Holiday rentals with a hot tub in North Side

4.85 out of 5 average rating, 313 reviews

Lux Urban 3BR/3BA Duplex + Parking!

LauraRating, 5 stars1 week 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, 117 reviews

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

AnneRating, 5 stars5 days ago

Matt was a wonderful host and very responsive. The house was exactly as described. It felt like a home away from home. Everything you need is provided for you. I was traveling with my teen sons and we enjoyed the hot tub each night and watched a movie while soaking and relaxing. The house is on the Southside of the city and which was a nice break from the buzz of downtown. The train is about a 20-25 minute walk and the White Sox stadium is right near there. I definitely recommend this place if you’re looking for a home in Chicago.

4.93 out of 5 average rating, 791 reviews

Treehouse in Schaumburg

Enchanted Garden Treehouse (Amenity*)

ShambhobiRating, 5 stars1 week ago

Daniel’s treehouse is a magical place!! From the lovely Japanese style garden to the hot tub - it was the best way to spend a little getaway near the city ❤️ will recommend with all my heart and cannot wait to come back again.

4.93 out of 5 average rating, 114 reviews

Condo in Chicago

The Fox Den

JamesRating, 5 stars2 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.

Top Guest favourite

Condo in Chicago

4.98 out of 5 average rating, 270 reviews

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

DawnRating, 5 stars4 days 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!

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What guests are saying

The Areal Oasis

4.9 out of 5 average rating, 42 reviews3 weeks ago

STAY HERE - no regrets. The apt building was easy to find with a pull thru drive to unload luggage and a lobby for my family to wait in while I parked. Parking was affordable and close by using the app as suggested, many within a 10-minute walk. Getting the key was easy and the apartment was clean and tidy, exactly as described. The city view was stunning, you can see Lake Michigan and on a very gusty morning we could see the massive wave whitecaps from the window. Plenty of household items available from plates and cups to linens and soap. The building was well maintained, safe and the residents friendly. The amenities (pool, gym, bball court, *jacuzzi was not open yet) and the rooftop lounge and views were all great! Stephanie was attentive and touched base a few times to check in, but we didn't need anything! Location is walkable to much of the city-the Willis tower, Millenium Park and the Shedd Aquarium/Field Museum. Train is close too! Target is literally next door- so handy!

Apartment in Chicago

What guests are saying

Superiorhaus Noble Square Sleeps 16 HotTub/RecRoom

4.98 out of 5 average rating, 52 reviews3 weeks ago

Tom was a fantastic host! Super responsive and helpful. His place was just amazing—gorgeous with so many amenities—hot tub, pool table, darts, etc. We had so much space to spread out and enjoy. The kitchen was extremely well-stocked-spices, condiments, cooking utensils. The location was great. We were a couple blocks from both the train and bus—so easy to pop on the bus to downtown-15 minute ride straight there. Parking was easy and excellent—a garage space as well as plenty of street parking with provided passes. Definitely recommend!!

Condo in Chicago

What guests are saying

Minutes to Wrigley Amazing Location - Sleeps 6

4.57 out of 5 average rating, 7 reviews2 months ago

I had surgery at the hospital around the corner and stayed here for few days as I couldn’t climb the steps to my apartment post surgery, highly recommend. There are two steps down into the apartment that I was easily able to handle, the shower in the back of the house has grab bars, and overall the house was very accessible and easy to navigate with my walker. Would stay again!

Apartment in Chicago

What guests are saying

Large Studio Apartment with no cleaning fee

4.82 out of 5 average rating, 11 reviews5 months ago

What a great stay! The boat was even better. He was immediately responsive and accommodated extra when caught in a pinch. He was very communicative and helpful. The place was very comfortable for both us and the dogs. It felt like home! Would recommend to anyone.

Apartment in Chicago

What guests are saying

Skyline Oasis: City & Lake Views

4.96 out of 5 average rating, 24 reviews2 months ago

Let me just say, the pictures don’t do this cute, cozy place justice! I’m big on hospitality and customer service, and Johana and Akos were beyond accommodating and communicative. I would dare to say this is the most accommodating place I’ve experienced so far! The space has such a good energy and flow to it — cozy, inviting, and with a beautiful sunset view from the kitchen window that you can enjoy right from the living room sofa. The views are stunning, and the building itself is upscale, clean, and even smells great! I enjoy playing some of the games that were pervaded( Uno and Jenga) and I appreciated that the TVs had all the apps, HBO, Disney, prime, Netflix etc. It’s in a great location, and I felt very safe throughout my stay. The only con would be some city noise, but it didn’t bother me at all. There’s a nearby train that doesn’t pass often, and again, it wasn’t an issue for me. I would definitely recommend this place!!

Apartment in Chicago

What guests are saying

Rooftop HotTub As Seen On "Married At First Sight"

4.85 out of 5 average rating, 53 reviews6 months ago

I booked this Air BNB for my girlfriend's birthday weekend and my surprise proposal! Ashlee was very responsive, super helpful, just an overall great host! She went out of her way to decorate the master bedroom for me with rose petals, tea lights, champagne and all! There were snacks in the kitchen, the place was clean and tidy, our group really felt at home! The vibes were everything, and so were the VIEWS from the rooftop!!!! Thank you Ashlee!!

Apartment in Chicago

What guests are saying

Luxurious 3BD Penthouse- Private Patio+Gym+Rooftop

5 out of 5 average rating, 6 reviews2 weeks ago

Avantika’s penthouse apartment was absolutely lovely. The space was comfortable and well-designed, with beautiful bedrooms and impeccably clean bathrooms. The kitchen was modern, spacious, and had everything we needed. Avantika was incredibly kind, helpful, and very responsive throughout our stay. We had a fantastic experience and will definitely be back!

Apartment in Chicago

What guests are saying

Luxury Penthouse w/ HOT TUB & Amazing Roof Deck

4.93 out of 5 average rating, 56 reviews3 weeks ago

James was a responsive host and the space looks just like the pictures, in a fantastic location in Chicago with easy walking to the L and all the great restaurants, bars, and shopping on Division and Milwaukee Ave. A few highlights: Our kids enjoyed the hot tub and though it is shared we didn’t see anyone else during our 1-wk stay. Plenty of space for the 6 of us with a nice open floor plan to hang out. The location was even better than I remembered, after living nearby about 10 years ago. James was very helpful and had clear instructions and typically responded in less than an hour. Some things to know: when we stayed there was a house next door getting gutted, and construction started at 6a on weekdays. Guests in the street-facing rooms may want white noise / earplugs esp if they are light sleepers. As other reviews state, the alley and garage space are tight. I’ve lived mostly in cities, but could not fit our minivan. There is some street parking a couple blocks away.

Condo in Chicago

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Holiday House Rentals with a hot tub

4.75 out of 5 average rating, 53 reviews

Home in Maywood

1610 Entire home for your visiting Chicago IL

EneidaRating, 5 stars4 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.

4.92 out of 5 average rating, 79 reviews

Home in Skokie

Quiet and welcoming house.

DeborahRating, 5 stars1 week ago

We stayed here for a family wedding in the Chicago area. Met all of our needs. Would stay again

4.93 out of 5 average rating, 72 reviews

Home in West Chicago

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

JesseRating, 5 stars2 months ago

We had a lovely ladies weekend. The place was perfect for a large social gathering, allowing space for both large groups to socialize together and for smaller groups to break off into other activities. The house also feels delightfully private down a long driveway. Worth noting that the driveway can be a bit hard to see, located just past a large hedge.

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Home in Bloomingdale

4.94 out of 5 average rating, 47 reviews

Whole House With Hot Tub And Spacious Bedrooms

KarinaRating, 5 stars1 week 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

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

AlexandraRating, 5 stars1 week ago

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

4.7 out of 5 average rating, 126 reviews

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

FarrariRating, 5 stars2 months ago

Pam and her property was an absolute joy. It truly was a peaceful experience. I definitely will be booking again.

4.84 out of 5 average rating, 50 reviews

Home in Palatine

Private Room w/ attached bath and personal kitchen

BrandonRating, 5 stars1 week ago

I stayed here for a couple of months for work and had a great experience. The place was equipped with all the necessary kitchen essentials, extra towels, and more. The neighborhood was very safe, quiet, and welcoming. Overall, I had a great experience.

Top Guest favourite