Holiday rentals in Cook County

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Top-rated holiday rentals in Cook County

Guests agree: these stays are highly rated for location, cleanliness and more.

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Guest favourite

Cabin

4.95 out of 5 average rating, 101 reviews

Cozy Log Cabin Near Indiana Dunes & Lake Michigan!

Less than 10 minutes from Indiana Dunes National Park and Lake Michigan, our beautiful log cabin sits on 2 acres while still being in the heart of Portage! Our large front deck overlooks state land giving a beautiful, private view out of our large windows. Our cozy cabin has 3 bedrooms and 3.5 bathrooms with fun, thoughtful touches for your family including video game consoles, movies, books, a LOT of games, a pool/ping pong table, 2 fire pits, and more! Age limit: 25+ years old Sorry no pets

Superhost

Home

4.57 out of 5 average rating, 23 reviews

Amazing Summer Pool Awaits You!

Vacation, Staycation or Business, you will love your stay at this beautiful paradise with heated pool and tri-level entertainment deck equipped with grill and outside seating and gazebo! Semi-secluded backyard, walking distance to bike path, playground, skate park, walking trails, restaurants and even the gym! Relax on the magnificent deck while watching the sunset This home is pet free and smoke free. Pool is available May-Sept. WiFi is available throughout and Smart TV in the family room.

Guest favourite

Flat

4.94 out of 5 average rating, 154 reviews

Sun drenched 2 bedroom 1 bath with Kitchen & W/D

Welcome to beautiful Roscoe Village! Come relax and enjoy a gorgeous loft-like condo that has a huge sun-drenched living room and opens up right to the kitchen. Enjoy cooking on your own in the spacious kitchen and rest easily at night in a spacious king bed in the main bedroom. We love and welcome pets - so no need to leave your fur baby at home. Uber to Wicker Park and Logan Square. You’ll have your own private entrance with a lock box to get into the condo. We look forward to hosting you!

Guest favourite

Cottage

4.92 out of 5 average rating, 50 reviews

Miller Beach Cozy Cottage with indoor fireplace

Have fun with the whole family at this stylish place. Have fun with your friends. Have a quite time if you need to escape from a crowd. Just simple as it is. Just enjoy being here, in a modern costal farmhouse loaded with almost everything you need for perfect and relaxing getaway. Please be a guest of our lovley restaurants, brewery, be a visitor of our small downtown, explore the beaches, dunes, and hiking trails of Lake Michigan and surrounding areas! Only 45min from Chicago!

Superhost

Home

4.9 out of 5 average rating, 108 reviews

Sunset beach house

Super beach location ,3 bedroom , 2 bath house with amazing view of the lake, 6 person hot tub open Sep-Nov, Apr-Jun, beach access, 100 steps from water Bright, sunny, dining in a sun room with the view of the lake. First floor two large bedrooms, bathroom ,gourmet kitchen, large living room, gas fireplace, dining room. Lower level -large smart tv in family room with comfortable sofa , big bedroom, bathroom and washer/dryer , grill, fire pit Do not accept pets and ESP due to allergies

Superhost

Flat

4.91 out of 5 average rating, 11 reviews

2-level PH w/ 2 Luxe Suites Combined; Spa Access

The top floor sprawling ranch with duplex down offers sky & outdoors views, privacy, & cathedral ceilings, it is connected to your rear 2nd floor suite with 10ft ceilings. A burgeoning neighborhood next to the 606 Trail Amenities: -Uber-fast Wifi streaming, -Hot tub house - 80" + 75" hi-def tv's - 3 sectional couches for living - Designed for an aristocratic feel - The touristy 606 Trail access 100ft away, - YMCA across the street with indoor Olympic size & kiddie-pools!

Superhost

Home

4.91 out of 5 average rating, 118 reviews

Peaceful & Private Hot Tub Vacation Home Getaway

A Rare gem 💎in the heart of Homewood. This Quaint 2-bedroom remodeled home is charming, sophisticated and discrete. It is minutes away from the Metra station, golf course and downtown Homewood shops. The energy is very calm and quiet ☯️. This is the home away from home where details are everything and the pictures do not capture the essence of this luxurious space. Experience the love, the joy and the peace that continues to leave its mark. Peace and Love - Michael and KP💞

Guest favourite

Home

5 out of 5 average rating, 8 reviews

Alluring Avondale Abode

Welcome to Alluring Avondale Abode, the perfect vacation rental for your next family trip or group getaway. A pet-friendly paradise, centrally located for easy travel to all the top attractions. A spacious kitchen, beautiful backyard deck, and patio create a wonderful backdrop for entertaining and relaxing. Find an array of fun games to keep all ages occupied. Book now and experience the laid-back vibe and unbeatable amenities that will make your vacation truly unforgettable.

Guest favourite

Flat

4.89 out of 5 average rating, 9 reviews

Miller Beach FairyForest Retreat

Escape to a whimsical retreat nestled atop the Indiana Dunes. Walk to the beach, only 3 blocks. Our mid-century modern three-bedroom apartment boasts a magical fairy forest theme, enchanting guests from the moment they arrive. Perched on a sand dune within the bio-swale ecosystem, each room offers treetop views. The true gem is our sprawling 400sqft screened porch, an elevated haven that immerses you in the tranquility of the woodland, evoking the sense you’re in a treehouse

Superhost

Home

4.93 out of 5 average rating, 134 reviews

Bayless Dune Lodge at West Beach - Indiana Dunes!

Bayless Dune Lodge at West Beach is a gorgeous, Lodge-themed home in Miller Beach, Indiana, a scenic community surrounded by the Indiana Dunes National Park! A short walk to one of the finest white sand beaches on Lake Michigan, the Lodge sits on nearly half an acre of land nestled into the "Bayless Dunes Nature Preserve." The property boasts a heated, in-ground swimming pool, pool-side lounge area, two outdoor dining areas, two spa-quality bathrooms and more!

Guest favourite

Home

4.96 out of 5 average rating, 48 reviews

Paradise in Schaumburg Low Cleaning Fee, 3 BR, 4Bd

Welcome to this inviting 3-bedroom, 1.5-bathroom home in a very safe and quiet neighborhood. Enjoy the tranquility while being close to all shopping, restaurants, and entertainment options. The spacious interior includes a bright living area and a functional kitchen. Additionally, an indoor park nearby offers a great place for year-round recreation. This home combines comfort, convenience, and a prime location, perfect for families and individuals alike.

Guest favourite

Campervan/Motorhome

5 out of 5 average rating, 8 reviews

Relaxing*1BR/1BA*Mini Golf*Fishing*Bands*Boating

🏕️ Cozy Queen Camper in a Gated Resort Community! 🎣🎉 Escape to our comfortable and cozy queen bedroom camper nestled in a gated resort community. Whether you're here for adventure or relaxation, there's something for everyone! With activities like fishing 🎣, boating 🚤, gaming 🎮, sports 🏀, mini golf ⛳, and even a private beach 🏖️, you're guaranteed a fun-filled stay. Enjoy live bands 🎶 and themed weekends 🎭 – there's never a dull moment.