Holiday rentals in Lake Bluff

4.96 out of 5 average rating, 126 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

4.86 out of 5 average rating, 108 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.

4.98 out of 5 average rating, 224 reviews

Home in Beach Park

B’s Farmhouse Cottage 2-bedroom duplex.

Experience the best of the midwest! Enjoy a newly remodeled "Magnolia Farm" inspired 2-bedroom duplex, all to yourself near everything you need. 50 Miles from Milwaukee, miles from Chicago, and 2 miles having your toes in the sand at Lake Michigan. We are minutes away from the Great Lakes Naval Station and the Cancer Treatment Center of America, Six Flags Great America, Gurnee Mills, and Great Wolf Lodge. Whatever brings you here make J&B's Farmhouse Cottage your home away from home today.

4.89 out of 5 average rating, 200 reviews

Guest suite in Zion

Non-smoking, attached mother-in-law suite.

25 minutes away from the Naval Station 5 minutes away from the beach. 10 minutes to Wisconsin. 1 hour 40 minutes to O’Hare Airport and downtown Chicago. 40 minutes to Milwaukee Airport 25 minutes to Six Flags and Great Wolf Lodge. Safe and quiet neighborhood with plenty of wildlife right in the back yard. This Mother in Law suite has tons of natural light. For nature lover’s this unit is close to the beach and there are walking trails nearby. Small children maybe heard from 7AM to 7PM.

Guest suite in Riverwoods

4.96 out of 5 average rating, 402 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.

4.92 out of 5 average rating, 124 reviews

Home in Waukegan

The Indigo Cottage

This is a newly remodeled single-family home! It is small but has everything you need to enjoy time with family and friends during your stay in the Chicagoland area! There are two bedrooms each with a queen bed, an updated bathroom, a dining room with seating for 6, a cozy living room with a Crate & Barrel pull-out queen sofa bed, and a nice, updated kitchen! There's a brand-new washing machine and dryer in the basement. There's a nice patio table outside too in the private yard. Welcome!

4.82 out of 5 average rating, 136 reviews

Flat in Waukegan

Cozy Corner, stylish 1bed near Navy Base!

Kick back and relax in this calm, stylish space. This is a newly remodeled 1 bedroom apartment. The Cozy Corner is designed to be a place of peace, for rest and relaxation. Feel right at home in this beautiful apartment. The kitchen is stocked with plenty of utensils and cookware for your favorite meal. Be sure to relax by the indoor fireplace and watch your favorite movies. Dedicated work space with desk and fast wifi perfect for traveling professionals. Longer stays discounted!

4.99 out of 5 average rating, 151 reviews

Home in Round Lake Beach

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!

Guest suite in Highland Park

4.97 out of 5 average rating, 146 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.

Guest house in Lake Forest

4.79 out of 5 average rating, 109 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

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Other great holiday rentals in Lake Bluff

4.78 out of 5 average rating, 58 reviews

Flat in Waukegan

Cozy Apartment I Naval Station

AlexRating, 5 stars3 weeks ago

I stayed for about two weeks while I was working in the area. It was the prefect location, close to highways and grocery stores. I travel with my dog and she was allowed in the rental which was a huge help. We went on many walks around the neighborhood which is very nice and quiet. The kitchen is so nice I think that was a favorite part. Thank you!

4.92 out of 5 average rating, 165 reviews

Flat in Highland Park

Lovely studio near the beach! (and heated floors!)

JohnnyRating, 5 stars1 week ago

Fantastic location /! close to the lake and restaurants .Close to my wife’s work. The place was perfect. Nice , comfortable, cozy and clean. Communication with Ariel is perfect. Can’t wait to come back again. Thank you for an excellent stay.

4.89 out of 5 average rating, 79 reviews

Home in North Chicago

Spacious 2-br, 1 bath home w/AC near Naval Base

KathleenRating, 5 stars2 weeks ago

This home was chosen because of it's proximity to Recruit Training camp Great Lakes! I wanted to make sure I could get to my son's bootcamp graduation quickly with no issues of traffic. That worked out perfectly especially with Sarges easy directions! As for this home, it is located on a one way street which was extremely easy to find. The home is adorable, extremely clean and well decorated!!! I would highly recommend. They accommodated an earlier check in as we had a few connecting flights from Los Angeles... The beds are extremely comfortable with nice sheets and pillows. The towels in the bathroom were nice and fluffy. Shower was really nice with a filtered shower head! Nice TVs thru out! Shampoos, conditioners, soap in shower. first aid kits, iron and iron board, blow dryer. Kitchen had plenty of essentials to utilize for home cooked meals. If you are coming for Navy bootcamp graduation... do not hesitate to book!! Perfect home to rent! Thank you again to the hosts!

4.82 out of 5 average rating, 87 reviews

Flat in Libertyville

131 E. Park Ave - Unit 306

DemetriaRating, 5 stars3 weeks ago

It was very peaceful. Able to open windows and get good, clean fresh air. Was nicely laid out and amenities worked. Appreciated the working elevator. I’d definitely stay again.

4.85 out of 5 average rating, 41 reviews

Flat in North Chicago

Close to Navy Base & Six Flags Great America

TayRating, 5 stars2 weeks ago

Lauren was very helpful and everything was nice in the Airbnb! Only thing to complain about would be the lack of curtains on windows in the living room, I stayed alone so I always felt like someone could see me. Second would just be the extra fees for some small things.

5 out of 5 average rating, 44 reviews

Flat in Highland Park

Full Apartment green oasis in law suite

JonRating, 5 stars1 day ago

Lola made me and my girlfriend feel very at home. She was always there if we ever had questions and she always made sure we were comfortable. Her kitchen downstairs is def the kitchen you’re looking for if you’re trying to cook dinner or breakfast. Overall, great BNB with a fantastic host. Thanks again Lola!!

5 out of 5 average rating, 64 reviews

Home in Highland Park

Modern & Private Basement Retreat with Kitchenette

MaryRating, 5 stars2 weeks ago

Great stay at Crystal's place! She was very responsive and helpful for check in. Even though this was in her home, it felt very private. It is immaculately kept and was comfortable with great amenities.