Vacation rentals in Winnetka

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Top-rated vacation rentals in Winnetka

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Guest favorite

Guesthouse in Evanston

4.98 out of 5 average rating, 202 reviews

Cottage in a Garden

Enjoy the serenity of our secret garden from your private guest house. Enjoy privacy on the covered sun porch. Watch butterflies float by in the pollinator garden. Listen to evening quiet on the patio overlooking the garden. Spin some records from the eclectic collection. Stroll the leafy neighborhood. Stop for a beer at award-winning Temperance Brewery. 5 minute walk to Divvy bike station gives you access to all of Chicago and CTA/Metra train. Short ride to lakefront, Northwestern, downtown.

Mar 12 – 19

ﺩ.ﺇ548 per night

Guest favorite

Home in Beach Park

4.98 out of 5 average rating, 161 reviews

B’s Farmhouse Cottage 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, miles from Chicago, and 2 miles having your toes in the sand at Lake Michigan. We are minutes away from the Great Lakes Naval Station and the Cancer Treatment Center of America, Six Flags Great America, Gurnee Mills, and Great Wolf Lodge. Whatever brings you here make J&B's Farmhouse Cottage your home away from home today.

Jan 28 – Feb 4

ﺩ.ﺇ480 per night

Guest favorite

Apartment in Arlington Heights

4.99 out of 5 average rating, 114 reviews

Ideal Location in Awesome Heights

Near the heart of downtown Arlington Heights and convenient to O’Hare. You can settle in at this cozy basement apartment with a super comfortable queen bed and all the amenities you’d need. Whether your visit to AH is for business or pleasure, city or suburbs, we look forward to hosting you. The private apartment works great for guests with a car or using public transit. Easy access to Metra station, AH restaurants, Des Plaines Theater, NW Community Hospital & Schaumburg Convention Center.

May 4 – 11

ﺩ.ﺇ524 per night

Guest favorite

Guest suite in Riverwoods

4.95 out of 5 average rating, 300 reviews

Master qtr close to nature & easy urban facilities

This amazing prairie style home sits on 2 acre land surrounded by lush lawn and majestic oak trees - a nature lover's dream with unparalleled serenity. Vacation-like setting blends country-like quiet with nearby conveniences including shopping, trains, restaurants, highways, Ravinia (18 MINs drive). 5 MINs to I 294. 20 MINS to O'HARE; 5 Mins to Discover, Baxter; 10 MINs to Walgreens Deerfield campus, TRINITY INT'L UNIVERSITY; 15 MINS to Lake Forest Academy. 25 MINs to Great Lakes Navy Base.

May 10 – 17

ﺩ.ﺇ514 per night

Guest favorite

Guest suite in Evanston

4.97 out of 5 average rating, 213 reviews

A guest suite centrally located, but so quiet...

IF... you want to race into the city to see a play, go for a jog along the lake, have a quick coffee with a friend or enjoy a fine restaurant to celebrate a special occasion, it's all here in the lovely lakeside town of EVANSTON, IL. You can enjoy it all while living in my guest suite w/private kitchen, private bath, private entry, shared laundry area and......., if you need it, garage parking, too! Enjoy my garden on warm summer days; in winter, you will love the heated floor!

Nov 23 – 30

ﺩ.ﺇ382 per night

Guest favorite

Townhouse in Hoffman Estates

4.91 out of 5 average rating, 292 reviews

a SIMPLE place

Booking the entire house with 100% privacy. It has 2 driveway parking spaces and street parking. Garage may be available. CHECK-IN and OUT are flexible. I set checkout at 11am (text me if you need late checkout). The space is perfect for a family of 4. It is located about 20 minutes from O'Hare airport and 40 minutes from Chicago downtown. Infants and pets are welcome (please text me for over size pets or more than 2 pets) Play pan is available upon request.

Nov 27 – Dec 4

ﺩ.ﺇ357 per night

Guest favorite

Apartment in Wilmette

4.86 out of 5 average rating, 119 reviews

Downtown Wilmette Micro Studio

During this time, we are taking extra precautionary measures to ensure our guests safety. Cute and private micro studio in phenomenal downtown Wilmette location. Steps from all local restaurants, shopping, and the Metra station. Walkable to Gillson Beach and the Linden CTA stop. Enter through the front gate to an open & shared yard with private, single access to the unit. Pets OK with additional pet fee (some breed / weight restrictions).

Jun 14 – 21

ﺩ.ﺇ477 per night

Guest favorite

Apartment in Wilmette

4.89 out of 5 average rating, 235 reviews

Spacious Garden Apartment with Sauna and Fireplace

English garden apartment in historic Wilmette home with a private entrance, sauna, washer/dryer, kitchenette, dining area, recreation room with pool table, vintage pinball machine, and a wood-burning fireplace with gas igniter. Two queen beds, 1 full-size sleeper sofa, and a single mattress are available for large families. Ideal access to Northwestern University for all events. Free WIFI and an internet-enabled flat-screen TV.

Jun 27 – Jul 4

ﺩ.ﺇ864 per night

Guest favorite

Guest suite in Evanston

4.83 out of 5 average rating, 326 reviews

Huge, cozy one bedroom semi-basement apartment

1000 SF Close both to Chicago area and the lake and the suburbs. It has a side separate entrance from the main house. One bedroom with one queen bed. A pull out couch too. A fully equipped kitchen. One full bathroom with a shower , no tub. A cozy living room with TV. This propery has surveillance cameras . Strict rules will be applied to violation of maximum capacity of 4 people. The place is not rented for parties !

Feb 10 – 17

ﺩ.ﺇ338 per night

Guest favorite

Apartment in Skokie

4.91 out of 5 average rating, 530 reviews

Cozy Garden Unit in Quiet Neighborhood

A cozy garden unit in the heart of skokie, off of a quiet residential street with plenty of street parking. Just a mile away from the Skokie-Dempster Yellow line train that leads to downtown Chicago, and within a mile from Old Orchard Mall and plenty of great eateries such as: Chick-fil-A, Portillo's, Culver's, Oberwies, Kaufman's Bagel, and more. 15 minutes away from Evanston and the Beautiful Lake Michigan shoreline!

Mar 13 – 20

ﺩ.ﺇ496 per night

Guest favorite

Guest suite in Highland Park

4.97 out of 5 average rating, 110 reviews

Charming in-law suite w/ use of deck and yard

Charming little house in Highland Park. In-law suite is in the basement and has it's own full size kitchen bathroom. We live up-stairs with our 3 little dogs so we will be available if you need anything during your stay. The in-law suite is set up like a studio and has one queen bed and a separate closet area. Please note- the suite is in the basement. You have shared use of the deck/yard

Jun 28 – Jul 5

ﺩ.ﺇ470 per night

Superhost

Apartment in Evanston

4.83 out of 5 average rating, 215 reviews

Adorable 1BR apartment near Northwestern

Cozy and comfortable one bedroom apartment with full kitchen and updated bath. Recently re-decorated with fresh carpet, paint and new queen bed. Located on the second floor of a single family 2-flat style home in a quiet, residential neighborhood. Ample, free street parking. One additional person can be accommodated with blow-up mattress.

Oct 10 – 17

ﺩ.ﺇ544 per night