Holiday rentals in Deerfield

4.9 out of 5 average rating, 128 reviews

Home in Highland Park

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.

4.97 out of 5 average rating, 73 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, 9 reviews

Home in Northbrook

6 Kings | Ping-Pong | Gazebo!

Discover a spacious retreat perfect for groups, featuring 6 king beds, multiple smart TVs (w/ complimentary Disney+ & Hulu), a ping pong table, & plenty of driveway parking! Enjoy meals at the dining or kitchen table, then relax in the large yard under the gazebo. With 3.5 baths, everyone has room to refresh. Its prime location offers quick access to the North Shore’s beaches or Chicago’s vibrant scene—perfect for families, work groups, or friends seeking comfort, entertainment, and convenience!

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, 153 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

4.83 out of 5 average rating, 122 reviews

Flat in Highland Park

Chic Studio in Downtown Highland Park - By Metra

Discover our elegant studio unit in Highland Park, now featuring FREE parking! This simple yet comfortable space is perfect for couples, concert-goers, and small families. You'll find all the essential amenities you need, including a fully stocked kitchen, laundry facilities, and reliable Wi-Fi. Our location is ideal for exploring downtown Highland Park, with convenient access to top attractions, restaurants, and shops. Book now and discover your perfect home away from home on the North Shore.

4.91 out of 5 average rating, 164 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, 400 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.

4.99 out of 5 average rating, 659 reviews

Guest suite in Geneva

A Suite within a Cozy cottage in Geneva Illinois.

Cozy private suite in the lower level. Guests have the suite to themselves. The bathroom is adjacent to the room and is private. There is a small fridge, a coffee maker, and a microwave oven. We are in Geneva, Illinois. We are LGBTQ+friendly. Our space is ideal for shorter stays and visitors on the go . Not suitable for staycations. Quiet area. Hosts live on the upper level and guests pass through our space to get to the suite. In a bind we can accommodate a 3rd guest and a pet. Welcome.

Guest house in Lake Forest

4.94 out of 5 average rating, 127 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.

Guest suite in Northbrook

4.91 out of 5 average rating, 88 reviews

ELEGANT 2BR/2BA NORTHSHORE GARDEN APARTMENT

Cozy In-law Garden Apartment -Lower Level Unit with High Ceilings -Separate PRIVATE Entry -Easy Self Check-in -Complementary Coffee, Tea & Snacks -Full Kitchen with Cooking Utensils -Dishwasher -Washer & Dryer -Roku TV -Comfortable Queen Beds with Designer Pillows -Off Street Parking -5 Min. to Chicago Botanic Garden -5 Min. to Northbrook Mall -10 Min to Lurie Children's Hospital & Surgery Center -10 Min. to Ravinia -20 Min. to Ohare International Airport -35 Min. to Downtown Chicago

Holiday rentals for every style

Get the amount of space that is right for you

Hotels

Stylish accommodation and amenities

Unique stays

Spaces that are more than just a place to sleep

Homes

Comfortable places with all the essentials

Popular amenities for Deerfield holiday rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Other great holiday rentals in Deerfield

4.96 out of 5 average rating, 190 reviews

Private room in Evanston

Welcoming Evanston Home

JoshuaRating, 5 stars2 weeks ago

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

Private room in Grayslake

4.91 out of 5 average rating, 79 reviews

T - Amazing Open Floor Plan, Across From Lake

JamalRating, 5 stars4 days ago

I had a great stay at Dr. Cheryl's home. I had stayed there once before, and everything was perfect both times. Dr. Cheryl is a great host and her house is beautiful and clean. Will definitely stay again. Very highly recommend.

4.91 out of 5 average rating, 104 reviews

Private room in Evanston

Room Mins to Downtown Chicago & Northwestern!

NataliaRating, 5 stars1 week 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.

4.89 out of 5 average rating, 383 reviews

Private room in Glenview

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.

4.88 out of 5 average rating, 17 reviews

Private room in Wheeling

Stunning Private Master Bedroom with own bathroom

OmarRating, 5 stars1 month 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.

4.8 out of 5 average rating, 363 reviews

Hotel room in Itasca

King Bed at Chicago Northwest + PET Friendly

JenniferRating, 5 stars2 weeks ago

had a wonderful stay. would stay again.

Hotel room in Libertyville

4.82 out of 5 average rating, 45 reviews

Spacious Budget-friendly Room w/ Kitchenette

KaidenRating, 5 stars3 weeks ago

Easy check in, super clean room with a nice bathroom, 24 hour access to the snack bar downstairs and checkin/checkout; overall a GREAT stay and well worth the price!