Vacation rentals in Winnetka

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Top-rated vacation rentals in Winnetka

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Guest favorite

Home in Wilmette

4.98 out of 5 average rating, 126 reviews

Unique porcelain-enamel paneled "Lustron" home

This rare modern post war home has a style all its own. Created by Carl Strandlund in Columbus Ohio, it consisted of prefabricated porcelain enamel covered panels inside and out making it durable and easy to clean. Easing the postwar housing shortage and its maintenance free design were its selling points. Great care has been taken to reflect its true character so enjoy the well thought out floor plan and huge yard. Close to Northwestern, Gilson park beach, and downtown Chicago via car or train.

Guest favorite

Guesthouse in Evanston

4.98 out of 5 average rating, 225 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.

Guest favorite

Rental unit in Highland Park

4.94 out of 5 average rating, 146 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.

Guest favorite

Guest suite in Riverwoods

4.95 out of 5 average rating, 350 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.

Guest favorite

Guesthouse in Lake Forest

4.95 out of 5 average rating, 114 reviews

The Green Door - safe and calm with walkability

This charming guesthouse in Lake Forest is only steps away from beautiful Market Square — the historic retail center of the community. Inside it features loads of light, in-unit washer and dryer, a well-equipped kitchen and a professionally designed stylish and calming interior. Outside, it has a vintage (ie. older) porch/breezeway with classic outdoor games. Walk to two grocery stores, bars/restaurants and our historic train station that connects to Chicago and various corporate shuttles.

Guest favorite

Rental unit in Evanston

4.97 out of 5 average rating, 453 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.

Guest favorite

Home in Highland Park

4.91 out of 5 average rating, 140 reviews

2-Acre Highland Park Retreat with Heated Pool ~ 5*

Experience luxury of this award winning 6BR 4Bath family home in picturesque Northshore private estate. Spend day by the private heated pool, enjoy beauty of gardens, explore local landmarks, starting with the gates of neighborhood Michael Jordan estate. The stylish design and rich amenity list will leave you in awe. ✔ Two-Acre Estate ✔ 6 Comfy BRs ✔ Multiple Living Areas ✔ Full Kitchen ✔ Backyard (Pool, Lounges, BBQ) ✔ Smart TVs ✔ High-Speed Wi-Fi ✔ Free Parking See more below!

Guest favorite

Guest suite in Evanston

4.97 out of 5 average rating, 232 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!

Guest favorite

Rental unit in Wilmette

4.9 out of 5 average rating, 252 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.

Guest favorite

Rental unit in Skokie

4.89 out of 5 average rating, 593 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!

Guest favorite

Guest suite in Highland Park

4.96 out of 5 average rating, 134 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

Guest favorite

Rental unit in Evanston

4.84 out of 5 average rating, 239 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.

Vacation rentals for every style

Get the amount of space that is right for you

Popular amenities for Winnetka vacation rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Stay near Winnetka's top sights

Writers Theatre8 locals recommend

Starbucks8 locals recommend

Skokie Lagoons6 locals recommend

Historic Wagner Farm5 locals recommend

Glencoe Beach4 locals recommend

Graeter's Ice Cream3 locals recommend

Other great vacation rentals in Winnetka

Guest favorite

Home in Skokie

4.91 out of 5 average rating, 70 reviews

Quiet and welcoming house.

Guest favorite

Rental unit in Skokie

4.89 out of 5 average rating, 53 reviews

Charming 2 bed/1 bath apt- walk 2 train/store/rest

Guest favorite

Guesthouse in Evanston

4.91 out of 5 average rating, 94 reviews

Cozy Guesthouse near NU - next to Lee Street Beach

Guest favorite

Rental unit in Highland Park

5 out of 5 average rating, 25 reviews

Full Apartment green oasis in law suite

Guest favorite

Cottage in Highland Park

4.97 out of 5 average rating, 70 reviews

Re-imagined 1880s cottage by Highwood, Metra, Lake

Guest favorite

Rental unit in Evanston

4.94 out of 5 average rating, 98 reviews

Cute & comfortable apartment on quiet street

Guest favorite

Home in Evanston

4.93 out of 5 average rating, 41 reviews

Sleepy sanctuary

Superhost

Rental unit in Highland Park

4.86 out of 5 average rating, 97 reviews

Chic Studio in Downtown Highland Park near Metra

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Quick stats about vacation rentals in Winnetka

Total rentals
10 properties
Nightly prices starting at
$20 before taxes and fees
Total number of reviews
160 reviews
Wifi availability
10 properties include access to wifi
Popular amenities
Kitchen, Wifi, and Pool
Local attractions
Tower Road Park/Beach, The Happ Inn Bar & Grill, and Spirit Elephant

Vacation rentals in Winnetka

Top-rated vacation rentals in Winnetka

Home in Wilmette

Guesthouse in Evanston

Rental unit in Highland Park

Guest suite in Riverwoods

Guesthouse in Lake Forest

Rental unit in Evanston

Home in Highland Park

Guest suite in Evanston

Rental unit in Wilmette

Rental unit in Skokie

Guest suite in Highland Park

Rental unit in Evanston

Vacation rentals for every style

Hotels

Unique stays

Homes

Popular amenities for Winnetka vacation rentals

Stay near Winnetka's top sights

Other great vacation rentals in Winnetka

Home in Skokie

Rental unit in Skokie

Guesthouse in Evanston

Rental unit in Highland Park

Cottage in Highland Park

Rental unit in Evanston

Home in Evanston

Rental unit in Highland Park

Quick stats about vacation rentals in Winnetka

Total rentals

Nightly prices starting at

Total number of reviews

Wifi availability

Popular amenities

Local attractions

Destinations to explore