Galewood Holiday Rentals
Apartment
10.0Exceptional
(43 Reviews)
2 Bedrooms
1 Bath
4 Guests
Parking
Balcony/Terrace
Kitchen
Air Conditioner
US $276/Night
7 Nights - US $1,934
Apartment
- Chicago
- ·
- Belmont Cragin
- 0.48 mi to center
10.0Exceptional
(5 Reviews)
3 Bedrooms
2 Baths
5 Guests
1345.49 ft²
- Parking
- Balcony/Terrace
- Air Conditioner
Internet
US $284/Night
7 Nights - US $1,991
Apartment
10.0Exceptional
(5 Reviews)
1 Bedroom
1 Bath
- Internet
Child Friendly
Security/Safety
Business Services
US $357/Night
7 Nights - US $2,497
Apartment
- Chicago
- ·
- Forest Park
- 0.93 mi to center
10.0Exceptional
(36 Reviews)
2 Bedrooms
1 Bath
4 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
US $218/Night
7 Nights - US $1,523
Apartment
- Chicago
- ·
- Belmont Cragin
- 1.14 mi to center
10.0Exceptional
(2 Reviews)
2 Bedrooms
1 Bath
4 Guests
904.17 ft²
Oceanfront- Parking
Ocean View
View
US $290/Night
7 Nights - US $2,028
Apartment
- Chicago
- ·
- Forest Park
- 1.03 mi to center
10.0Exceptional
(20 Reviews)
2 Bedrooms
1 Bath
6 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
US $216/Night
7 Nights - US $1,510
Apartment
- Chicago
- ·
- Belmont Cragin
- 1.14 mi to center
10.0Exceptional
(12 Reviews)
2 Bedrooms
1 Bath
4 Guests
900 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $301/Night
7 Nights - US $2,108
Apartment
10.0Exceptional
(11 Reviews)
2 Bedrooms
1 Bath
4 Guests
904 ft²
- Balcony/Terrace
- Kitchen
- Air Conditioner
- Internet
US $414/Night
7 Nights - US $2,901
Apartment
10.0Exceptional
(9 Reviews)
2 Bedrooms
1 Bath
4 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $282/Night
7 Nights - US $1,972
Luxury Holiday Rentals in Galewood
Over 437+ Luxury Holiday Rentals in or Near Galewood
Apartment
10.0Exceptional
(11 Reviews)
5 Bedrooms
2 Baths
6 Guests
1800 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $4,597/Night
7 Nights - US $32,180
Apartment
- Chicago
- ·
- Elmwood Park
- 0.29 mi to center
2 Bedrooms
1 Bath
6 Guests
- Parking
- Air Conditioner
- Internet
Pet Friendly
US $3,000/Night
7 Nights - US $21,000
Apartment
10.0Exceptional
(1 Review)
2 Bedrooms
1 Bath
6 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
US $2,837/Night
7 Nights - US $19,861
House
- Chicago
- ·
- South Austin
- 0.66 mi to center
7 Bedrooms
3 Baths
18 Guests
538.2 ft²
- Balcony/Terrace
- View
- Air Conditioner
- Internet
US $2,082/Night
7 Nights - US $14,573
House
10.0Exceptional
(1 Review)
6 Bedrooms
3 Baths
16 Guests
- Air Conditioner
- Internet
- Child Friendly
Laundry
US $1,412/Night
7 Nights - US $9,885
House
5 Bedrooms
3 Baths
16 Guests
2195.84 ft²
- Parking
- Balcony/Terrace
- Air Conditioner
- Internet
US $1,278/Night
7 Nights - US $8,947
New
House
10.0Exceptional
(11 Reviews)
4 Bedrooms
5 Baths
9 Guests
5000 ft²
Hot Tub- Parking
- Balcony/Terrace
- Kitchen
US $1,118/Night
7 Nights - US $7,825
House
10.0Exceptional
(5 Reviews)
8 Bedrooms
3 Baths
18 Guests
- Kitchen
- Air Conditioner
- Internet
- Pet Friendly
US $1,017/Night
7 Nights - US $7,118
House
9.0Exceptional
(4 Reviews)
8 Bedrooms
3 Baths
10 Guests
3200 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $957/Night
7 Nights - US $6,701
Top-Rated Holiday Rentals with a Pool in Galewood
Over 7+ The Best Private Villas and Holiday Rentals in Galewood with a Pool
Hotel
- Chicago
- ·
- Belmont Cragin
- 0.15 mi to center
9.0Exceptional
(2 Reviews)
1 Bath
567 ft²
- Parking
Pool- Kitchen
- Air Conditioner
US $376/Night
7 Nights - US $2,635
Hotel
1 Bath
- Parking
- Pool
- Kitchen
- Air Conditioner
US $410/Night
7 Nights - US $2,869
House
- Chicago
- ·
- Forest Park
- 0.87 mi to center
9.8Exceptional
(16 Reviews)
2 Bedrooms
1 Bath
5 Guests
- Parking
- Pool
- Kitchen
- Air Conditioner
US $191/Night
7 Nights - US $1,335
House
4.0Average
(2 Reviews)
2 Bedrooms
2 Baths
10 Guests
- Pool
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $349/Night
7 Nights - US $2,443
Apartment
2 Bedrooms
1 Bath
4 Guests
1700 ft²
- Hot Tub
- Parking
- Pool
- Ocean View
US $327/Night
7 Nights - US $2,292
Apartment
1 Bedroom
1 Bath
3 Guests
700 ft²
- Parking
- Pool
Spa- Ocean View
US $150/Night
7 Nights - US $1,048
Apartment
- Chicago
- ·
- Forest Park
- 1.26 mi to center
1 Bedroom
1 Bath
3 Guests
- Pool
- Kitchen
- Air Conditioner
- Internet
US $83/Night
7 Nights - US $581
Pet-Friendly Holiday Rentals in Galewood
Over 176+ Pet-Friendly Holiday Rentals in or Near Galewood
Apartment
- Chicago
- ·
- Belmont Cragin
- 0.18 mi to center
10.0Exceptional
(2 Reviews)
2 Bedrooms
1 Bath
5 Guests
- Balcony/Terrace
- Kitchen
- Air Conditioner
- Internet
US $369/Night
7 Nights - US $2,586
Apartment
- Chicago
- ·
- Belmont Cragin
- 0.18 mi to center
9.3Exceptional
(3 Reviews)
1 Bedroom
1 Bath
5 Guests
10763.91 ft²
- Parking
- View
- Air Conditioner
- Internet
US $283/Night
7 Nights - US $1,978
Cottage
- Chicago
- ·
- Forest Park
- 1.04 mi to center
1 Bedroom
1 Bath
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $475/Night
7 Nights - US $3,324
Condo
- Chicago
- ·
- Elmwood Park
- 0.29 mi to center
10.0Exceptional
(1 Review)
2 Bedrooms
1 Bath
13 Guests
- Kitchen
- Air Conditioner
- Internet
- Pet Friendly
US $134/Night
7 Nights - US $935
Apartment
9.3Exceptional
(3 Reviews)
3 Bedrooms
2 Baths
8 Guests
107.64 ft²
- Hot Tub
- Parking
- Air Conditioner
- Internet
US $216/Night
7 Nights - US $1,510
House
9.8Exceptional
(29 Reviews)
2 Bedrooms
1 Bath
4 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
US $251/Night
7 Nights - US $1,756
Apartment
9.6Exceptional
(34 Reviews)
2 Bedrooms
1 Bath
6 Guests
900 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $282/Night
7 Nights - US $1,975
Apartment
- Chicago
- ·
- Forest Park
- 0.95 mi to center
9.6Exceptional
(14 Reviews)
2 Bedrooms
1 Bath
5 Guests
1000 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $221/Night
7 Nights - US $1,548
House
9.6Exceptional
(8 Reviews)
1 Bedroom
1 Bath
4 Guests
850 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $214/Night
7 Nights - US $1,495
Large Holiday Rentals and Private Villas in Galewood
Over 66+ Large Holiday Rentals and Private Villas in or Near Galewood
House
8.8Fabulous
(13 Reviews)
7 Bedrooms
4 Baths
14 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $614/Night
7 Nights - US $4,296
Bed & Breakfast
9.8Exceptional
(39 Reviews)
5 Bedrooms
5 Baths
10 Guests
374.05 ft²
Breakfast- Parking
- Balcony/Terrace
- Air Conditioner
US $307/Night
7 Nights - US $2,147
US $857/Night
7 Nights - US $6,001
Apartment
10.0Exceptional
(136 Reviews)
3 Bedrooms
1 Bath
10 Guests
1000 ft²
- Breakfast
- Parking
- Balcony/Terrace
- Kitchen
US $181/Night
7 Nights - US $1,265
Apartment
9.8Exceptional
(8 Reviews)
4 Bedrooms
1 Bath
10 Guests
1797.57 ft²
- Parking
- Air Conditioner
- Internet
- Laundry
US $204/Night
7 Nights - US $1,425
House
10.0Exceptional
(9 Reviews)
5 Bedrooms
4 Baths
14 Guests
3000 ft²
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
US $846/Night
7 Nights - US $5,921
House
10.0Exceptional
(7 Reviews)
6 Bedrooms
3 Baths
16 Guests
3000 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $784/Night
7 Nights - US $5,488
House
- Chicago
- ·
- Forest Park
- 0.66 mi to center
10.0Exceptional
(7 Reviews)
5 Bedrooms
3 Baths
16 Guests
- Balcony/Terrace
- Kitchen
- Air Conditioner
- Internet
US $748/Night
7 Nights - US $5,238
Apartment
10.0Exceptional
(5 Reviews)
4 Bedrooms
1 Bath
10 Guests
1798 ft²
- Parking
- Kitchen
- Air Conditioner
- Internet
US $403/Night
7 Nights - US $2,821
Wheelchair Accessible Holiday Homes in Galewood
Over 16+ Wheelchair Accessible Holiday Homes in or Near Galewood
Apartment
10.0Exceptional
(1 Review)
2 Bedrooms
2 Baths
4 Guests
1000 ft²
- Balcony/Terrace
- Kitchen
- Air Conditioner
- Internet
US $546/Night
7 Nights - US $3,823
Hotel
6.4Good
(32 Reviews)
8 Baths
355.21 ft²
- Breakfast
- Parking
- Kitchen
- Air Conditioner
US $152/Night
7 Nights - US $1,066
Hotel
9.2Exceptional
(1143 Reviews)
1 Bath
- Parking
- Kitchen
- Air Conditioner
- Internet
US $121/Night
7 Nights - US $847
Apartment
8.0Excellent
(2 Reviews)
2 Bedrooms
2 Baths
4 Guests
1000 ft²
- Balcony/Terrace
- Kitchen
- Air Conditioner
- Internet
US $233/Night
7 Nights - US $1,630
Apartment
2 Bedrooms
2 Baths
4 Guests
1000 ft²
- Balcony/Terrace
- Kitchen
- Air Conditioner
- Internet
US $588/Night
7 Nights - US $4,119
House
8.6Fabulous
(14 Reviews)
2 Bedrooms
1 Bath
5 Guests
9580 ft²
- Balcony/Terrace
- Kitchen
- Air Conditioner
- Internet
US $388/Night
7 Nights - US $2,719
Apartment
10.0Exceptional
(1 Review)
2 Bedrooms
2 Baths
4 Guests
963 ft²
- Kitchen
- Air Conditioner
- Pet Friendly
- Child Friendly
US $85/Night
7 Nights - US $595
Apartment
2 Bedrooms
2 Baths
4 Guests
955 ft²
- Parking
- Kitchen
- Air Conditioner
- Pet Friendly
US $152/Night
7 Nights - US $1,061
Apartment
1 Bedroom
1 Bath
2 Guests
780 ft²
- Parking
- Kitchen
- Air Conditioner
- Internet
US $138/Night
7 Nights - US $966
Galewood Private Villas and Holiday Homes Under $200
Over 163+ Galewood Private Villas and Holiday Homes Under $200
Apartment
10.0Exceptional
(3 Reviews)
1 Bedroom
1 Bath
2 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
US $145/Night
7 Nights - US $1,015
Apartment
9.8Exceptional
(4 Reviews)
2 Bedrooms
1 Bath
4 Guests
699.65 ft²
- Parking
- Air Conditioner
- Internet
- Child Friendly
US $132/Night
7 Nights - US $921
New
Apartment
10.0Exceptional
(2 Reviews)
2 Bedrooms
1 Bath
6 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $195/Night
7 Nights - US $1,365
Apartment
9.2Exceptional
(6 Reviews)
3 Bedrooms
1 Bath
6 Guests
236.81 ft²
- Parking
- Balcony/Terrace
- Air Conditioner
- Internet
US $162/Night
7 Nights - US $1,137
Apartment
10.0Exceptional
(2 Reviews)
1 Bedroom
1 Bath
4 Guests
1000 ft²
- Balcony/Terrace
- Kitchen
- Air Conditioner
- Internet
US $189/Night
7 Nights - US $1,325
Apartment
10.0Exceptional
(2 Reviews)
1 Bedroom
1 Bath
2 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
US $178/Night
7 Nights - US $1,249
Apartment
- Chicago
- ·
- Forest Park
- 0.59 mi to center
10.0Exceptional
(1 Review)
2 Bedrooms
1 Bath
4 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $197/Night
7 Nights - US $1,378
Apartment
9.8Exceptional
(77 Reviews)
1 Bedroom
1 Bath
3 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $181/Night
7 Nights - US $1,266
House
9.8Exceptional
(36 Reviews)
2 Bedrooms
1 Bath
4 Guests
- Breakfast
- Parking
- Balcony/Terrace
- Kitchen
US $142/Night
7 Nights - US $992
Instantly Bookable Holiday Homes in Galewood
Over 236+ Instantly Bookable Holiday Homes in or Near Galewood
Condo
- Chicago
- ·
- Forest Park
- 1.12 mi to center
10.0Exceptional
(8 Reviews)
2 Bedrooms
1 Bath
4 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
US $249/Night
7 Nights - US $1,741
Apartment
1 Bedroom
1 Bath
2 Guests
- Air Conditioner
- Internet
- Laundry
- Security/Safety
US $230/Night
7 Nights - US $1,611
House
10.0Exceptional
(3 Reviews)
2 Bedrooms
1 Bath
4 Guests
1200 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $328/Night
7 Nights - US $2,296
Apartment
10.0Exceptional
(2 Reviews)
1 Bedroom
1 Bath
2 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
US $327/Night
7 Nights - US $2,288
Apartment
10.0Exceptional
(1 Review)
2 Bedrooms
1 Bath
6 Guests
13993 ft²
- Parking
- Kitchen
- Air Conditioner
- Internet
US $391/Night
7 Nights - US $2,734
House
9.8Exceptional
(16 Reviews)
2 Bedrooms
1 Bath
6 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $173/Night
7 Nights - US $1,214
Apartment
9.6Exceptional
(110 Reviews)
2 Bedrooms
2 Baths
6 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
US $307/Night
7 Nights - US $2,149
Apartment
- Chicago
- ·
- North Austin
- 0.54 mi to center
9.6Exceptional
(9 Reviews)
2 Bedrooms
1 Bath
4 Guests
- Kitchen
- Air Conditioner
- Internet
- Child Friendly
US $221/Night
7 Nights - US $1,546
Apartment
- Chicago
- ·
- Forest Park
- 1.14 mi to center
9.6Exceptional
(4 Reviews)
2 Bedrooms
1 Bath
6 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
US $257/Night
7 Nights - US $1,800
Book a Last Minute Place to Stay in Galewood
About Casai's Private Villas and Holiday Rentals in Galewood
Discover more than 446 vacation rentals available in Galewood. These rentals, ranging from vacation rentals to Casai Homes and other short-term private accommodations, offer top-notch amenities with unbeatable value, ensuring both comfort and luxury. Enjoy more space and value when you stay at a Casai property in Galewood.
Seeking last-minute deals or the best available offers for cottages, condos, private villas, and spacious vacation homes? With Casai in Galewood, you can effortlessly compare various deals with just a click. Whether you're looking for a Casai with exceptional swimming pools, hot tubs, pet-friendly options, or large master suite bedrooms equipped with large screen televisions, you'll find a variety of options near Galewood. On average, places to stay near Galewood offer 932.79 ft², with nightly prices averaging US $321.
With Casai, finding and comparing holiday rentals in Galewood is easy and secure, often at a 30-40% discount compared to hotel prices. Simply search for your destination and secure your reservation today.
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Top Accommodation Types in Galewood
| Type | Count |
|---|---|
| Holiday Apartments | 269 |
| Vacation Homes | 139 |
| Cottages | 3 |
Use these Quick Filters to Find a Holiday Rental in Galewood
★ Pro Tip: Casai simplifies the process of comparing the finest listings across various online vacation rental platforms, including Booking.com and more. Utilize the Advanced Filter feature located at the top to effortlessly switch between Casai homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals, eco-friendly properties, and different property types. Explore various cancellation policies, prices, and numerous options to find the ideal accommodation for your next vacation in Galewood.
Weather in Galewood, IL
View the weather forecast for Galewood before booking your Galewood 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
Frequently Asked Questions About Galewood?
What are the top holiday rentals in Galewood?
With numerous options available in Galewood, planning to stay in the area? Consider booking a few nights at one of these properties, rated as the Top Holiday Rentals in Galewood:
- Updated Forest Park 3 BR Bungalow
- Cozy Comfy Clean 420 Compliant FREE Parking QUIET Neighborhood A GUEST FAVORITE!
- 8 MILES FROM DOWNTOWN CHICAGO!
- Clean and Comfy Updated Apt in Convenient Location
- Oak Park Victorian by FLW Studio
- Large, modern 2 bedroom in the heart of Forest Park
- Space&style New rehab, first flr + bsmt of duplex, driveway prkng, walk to train
- Tranquil Portage Park Stay
- 4-bedroom townhome in Frank Lloyd Wright District-FREE PARKING, Patio, Yard
- Spacious brand new condo - 15 min from downtown Chicago! Sleeps 6
Which holiday homes in Galewood are best for families?
If you're searching for a family-friendly holiday home in Galewood, consider one of the following properties. Each comes highly recommended, with excellent reviews for families or groups staying in Galewood:
- Stylish 2 Bedroom Aparment with Games and Free Parking
- Tree-Lined Serenity Condo in Forest Park, Near Train & Madison St
- Historic Oak Park Residence
How many Casai.com holiday rentals are available in Galewood?
As of 2026, Casai boasts over 446 properties listed in the Galewood area, with more being added continually. By consolidating listings from various websites, Casai provides an extensive selection of the finest Casai properties in Galewood.
Nearby Neighborhood (2)
| Neighborhood | Property Count |
|---|---|
| Austin Vacation Rentals in Chicago, Illinois | 554 |
| North Austin Vacation Rentals in Chicago, Illinois | 600 |
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