
Holiday houses in Lake View
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Top-rated holiday rentals in Lake View
Guests agree: these stays are highly rated for location, cleanliness and more.

3br W/ Elevator, Patio & Laundry Near the Red Line
My 3 bedroom apartment in Sheridan Park is a stunning place to call home in Chicago! You'll love the neighborhood; its vibrant food and art scene is uniquely diverse in Chicago. A mile north of Wrigley Field - Just to the east, Montrose Beach is a nice break from the city. If work is what brings to you to town, the nearby Brown line will take you right to the Loop. I provide all the essentials to make your stay easy and comfortable. (Balcony maintained for Summer Season, Memorial Day-Labor Day)

Retro Designer Home | Walk to Wrigley, Bars & Lake
Stay in prime Lakeview East, one of Chicago’s most walkable and safest neighborhoods, perfectly located near everything. • 12 mins walk to Wrigley Field • 6 mins walk to Lake Michigan & lakefront trails • 2 mins walk to top restaurants, bars, nightlife, shopping & entertainment • 8 mins walk to CTA Redline, access to downtown Chicago & airport • Extremely walkable, safe & vibrant area Live in the center of it all while enjoying a stylish designer apartment in one of Chicago’s best locations.

Wrigleyville Condo 2 Blks from Lake & Train
I think you'll enjoy my spacious East Lakeview condo. The location is super convenient just 2 blks from Sheridan red line & 2 blks from the lake. Easy proximity 4 blks to Wrigley Field & restaurants/nightlife in Wrigleyville & Boystown. Amazing restaurant next door w/back patio- El Mariachi w/the freshest chips & guacamole! Starbucks, playground, and Divvy Bike station at the corner. 1 mi to Montrose Beach. All downtown sight-seeing easily accessible from Lake Shore Dr or red line 2 blks away.

Sun drenched 2 bedroom 1 bath with Kitchen & W/D
Welcome to beautiful Roscoe Village! Come relax and enjoy a gorgeous loft-like condo that has a huge sun-drenched living room and opens up right to the kitchen. Enjoy cooking on your own in the spacious kitchen and rest easily at night in a spacious king bed in the main bedroom. We love and welcome pets - so no need to leave your fur baby at home. Uber to Wicker Park and Logan Square. You’ll have your own private entrance with a lock box to get into the condo. We look forward to hosting you!

Grace House | Cozy, contemporary + convenient 2-BR
Make yourself at home in our newly renovated, spacious and immaculately clean 2-bedroom, 1-bath condo — perfect for your next family, work or friends' trip. Located on a tree-lined street in a family-friendly neighborhood and walkable to shops, restaurants, cafes, bars and more. A stone's throw to Southport Corridor/Wrigleyville/Lakeview, Lincoln Square, Roscoe Village and everything the Northside has to offer. Gigabit internet w/ WiFi and everything you need to live and thrive in Chicago.

RockStar Pad W3A BoysTown/Wrigley Field/Parking
HAVE IT ALL @ W3A Chicago Wrigley Field/Boystown/Lakeview -Newly renovated like new in safe centrally located East Lakeview. -10 min walk to Wrigley Field, Boys town, beaches, super markets, restaurants with late night dining. 5 min walk to Metro Sheridan Red Line (direct downtown), private enclosed parking $10/night & or free permits for street parking -600 thread count linens, fluffy soft pillows, house coats, high speed WiFi, Sonos speakers, stylish design & in unit washer & dryer

A Whimsical Fairy-tale Loft in Ravenswood Chicago
Welcome to Bluebird Inn, an intimate, thoughtfully designed urban inn that will serve as an oasis as you embark on your exploration of Chicago. Nestled above the Long Room, a beloved neighborhood tavern and coffee house (Bad Johnny's, Nice Guy Food Co., Cash's Kitchen and AJ's Bakery & Diner), you can start your day downstairs with breakfast and coffee and stop in for a nitecap before heading up to retire for the evening. Settle in & enjoy the amenities and approachable luxury.

Foosball, Steps from Wrigley, Private Parking
Our apartment is ideally located near Wrigley Field and just steps from the Red Line, making it extremely convenient for exploring Chicago. Because of this prime location, occasional train and street noise can be heard. To help you sleep comfortably, we provide ear plugs. Many of our guests still enjoy the vibrant city atmosphere while finding the apartment cozy and restful. Perfect For: Guests who love being in the heart of Chicago and don’t mind a bit of city life sounds.

Spacious 2 Bedroom in the heart of Lakeview!
Come enjoy this warm and spacious 2br/1ba vintage apartment in the heart of Lakeview! 10 Minute walk to Wrigley Field and steps away from many dining and shopping options. Fully stocked kitchen, dining room (seats six), decorative fireplace, TV w/ Fire Stick, two bedrooms with queen beds, office space for working remote, and large private deck with gas grill. Very close to Lake Shore Drive, short walk to the Belmont L, and easy access to many buses. Two night minimum stay.

Lakeview Home with Patio
Enjoy this thoughtfully curated apartment in the Lakeview neighborhood of Chicago. Home features two bedrooms with queen beds, one bathroom, and an outdoor patio with full dining table, fire pit, and TV! Right off the Southport Corridor, this quiet tree-lined street is walking distance to Wrigley Field, countless restaurants / bars, and the lake. Street parking is free and very easy! Can guarantee you will always find a spot within one or two blocks of the property!

Beautiful Remodel in Sought After Wrigleyville
Modern comfort meets unbeatable location in this freshly renovated 1BR/1BA Wrigleyville gem. Enjoy the "new unit" feel with fresh paint, new appliances, and soaring 10-ft ceilings. Nestled in Lakeview, you're steps from top restaurants, bars, theaters, and iconic attractions. Perfect for travelers seeking style, convenience, and a true Chicago experience. Public transit is a block away and Spothero parking behind the building.

Quirky Quarters at Wrigley
I think you are just going to love my apartment. The space features wonderful large street level windows in the living room and has all of the quirky charm that vintage buildings offer up. The location literally can't be beat, with the apartment a ten minute walk from Wrigley Field, the bustling Southport shopping corridor, and both the red line and brown line subway stations. There is no parking available with the apartment.
Popular amenities for Lake View holiday rentals
Stay near Lake View's top sights
Other great holiday rentals in Lake View

Bright 1BR unit w/ elevator & Wifi

The Winslow - Chic Studio by Wrigley Field

Kasa | Spectacular City Views | Chicago

Windsor Castle | 4 BR 3.5 Bath Near Lake & Wrigley

Guest Favorite Getaway | Lakeview | Near Wrigley

Mid-Century Modern | Walk to Wrigley

Wrigley Flat - Short walk to Wrigley Field

Wrigleyville 2 bed 2 bath + Office Newly Rehabbed
Quick stats about holiday rentals in Lake View

Total holiday rentals
Explore 660 holiday rentals in Lake View

Nightly prices starting at
Lake View holiday rentals start at $35 NZD per night before taxes and fees

Verified guest reviews
Over 54,720 verified reviews to help you choose

Family-friendly holiday rentals
340 properties offer extra space and kid-friendly amenities

Pet-friendly accommodation
Find 240 rentals that welcome pets

Rentals with dedicated workspaces
400 properties have a dedicated workspace

Wi-Fi availability
660 of Lake View holiday rentals include Wi-Fi access

Popular amenities for guests
Guests love Gym, BBQ grill and Laptop-friendly workspace across Lake View rentals

4.8 Average rating
Lake View stays are highly rated by guests—averaging 4.8 out of 5!
Destinations to explore
- Rentals with a washing machine and dryer Lake View
- Condo rentals Lake View
- Rentals with lake access Lake View
- Rentals with a patio Lake View
- Rentals with breakfast Lake View
- Rentals with a fireplace Lake View
- Family-friendly rentals Lake View
- House rentals Lake View
- Fitness-friendly rentals Lake View
- Apartment rentals Lake View
- Pet-friendly rentals Lake View
- Rentals with beach access Lake View
- Bed and breakfasts Lake View
- Rentals with outdoor seating Lake View
- Rentals with a fire pit Lake View
- Wrigley Field
- Lincoln Park
- United Center
- Soldier Field
- Grant Park
- Navy Pier
- Millennium Park
- Naval Station Great Lakes
- 875 North Michigan Avenue
- Indiana Dunes State Park
- Six Flags Great America
- Shedd Aquarium
- The Field Museum
- Humboldt Park
- Chicago River Walk
- University of Chicago
- SeatGeek Stadium
- Guaranteed Rate Field
- Lincoln Park Zoo
- Loyola University Chicago
- Donald E Stephens Convention Center
- Union Park
- Frank Lloyd Wright Home and Studio
- Wilmot Mountain Ski Resort





