Holiday rentals in Winnetka

4.95 out of 5 average rating, 65 reviews

Home in Wauconda

The Adorable "Blue Breeze"!

Enjoy time at our centrally-located, family-friendly home. Close by, you'll find a public fishing dock and the popular Phil's Beach. A peaceful space with an outside patio and grill, perfect for relaxing at end of day. We also have a large driveway that can accommodate your boat making it easy to enjoy a day on Bangs Lake or a short 15 min trip to Fox Lake. Nearby attractions include the Volo Museum, Jurassic Gardens, and Lake County Discovery Museum. Please note the backyard is not fenced in.

4.86 out of 5 average rating, 65 reviews

Home in Twin Lakes

beach access, pet friendly yard, hot tub, 5 bedrms

4,000 sq ft 5 bedroom, 3.5 bath home. Short walk to Musial beach on Lake Elizabeth. Perfect for large families with multiple living areas. Island Kitchen with fireplace & den. 3 season room. Master bedrm with walkin shower. Large 2nd floor family room with lg tv, vinyl records and shuffle board! Outdoor grill & fire pit & free firewood. Close to Grand Geneva Resort, Lake Geneva and Wilmot Mtn. Boat dock available on Lake Elizabeth. Turnkey boat rental available. Short walk to Roadhouse bar.

4.94 out of 5 average rating, 179 reviews

Flat in West Lake View

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!

4.9 out of 5 average rating, 129 reviews

Home in Antioch

Lakefront, beautiful views, spacious and private.

With panoramic views of the lake, you’ll love the stunning sunsets, private beach, pier, and kayaks. Experience outstanding fishing and walk to downtown for restaurants, bars, shopping, theater, and concerts in the park. Skiing at Wilmot/Vail is just a short drive away. Inside, unwind by two fireplaces, three TV screens, or play a game on the pool table. The large wet bar and expansive kitchen are perfect for gatherings, with additional space in the dining areas, private office, and gym.

4.94 out of 5 average rating, 16 reviews

Home in Winthrop Harbor

The Harbor House - Amazing!

The Harbor House is simply AMAZING! Set on over an acre, this private beautiful home is perfect for making beautiful family and group memories. The spacious interior features a great room as well as a separate family room. The expansive kitchen is fully equipped. Smart TV's in all BR's, the GR and FR. Full size washer and dryer. This home boasts an expansive private yard featuring plenty of outdoor seating with a gas grill and firepit. Ample parking. RV parking (50 amp).

4.99 out of 5 average rating, 144 reviews

Home in Round Lake Beach

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!

5 out of 5 average rating, 12 reviews

Home in Avondale

Alluring Avondale Abode

Welcome to Alluring Avondale Abode, the perfect vacation rental for your next family trip or group getaway. A pet-friendly paradise, centrally located for easy travel to all the top attractions. A spacious kitchen, beautiful backyard deck, and patio create a wonderful backdrop for entertaining and relaxing. Find an array of fun games to keep all ages occupied. Book now and experience the laid-back vibe and unbeatable amenities that will make your vacation truly unforgettable.

5 out of 5 average rating, 5 reviews

Home in Twin Lakes

Rustic Cottage Downtown Twin Lakes

Embrace the allure of the lake in our cozy rustic retreat nestled directly across the street from Lake Mary in the heart of Twin Lakes. This wonderful cottage provides a unique blend of rustic charm and modern comfort, featuring a warm, woodsy interior, lots of natural light and gas fire pit for enjoying warm breezes and westward facing sunsets. This cabin is the perfect getaway for those seeking to reconnect with water and find solace in the beauty of Wisconsin lake life.

4.92 out of 5 average rating, 12 reviews

Flat in Logan Square

2-level PH w/ 2 Luxe Suites Combined; Spa Access

The top floor sprawling ranch with duplex down offers sky & outdoors views, privacy, & cathedral ceilings, it is connected to your rear 2nd floor suite with 10ft ceilings. A burgeoning neighborhood next to the 606 Trail Amenities: - Uber-fast Wifi streaming, - Hot tub house - 80" + 75" hi-def tv's - 3 sectional couches - European decor - 2 kitchens - The popular 606 Trail access is 100 ft away, - YMCA across the street with indoor Olympic size & kiddie-pools!

4.87 out of 5 average rating, 125 reviews

Home in Fox Lake

Lakefront Paradise

Relax and have fun with the family and friends at this unique getaway! We are situated directly on the lakefront with private access to our pier where you can enjoy world class sunset views. Jump in and go swimming, roast s'mores over a campfire right next to the water, grill up some burgers on the spacious deck or get some rest in our luxurious suites in this newly renovated (June 2021) home.

4.85 out of 5 average rating, 73 reviews

Home in Round Lake Beach

Lake/Beach Getaway (Remodeled)

Have fun with the whole family at this stylish home. Everything has been recently renovated. This is directly across from a beach, which is perfect for winter and summer activities. We supply 2 kayaks, fishing poles (Bring your fishing boat)This place has 3 bedrooms, and a total of 5 beds. There is also a lot of dining and shopping, nearby. This is a hidden gem and brand new to AirBnb.