Vacation rentals in Lake Forest

A bright living area features two upholstered chairs and a gray sofa, arranged around a white coffee table. Natural light enters through large windows, draped with gray curtains. A decorative bowl with flowers adds a touch of color to the space.

4.9 out of 5 average rating, 131 reviews

Rejuvenate and Relax in the North Shore

Set in the midst of an affluent neighborhood, this spacious and sunny four bedroom retreat offers all the comforts of a home away from home. With it's perfect location close to Lake Michigan, Chicago Botanical Garden, Ravinia, Naval Base, and Six Flags Great America to name a few, our family home is within reach to Chicago as well. If you feel very adventurous, just leave your car in garage, pick up a bike and ride the Lake Shore Bike trail all the way to downtown Chicago, enjoying the beautiful scenery. If you feel less adventures but still would like to enjoy beautiful scenery, you can do it by taking a train. Metra can get you downtown Chicago in less than 45 min. and the stop is within walking distance.

4.82 out of 5 average rating, 34 reviews

A cozy outdoor patio area features a round table with four chairs, complemented by a large umbrella for shade. A chaise lounge rests beside the table, all set on a paved surface surrounded by greenery and a wooden fence for privacy.

Home in Lake Forest

Parkside Cottage Near the Train

This special place is close to everything, making it easy to plan your visit. The property is nextdoor to South Park with tennis, pickelball, baseball and basketball courts. The bike path to uptown is directly behind the house. It does back up to the train you can take to downtown Chicago, just 30 minutes away. The property is 1 Mile to the public beach and uptown Lake Forest and only .5 mile to Lake Forest College. It has a unique charm having been built in 1920. There's only one toilet.

The cozy living room is designed with soft seating arrangements and a wooden coffee table at the center. Natural light flows through nearby windows, enhancing the inviting atmosphere. A chandelier and wall mirror add character, while decorative accents on the table provide visual interest.

4.96 out of 5 average rating, 129 reviews

Charming Ranch-Style Cottage

Escape the hustle and bustle of the city in this relaxing, cozy, cottage that is a few blocks away from downtown Highland Park and Highwood, with great restaurants, bars and coffee shops. It is perfect for single travelers, couples, or a small family. We are grateful for the amazing Airbnb hosts across the globe, who opened their homes to us, and made our trips so memorable. So when we bought our own home, it was only right that we would return the favor and open our home to fellow adventurers

Apartment in Highland Park

A cozy studio apartment features a spacious bed with crisp linens, complemented by a modern black and white wall art piece. A small dining table is positioned nearby, alongside a decorative plant and a lamp providing soft light. Natural light enters through a window dressed with blinds.

4.86 out of 5 average rating, 111 reviews

Chic Studio in Downtown Highland Park near Metra

Welcome to downtown Highland Park! Experience comfort and convenience in our cozy studio apartment with FREE parking. Just a 5-minute walk to the Metra, and within a leisurely 15-minute stroll, enjoy breathtaking views of Lake Michigan. Explore historic Fort Sheridan Forest Preserve and beach, only a quick 5-minute drive away. Discover delightful dining, gelato shops, parks, and more—all within walking distance. Our well-appointed apartment ensures a memorable stay in this vibrant neighborhood.

Apartment in Highland Park

A charming entryway is featured, showcasing a white shingled exterior with green shutters. Two metal chairs surround a small round table, providing a cozy outdoor seating area. The front door is framed by a gabled roof, inviting guests into the studio.

4.92 out of 5 average rating, 170 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 suite in Riverwoods

A well-defined stone pathway leads to the entrance of the prairie-style home, bordered by lush green grass and neatly trimmed hedges. Hanging flower baskets add vibrant touches above the cozy seating area, surrounded by the serene backdrop of towering oak trees.

4.96 out of 5 average rating, 411 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.

Guesthouse in Lake Forest

The living area features a velvet sofa adorned with colorful pillows, complemented by a matching armchair. A glass coffee table is centered on a patterned area rug, with a bookshelf displaying decorative items and books in the background.

4.95 out of 5 average rating, 129 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.

An aerial view of the family home reveals a spacious layout surrounded by lush green lawns. A heated swimming pool is situated in the backyard, bordered by lounge chairs and shaded areas, while a circular driveway leads to the entrance, enhancing the estate's inviting appeal.

4.91 out of 5 average rating, 145 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 suite in Highland Park

A modern kitchen features sleek cabinetry and granite countertops, with an island and two bar stools. Stainless steel appliances, including a refrigerator and stove, are prominent. Soft overhead lighting enhances the neutral color palette, and an adjacent pantry is visible through an open door.

4.97 out of 5 average rating, 147 reviews

Charming in-law suite w/ use of deck and yard

Charming home in Highland Park. The space is my in-law suite which is in the lower level of my home and has its own full size kitchen and 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,a separate closet area and laundry. Please note- the suite is in the basement, but there is natural light. You have shared use of the deck/yard if desired.

Guesthouse in Lake Forest

A cozy bedroom features a black metal bed frame adorned with soft pillows in pink and green hues. Textured white bedding is spread across the bed. Natural light filters through the large windows, complemented by light-colored curtains, and a nightstand sits beside the bed.

4.79 out of 5 average rating, 111 reviews

Designer's Dream in the North Shore!

Welcome to the newly designed cottage at Longmeadow. A tranquil escape from the city hustle of Downtown Chicago. Enjoy the serene setting while close proximity to town amenities, public transit and beautiful trails and parks. A cozy retreat in the wintertime to snuggle up with a great book and hot cocoa. It's also a perfect summer cottage for adventurers looking to take advantage of the beautiful landscape ! Check us out on: Instagram! longmeadowcottage

A charming brick home is set amidst a lush green lawn, framed by trees and bushes. The two-story structure features a distinctive sloped roof and a welcoming front porch. Natural light enhances the inviting exterior on a clear blue sky day.

4.91 out of 5 average rating, 74 reviews

A Wonderful Getaway Home on the North Shore!

A perfect place to visit the northern highlights of Chicago! 1/4 mile from Ravinia! 1.5 miles from the Botanic Gardens! 30 minutes from Chicago (an hour and a half from Milwaukee). Close to trains, planes, and easy automobile access. A two-bedroom gem in the heart of so many wonderful things. Other local places include Northwestern University, Lake Forest, Winnetka, and Lake County. I have a cat living here, but he will accompany me when I leave.

4.93 out of 5 average rating, 107 reviews

A spacious living area features modern furniture, including a leather sofa and armchairs arranged around a coffee table. A dining table with blue chairs is visible, complemented by large windows allowing natural light. The room has a warm and neutral color palette.

Loft in Libertyville

Historic Downtown Libertyville Loft

Enjoy a stylish experience at this centrally-located 1600 square foot place. Located in the heart of Downtown Libertyville, half way between Chicago and Milwaukee. Close to Six Flags, Great Lakes Navy Base, Lake Michigan beaches, forest preserves, train station and the Chain of Lakes. Downtown Libertyville is a trendy town offering several restaurants, shops and fun events. Book one of the only units truly Downtown Libertyville.

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Popular amenities for Lake Forest vacation rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Other great vacation rentals in Lake Forest

Private room in Woodstock

A small sitting area is evident, featuring a light-colored sofa with dark pillows, positioned against walls adorned with framed artwork. Two large windows covered with blinds allow natural light to fill the room. A dark side table sits beside the sofa, on top of a patterned area rug.

4.93 out of 5 average rating, 397 reviews

Mini Suite in the House of Odd

4.94 out of 5 average rating, 198 reviews

A tree-lined street in a quiet neighborhood is visible, with well-maintained lawns and charming homes featuring brick exteriors. A single green chair is positioned on a grassy area, inviting relaxation amidst the landscaped surroundings.

Private room in Evanston

Welcoming Evanston Home

Private room in Crystal Lake

A cozy bedroom features a spacious bed dressed in white linens and decorative pillows. A nightstand is placed beside the bed, and a piece of wall art adds a touch of elegance. Natural light enters through a window, with beige curtains framing it, and a patterned rug is laid on the floor.

4.89 out of 5 average rating, 158 reviews

Master Bedroom w/Bathroom - safe and cozy

Private room in Grayslake

An aerial view of a cozy living space features a light brown sofa adorned with patterned cushions, complemented by a matching armchair. A decorative area rug lies on polished wooden floors, while a small table holds a book. Large windows bring in natural light, framed by blue curtains.

4.92 out of 5 average rating, 83 reviews

T - Amazing Open Floor Plan, Across From Lake

4.99 out of 5 average rating, 660 reviews

The exterior of the home features light-colored siding and red shutters, complemented by neatly trimmed shrubs. A stone pathway leads to a white front door, flanked by large windows that allow for ample natural light. Lush green grass surrounds the entrance.

Private room in Geneva

Room within a Cozy Cottage

Private room in Norwood Park

4.77 out of 5 average rating, 321 reviews

Chicago River Room near USMLE

4.9 out of 5 average rating, 41 reviews

Private room in Skokie

Cozy Private Room