Vacation rentals with a hot tub in Near North Side, Chicago

4.85 out of 5 average rating, 314 reviews

A spacious living area features a blend of warm wall colors and modern decor. Comfortable seating includes a light-colored sofa and a wooden chair. A fireplace is highlighted on one wall, accompanied by a ceiling fan and natural light from large windows.

Home in West Town

Lux Urban 3BR/3BA Duplex + Parking!

LauraRating, 5 stars2 weeks ago

Our host was extremely tentative and helpful. We really enjoyed our stay at the home. It was big enough to accommodate our family plus a few other visitors, plenty of beds, plenty of living space so people didn’t have to be on top of each other. Very close to downtown and the blue line which made going to the airport and downtown much more accessible. we didn’t even have to rent a car.

4.96 out of 5 average rating, 119 reviews

A spacious hot tub is situated under a pergola, surrounded by wooden fencing. The water glows in blue, with bubbles visible. A flat-screen TV is mounted nearby, providing entertainment for guests while they relax.

Home in Bridgeport

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

ErikaRating, 5 stars1 week ago

Our time at Matthew’s place was phenomenal! Everything is as pictured, but the pictures doesn't do much just for how nice this house was. I'm an extreme clean freak when traveling, and usually bring my own cleaning products, but I had nothing to worry about here. If you're considering this home, DO IT!

4.93 out of 5 average rating, 792 reviews

A treehouse elevated above ground showcases a wooden exterior with a balcony. An inviting staircase leads to the entrance, surrounded by lush greenery and vibrant leaves creating a natural setting. The sturdy structure is supported by wooden beams, blending harmoniously with the surrounding trees.

Treehouse in Schaumburg

Enchanted Garden Treehouse (Amenity*)

Maggie JeanRating, 5 stars6 days ago

We stayed one night in Daniel’s treehouse and it was AMAZING! I was hesitant with it being in a neighborhood, but it truly felt so private and like we were surrounded by nature. The koi pond with the fish was so fun, we loved the hot tub at night and also sitting by the fireplace. Daniel was responsive and gave us all the information we needed. Highly highly recommend!!

4.93 out of 5 average rating, 115 reviews

A retro-style kitchen features teal appliances, including a refrigerator and a stove. White cabinetry with glass inserts is complemented by a tiled backsplash. Warm wood surfaces add contrast to the space, with smooth flooring and ambient lighting creating a bright and functional cooking area.

Condo in Lincoln Square

The Fox Den

JamesRating, 5 stars3 weeks ago

This place was great from the balcony to the fenced in area behind the house. Parking was easy and free on the side streets. The retro appliances really stood out in the kitchen. Wonderful are for dogs to go out easily and safe to be able to walk them. A few parks nearby. Great place to stay with lots to do within walking distance.

4.94 out of 5 average rating, 199 reviews

A hot tub with bubbling water is illuminated by soft blue lights, surrounded by wooden fencing. String lights overhead add a warm ambiance, creating a serene outdoor space for relaxation.

Condo in Little Italy

Private hot tub - King bed suite - Free parking

MarkRating, 5 stars2 weeks ago

what a great location! walkable to great restaurants, breakfast, lunch and dinner. nice private area by the hot tub. was an amazing experience and I cannot wait to return. Cody was super responsive, we had a last minute shuffle and he was able to accommodate it at a more than reasonable cost. would recommend!

4.96 out of 5 average rating, 135 reviews

An outdoor patio is showcased, featuring a rectangular fire table surrounded by four cushioned chairs. The wooden decking contrasts with the subdued colors of the furniture. A partial cover is draped over one corner, providing shade from the sun.

Condo in West Town

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

JadenRating, 5 stars4 days ago

Absolutely loved Cynthia and Thomas's place! They were proactive in their communication and responded promptly. The space itself was beautiful and very clean upon arrival. I loved the small balcony area and the bathroom! The bathroom itself was worth the price for an amazing shower and spa experience. The house was so peaceful and quiet, but it was also located near so many things to do. Definitely looking forward to staying again in the future!

4.98 out of 5 average rating, 270 reviews

An elegantly furnished dining area features a wooden table with a textured runner. Dark leather chairs surround the table, and a modern chandelier hangs above. The open kitchen, equipped with stainless steel appliances and bar seating, is visible in the background.

Condo in Logan Square

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

DawnRating, 5 stars1 week ago

What an unbelievable find! This garden apartment is an 8 minute walk to my daughter’s apartment! I was looking for a place close to hers for a weekend visit. This place was perfect and it had a garage to park my car in! The interior was pristine. Beautifully decorated, the bed was comfy, big beefy towels for the shower, and you wanted for nothing! This place was fully stocked with necessities! I would recommend this place to anyone looking for an extremely nice stay in a great neighborhood with the added security of a garage to park in! Oh and there is a nice patio in the back yard if you want to sit outside on a nice day and relax! I will definitely be coming back the next time I come to visit! Thanks Bryan!

Apartment in Belmont Cragin

A hot tub is positioned in a vibrant game room, surrounded by colorful murals depicting a beach and lively graphics. Water glistens in the tub, inviting relaxation and enjoyment after a day of activities.

4.98 out of 5 average rating, 105 reviews

Belmont Pleasures - hot tub / arcade gaming room

TaraRating, 5 stars2 days ago

What could I say… the place was amazing!! My grandson and his friends had a terrific time. Me and my family enjoyed the couple for days we stayed here, the amount of things you can do in the house was amazing, will definitely will be booking all my grandkids parties here.

Vacation rentals for every style

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Popular amenities for Near North Side, Chicago hot tub rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a hot tub

4.75 out of 5 average rating, 53 reviews

The exterior of a two-story house is showcased, featuring a set of wooden steps leading to a porch. A grassy area surrounds the house, which is framed by landscaping. A barbecue grill is positioned near the base of the stairs.

Home in Maywood

1610 Entire home for your visiting Chicago IL

EneidaRating, 5 stars5 months ago

House was easy to find. It was very nice and clean. About 15 minutes to downtown. Will highly recommend. I will definitely be staying again.

4.93 out of 5 average rating, 81 reviews

A cozy brick facade is showcased, featuring a sunroom with large glass windows and a well-maintained lawn. Pathways lead to the entrance, surrounded by lush greenery and neatly trimmed hedges, creating a welcoming outdoor atmosphere.

Home in Skokie

Quiet and welcoming house.

JustinRating, 5 stars6 days ago

Tsegie was gracious, responsive, and helpful. The home had every amenity listed, and the neighborhood was quiet with plentiful street parking. A few areas needed cleaning, but Tsegie had the housekeeper over within an hour to address. There were plenty of towels and linens, and my two kids (5 and 2.5) loved the backyard, which is spacious and fully fenced. Checking in and out was a breeze, and there was a fantastic new TV (75 inch?) with a soundbar for a cozy and entertaining living room. The basement is huge with an open floor for more kid-friendly play space, and a jacuzzi tub in the bathroom that was also a hit with the kids. A few items could use attention, like a few out light bulbs, a tub that needs paint, and a broken drawer. But overall, the place was in good shape. There were holiday decorations out, but other than that, the pictures were accurate. Very well regulated thermostat had the temp perfect throughout. I recommend this rental for families or those needing extra space.

4.94 out of 5 average rating, 48 reviews

A spacious basement game area features a classic pool table with a vibrant green felt surface, complemented by cues and an arranged set of colored balls. Nearby, a seating area with leather couches and an arcade machine is visible along the wooden-paneled wall.

Home in Bloomingdale

Whole House With Hot Tub And Spacious Bedrooms

KarinaRating, 5 stars2 weeks ago

Amazing stay! This place has everything you need for both short and long visits. The location is extremely safe and convenient with shops within walking distance. My family and I thoroughly enjoyed the entire property, especially the game room and TV room which were perfect for entertainment. Moiz, the host, was very kind and quick to respond to any needs we had. Thank you for everything! We would definitely stay here again

4.79 out of 5 average rating, 39 reviews

A spacious living area is highlighted by large windows allowing natural light to fill the room. A modern sectional sofa sits adjacent to a glass coffee table, while a dining area with elegant chairs and a chandelier completes the setting. Unique wall art adds character to the space.

Home in Logan Square

5BR/4BA Home - Theatre, Hot Tub, Sauna, Rooftop!

AlexandraRating, 5 stars2 weeks ago

This house was so beautiful and hosted my friends and I for my birthday. It was everything I hoped for!

4.88 out of 5 average rating, 72 reviews

A three-story house features a welcoming entrance surrounded by greenery. The front patio holds steps leading to the main door, with elegant glass doors partially illuminated by soft lighting. A decorative fence encloses the property, enhancing privacy while showcasing the well-groomed landscaping.

Home in Lake View

Entire house in Lakeview with yard and garage

AnnieRating, 5 stars1 week ago

The absolute best location for all that Chicago has to offer. With a family of 6 it’s rare to find a place where everyone can fit… even the dog:)

5 out of 5 average rating, 6 reviews

An open living space is highlighted by a stone fireplace and a large television mounted above it. A comfortable sectional sofa surrounds a round coffee table, while natural light fills the room through large windows. A dining area can be seen in the background.

Home in Homewood

Fore! Peace & Love @ Golf House

TamiekaRating, 5 stars4 months ago

Michael & KP’s place was amazing! Communication was excellent! My family and I absolutely loved our time here. The Christmas Tree and Decor were beautiful!! There was more than enough room for everyone to be comfortable. Michael & KP were amazing went above and beyond. Every room had a tv including the kitchen which was awesome. There was a nice selection of games in the game room for the family to enjoy. My family and I created beautiful memories here! Thank you guys for hosting us. Overall an A+ and we will be returning.