Holiday rentals with a hot tub in North Side

4.85 out of 5 average rating, 317 reviews

Lux Urban 3BR/3BA Duplex + Parking!

**PLEASE READ FULL DESCRIPTION BELOW AND CLICK "CONTACT HOST" BEFORE REQUESTING A BOOKING** Downtown urban designer home near Blue Line subway (direct to Loop or O'hare), Salt Shed Theater, Michigan Ave., United Center & nightlife. Perfect for families, business groups, or modern travelers which can sleep 12+. Spacious duplex unit with huge deck in trendy, central River West neighborhood. Walk to restaurants, cafes, nightlife. 2 subway stops to Loop, 40 minutes direct to airports. Parking avail!

4.96 out of 5 average rating, 123 reviews

Modern Lux Getaway w/ Hot Tub, Lrg Yard, Parking

1 King, 1 Queen, 1 Sofa Bed, 2 Air Mattresses (1 Full, 1Queen) 1 Pack n Play Enjoy your stay in this cozy modern home that sits on an oversized lot with luxury amenities and a spacious front yard with exceptional landscaping. The property has a car port in back which allows parking for 2 cars. The ideal getaway to grill up some food and relax in the jacuzzi hot tub year round! We are pet friendly! NO CHORES! Please reach out with any questions you may have before booking Hot tub 5-6 Person Spa

4.85 out of 5 average rating, 156 reviews

Home in Whiting

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

4.93 out of 5 average rating, 804 reviews

Treehouse in Schaumburg

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!

Guest suite in Riverwoods

4.96 out of 5 average rating, 402 reviews

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.

4.88 out of 5 average rating, 311 reviews

Guesthouse in Chicago

Private Coach house near Lincoln Square!

Lovely 625 Sq Ft detached, single-story coach house(100 years old) located in Bowmanville, nestled between Andersonville, and Lincoln Square. This little piece of heaven offers the privacy of a detached home with a fenced oversized yard perfect for puppies to run around in or enjoy a beer from one of our many local breweries. The house provides a full-size kitchen and bath with a walk Less than 1 mile to the closest CTA and 1.5 from Wrigley. Pets Allowed! Bathroom/Shower updated Feb 2025!

4.92 out of 5 average rating, 36 reviews

Apartment in Chicago

2Bed 2Bath 15min to Wrigley with Parking& Balcony

Discover our 1200 sqft condo in Irving Park. Ideal for families and pet-friendly, it features 2 queen beds, 1 sofa bed, 1 air mattress, 2 newly renovated baths (one with jacuzzi), & a private balcony. In-unit laundry and a dedicated parking spot are included. The bus stop in front takes you to the lake at Montrose Beach in 15 minutes. 10 minute by bus or car to Wrigley Field. Walk to the Blue Line subway, parks, convenience stores, and restaurants. Your Northside Chicago retreat awaits

4.94 out of 5 average rating, 208 reviews

Condo in Chicago

Private hot tub - King bed suite - Free parking

Welcome to this urban retreat in the heart of Chicago's Little Italy neighborhood. Conveniently located adjacent to Chicago's downtown Loop and West Loop neighborhoods, you will find endless opportunities to experience the best of Chicago. At the end of your day, enjoy a relaxing soak in your private outdoor hot tub (open year-round) before sinking in to your Tempur-Pedic king bed for a restful night's sleep. Complimentary off-street parking provides rare convenience near the city center.

4.97 out of 5 average rating, 146 reviews

Condo in Chicago

Downtown Chicago - Spa Bath, Patio, 3 blocks to L

Explore Chicago's charm just moments from downtown! This Airbnb boasts a spa bath with a luxurious rain shower and jetted tub, a fully equipped kitchen for culinary adventures, comfortable reclining sofas for relaxation, and ample space to unwind. Sleep like royalty in the master bedroom's king bed, and a queen murphy bed in the living area ensures a comfortable stay for up to four guests. Step outside to the patio with a fire pit for cozy evenings. Your Windy City getaway begins here!

4.98 out of 5 average rating, 278 reviews

Condo in Chicago

Urban Luxury 1BR/2BA Logan Square Condo w/Garage

Luxurious 1BR/2BA garden-level condo in vibrant Logan Square! Comfortably furnished with tons of light and amenities, conveniently located one block from the Logan Square Blue Line Station and located on a quiet street. Steps from all of the hip restaurants and nightlife in Logan Square. Huge back yard and patio with fire pit for guest use. Free on-site garage parking with remote. And, if using public transit, the Logan Square is 8 stops, ~15-20 minutes from the Loop downtown!

4.92 out of 5 average rating, 107 reviews

Home in Carol Stream

Lake House Hot Tub-Billiards-Kayak Waterfront Stay

Our beautiful home is the perfect place to gather with friends & family, relax, refresh, fish, have fun with your loved ones. It's the perfect home away from home with great views of the lake and on a quiet cul-de-sac. Stunning views of the lake while grilling or the firepit from the completely upgraded patio & the hot tub 🥂 🐶Up to 2 furry babies are allowed & they'll love the almost 1 acre fenced-in yard! (pet fee is extra & must be included at time of booking)

4.98 out of 5 average rating, 119 reviews

Apartment in Chicago

Belmont Pleasures - hot tub / arcade gaming room

Welcome home! If you’re looking for a unique experience to enjoy with your friends and family come have some fun in this beautiful luxury home, located in belmont-cragin neighborhood Chicago IL 60634 The spacious house includes 3 bedrooms, 4 full bunkbeds , 2 queen beds , 2 sofa queen beds , 2 & 1/2 bathrooms . Whether you’re looking to book for a birthday, bachelor/bachelorette gathering, or trip with family and friends, this place has something for everyone.

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Holiday House Rentals with a hot tub

4.93 out of 5 average rating, 86 reviews

Home in Skokie

Quiet and welcoming house.

SupatchaRating, 5 stars2 weeks ago

We had a great stay at Tsegie’s beautiful home. The house was not only very clean and well-maintained, but also tastefully decorated and comfortable. It’s located in a quiet, safe residential neighborhood with friendly neighbors — perfect for those who have a car, as there’s plenty of free street parking available. Tsegie is a professional and responsive host — very kind and easy to communicate with. We especially appreciated the spacious basement, which was great for indoor activities without disturbing anyone. Our toddler loved the front lawn — it became his favorite play area during the stay. If you're visiting Chicago with a car and prefer a peaceful, suburban atmosphere, this is a wonderful option. I was traveling with a young child and felt very safe and comfortable here. We’d love to stay in this area again on our next trip.

Superhost

Home in West Chicago

4.93 out of 5 average rating, 74 reviews

6 Bedrm/3 Bath Retreat/Reunion, Hot Tub, Fireplace

Eva MarieRating, 5 stars1 month ago

We were a group of 13 women and 5 children, and this location was perfect for us. It was quiet, beautiful, and had enough beds for everyone. The kids had a great time in the tree house and yard, the kitchen was well suited for our meal prep, and the home, was clean and neat. We never heard or saw our hostess who stays on the property, but she communicated by message as needed. The driveway was hard to spot on arrival, but once we knew where it was it wasn't a problem. I would recommend this home for a large group and would stay there again, myself!

4.92 out of 5 average rating, 52 reviews

Home in Bloomingdale

Now Open: Heated Pool with Entire House

AmyRating, 5 starstoday

Really great place to stay, super responsive host! The pool was pretty great and so was the hot tub! Great location too, lots of stores, restaurants around, and parks like the Busse Woods (it’s huge and lots of walking paths)!

4.86 out of 5 average rating, 77 reviews

Entire house in Lakeview with yard and garage

AnhthuRating, 5 stars1 month ago

Loved our stay at Arturo’s place. The location was super convenient and only a 10 minutes walk to the red line. We were able to grab coffee and food within a 5 minutes walk. We will definitely stay again if we’re in town.

Superhost

4.88 out of 5 average rating, 56 reviews

Luxury Loft with Private Pool and Movie Theater

RyanRating, 5 stars1 week ago

Damani was a great host, really responsive and easy to communicate with! The house was exactly as advertised and really nice! The pool was great!

Superhost

4.69 out of 5 average rating, 128 reviews

6-Bed Family Mini-Mansion for 12 Parking & Hot Tub

AnastasiaRating, 5 stars1 month ago

I truly fell in love with this home. Spot on with the photos and descriptions. Very easy to communicate with Pam, and she offered as much assistance a needed, if needed. If you have a larger group needing accommodations this is a great space. The location was very close to the expressway and is 30 minutes from Navy Pier and downtown Chicago.

4.93 out of 5 average rating, 72 reviews

7 Bed Oasis with 5 Baths, Hot Tub, Sauna, Game Rm

TiokoRating, 5 stars2 months ago

Patty was extremely responsive prior to our visit to Chicago, during and post our stay. She also immediately addressed and resolved our cosmetic and minor concerns. Patty was beyond accommodating, kind, accessible, and understanding of our needs and expectations as we were traveling from three different states and with family members ranging for the age of 3 to 85. We booked this Airbnb for our family of 16 for Easter weekend and EVERYONE loved it. It was important that our elders were comfortable, safe and enjoyed themselves, they were sooo impressed and happy. The space is huge and perfect for entertainment. There are a ton of activities available and enough room for everyone/couples to have their own bed/room. With 1.5 kitchens including two stoves, it was convenient, as we cooked breakfast, lunch, and dinner each day in large quantities. The home was beautiful, comfy and we felt right at home! We highly recommend and can’t wait to book this Airbnb for our next trip to Chicago!