
Apartment holiday rentals in Waukegan
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Top-rated apartment rentals in Waukegan
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Whole Flat in Private Club. Walk to L, Dining & Shows
Find unrivaled amenities in the newly restored Lawrence House, a Deco gem lauded a “unique architectural treasure” by the Chicago Architecture Foundation. Bask in an over-sized double lounger on the roof-top deck with 360-degree skyline views. Detox in the state-of-the-art fitness center with boxing gym. Soak in the 50-foot mosaic-tiled pool. Come home to a sunny, open-layout flat, with a cozy private bedroom, spa-like bathroom, fully-equipped kitchen, and free washer/dryer. Work or play in the terrazzo-floored Grand Lobby with club seating, adjoining cafe, craft cocktail bar and restaurant. Newly restored, sunny and spacious, immaculate, hotel-styled one-bedroom apartment with all new fixtures and appliances. Cozy bedroom with comfortable queen bed, flat screen TV, and large closet. Living room with couch that pulls out to a full-sized bed, club chair, large flat screen TV, and drop-leaf table for working. Stocked kitchen with everything you need to cook full meals, a new Smeg fridge, granite counters, and bar-stool seating. A queen-sized Serta air mattress allows up to 5 people to sleep comfortably. Central heat and air conditioning. Free washer/dryer in unit. Just-restored Art Deco building, called a "unique architectural treasure" by the Chicago Architecture Foundation. Unrivaled, private-club styled amenities. State of the art fitness center. Mosaic-tiled 50-foot pool. Roof-top lounge and deck with 360-degree skyline views, and tons of over-sized double loungers. Garden patio with fire pit, grills and picnic tables. Grand Lobby with cafe and craft cocktail bar, club seating, striking stained-glass skylight, ornate plaster moldings and terrazzo floor. Privacy guaranteed. The entire apartment is yours. You may also use the building's gorgeous amenities: fitness center, pool, roof-top lounge and deck, and garden patio. We have a self check-in and check-out system to provide you the most flexibility. However, we are always available to answer any questions, address any concerns, and provide recommendations. In the heart of Chicago's premier live-music and entertainment district, steps from two major concert venues and a legendary jazz lounge. Walk to dozens of restaurants and bars. Two blocks to the Beach. One block to the Red Line 'L' train, which goes straight to Wrigley Field in 5 minutes, and the Loop in 20 minutes. To learn more about the area, check out the Chicago Sun-Times feature on Uptown by googling: “sun times uptown neighborhood” One block to Red Line 'L' station. Free street parking with permits provided. Pets may live in the building but there are no pets allowed in this unit. In the heart of Chicago's premier live-music and entertainment district, steps from two major concert venues and a legendary jazz lounge. Walk to dozens of restaurants and bars. Two blocks to the Beach. One block to the Red Line 'L' train [temporarily 3 blocks while my station is rebuilt], which goes straight to Wrigley Field in 5 minutes, and the Loop in 20 minutes. To learn more about the area, check out the Chicago Sun-Times feature on Uptown by googling: “sun times uptown neighborhood guide”

Modern Avondale Apt | Great Food & Free Parking
Clean & modern Avondale apt close to Blue Line, perfect for urban explorers! Stylish decor, comfy bed, and a cozy ambiance await. Explore nearby cafes, bars, and boutiques, or hop on the train for downtown adventures. Easy to access & great neighborhood. Easy permit parking (free passes provided) on street allows for the ability to drive or take public transportation wherever you want to explore. Avondale has been voted one of the best neighborhoods in Chicago! Come see what the fuss is about.

Walk to downtown McHenry. Heart of the Fox River
NO PETS Entire 2nd. floor. 1 block away from downtown, Fox River Riverwalk & Pokémon Gym. Full stocked kitchen, books, games, toys & extra amenities to make your stay beyond relaxing. 4:20 allowed in backyard & not in view of under the age of 21. Private smoking area in front too. Minutes away from 2 State Parks, 1 with free boat/kayak launch. Several marinas, boat rental, golf courses & huge variety of entertainment. Look at Bettye's Guidebook for more information & nearby entertainment.

Charming Riverfront Stay | Heart of Downtown
Welcome to The Riverfronts! Three boutique hotel rooms perfectly situated along the river in downtown West Dundee, offering scenic views and modern comforts. ✔ Riverfront Location: Enjoy the scenic riverwalk just steps away. ✔ Prime Downtown Spot: In the heart of downtown Dundee, minutes from top attractions and dining. ✔ Exclusive Group Booking: Reserve just one or all three units for your entire party. ✔ Outdoor Firepit: Unwind by the firepit, perfect for evening gatherings. ✔ Sleeps 4: Each

Downtown-Treetop Deck-2Bd/2Bth
Discover this one-of-a-kind, shabby-chic second-floor apartment in the heart of Downtown Kenosha — just steps from coffee shops, restaurants, museums, and the shores of Lake Michigan. Ideal for travelers who want everything within walking distance. Relax and unwind on the spacious, completely private back deck — your own hidden oasis tucked among treetops and historic neighborhood buildings. Perfect for stays up to four guests. Please note: This property is not suitable for young children.

Modern Garden apartment (WHOLE UNIT)
Freshly Remodeled , Lower Level garden apartment one bedroom one bath. Older building with wooden floors. If hearing people upstairs walking can bother you , do NOT book it please .Very Spacious with its open concept layout. Parking is right next to the main entrance of the building. 24/7 perimeter monitoring cameras. The Condo is very close to the Metra Train. It is !5 min away from O'Hare airport and 10min to outlets Absolutely NO parties, NO gathering Quiet hours 10 pm till 6.00 am

J’s Farmhouse Cottage. 2 bedroom duplex.
Formerly known as Magnolia Farmhouse inspired. 2 bedroom duplex. Experience the best of the midwest! Enjoy a newly remodeled, "Magnolia Farm" inspired 2-bedroom duplex, all to yourself near everything you need. 50 miles from Milwaukee, 45 miles from Chicago, and 2 miles from having your toes in the sand at Lake Michigan! We are minutes away from the Great Lakes Naval Station (9 mi) and the Cancer Treatment Center of America, Six Flags Great America, Gurnee Mills, and Great Wolf Lodge.

A Quiet Stay While You Are Away Oak Park
Welcome to our cozy and comfortable home located in a quiet neighborhood. Our space is perfect for couples, solo travelers, small families, and long-term stays. This is a beautiful, modernist home located in the Frank Lloyd Wright District Neighborhood, a designated historic district known for its collection of homes designed by the famous architect Frank Lloyd Wright. This district features a collection of some of his iconic designs and is a destination for architecture enthusiasts.

Cozy guest studio, great for couples!
This unique place has a style all its own. Enjoy this beautiful, cozy guest studio with modern touches and well furnished living area, small kitchenette with mini fridge and microwave to reheat a quick bite before heading to the city, full bathroom with rainfall shower and handheld sprayer to help you relax after a long day. Flat screen TV with Xfinity streaming device so you can connect your accounts and enjoy your favorite shows and movies for a quiet stay in.

Sherwood House
Enjoy the ambience of the Sherwood House, an 1884 Victorian built for Judge David Sherwood. Use of entire first floor apartment including a full kitchen is perfect for longer term stays. Original features include multiple stained glass windows, beautiful wood work, multiple decorative fireplaces and hardwood floors. Located just blocks from downtown Elgin, walk to shops, restaurants, the casino, bike trail or Metra. WiFi and off street parking.

Calm here! Cozy, spacious, comfortable, lg space
Large, Cozy, suite w sweet kitchenette for “portable” meals; full-size refrigerator/ freezer; a writing desk for work. Many little ( in case you forgot) items to keep you comfy. This is a quiet town on the gorgeous Lake Michigan. Near: 6 Flags, Great Lakes Navy Base; Cancer Treatment Centers of America & the city Chicago via the Metra in town. Convenient & Quiet. I have 3 dogs. They are kind, outgoing and will want to meet you.

Chic retreat near the best of Lakeview & Wrigley
Stylish, centrally-located getaway perfect for a visit to the Windy City! This charming space was freshly renovated in early 2022 with ample space (nearly 1500 sq ft), a Peloton exercise bike, and kitchenette. Located in the trendy Southport Corridor blocks from the best of Chicago's north side; shopping, fine dining, bars, Wrigley Field, close to Brown line train public transit with Whole Foods at the end of the block!
Popular amenities for Waukegan apartment rentals
Weekly apartment rentals

Downtown Libertyville Apt Near Naval Base

Luxury 2BR Apartment in River West

Apt Minutes from Naval Station

cozy grand studio 2nd floor/near lake/public tran.

The Modern Rooftop Retreat

Flat on Hamilton Court

COZY unit near Michigan Lake 2nd floor/no elevator

Treetop Vista • Spacious Luxe Near DT Chi+Parking
Private apartment rentals

Walk to: Metra to Chicago & Downtown Elmhurst

Cozy Garden Unit In Edgewater

Explore Lincoln Park from a Polished Apartment

Quirky Quarters at Wrigley

Entire 1st Floor Apt near O'Hare/ORD & Blue Line

Huge Sofa-King Bed-Easy Parking-Private Deck-Retro

Peaceful Elgin APT King Bed

Chain O' Lakes 3/1.5 Beach Penthouse and Boat Dock
Apartment rentals with a hot tub

Spacious Beautiful Condo

Skyline Oasis: City & Lake Views

Luxury 3BD Penthouse – Private Patio+Skyline Views

33rd-Floor Penthouse with Breathtaking Views

Winter Escape 1 BR in Wicker Parl|1 FREE G Parking

Belmont Pleasures - hot tub / arcade gaming room

2Bed 2Bath 15min to Wrigley with Parking& Balcony

Checkerboard Studio, Private Outdoor Hot Tub, Yard
When is the best time to visit Waukegan?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $107 SGD | $106 SGD | $104 SGD | $104 SGD | $116 SGD | $126 SGD | $124 SGD | $117 SGD | $111 SGD | $103 SGD | $114 SGD | $104 SGD |
| Avg. temp | -4°C | -2°C | 4°C | 10°C | 16°C | 21°C | 24°C | 23°C | 19°C | 12°C | 5°C | -1°C |
Quick stats about flat rentals in Waukegan

Total holiday rentals
Explore 50 holiday rentals in Waukegan

Nightly prices starting at
Waukegan holiday rentals start at $65 SGD per night before taxes and fees

Verified guest reviews
Over 3,290 verified reviews to help you choose

Family-friendly holiday rentals
30 properties offer extra space & child-friendly amenities

Pet-friendly holiday rentals
Find 20 rentals that welcome pets

Rentals with dedicated workspaces
30 properties have a dedicated workspace

Wifi availability
50 of Waukegan holiday rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Waukegan rentals

4.7 Average rating
Waukegan stays receive an average rating of 4.7 out of 5 from guests
Destinations to explore
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- Rentals with breakfast Waukegan
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- Rentals with a fireplace Waukegan
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- House rentals Waukegan
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- Lincoln Park
- Millennium Park
- Wrigley Field
- United Center
- Navy Pier
- Six Flags Great America
- 875 North Michigan Avenue
- Humboldt Park
- Shedd Aquarium
- Alpine Valley Resort
- Guaranteed Rate Field
- The Field Museum
- Oak Street Beach
- Wicker Park
- Lincoln Park Zoo
- Garfield Park Conservatory
- Frank Lloyd Wright Home and Studio
- The Beverly Country Club
- Museum of Science and Industry
- Brookfield Zoo
- Wilmot Mountain Ski Resort
- Willis Tower
- Illinois Beach State Park
- The 606




