Pet-friendly holiday rentals in Highland Park

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!

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.

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.

New 3bd/1.5 bth Apt w/private prkg

A perfect hideaway! This quiet, secluded unit is nestled in lush greenery within walkng dist (1.5M) to NWU. Enjoy our renowned restaurants and theaters, plus easy access to downtown Chgo’s many attractions via the Metra; Sleeps up to 7 guests, with 2 queen beds, 2 single beds, and an 8-foot couch in Liv rm; Ultra-modern kitchen equipped with everything; Dedicated parking space in rear of the bldng; free high-speed Wi-Fi is included. Host lives nearby and responds promptly to any inquiries

SW Evanston Private, Stylish, Spacious Suite

Comfort and convenience abound in this stylish suburban suite! Mid-century and vintage motif meets modern touches and style. Guests have the entire basement, with a private bedroom, bathroom, huge living space, and a private entrance in a quiet house on a beautiful treelined street. Backyard access, coffee, easy street parking. Walking distance to parks and public transportation, a short drive to downtown Evanston and the lakefront, easy access to Chicago, Northwestern. Loyola, Skokie.

TheGlassCabin @ HackmatackRetreat

The Pond House, a vintage glass cabin filled with art, water views & eclectic vibes privately perched on the sacred grounds of Hackmatack Retreat Center. Native prairie, a winding slow river, two ponds, 200+ year old oaks & big sky- Countless places to curl up, gathering, focus-- nooks and crannies indoors and out, we offer “time out for time in” amidst this noisy world. Minutes from 2 small towns, all amenities, we're all about peace & ease-- let us custom curate your experience !

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.

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.**

Lovely top floor 2BR/2BA, steps from everything!

BEST LOCATION IN LOGAN SQUARE/AVONDALE! Brand new stylish TOP floor 2 bed/2 bath located in the heart of the highly desirable Avondale neighborhood. This luxurious space is situated 15 minutes drive to Wrigley Field, 7 minutes walk from the CTA Belmont Blue Line, only minutes away from O'Hare airport, downtown Chicago and The Loop. Conveniently close to expressway. Steps from award winning restaurants, popular bars, great coffee shops, clubs, galleries and exclusive shops.

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

Welcome to our cozy and comfortable Airbnb, perfectly located near Naval Station Great Lakes (approximately 5-7 min., 2 miles), Six Flags Great America, and just an hour from downtown Chicago! Whether you're visiting for Navy graduation, family time, business, or a weekend getaway, our home offers the perfect balance of convenience and relaxation. We take pride in providing excellent hospitality and a smooth, stress-free experience from check in to check out.

Victorian House in Heart of Rogers Park

Newly restored Victorian house giving you a touch of Chicago's history with modern comfort. Feel at home away from home with fully equipped kitchen, entire house, and outdoor spaces with beautifully landscaped garden for lounging, grilling, and chilling. Large screen TV in living room and TVs in each bedroom. Fast Wi-Fi throughout the house. Walking distance to public transit, restaurants, bars, beach and shopping. Designated parking. #TheCatalpa

Historic Downtown Libertyville Loft

Enjoy a stylish experience at this centrally-located 1600 square foot place. Located in the heart of Downtown Libertyville, half way between Chicago and Milwaukee. Close to Six Flags, Great Lakes Navy Base, Lake Michigan beaches, forest preserves, train station and the Chain of Lakes. Downtown Libertyville is a trendy town offering several restaurants, shops and fun events. Book one of the only units truly Downtown Libertyville.