Holiday rentals in Glencoe

4.97 out of 5 average rating, 72 reviews

Home in Northbrook

*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.

5 out of 5 average rating, 40 reviews

Flat in Highland Park

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.

4.97 out of 5 average rating, 152 reviews

Home in Wilmette

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.

4.97 out of 5 average rating, 121 reviews

Home in Highland Park

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

5 out of 5 average rating, 28 reviews

Home in Highland Park

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

4.86 out of 5 average rating, 107 reviews

Flat in Highland Park

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.

4.91 out of 5 average rating, 163 reviews

Flat in Highland Park

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

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.

5 out of 5 average rating, 38 reviews

Guest house in Evanston

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.

4.98 out of 5 average rating, 256 reviews

Guest suite in Evanston

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!

4.91 out of 5 average rating, 69 reviews

Home in Highland Park

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.

4.9 out of 5 average rating, 265 reviews

Flat in Wilmette

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. **Please note the apartment is located on the garden level and does NOT include the entire home.**

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Other great holiday rentals in Glencoe

Private room in West Rogers Park

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!

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.

4.8 out of 5 average rating, 108 reviews

Private room in Skokie

Room w/ Amenities Mins to Downtown Chicago & NU!

RamRating, 5 stars1 week ago

Musa's place was extremely comfortable, very nice and easy to find! Check-in instructions were very clear, and the area itself is very peaceful. Surrounding streets are walkable as well, and it's a very short drive to a train station to quickly get downtown if needed.

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!

4.98 out of 5 average rating, 179 reviews

Private room in Evanston

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!!

4.89 out of 5 average rating, 383 reviews

Private room in Glenview

Garden Suite with Private Full Bath-Adults Only

DarylRating, 5 stars1 month 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.

5 out of 5 average rating, 16 reviews

Private room in Wheeling

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.