Vacation rentals with outdoor seating in Highland Park

Enchanted Garden Treehouse (Amenity*)

Summer is here, flowers are blooming, the treehouse is air conditioned and cozy, and the hot tub ready! Relax in our luxurious, very private, 4' deep cedar hot/cool tub nestled in the evergreens, while the moon and stars swirl overhead, the waterfall tumbles into the koi pond, and the fire table and torches blaze. The running stream makes this a wildlife refuge, with tons of birds, squirrels, rabbits, foxes and hawks. We are 420 friendly. Come experience the magic and make a special memory!

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.

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.

2-Acre Highland Park Retreat with Heated Pool ~ 5*

Experience luxury of this award winning 6BR 4Bath family home in picturesque Northshore private estate. Spend day by the private heated pool, enjoy beauty of gardens, explore local landmarks, starting with the gates of neighborhood Michael Jordan estate. The stylish design and rich amenity list will leave you in awe. ✔ Two-Acre Estate ✔ 6 Comfy BRs ✔ Multiple Living Areas ✔ Full Kitchen ✔ Backyard (Pool, Lounges, BBQ) ✔ Smart TVs ✔ High-Speed Wi-Fi ✔ Free Parking See more below!

The Vanderpool House

The Vanderpool House has a Private Suite in a historic 100 year old Chicago Bungalow just 2 blocks away from the 2nd largest transit center in Chicago. The Blue Line L stop will take you downtown, the airport, or the Rosemont Convention Center. The Metra train will take you downtown or the northwest suburbs and you have 13 bus lines will take you anywhere else. Onsite parking is available at no extra charge. Theaters, Neighborhood Restaurants, Art Museums within walking distance.

Spacious Garden Apartment with Sauna and Fireplace

English garden apartment in historic Wilmette home with a private entrance, sauna, washer/dryer, kitchenette, dining area, recreation room with pool table, vintage pinball machine, and a wood-burning fireplace with gas igniter. Two queen beds, 1 full-size sleeper sofa, and a single mattress are available for large families. Ideal access to Northwestern University for all events. **Please note the apartment is located on the garden level and does NOT include the entire home.**

Cozy Neighborhood Escape | Near NU-Chicago-Beaches

This is a beautiful, newly renovated apartment that is cozy and contemporary! This unit is located in Evanston’s arts district, surrounded by local shops, tree lined streets, and is a short distance to restaurants, the lakefront, and Northwestern University. Evanston is a suburb just north of Chicago with easy access to the city either by car or public transit. This apartment sleeps up to 4 people and is a 1 bedroom, 1 bath with a sofa sleeper. Don’t miss out. Book Now!

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.

Near Northwestern | Chicago-Sunny & Serene Airbnb

Spacious & private 1 bedroom /1 bath guest suite, with backyard/patio access. Private entrance and walkway with keypad entry. This suite is attached to a single family home. One comfy bedroom, one bath, kitchenette with amenities, (no stove or kitchen sink) sun room/breakfast bar, laptop friendly workspace with desk, wi-fi, relaxing living area. Full cable package. Queen air mattress is available No pets allowed. The home is not wheelchair or ADA compliant.