Vacation rentals in Highland Park

4.86 out of 5 average rating, 65 reviews

A charming two-story house is set within a lush green lawn, featuring large trees that provide shade. The front porch is approachable and includes a railing, while an American flag gently waves. A fence encloses the backyard, creating a private outdoor space.

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.

Apartment in West Lake View

A spacious living room features large windows allowing natural light to fill the space. A comfortable light-colored sectional sofa is situated in front of a glass coffee table, with a medium-sized rug underneath. A wooden side table and a television mounted on the wall are also visible.

4.94 out of 5 average rating, 177 reviews

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!

4.97 out of 5 average rating, 143 reviews

A serene pathway lined with lush greenery features tall trees and blooming flowers. An inviting red chair is positioned in the background. A friendly sign indicating 'KEEP RIGHT' guides guests along the landscaped route toward the cottages.

Bungalow in Lake Geneva

Private Cozy Cottage Lake Geneva, WI

Come stay at our top rated Bed & Breakfast, located two blocks from the beautiful Lake Geneva. Relax in our California king suites, each contains a spa tub and shower, with heated floors and towel rails in the bathroom. Your complimentary breakfast basket is placed in your fridge prior to arrival, as well as complimentary gift of wine & cheese. Free WIFI is available on the property. No Pets, ADULTS over 21 ONLY. *NOTE all guests are required to pay a 8% Lake Geneva Bed Tax at check in.

4.9 out of 5 average rating, 129 reviews

A sunny four-season sunroom features a turquoise ceiling and large windows showcasing outdoor views. Comfortable seating includes a wicker chair and a patterned area rug. Decorative elements include a potted plant and a vase of flowers, creating a relaxed and inviting space.

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, 34 reviews

The Clean Slate, Walk to down town, pet friendly

The Clean Slate is the latest offering from Lake Geneva luxury Rentals. Half mile walk to downtown. Pet friendly The house can accommodate 8 guests, but can be rented with its sister property, The White House, to accommodate larger groups. Contact host to inquire about renting both houses. This newly built home will surely delight. Tastefully decorated with all modern amenities. Easy access to downtown Lake Geneva’s shops, restaurants, Riviera Beach, and Geneva Lake Shore Path.

Top guest favorite

Home in Round Lake Beach

4.99 out of 5 average rating, 144 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!

5 out of 5 average rating, 5 reviews

The exterior of the rustic cottage showcases a wooden deck with a picnic table and outdoor seating area. A patio umbrella provides shade, while vibrant greenery surrounds the space. Sunlight casts a warm glow on the inviting structure, accentuated by a clear blue sky.

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.

4.95 out of 5 average rating, 44 reviews

1 block to the Lake, then 2 blocks to Downtown

Renovated vintage cottage is blocks from the lake, 4 blocks to Riviera Beach, and a short walk to downtown. Stunning cottage boasts original stained glass with gorgeous renovated kitchen including granite countertops and stainless steel appliances. Fully stocked kitchen with plates, utensils, pots, pans and mixing bowls. Cabinets and drawers clearly labeled. Child plates, bowls, cups and kid utensils. Many games, toys, puzzles and books for kids too! Patio table outside.

Apartment in Logan Square

A modern kitchen and dining area features an expansive island with seating for four and an elegant dining table surrounded by stylish chairs. Four skylights allow natural light to fill the space, highlighting the blue walls and contemporary decor.

4.92 out of 5 average rating, 12 reviews

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!

A bright and airy entryway features a wooden bench against a large window. A staircase with a modern railing leads to the upper level, while a potted plant adds a touch of greenery to the space. The walls are painted in soft gray tones.

4.97 out of 5 average rating, 153 reviews

NEW! Cozy Downtown Farmhouse, 5BR 3 BA Sleeps 15!!

Our gorgeous home is set in the heart of downtown Lake Geneva. 5 bedroom, 3 bathroom home that is two blocks from the lake and a few blocks from downtown shopping and restaurants. We just completed an extensive renovation of the home and it is now ready for you to stay for your dream vacation. Our homes are fully licensed and legal for short term rentals. We also rent the home two doors down and another in nearby Williams Bay!

A well-maintained house features a spacious composite deck, bordered by white railings. Large windows provide natural light to the interior. Lush green grass surrounds the deck, complementing the clear blue sky and leafy trees in the background.

5 out of 5 average rating, 26 reviews

Modern Downtown Lake Geneva Charm - Sleeps 8

Beautiful 3 bedroom home located in the heart of Lake Geneva and walking distance to restaurants, bars, & the beach. This recently remodeled house is the perfect place for an escape. With an open kitchen concept, leading out to a large composite (Trex®) deck, there is no shortage of space for any activity or just to get back to a quieter more relaxing pace. *** This property is Licensed & Legal for weekend rentals ***

4.87 out of 5 average rating, 124 reviews

An airy living space is highlighted by large windows offering views of the lake. A wooden dining table accommodates six, while a comfortable seating area is arranged around a fireplace. A large flat-screen TV is mounted above the fireplace, enhancing the room's modern aesthetic.

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.

Vacation rentals for every style

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Popular amenities for Highland Park vacation rentals

Self check-in

Gym

BBQ grill

Laptop-friendly workspace

Wifi

Stay near Highland Park's top sights

Chicago Botanic Garden167 locals recommend

Ravinia Festival West Lot33 locals recommend

Ravinia Festival Box Office14 locals recommend

Northbrook Court11 locals recommend

Jewel-Osco9 locals recommend

Lake-Cook Rd & Turnbull Woods Ct station8 locals recommend

Other great vacation rentals in Highland Park

4.76 out of 5 average rating, 29 reviews

A spacious deck overlooking Pistakee Lake features a wooden surface and multiple seating areas. Two chairs are positioned around a small table, while the tranquil water reflects a cloudy sky. Nearby, boat docks can be seen along the shoreline, enhancing the lakefront view.

Home in Fox Lake

Pistakee Lake Getaway

4.89 out of 5 average rating, 55 reviews

A tranquil view of the lake is captured at sunset, with golden hues reflecting on the water. A torch stands in the foreground, gently illuminating the scene, while trees frame the image along the edge of the deck.

Home in Fox Lake

Stunning Lake Views, Huge Deck, Water Fun!

Top guest favorite

A bright living area is showcased with large windows that invite natural light. Comfortable seating arrangements are provided by two armchairs and a spacious sofa. A rustic rug anchors the space, complemented by a decorative coffee table and a bench along the staircase.

Home in Schaumburg

5 out of 5 average rating, 51 reviews

Great location-King beds-Kids playroom

4.86 out of 5 average rating, 42 reviews

A cozy living area is presented, featuring a stone fireplace as a focal point. Two armchairs are positioned around a coffee table, with decor additions providing a touch of greenery. Natural light enters through nearby windows, illuminating the light-colored walls and hardwood floors.

Apartment in Albany Park

Elegant 4Bedroom with Free Parking in Albany Park

Apartment in Jefferson Park

A modern kitchen is equipped with sleek stainless steel appliances, including a microwave and dishwasher. Light countertops complement dark cabinetry, while a small countertop with two barstools provides a casual dining option. Natural light filters in through a window near the door.

4.63 out of 5 average rating, 24 reviews

City Gem: Stylish 3BR for Urban Explorers

4.92 out of 5 average rating, 116 reviews

The image showcases a sandy beach area beside a calm water channel. Colorful kayaks and a canoe are positioned along the shoreline. A spacious green lawn is framed by large trees, with blue lawn chairs and a hammock visible in the background.

Home in Antioch

Entertain on The Chain! water sports and sauna.

4.93 out of 5 average rating, 137 reviews

A comfortable living area features a sectional sofa adorned with decorative pillows, complemented by a cozy armchair. Natural light floods in through large windows, offering a view of the lakeside. A decorative table and plants add warmth to the space.

Cottage in Wonder Lake

The Cozy Lake House/ Perfect Winter Getaway!DM ?s