Condo/Apartment
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Villa
Find the best place to stay - Grand Boulevard
Showing deals for: 13 Oct - 16 Oct
Just Minutes from Downtown Chicago
Sleeps 6 · 1 bedroom · 1+ bathroom
10 out of 10
exceptional
(1 review)
The current price is NZ$1,025
for 3 nights, 1 home
NZ$342 per night
includes taxes & fees

Just Minutes from Downtown Chicago
Sleeps 6 · 1 bedroom · 1+ bathroom
9.0 out of 10
wonderful
(2 reviews)
The current price is NZ$1,025
for 3 nights, 1 home
NZ$342 per night
includes taxes & fees

Bronzeville Manor walking distance to hospitals
Sleeps 4 · 1 bedroom · 1 bathroom
10 out of 10
exceptional
(15 reviews)
The current price is NZ$1,532
for 3 nights, 1 apartment
NZ$511 per night
includes taxes & fees

Renovated 6 Bedroom 5 Bathroom Home 10 Minutes from Downtown Chicago
Sleeps 15 · 6 bedrooms · 5 bathrooms
9.4 out of 10
exceptional
(12 reviews)
The current price is NZ$5,414
for 3 nights, 1 home
NZ$1,805 per night
includes taxes & fees
- Peace of mindOur Book with Confidence guarantee gives you 24/7 support
- More quality timeFrom booking to staying, the whole process is simple and enjoyable
- All the privacy of homeEnjoy full kitchens, laundry, pools, gardens and more
- More for lessMore space, more privacy, more amenities — more value