Family-friendly vacation rentals in Highland Park

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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.

Family · Indoor spaces · Sleep quality

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.

Indoor spaces · Family · Quiet

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Cozy 2-Bedroom Cottage Near Downtown Highland Park

Step into a warm, inviting retreat where comfort meets character! This beautifully updated suite features two cozy bedrooms, a private bathroom, and thoughtfully decorated living spaces in a modern farmhouse style. Nestled in the heart of Highland Park, you’re steps from great restaurants, boutique shops, scenic trails, and parks, plus a golf course across the street and just 1.5 miles from Lake Michigan. Whether it’s a family getaway or a business trip, it’s your perfect home away from home!

Indoor spaces · Kitchen · Shared spaces

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Guest favorite

*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.

Family · Indoor spaces · Checkout

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.

Indoor spaces · Kitchen · Value

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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.

Indoor spaces · Family · Check-in

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Guest favorite

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.

Family · Indoor spaces · Bathroom

Top guest favorite

Guest favorite

Charming space 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. I live up-stairs with my 3 small dogs so I 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 (stairs), but there is natural light. You have use of the deck/yard if desired. No stays over 3 weeks.

Indoor spaces · Kitchen · Comfort

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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

Indoor spaces · Family · Long stay

Your relaxing stay in Highland Park

Whether you are looking to escape the city hustle and bustle, visiting Lake Forest College, the Naval Station or moving cross country, our bright and spacious suite is the perfect spot to check in and relax for a few nights. Featuring a separate entrance and a beautiful, private newly remodeled bathroom. 43 4K Smart HDTV with Netflix and Prime and super fast WiFi available for streaming. Kitchenette with a microwave, mini fridge, sink and cups/plates/010/053/2026cutlery.

Family · Indoor spaces · Nearby

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The NICEST place in Evanston for Families 1500Main

Fully Furnished 2-story, 2 bedroom attached Duplex with a King bed in the Primary bedroom and a pair of Twin beds in the 2nd bedroom. Couch on main floor is also a sofa bed that sleeps two if needed. Main floor is wide open floor plan. This space has been set up specifically for short-term rentals of 1-2 weeks or months and has previously been used by Guests looking for homes in the Evanston area or having construction done. We cater to Families visiting Northwestern University.

Family · Kitchen · Backyard

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

Family · Kitchen · Long stay