Vacation rentals in Glencoe

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Top-rated vacation rentals in Glencoe

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Top guest favorite

The ranch style home is set against a backdrop of vibrant autumn foliage. A large tree with orange leaves stands prominently in the front yard, complemented by well-maintained landscaping. A driveway leads to an attached garage, while outdoor seating is visible on a neatly manicured lawn.

Home in Northbrook

4.97 out of 5 average rating, 72 reviews

*King bed *Outdoor Living *Sought-After Area

Welcome to our sophisticated ranch style home, nestled in the serene, central Chicago neighborhood of Northbrook. This carefully curated home offers a peaceful retreat in a walkable neighborhood with nearby shopping and dining. With its elegant decor, comfortable furnishings, and modern amenities, the home provides a haven of relaxation. Whether you're enjoying a cup of coffee on the private patio or exploring the area, this home provides the perfect backdrop for a memorable vacation experience.

Top guest favorite

A modern bathroom showcases a glass-enclosed shower with a rainfall showerhead. Natural light enters through a glass block window. A sleek vanity with a round mirror is positioned above the sink, while stylish tile covers the floor and walls.

Apartment in Highland Park

5 out of 5 average rating, 40 reviews

Full Apartment green oasis in law suite

Forget your worries in this spacious 1 bedroom, 1 bath apartment. Large windows & great natural light. There are new Curtains in the Living Room. Designated Parking on site in long driveway. Full kitchen with full sized stainless steel appliances, private stackable washer and dryer machines & beautiful tile throughout. Bring slippers tile can be chilly to touch - if barefoot. Starbucks, parks, restaurants, dry cleaners & Jewel walking distance from apartment. Whole Foods & Target 7 min. drive.

Top guest favorite

A modern kitchen area features a coffee maker alongside a selection of coffee supplies. A neatly arranged shelf holds various packaged items, with an organized rack of spices mounted on the wall. A white serving tray is positioned prominently for added convenience.

Home in Wilmette

4.97 out of 5 average rating, 152 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.

Top guest favorite

A vibrant scene featuring a field of yellow flowers, surrounded by lush green foliage and trees. The sunlight filters through the leaves, creating a serene atmosphere. The mix of wildflowers and grasses creates a natural landscape that invites exploration.

Home in Highland Park

4.97 out of 5 average rating, 121 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

Superhost

The kitchen features light-colored cabinetry with glass doors displaying decorative dishware. A stylish countertop made of granite is complemented by a backsplash patterned in soft tones. Countertop appliances, including a coffee maker and toaster, are positioned for convenience, while natural light fills the space from a nearby window.

Home in Highland Park

5 out of 5 average rating, 28 reviews

Sanctuary on the Ravine

Take it easy at this unique and tranquil get away, walking distance to Ravinia and Beaches 3 Blocks.This historic, beautifully decorated and well maintained home has a lovely, peaceful & serene setting. Multiple indoor and outdoor seating arrangements. Fully stocked kitchen that opens to family room looking out onto several multilevel brick patios and a quiet, private ravine. The extra large living room has a down feathered sectional couch that seats up to 10 people. No parties or gatherings

Superhost

A clean and functional bathroom is equipped with essential fixtures. A bathtub and shower combination is complemented by a dark shower curtain featuring white polka dots. A mirror hangs above a white vanity with a sink, and decorative items add a touch of greenery.

Apartment in Highland Park

4.86 out of 5 average rating, 107 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.

Guest favorite

Townhouse in Winnetka

4.95 out of 5 average rating, 44 reviews

Warm and Cheerful 3 Bedroom Winnetka Townhouse

Stay in comfort in the ChicagoLand north shore in a 3 bedroom, 1.5 bath, 2-car garage townhome only blocks from Metra rail, grocery, and restaurants. Upstairs, The master bedroom has a king sized bed, two closets, and a dresser. The 1st guest bedroom has a full bed, a dresser, a single closet and a desk, and the 2nd guest bedroom has a full bed, a dresser and a single closet. On the ground floor the living room/dining room has a sofa, a settee, a few chairs, a 55" TV and a table for four.

Guest favorite

A welcoming entrance to the property is presented, featuring a paved driveway flanked by lush greenery. A black fence borders the pathway, leading towards a single-story house in the background, surrounded by trees and well-maintained landscaping.

Apartment in Highland Park

4.91 out of 5 average rating, 164 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.

Top guest favorite

The spacious master bathroom features a two-person jacuzzi tub and a separate walk-in shower. Natural light is provided by large windows, enhancing the warm wood cabinetry and neutral stone surfaces. Fluffy towels are neatly arranged alongside personal care items on the countertop.

Guest suite in Riverwoods

4.96 out of 5 average rating, 399 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.

Top guest favorite

Guesthouse in Evanston

5 out of 5 average rating, 38 reviews

Mr. Hughes’ Attic, an 80s-themed hideaway

Welcome to Mr. Hughes' Attic, a private coach house that pays homage to John Hughes (who filmed many of his movies nearby!) Located in NW Evanston, your stay includes a queen bed, full kitchen, laundry, full bath, dedicated workspace, private balcony, free parking, streaming TV, and more. We're a short walk to Central St shops, restaurants, and the Metra train, a five-minute drive to Northwestern, and less than 30 minutes to Chicago. Not wheelchair or ADA accessible. License# STR004.

Top guest favorite

The exterior features a charming two-story home with a welcoming front porch. A set of stairs leads to the entrance, surrounded by well-maintained greenery and blooming flowers. Sunlight filters through the trees, creating a warm and inviting atmosphere.

Guest suite in Evanston

4.98 out of 5 average rating, 256 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 private guest suite w/kitchenette, 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!

Top guest favorite

A charming house is depicted against a twilight sky, where warm light spills from multiple windows. The front door is slightly ajar, inviting exploration. Lush greenery frames the entryway and path, leading to a welcoming atmosphere in a tranquil setting.

Home in Highland Park

4.91 out of 5 average rating, 69 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 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: Northwestern University, Lake Forest, Winnetka, Lake County ... I have a cat living here, but he will accompany me when I leave. I just wanted to let you know if you have allergies.

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Popular amenities for Glencoe vacation rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Other great vacation rentals in Glencoe

Guest favorite

A well-maintained hospital exterior is featured, showcasing a clear sign directing to the Emergency entrance. Brightly colored flowers line the pathway, complemented by manicured greenery and trees. The modern brick building stands against a clear blue sky, indicating a welcoming and accessible environment.

Private room in Evanston

4.96 out of 5 average rating, 190 reviews

Welcoming Evanston Home

JoshuaRating, 5 stars1 week ago

Jennifer was a very hospitable host and I had a very pleasant stay. The room was very clean and quiet!

Guest favorite

A cozy twin bed is dressed in a light quilt, complemented by decorative pillows. A nightstand with a lamp and floral arrangement adds warmth to the space, alongside a decorative box. Soft, neutral tones create a calming atmosphere.

Private room in Highland Park

4.89 out of 5 average rating, 213 reviews

Perfect for Individual Travelers #1

RuthRating, 5 stars1 month ago

Simple cozy bedroom for cheaper than a hotel. Just what I needed. Definitely will stay here again if I’m in the area. Nina was super accommodating and I felt right at home.

Guest favorite

A private bathroom is visible, featuring light blue walls and beige tiled flooring. A white toilet is positioned next to a small potted plant. A sink with a countertop is shown, accompanied by a large mirror illuminated by bright lights above. A shower area is enclosed with beige tiles.

Private room in Mount Prospect

4.89 out of 5 average rating, 113 reviews

S2 Private studio in the house. 15min to O'Hare

SamRating, 5 stars2 weeks ago

Easy to communicate with and had a simple yet clean and comfortable space - thank you!

Top guest favorite

A spacious outdoor deck is featured, furnished with circular chairs and steps leading to a lush backyard. Surrounding greenery enhances the serene environment. A small glass table and wooden chairs are arranged on a stone patio, providing a comfortable space for relaxation.

Private room in Evanston

4.98 out of 5 average rating, 179 reviews

Peaceful Suite with natural light. Shared bath

KaeleeRating, 5 stars1 week ago

Irene and Mike were lovely hosts and super helpful. The room was beautifully decorated, light, airy, and super clean. The bed was extremely comfortable and the location was great— in a peaceful neighborhood but also just a short walk from many nice shops and restaurants. I saw at least 4 rabbits in the yard each day of my stay— it felt like a fairytale! I will definitely stay here again during my next visit to Evanston!!

Guest favorite

Contemporary walnut sliding barn doors are showcased, featuring a rich, dark wood texture with natural grain patterns. The doors are mounted on a sleek black track, adding a modern touch to the space.

Private room in Glenview

4.89 out of 5 average rating, 383 reviews

Garden Suite with Private Full Bath-Adults Only

DarylRating, 5 stars2 months ago

Great place. It was clean and spacious, I got my own bathroom, I got to do laundry, there’s free coffee, it’s close to the airport, the neighbourhood is beautiful. The smart TV was initially having problems during my stay but Nancy and Brent were very proactive in trying to fix it, which they did, and I got to enjoy watching Netflix in my last days. This place offers great value for money, 10/10 would highly recommend, and would actually book this place again in the future.

Guest favorite

An aerial view showcases the winding Lakeshore Drive alongside Lake Michigan. Lush greenery lines the waterfront path, with boats gently cruising on the water. The Chicago skyline rises in the background, characterized by various distinctive buildings against a clear blue sky.

Private room in Evanston

4.91 out of 5 average rating, 103 reviews

Room Mins to Downtown Chicago & Northwestern!

NataliaRating, 5 stars5 days ago

Musa was very friendly and helpful the entire time we stayed at his place. The house is big, neat and located in a nice and calm neighbourhood, ideal if you want to rest after a day in downtown. Good shops nearby so I recommend go for a walk around the beautiful Evanston.

Top guest favorite

The exterior of a townhouse is depicted, featuring a well-maintained grassy area in the foreground. The building showcases a combination of brick and siding, with large windows allowing natural light to enter. Trees are visible, contributing to the serene environment.

Private room in Wheeling

5 out of 5 average rating, 16 reviews

Stunning Private Master Bedroom with own bathroom

OmarRating, 5 stars3 weeks ago

Great stay for a few days. Place was nice and peaceful. Highly recommend this to anyone wanting to go to Chicago but wants to stay outside of downtown.

Superhost