Holiday rentals with a hot tub in Cook County

Couples Getaway, Jacuzzi, Sauna, Pool is Open

Couples Getaway | Private Suite w/ Jacuzzi, Sauna, Pool & Gym Indulge in a luxurious, private retreat designed for couples! This beautifully styled guesthouse suite is attached to the main house but completely private—you’ll have your own private entrance for total seclusion. Enjoy spa-like relaxation with a jacuzzi, sauna, pool access, and a fully equipped gym. Perfect for honeymoons, anniversaries, or weekend escapes, our space blends comfort, privacy, and elegance for an unforgettable stay.

The Spa of Downtown Whiting

so close to Chicago but so far away. NEWLY REMODELED AND COMPLETELY FURNISHED. There's so much to enjoy in this incredible converted 2 flat, now a single unit. WE COMPLETELY RIPPED ON AND REDID THE ENTIRE INTERIOR. 1ST Flr-spa w/ 2 person jacuzzi, shower, continuous hot water, family room, kitchen 2nd flr, sitting room w/ TV and surround sound, 2 bedrooms, w/ bathroom and bath/shower. -FRONT BALCONY, -SPEAKERS THROUGHOUT -BLOCKS FROM THE BEACH & WOLFE LAKE -PERFECT LOCATION FOR PIEROGIFEST

Beachfront- Lake Michigan-Hot Tub-Heated Pool

Lake Michigan - Beachfront w/Heated In-Ground Pool- Hot Tub - Indiana Dunes National Park - Private Basement Guest Suite - 2 Bedroom/2 Bathrooms - Beautifully Decorated This guest suite has everything you need for a comfy and relaxing stay. Enjoy the 3-person hot tub, perfect for unwinding after a day of adventure. In the summer months, enjoy the heated, in-ground pool. Hiking, beaches and so much more await—and less than an hour’s drive to Chicago. Heated Pool Open from Mid-May to Mid-Oct.

SYLVIA's CHARMING & RELAXING COTTAGE

Escape to beautiful Miller Beach! It is in a very friendly community, and the charming cottage is located only a 5min walk from the stunning beach. This house has a very private deck with an outstanding view of the green scenery, and the jacuzzi is also ready to be jumped into throughout all seasons. Walks on the beach here are very relaxing, as you will find the sugar-like sand to be pristine. When you stay at this cottage, you will never want to leave! You will enjoy and relax here for sure!

Lakefront Hot Tub-Fishing-Kayak & Pool Table Suite

Very large guest suite w/3 separate areas. Just like your own apartment, just not your own entrance. Great for friends traveling together! ENTRANCE IS THRU THE MAIN PART OF THE HOUSE. This is just for the basement but you have complete privacy down there. Fenced-in yard, hot tub, patio, bbq, firepit, enjoy fishing or sitting watching the sunsets. Stocked lake, walking path, 3 parks! Check out the pictures to see all our home has to offer! Full kitchen,laundry room & yard are shared space

The Private Relaxation Oasis Near the Beach

Welcome to our spacious 4 bed, 3 bath oasis perfect to relax, entertain, family gatherings, friend reunions, beach vacations or corporate retreats! Our house boasts a large living room and rec room with a 75'' flatscreen TV, a dedicated workstation, a fully-equipped kitchen, and a cozy fireplace.The entertainment enthusiasts, enjoy a theatre area, reclining seats, pool table, arcade selection, & board games. The private hot tub is perfect for unwinding at night or cooling off during the day.

Fore! Peace & Love @ Golf House

Welcome to "The Golf House"! Our 4-bed, 3-bath home sleeps 8 people comfortably and, features an open living space with a stunning golf course view, a full kitchen, and a huge deck. Enjoy natural sunlight or the stars through the skylight both in the master bedroom and bathroom. The home has hardwood floors, and TVs in each bedroom. Plus, a heated meditation room for relaxation. Ideal for families, women retreats, networking events etc. Experience luxury and tranquility right by the greens!

Stunning modern home with a lovely backyard

Beautiful modern home in Evergreen Park, not far from Chicago! Features one bedroom, a sofa bed, and two full bathrooms. Enjoy a fully equipped kitchen perfect for home-cooked meals. Step outside to a private backyard patio with an inflatable hot tub(months of May-September: MUST REQUEST) and cozy fireplace, ideal for relaxing evenings. Experience the perfect blend of peaceful suburban comfort and easy access to all the excitement, dining, and attractions the city of Chicago has to offer!

Enchanted Garden Treehouse (Amenity*)

Summer's here, the treehouse air conditioned and cozy, and the hot tub ready! Relax in our luxurious, 420 friendly, very private, 4' deep cedar hot 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 stream makes this a wildlife refuge, with many birds, squirrels, rabbit & fox. Come experience the magic and make a special memory! See why Chgo Magazine rates us top 3 staycations in Chgo!

Cul De Sac Jacuzzi home | Near Chicago

🏡 Location • 35-minute drive from downtown Chicago • Near forest preserves and local attractions 🍳 Kitchen • Stove/oven • Fully equipped kitchen cookware • Complimentary snacks & drinks 🧼 Laundry • In unit wash and dry • Complimentary detergent 📺 Entertainment Indoor: • Air hockey table • Board games • Fireplaces • TV Outdoor: • Fireplace • Gas grill 🛀 Bathing • Jacuzzi in one bathroom 🛌 Sleeping • 1 futon, 2 twin size beds and 1 queen • TV's in all rooms

Entire Cozy Townhouse

Take it easy at this unique and tranquil getaway. Comfortable and convenient to everything. The lake is a 5-10 minute walk, and so are the grocery stores. The train is right outside the house, literally across the street. The CTA purple and red line trains run through the city and some suburbs. The train will take you to downtown Evanston in 10 minutes ...or to downtown Chicago in 20 minutes. Ask me about the bikes and cars available for rent. This property is not ADA compliant.

Fun game-room suite with hot tub & optional Yurt

Activities includes: PS5 Disc w/TV Xbox Series X w/TV Outdoor heated Jacuzzi 27' above ground pool Pool and Air hockey table Arcade machine with 12 games Life Size Connect 4 Board games Basketball machine Electric fire place Queen & full size beds Full size sofa pull out sleeper Gazebo with two twin beds (seasonal) Fresh Eggs with chickens seasonal Gas Grill-propane included Romantic Robe for 2 (in colder months must request) Event Yurt add on $225 up to 25 additional guest