1323+ Private Villas and Holiday Rentals in Lincoln Square |
Lincoln Square Holiday Rentals
Apartment
- Chicago
- ·
- Wrigleyville
- 0.23 mi to center
5 Bedrooms
2 Baths
12 Guests
23681 ft²
Fireplace/Heating
Balcony/Terrace
Pet Friendly
Kitchen
US $1,136/Night
7 Nights - US $7,953
Apartment
- Chicago
- ·
- Lake View East
- 0.30 mi to center
10.0Exceptional
(14 Reviews)
1 Bedroom
1 Bath
2 Guests
699.65 ft²
Internet
Child Friendly
US $256/Night
7 Nights - US $1,792
House
10.0Exceptional
(25 Reviews)
1 Bedroom
1 Bath
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
Parking
US $531/Night
7 Nights - US $3,717
Apartment
- Chicago
- ·
- Roscoe Village
- 0.31 mi to center
4 Bedrooms
2 Baths
8 Guests
- Fireplace/Heating
- Kitchen
- Parking
Air Conditioner
US $1,003/Night
7 Nights - US $7,023
Apartment
10.0Exceptional
(12 Reviews)
1 Bedroom
1 Bath
4 Guests
452.08 ft²
Private Pool
Oceanfront- Fireplace/Heating
Pool
US $117/Night
7 Nights - US $819
Apartment
- Chicago
- ·
- Wrigleyville
- 0.09 mi to center
2 Bedrooms
2 Baths
8 Guests
- Fireplace/Heating
- Pet Friendly
- Air Conditioner
- Internet
US $627/Night
7 Nights - US $4,390
Apartment
2 Bedrooms
1 Bath
5 Guests
849 ft²
- Fireplace/Heating
- Kitchen
- Parking
- Internet
US $487/Night
7 Nights - US $3,406
Apartment
2 Bedrooms
1 Bath
4 Guests
754 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $442/Night
7 Nights - US $3,093
Apartment
- Chicago
- ·
- Ravenswood
- 0.23 mi to center
1 Bedroom
1 Bath
3 Guests
- Fireplace/Heating
- Kitchen
- Parking
- Air Conditioner
US $257/Night
7 Nights - US $1,799
Luxury Holiday Rentals in Lincoln Square
Over 1314+ Luxury Holiday Rentals in or Near Lincoln Square
House
4 Bedrooms
2 Baths
10 Guests
2497.23 ft²
- Parking
- Internet
- Child Friendly
Security/Safety
US $3,786/Night
7 Nights - US $26,500
Apartment
- Chicago
- ·
- West Ridge
- 0.23 mi to center
3 Bedrooms
2 Baths
1 Guest
Hot Tub- Fireplace/Heating
- Pet Friendly
- Kitchen
US $3,482/Night
7 Nights - US $24,371
House
- Chicago
- ·
- North Center
- 0.50 mi to center
10.0Exceptional
(1 Review)
4 Bedrooms
3 Baths
10 Guests
5000 ft²
- Fireplace/Heating
Ocean View- Balcony/Terrace
View
US $3,157/Night
7 Nights - US $22,097
Apartment
4 Bedrooms
2 Baths
10 Guests
- Fireplace/Heating
- Air Conditioner
- Internet
- Child Friendly
US $2,457/Night
7 Nights - US $17,200
House
10.0Exceptional
(57 Reviews)
6 Bedrooms
5 Baths
17 Guests
5000 ft²
- Oceanfront
- Hot Tub
Spa- Fireplace/Heating
US $2,172/Night
7 Nights - US $15,205
House
- Chicago
- ·
- Wrigleyville
- 0.22 mi to center
7.4Very Good
(3 Reviews)
9 Bedrooms
4 Baths
20 Guests
30139 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $2,150/Night
7 Nights - US $15,051
Apartment
- Chicago
- ·
- Wrigleyville
- 0.27 mi to center
10.0Exceptional
(1 Review)
9 Bedrooms
5 Baths
16 Guests
- Fireplace/Heating
- Kitchen
- Air Conditioner
- Internet
US $1,923/Night
7 Nights - US $13,459
Apartment
10.0Exceptional
(2 Reviews)
4 Bedrooms
2 Baths
10 Guests
26910 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $1,882/Night
7 Nights - US $13,176
Apartment
- Chicago
- ·
- Wrigleyville
- 0.20 mi to center
10.0Exceptional
(2 Reviews)
5 Bedrooms
3 Baths
10 Guests
2497.23 ft²
- Parking
- Air Conditioner
- Internet
- Child Friendly
US $1,867/Night
7 Nights - US $13,067
Top-Rated Holiday Rentals with a Pool in Lincoln Square
Over 38+ The Best Private Villas and Holiday Rentals in Lincoln Square with a Pool
Apartment
10.0Exceptional
(14 Reviews)
1 Bedroom
1 Bath
3 Guests
450 ft²
- Fireplace/Heating
- Pool
- Balcony/Terrace
- Kitchen
US $547/Night
7 Nights - US $3,826
Bed & Breakfast
- Chicago
- ·
- Roscoe Village
- 0.04 mi to center
9.8Exceptional
(100 Reviews)
1 Bedroom
1 Bath
2 Guests
650 ft²
- Fireplace/Heating
- Pool
- Balcony/Terrace
- Kitchen
US $418/Night
7 Nights - US $2,924
Bed & Breakfast
- Chicago
- ·
- Magnolia Glen
- 0.05 mi to center
9.2Exceptional
(497 Reviews)
1 Bedroom
1 Bath
- Fireplace/Heating
- Pool
- Balcony/Terrace
Breakfast
US $210/Night
7 Nights - US $1,467
Apartment
1 Bedroom
1 Bath
2 Guests
620 ft²
- Fireplace/Heating
- Pool
- Pet Friendly
- Kitchen
US $345/Night
7 Nights - US $2,415
Apartment
1 Bedroom
1 Bath
2 Guests
620 ft²
- Fireplace/Heating
- Pool
- Pet Friendly
- Kitchen
US $271/Night
7 Nights - US $1,897
Apartment
1 Bedroom
1 Bath
2 Guests
624.31 ft²
- Pool
- Pet Friendly
- Air Conditioner
- Internet
US $242/Night
7 Nights - US $1,694
Apartment
10.0Exceptional
(19 Reviews)
1 Bedroom
1 Bath
4 Guests
- Fireplace/Heating
- Pool
- Ocean View
- Balcony/Terrace
US $208/Night
7 Nights - US $1,453
House
- Chicago
- ·
- West Ridge
- 0.80 mi to center
10.0Exceptional
(2 Reviews)
3 Bedrooms
2 Baths
6 Guests
- Private Pool
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $350/Night
7 Nights - US $2,450
House
9.6Exceptional
(40 Reviews)
3 Bedrooms
1 Bath
4 Guests
1250 ft²
- Hot Tub
- Spa
- Fireplace/Heating
- Pool
US $396/Night
7 Nights - US $2,771
Pet-Friendly Holiday Rentals in Lincoln Square
Over 528+ Pet-Friendly Holiday Rentals in or Near Lincoln Square
Apartment
- Chicago
- ·
- Rogers Park
- 0.38 mi to center
1 Bedroom
1 Bath
5 Guests
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
- View
US $255/Night
7 Nights - US $1,785
Apartment
10.0Exceptional
(8 Reviews)
2 Bedrooms
1 Bath
4 Guests
914.93 ft²
- Fireplace/Heating
- Pet Friendly
- Air Conditioner
- Internet
US $618/Night
7 Nights - US $4,329
Bed & Breakfast
7.8Very Good
(641 Reviews)
1 Bedroom
1 Bath
- Pet Friendly
- Parking
- Internet
- Security/Safety
US $154/Night
7 Nights - US $1,075
New
Apartment
- Chicago
- ·
- West Ridge
- 0.73 mi to center
3 Bedrooms
2 Baths
8 Guests
- Fireplace/Heating
- Pet Friendly
- Air Conditioner
- Internet
US $205/Night
7 Nights - US $1,434
Apartment
- Chicago
- ·
- Wrigleyville
- 0.09 mi to center
10.0Exceptional
(2 Reviews)
2 Bedrooms
1 Bath
4 Guests
1194.79 ft²
- Pet Friendly
- Internet
- Child Friendly
- Security/Safety
US $500/Night
7 Nights - US $3,500
Apartment
10.0Exceptional
(169 Reviews)
2 Bedrooms
1 Bath
6 Guests
1000 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $360/Night
7 Nights - US $2,519
Apartment
- Chicago
- ·
- Roscoe Village
- 0.17 mi to center
10.0Exceptional
(97 Reviews)
2 Bedrooms
1 Bath
6 Guests
1200 ft²
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
- View
US $318/Night
7 Nights - US $2,225
Apartment
10.0Exceptional
(76 Reviews)
2 Bedrooms
1 Bath
4 Guests
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $248/Night
7 Nights - US $1,737
Apartment
10.0Exceptional
(65 Reviews)
2 Bedrooms
2 Baths
4 Guests
1500 ft²
- Fireplace/Heating
- Pet Friendly
- Kitchen
- Parking
US $500/Night
7 Nights - US $3,501
Large Holiday Rentals and Private Villas in Lincoln Square
Over 145+ Large Holiday Rentals and Private Villas in or Near Lincoln Square
Apartment
9.6Exceptional
(4 Reviews)
1 Bedroom
1 Bath
12 Guests
1001 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $452/Night
7 Nights - US $3,163
House
- Chicago
- ·
- West Bucktown
- 0.54 mi to center
10.0Exceptional
(1 Review)
5 Bedrooms
3 Baths
12 Guests
- Balcony/Terrace
- Breakfast
- Pet Friendly
- Kitchen
US $850/Night
7 Nights - US $5,950
Apartment
9.2Exceptional
(5 Reviews)
2 Bedrooms
1 Bath
10 Guests
969 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $341/Night
7 Nights - US $2,385
Apartment
- Chicago
- ·
- Irving Park
- 0.24 mi to center
9.7Exceptional
(104 Reviews)
6 Bedrooms
6 Baths
12 Guests
453.88 ft²
- Fireplace/Heating
- Parking
- Air Conditioner
- Internet
US $206/Night
7 Nights - US $1,441
Condo
10.0Exceptional
(117 Reviews)
3 Bedrooms
3 Baths
10 Guests
2200 ft²
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $587/Night
7 Nights - US $4,111
Apartment
10.0Exceptional
(106 Reviews)
4 Bedrooms
3 Baths
16 Guests
2300 ft²
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $1,200/Night
7 Nights - US $8,403
House
10.0Exceptional
(93 Reviews)
3 Bedrooms
3 Baths
20 Guests
2000 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $853/Night
7 Nights - US $5,968
Apartment
- Chicago
- ·
- Wrigleyville
- 0.15 mi to center
10.0Exceptional
(64 Reviews)
5 Bedrooms
2 Baths
11 Guests
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $922/Night
7 Nights - US $6,456
House
10.0Exceptional
(59 Reviews)
4 Bedrooms
2 Baths
10 Guests
4000 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $1,679/Night
7 Nights - US $11,754
Wheelchair Accessible Holiday Homes in Lincoln Square
Over 132+ Wheelchair Accessible Holiday Homes in or Near Lincoln Square
Apartment
10.0Exceptional
(53 Reviews)
1 Bedroom
1 Bath
2 Guests
441 ft²
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $287/Night
7 Nights - US $2,009
Apartment
8.5Fabulous
(10 Reviews)
1 Bedroom
1 Bath
4 Guests
904.17 ft²
- Air Conditioner
- Internet
- Child Friendly
Wheelchair Accessible
US $125/Night
7 Nights - US $875
Hotel
- Chicago
- ·
- Ravenswood
- 0.75 mi to center
9.8Exceptional
(397 Reviews)
1 Bath
- Balcony/Terrace
- Pet Friendly
- Kitchen
- Parking
US $341/Night
7 Nights - US $2,384
Apartment
- Chicago
- ·
- Edgewater Beach
- 0.35 mi to center
10.0Exceptional
(1 Review)
2 Bedrooms
2 Baths
4 Guests
1000 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $520/Night
7 Nights - US $3,639
Apartment
- Chicago
- ·
- Ravenswood
- 0.45 mi to center
8.2Excellent
(6 Reviews)
1 Bedroom
1 Bath
2 Guests
602.78 ft²
- Air Conditioner
- Internet
- Wheelchair Accessible
US $57/Night
7 Nights - US $399
Apartment
9.0Exceptional
(20 Reviews)
1 Bedroom
1 Bath
2 Guests
441 ft²
- Oceanfront
- Fireplace/Heating
- Ocean View
- View
US $287/Night
7 Nights - US $2,009
Apartment
8.6Fabulous
(17 Reviews)
1 Bedroom
1 Bath
2 Guests
441 ft²
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $347/Night
7 Nights - US $2,427
Apartment
8.4Excellent
(10 Reviews)
1 Bedroom
1 Bath
2 Guests
4844 ft²
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $213/Night
7 Nights - US $1,493
Apartment
- Chicago
- ·
- Edgewater Beach
- 0.35 mi to center
2 Bedrooms
2 Baths
4 Guests
1000 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $567/Night
7 Nights - US $3,968
Lincoln Square Private Villas and Holiday Homes Under $200
Over 430+ Lincoln Square Private Villas and Holiday Homes Under $200
Condo
- Chicago
- ·
- West Ridge
- 0.42 mi to center
3 Bedrooms
1 Bath
8 Guests
- Fireplace/Heating
- Air Conditioner
- Internet
- Child Friendly
US $115/Night
7 Nights - US $803
Apartment
- Chicago
- ·
- Roscoe Village
- 0.04 mi to center
10.0Exceptional
(2 Reviews)
3 Bedrooms
1 Bath
6 Guests
1399.31 ft²
- Breakfast
- Parking
- Air Conditioner
- Internet
US $195/Night
7 Nights - US $1,367
New
Apartment
- Chicago
- ·
- North Park
- 0.58 mi to center
1 Bedroom
1 Bath
2 Guests
- Fireplace/Heating
- Air Conditioner
- Internet
Laundry
US $100/Night
7 Nights - US $700
Apartment
10.0Exceptional
(1 Review)
1 Bedroom
1 Bath
2 Guests
1248.61 ft²
- Fireplace/Heating
- Balcony/Terrace
- View
- Pet Friendly
US $95/Night
7 Nights - US $668
Apartment
10.0Exceptional
(57 Reviews)
1 Bedroom
1 Bath
3 Guests
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $193/Night
7 Nights - US $1,348
Apartment
- Chicago
- ·
- Rogers Park
- 0.41 mi to center
10.0Exceptional
(54 Reviews)
1 Bedroom
1 Bath
6 Guests
750 ft²
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $200/Night
7 Nights - US $1,399
Apartment
- Chicago
- ·
- Edgewater Beach
- 0.16 mi to center
10.0Exceptional
(42 Reviews)
1 Bedroom
1 Bath
3 Guests
- Fireplace/Heating
- Kitchen
- Parking
- Air Conditioner
US $193/Night
7 Nights - US $1,348
House
10.0Exceptional
(38 Reviews)
2 Bedrooms
1 Bath
6 Guests
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $181/Night
7 Nights - US $1,265
Instantly Bookable Holiday Homes in Lincoln Square
Over 697+ Instantly Bookable Holiday Homes in or Near Lincoln Square
Hotel
2 Baths
- Fireplace/Heating
- Kitchen
- Air Conditioner
- Internet
US $441/Night
7 Nights - US $3,090
Apartment
- Chicago
- ·
- West Ridge
- 0.57 mi to center
10.0Exceptional
(6 Reviews)
1 Bedroom
1 Bath
5 Guests
- Oceanfront
- Fireplace/Heating
- Ocean View
- View
US $190/Night
7 Nights - US $1,330
Hotel
1 Bath
- Fireplace/Heating
- Kitchen
- Air Conditioner
- Internet
US $394/Night
7 Nights - US $2,758
Apartment
- Chicago
- ·
- Roscoe Village
- 0.19 mi to center
10.0Exceptional
(203 Reviews)
2 Bedrooms
1 Bath
4 Guests
900 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $288/Night
7 Nights - US $2,019
Apartment
- Chicago
- ·
- North Center
- 0.68 mi to center
10.0Exceptional
(134 Reviews)
2 Bedrooms
1 Bath
6 Guests
1000 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $249/Night
7 Nights - US $1,740
Apartment
- Chicago
- ·
- Magnolia Glen
- 0.09 mi to center
10.0Exceptional
(113 Reviews)
2 Bedrooms
2 Baths
5 Guests
1650 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $606/Night
7 Nights - US $4,240
Apartment
- Chicago
- ·
- Andersonville
- 0.33 mi to center
10.0Exceptional
(74 Reviews)
2 Bedrooms
1 Bath
4 Guests
1000 ft²
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $230/Night
7 Nights - US $1,612
Apartment
- Chicago
- ·
- Rogers Park
- 0.64 mi to center
10.0Exceptional
(57 Reviews)
2 Bedrooms
2 Baths
5 Guests
1100 ft²
- Hot Tub
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $370/Night
7 Nights - US $2,591
Condo
10.0Exceptional
(53 Reviews)
2 Bedrooms
2 Baths
5 Guests
1200 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $463/Night
7 Nights - US $3,243
Book a Last Minute Place to Stay in Lincoln Square
About Casai's Private Villas and Holiday Rentals in Lincoln Square
Discover more than 1323 vacation rentals available in Lincoln Square. 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 Lincoln Square.
Seeking last-minute deals or the best available offers for cottages, condos, private villas, and spacious vacation homes? With Casai in Lincoln Square, 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 Lincoln Square. On average, places to stay near Lincoln Square offer 776.95 ft², with nightly prices averaging US $433.
With Casai, finding and comparing holiday rentals in Lincoln Square 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 Lincoln Square
| Type | Count |
|---|---|
| Holiday Apartments | 968 |
| Vacation Homes | 181 |
| Villas | 1 |
Use these Quick Filters to Find a Holiday Rental in Lincoln Square
★ 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 Lincoln Square.
Weather in Lincoln Square, IL
View the weather forecast for Lincoln Square before booking your Lincoln Square 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 Lincoln Square?
What are the top holiday rentals in Lincoln Square?
With numerous options available in Lincoln Square, planning to stay in the area? Consider booking a few nights at one of these properties, rated as the Top Holiday Rentals in Lincoln Square:
- Luxury Loyola 3 Bedroom, 2 Bath, Near Subway and Beach
- Great Location-Beautiful Friendly Andersonville Neighborhood
- Roscoe Village Inn -Guesthouse - Walk to Chicago's Wrigley Field
- Single Family Home! Sleeps 8 Lincoln Park/Lakeview
- Lakeview/LincolnPark 2BR/1BA Updated Vintage Apartment in walkable neighborhood
- North Center - Modern, Safe, Family-Friendly, Solar-Powered Apartment
- Wrigleyville Condo, Sleeps 10, 1/2 block from Wrigley Field
- The entire FLAT. Stay Like You Own! Central AIR. TWO FULL BATHROOMS. Unique.
- Dramatic Wrigley Loft +PRIVATE Rooftop, Center of Wrigley, Ranked GUEST FAVORITE
- Roscoe Village- Only steps to cute shops & dining! Sleeps 4-6
Which holiday homes in Lincoln Square are best for families?
If you're searching for a family-friendly holiday home in Lincoln Square, consider one of the following properties. Each comes highly recommended, with excellent reviews for families or groups staying in Lincoln Square:
- Best Lincoln Square Location - Spacious 2 bedroom
- Modern 3BR Apt in Boystown, 12-min walk to Wrigley - Stratford 1S
- Hotel Zachary Chicago, a Tribute Portfolio Hotel
How many Casai.com holiday rentals are available in Lincoln Square?
As of 2026, Casai boasts over 1323 properties listed in the Lincoln Square area, with more being added continually. By consolidating listings from various websites, Casai provides an extensive selection of the finest Casai properties in Lincoln Square.
People Also Ask
Finding the best prices in Lincoln Square
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