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Vacation rentals in Winnetka

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Top-rated vacation rentals in Winnetka

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Home in Wilmette

4.98 out of 5 average rating, 111 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.

Guesthouse in Evanston

4.98 out of 5 average rating, 215 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.

Home in Beach Park

4.98 out of 5 average rating, 176 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.

Rental unit in Highland Park

4.95 out of 5 average rating, 133 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.

Guesthouse in Lake Forest

4.94 out of 5 average rating, 103 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 suite in Riverwoods

4.95 out of 5 average rating, 316 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.

Home in Highland Park

4.91 out of 5 average rating, 133 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!

Home in Round Lake Beach

4.99 out of 5 average rating, 105 reviews

Round Lake Getaway Retreat

Looking for a calming, peaceful lakeside getaway for you and your loved one? Come stay at our remodeled retreat with private waterfront access to Round Lake. Enjoy peace and reflection meditating on the spirited lake waters rolling into shore. Wake up to inspirational lake views with soul warming coffee, tea or cocoa. Savor deep or lazy conversation with your loved one, surrounded by dreamy décor and captivating nature. Come and relax, restore, and rejuvenate by the lake!

Townhouse in Hoffman Estates

4.91 out of 5 average rating, 304 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.

Rental unit in Wilmette

4.89 out of 5 average rating, 244 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.

Rental unit in Skokie

4.89 out of 5 average rating, 554 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 suite in Highland Park

4.96 out of 5 average rating, 122 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

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Popular amenities for Winnetka vacation rentals

Free parking on premises

Air conditioning

Other great vacation rentals in Winnetka

Guesthouse in Evanston

4.9 out of 5 average rating, 83 reviews

Cozy Guesthouse near NU - next to Lee Street Beach

Home in Northbrook

4.97 out of 5 average rating, 29 reviews

*King bed *Outdoor Living *Sought-After Area

Home in Skokie

4.89 out of 5 average rating, 70 reviews

Luxe-Haus of Love—The 1938 Cape Cod |Heated FLRS |

Home in Evanston

4.9 out of 5 average rating, 31 reviews

Sleepy sanctuary

Home in Highland Park

5 out of 5 average rating, 26 reviews

Sanctuary on the Ravine

Condo in Skokie

4.95 out of 5 average rating, 43 reviews

Parking Terrace Near Universities Up to 10%OFF

Home in Evanston

5 out of 5 average rating, 23 reviews

Wanderlust Cottage

Home in Highland Park

4.96 out of 5 average rating, 80 reviews

Charming Ranch-Style Cottage

Frequently Asked Questions

How is the weather in Winnetka?
Winnetka experiences a continental climate with hot summers and cold winters. In summer, temperatures can reach up to 85°F (29°C), while in winter, it can drop to around 20°F (-6°C). Enjoy winter activities like snowshoeing or cross-country skiing at the Winnetka Golf Club.
What are some of the best things to do in Winnetka?
Winnetka is a vibrant destination with a rich history and nature. You can explore the historical landmarks such as the Winnetka Historical Society Museum, enjoy the serene environment at the Skokie Lagoons, or immerse yourself in cultural experiences at the Winnetka Community House.
What is the best time of year to visit Winnetka?
The most frequented time to visit Winnetka is during the summer months when the weather is warm and outdoor activities are in full swing. One of the popular events is the Summer Art Fair, where local artists showcase their creativity.
What are the best places to stay in Winnetka?
Popular areas to stay in Winnetka include the vibrant downtown area, which has numerous shopping and dining options, and the serene Hubbard Woods neighborhood, known for its beautiful homes and parks.
What are the best places to visit in Winnetka?
There are many significant places to visit in Winnetka. These include the historical Baha'i House of Worship, the lush Winnetka Golf Club, and the vibrant Winnetka Farmer's Market.
What are some hiking trails in Winnetka?
Winnetka is ideal for the outdoor enthusiast. You can explore the Green Bay Trail, a beautiful path for hiking and cycling, or take a leisurely walk along the Skokie Lagoons trail, both offering picturesque views of the area.
What are some family activities to do in Winnetka?
Families can enjoy a host of activities in Winnetka. You can explore the Hubbard Woods Park, visit the Winnetka Public Library for family-friendly events, or enjoy a picnic near the majestic Tower Road Beach.
What are some of the best day trip ideas in Winnetka?
For a day trip around Winnetka, consider a drive to the nearby city of Evanston for a visit to the Northwestern University campus, or explore the lush Chicago Botanic Garden, just a short journey away in Glencoe.

Destinations to explore