
Vacation rentals in Highland Park
Find and book unique accommodations on Airbnb
Top-rated vacation rentals in Highland Park
Guests agree: these stays are highly rated for location, cleanliness, and more.

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.

*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.

Cozy 2 bedroom house/w garage in Skokie
Charming 2B/1.5B house in Skokie IL. This Airbnb boasts plenty of amenities including WIFI, Roku TV's, fully furnished, a beautiful backyard, workout gym and sauna in the basement and a kitchen with top of the line appliances. The house sits on a quiet residential street just 2 minutes away from the nearest interstate taking you to beautiful Downtown Chicago in about 25min . Downtown Skokie is a few minutes away, plenty of shopping options 5min to Village Crossing and 15min to Old Orchard Mall.

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.

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.

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.

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.

Penthouse In The Historic Hobbs
Experience luxury and historic charm at the Penthouse in the Historic Hobbs. Built in 1892, and restored in 2023, this new one bedroom corner unit offers a panoramic view of the Aurora skyline. Cook a delicious meal in the fully stocked kitchen. Dine at the bespoke table in the window bay under the iconic onion dome. Relax on the cozy sofa and enjoy a movie on the big screen TV. Rest in the plush king-sized bed. This urban retreat is near coffee, shopping, art and entertainment.

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.

Cozy French Inspired Cottage in rural setting
Relax and escape to our charming, one of a kind cottage. Beautifully decorated with period furniture and tastefully updated with modern amenities. The cottage offers slate tile and hardwood floors. Original pine floors line the upstairs loft bedrooms. Cook in a French inspired country kitchen with butcher block counter tops. Rural setting, yet minutes away from everything! Downtown is a 20 min. walk and the Metra will take you to the city in 45 minutes!

Beautifully decorated ranch near beach & shops
Beautifully decorated ranch, minuets from lakefront beach, downtown Lake Forest, and commuter rail to downtown Chicago. Spacious home with almost 3000 square feet, open floor plan for enjoyment, master suite with soaking tub and shower, family room with gas burning fireplace opens to kitchen, flat screen TVs throughout, WiFi, exceptionally clean, and neat.

Cozy 2-Bedroom Cottage Near Downtown Highland Park
Step into comfort and character in this beautifully updated home’s front suite. Featuring two comfortable bedrooms, a private bathroom, and cozy living spaces decorated in modern farmhouse style. Enjoy a well equipped kitchenette, free coffee & tea, and a prime Highland Park location. Walk to shops, restaurants, parks, and easy access to Chicago.
Popular amenities for Highland Park vacation rentals
Other great vacation rentals in Highland Park

Stunning & Stylish Downtown Studio - Highland Park

North Shore - Home Away From Home

Casa 22 Luxury & Modern 3BD 2BA Home in Skokie

Full Apartment green oasis in law suite

A Wonderful Getaway Home on the North Shore!

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

3 Luxury Master Suites by Gardens, Lake & Chicago

Elegant 2BR/2BA Northshore Garden Apartment
When is the best time to visit Highland Park?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $238 CAD | $227 CAD | $265 CAD | $238 CAD | $269 CAD | $351 CAD | $328 CAD | $299 CAD | $282 CAD | $294 CAD | $290 CAD | $241 CAD |
| Avg. temp | -4 °C | -2 °C | 4 °C | 10 °C | 16 °C | 21 °C | 24 °C | 23 °C | 19 °C | 12 °C | 5 °C | -1 °C |
Frequently Asked Questions
Are there family-friendly vacation rentals in Highland Park?
Highland Park has more than 30 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.
How much does it cost to stay in apartment rentals in Highland Park?
Experience the best of Highland Park with our apartment rentals, starting at about $30 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Are there pet-friendly vacation rentals in Highland Park?
Four-legged friends are welcome in Highland Park. Choose from more than 20 vacation rentals for guests traveling with pets.
Are there vacation rentals with a dedicated workspace in Highland Park?
Yes! Work meets play with ease at over 30 vacation rentals in Highland Park featuring dedicated workspaces. Stay connected and productive in your home away from home.
Where should I stay in Highland Park?
Make yourself at home in Highland Park by choosing from our most frequently booked neighborhoods. We have over 70 vacation rentals in Deerfield, over 70 vacation rentals in Highwood, and over 80 vacation rentals in Highland Park.
Do house rentals in Highland Park have air conditioning?
Absolutely! We offer over 30 house rentals with air conditioning in Highland Park. Enjoy a tailored experience with all the comforts you desire.
Do apartment rentals in Highland Park have a kitchen?
Absolutely! We offer over 10 apartment rentals with a kitchen in Highland Park. Enjoy a tailored experience with all the comforts you desire.
Do apartment rentals in Highland Park have wifi?
Absolutely! We offer over 10 apartment rentals with wifi in Highland Park. Enjoy a tailored experience with all the comforts you desire.
Do apartment rentals in Highland Park have free parking?
Absolutely! We offer over 10 apartment rentals with free parking in Highland Park. Enjoy a tailored experience with all the comforts you desire.
What are the most popular amenities for House Rentals in Highland Park?
Enhance your stay in our House Rentals with the most popular amenities: over 20 homes with a kitchen, over 30 homes with free parking, over 30 homes with wifi, over 30 homes with air conditioning, and more. Indulge in the ultimate retreat, tailored to your preferences.
Quick stats about vacation rentals in Highland Park

Total vacation rentals
Explore 50 vacation rentals in Highland Park

Nightly prices starting at
Highland Park vacation rentals start at $41 CAD per night before taxes and fees

Verified guest reviews
Over 2,360 verified reviews to help you choose

Family-friendly vacation rentals
30 properties offer extra space and kid-friendly amenities

Pet-friendly vacation rentals
Find 20 rentals that welcome pets

Rentals with dedicated workspaces
30 properties have a dedicated workspace

Wifi availability
50 of Highland Park vacation rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi, and Pool across Highland Park rentals

4.9 Average rating
Highland Park stays are highly rated by guests—averaging 4.9 out of 5!
Destinations to explore
- Chicago Vacation rentals
- Platteville Vacation rentals
- Downtown Chicago Vacation rentals
- Indianapolis Vacation rentals
- Southern Indiana Vacation rentals
- Detroit Vacation rentals
- Columbus Vacation rentals
- St. Louis Vacation rentals
- Louisville Vacation rentals
- Cincinnati Vacation rentals
- Wisconsin River Vacation rentals
- Milwaukee Vacation rentals
- Lincoln Park
- Millennium Park
- Wrigley Field
- United Center
- Grant Park
- Navy Pier
- 875 North Michigan Avenue
- Soldier Field
- Six Flags Great America
- Humboldt Park
- Alpine Valley Resort
- Shedd Aquarium
- Guaranteed Rate Field
- The Field Museum
- Wicker Park
- Wilmot Mountain Ski Resort
- Lincoln Park Zoo
- Garfield Park Conservatory
- Oak Street Beach
- Frank Lloyd Wright Home and Studio
- Brookfield Zoo
- Willis Tower
- Illinois Beach State Park
- University of Chicago




