Holiday rentals in Bannockburn

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Top-rated holiday rentals in Bannockburn

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Top guest favourite

Cottage in Highland Park

4.98 out of 5 average rating, 93 reviews

Re-imagined 1880s cottage by Highwood, Metra, Lake

Step inside Step back in time Cozy, 1880 built, re-imagined, ravine edged garden cottage Your home away from home. Escape the city and relax in our newly renovated historic cottage and gardens. Peaceful yet centrally located, vintage yet modern, Mere Cottage has so much to offer. Inside: You'll enjoy updated amenities in harmony with a distinctive vintage charm. The common area has an open layout, perfect for socializing. The kitchen and pantry (my favorite room!) are new from top to bottom and are fully stocked with any cooking gadgets you may need. Two bedrooms are joined by a Jack & Jill bathroom. The living room has a sofa that pulls out into full size bed. Outside: Jordan and I had fun redesigning the grounds from front to back. Enjoy the front garden from the rocking chair on our wrap around porch. Out back we've added a vegetable and perennial garden for you to take in. Dinner out on the back deck overlooking the garden is highly recommended! Guests have access to the entire home and grounds. Jordan and I live in the neighborhood and will be available if you need us! Our cottage is located in Highland Park, about 25 miles north of Chicago on Lake Michigan. We like to think we have the best of both worlds- being in a quiet residential neighborhood with walking access to numerous amenities right around the corner. We're a quick 5 minute walk to Highwood (the north shore’s restaurant district) and an 8 minute walk to the Metra train that can take you from Chicago to Kenosha and any place in between. We're also right on the North Shore bike path (bring your bikes!). Fort Sheridan is also close by and worth exploring for its interesting history, architecture, and nature trails. On foot: Many errands can be done on foot. We have some of the best restaurants and watering holes north of Chicago within walking distance. There is also a Walgreens convenience store 2 blocks away. By car: Getting around by car is also easy. Parking is readily available almost anywhere you'll visit. You can get to downtown Chicago in 30 minutes in ideal traffic. Train: The Metra (our train system) can also conveniently get you to and from various attractions including downtown Chicago (a scenic 45 minute ride), Ravinia music venue, the Chicago Botanic Gardens, Great Lakes Naval Base and many more. Bike: Pack your bikes! We're located on the north shore bike trail. Head north on the trail to check out the beautiful Fort Sheridan, Lake Forest, and quaint Lake Bluff. Head south to Ravinia, Chicago Botanic Garden, and numerous other beautiful villages along Lake Michigan. I bike often and will gladly point you to some great hidden gems! If you're flying into O'hare, we recommend taking an Uber to our cottage. We're about a 30 minute drive from the airport. Six Flags Great America is also a 25 minute drive away. Keep in mind that the bathroom is a Jack & Jill and is accessed from either bedroom. There is no access from the common area, so it could pose an issue at night when sleeping our max number of 6. Please keep things tidy and wash any dishes used during your stay. Out of respect for our neighbors (this home is located in a quiet residential neighborhood), no parties or large gatherings are allowed. No pets allowed.

Top guest favourite

Home in Northbrook

4.98 out of 5 average rating, 86 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.

Superhost

Flat in Highland Park

4.84 out of 5 average rating, 124 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 favourite

Flat in Highland Park

4.91 out of 5 average rating, 182 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 favourite

Guest suite in Riverwoods

4.95 out of 5 average rating, 427 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.

Guest favourite

Guest house in Lake Forest

4.94 out of 5 average rating, 134 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 favourite

Flat in Libertyville

5 out of 5 average rating, 23 reviews

305

Kick back and relax in this calm, stylish space. This peaceful, quiet apartment is walking distance to beautiful downtown Libertyville. The building is very nicely maintained with an elevator. Located 7 miles from Great Lakes Naval Base and 35 miles from downtown Chicago. The unit is very clean with all brand new furnishings and appliances including HD tv's in both the living room and bedroom. Free ample parking. On-site laundry one floor down. Fast wifi with a dedicated work space.

Top guest favourite

Home in Round Lake Beach

4.99 out of 5 average rating, 167 reviews

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!

Superhost

Home in Lake Forest

5 out of 5 average rating, 4 reviews

Spacious Home-Great Lakes Close-Quiet Location

Executive Housing and Temp Relocation requests welcome — Top Ranked Lake Forest School District Kick back and relax at this charming 5BR, 4BA Lake Forest home—just a mile to the beach Tucked on a quiet street with a backyard that feels like your own private park, it’s perfect for family fun or a peaceful escape. Cook up something tasty in the full kitchen, play in the yard, or stroll to nearby shops and trails. Just an hour from downtown Chicago but feels like a world away.

Top guest favourite

Guest suite in Highland Park

4.97 out of 5 average rating, 153 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.

Superhost

Guest house in Lake Forest

4.8 out of 5 average rating, 116 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

Guest favourite

Home in Highland Park

4.91 out of 5 average rating, 78 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.