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Vacation rentals in Winnetka

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Top-rated vacation rentals in Winnetka

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Apartment in Park Ridge

4.79 out of 5 average rating, 319 reviews

Modern Garden apartment (WHOLE UNIT)

Freshly Remodeled , Lower Level Condo one bedroom one bath. The Condo is very large for a one bedroom. Very Spacious with its open concept layout. Parking is right next to the main entrance of the building. Perfect place to relax Perfect and safe place to rest . 24/7 perimeter monitoring cameras. The Condo is very close to the Metra Train. It is !5 min away from O'Hare airport and 10 min from Chicago outlets etc. It is not a party room . No parties or large gathering .... Garden Apartment

Nov 21 – 28

G$30,393 GYD per night

Guesthouse in Evanston

4.98 out of 5 average rating, 201 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.

Nov 19 – 26

G$31,305 GYD per night

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 12 – 19

G$27,317 GYD per night

Apartment in Arlington Heights

4.99 out of 5 average rating, 112 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.

Jun 11 – 18

G$29,798 GYD per night

Apartment in Highland Park

4.94 out of 5 average rating, 122 reviews

Lovely studio near the beach! (and heated floors!)

Get away from the city to this studio in Highland Park. The newly renovated space has everything you need for a relaxing getaway—huge comfy couch, brand new bed with Brooklinen + Parachute bedding, pristine bathroom, and lots of amenities. Downtown Highland Park, Highwood, + the beach are just a walk away. There's access to grocery stores, restaurants, and shops, and you can retreat to the quiet of your studio when you're ready to unwind. Ps. For the winter months: We've got heated floors.

Feb 15 – 22

G$40,464 GYD per night

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 26 – Jun 2

G$34,747 GYD per night

Apartment in Evanston

4.97 out of 5 average rating, 406 reviews

Charming, Sunny Apartment with Backyard Garden

House of the Blue Doors Enjoy staying with us in this spacious 1st floor flat. Furnished by the resident designer in tasteful neutrals, original curated artwork, one of a kind furniture and accent pieces. Sip morning coffee or a glass of wine in the sunlit kitchen or front porch, fire up the backyard grill for a barbecue. Soak in the award winning Chicago ceramic artist designed and made floor in the bathroom. Close to Northwestern, Chicago, Lake Michigan, everything Evanston offers.

Mar 27 – Apr 3

G$31,816 GYD per night

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!

Mar 9 – 16

G$31,147 GYD per night

Townhouse in Hoffman Estates

4.91 out of 5 average rating, 291 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.

Dec 19 – 26

G$20,303 GYD per night

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

G$27,155 GYD per night

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 23 – 30

G$49,115 GYD per night

Guest suite in Evanston

4.83 out of 5 average rating, 323 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 !

Aug 22 – 29

G$19,207 GYD per night

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Popular amenities for Winnetka vacation rentals

Free parking on premises

Air conditioning

Other great vacation rentals in Winnetka

Home in Wilmette

4.98 out of 5 average rating, 92 reviews

Unique porcelain-enamel paneled "Lustron" home

Sep 26 – Oct 3

G$35,271 GYD per night

Guesthouse in Lake Forest

4.95 out of 5 average rating, 95 reviews

The Green Door - safe and calm with walkability

Feb 4 – 11

G$20,525 GYD per night

Apartment in Highland Park

5.0 out of 5 average rating, 37 reviews

Stunning & Stylish Downtown Studio - Highland Park

May 8 – 15

G$20,665 GYD per night

Townhouse in Winnetka

4.96 out of 5 average rating, 26 reviews

Warm and Cheerful 3 Bedroom Winnetka Townhouse

Oct 18 – 25

G$81,292 GYD per night

Apartment in Wilmette

4.84 out of 5 average rating, 19 reviews

The Shop - Trendy Studio in the heart of Wilmette

Jun 15 – 22

G$41,242 GYD per night

Guesthouse in Evanston

4.91 out of 5 average rating, 76 reviews

Cozy Guesthouse near NU - next to Lee Street Beach

Feb 18 – 25

G$33,530 GYD per night

Home in Northbrook

5.0 out of 5 average rating, 14 reviews

Northbrook Retreat with Ample Outdoor Space

Jun 27 – Jul 4

G$75,450 GYD per night

Home in Skokie

5.0 out of 5 average rating, 25 reviews

Culinary DREAM - Pizza Oven/BBQ/Smoker

Nov 25 – Dec 2

G$116,538 GYD per night

Destinations to explore