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Holiday rentals with breakfast in South Side

Find and book unique Holiday Accommodation with Breakfast on Airbnb

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Popular amenities for South Side Holiday Accommodation with Breakfast

Holiday House Rentals with breakfast

Guest favourite
Home in Gary
4.95 out of 5 average rating, 173 reviews

Kayaker’s Dune Cottage

MariRating, 5 stars1 month ago
This was a great kid friendly place to stay. Michael's dad brings fresh baked muffins. There is access to a water way in the back yard and across the street a beautiful trail to the dunes. Lots of games and things to do in the house.
Superhost
Home in Chicago
4.86 out of 5 average rating, 65 reviews

◆◆◆ Work, Play, Eat | 5B/3BA Near Everything ◆◆◆

PhoolRating, 5 stars2 months ago
FANTASTIC!! Great host! Awesome location! Clean house with everything needed available.. my kids loved the house, it felt like home away from home. Peaceful … Wish I could give more stars than 5!!!
Superhost
Home in Chicago
4.56 out of 5 average rating, 135 reviews

Huge 2 Story Home/7miles from Downtown Chicago!

CrystalRating, 5 stars1 day ago
My family and I enjoyed our stay, if you can look past the neighborhood(that wasn’t extremely bad) it was a very welcoming stay. I would book with Kevin for future visits
Guest favourite
Home in Chicago
4.99 out of 5 average rating, 79 reviews

Luxe SFH Bucktown Retreat with Garage Parking

JacquieRating, 5 stars3 months ago
The home was beautiful, clean, easily accessible and located in a great area. We had many options for restaurants within a few minutes drive. Easy access to downtown for exploring. Very comfortable amenities and well stocked kitchen. We would stay here again!
Superhost
Home in Bolingbrook
4.73 out of 5 average rating, 22 reviews

Private 3BR w/ Backyard | LCP Collection

CarltonRating, 5 stars10 months ago
this was a great place lovely 😍 will book again and who ever reading this should book to
Superhost
Home in Chicago
4.82 out of 5 average rating, 11 reviews

Cozy 4-Bedroom House with Patio

RodrigoRating, 5 stars6 months ago
Tudo perfeito, Thatheu é um excelente anfitrião, sempre responde rapidamente, a acomodação é perfeita, com uma estrutura excelente e a localização é muito boa, pois tem ônibus e uma estação de metrô bem pertinho que leva ao aeroporto e também para os principais pontos turísticos da cidade. Thatheu deixou água, leite e outras coisinhas, super gentil. O bairro é muito tranquilo, com boa estrutura de restaurante, mercado, lavanderia, dollar tree…
Guest favourite
Home in Westmont
4.89 out of 5 average rating, 84 reviews

Pretty Westmont Cottage & enclosed yard fenced.

PeterRating, 5 stars6 days ago
Attentive host who still respected our privacy. Nice co,y place in a great location/neighborhood
Superhost
Home in Gary
4.91 out of 5 average rating, 75 reviews

Laurna Dune

JennaRating, 5 stars1 day ago
Wonderful stay. Angela’s place was very welcoming, clean, and had everything we needed and more. The beds were super comfortable we slept just as well as we do at home. Check in and check out was incredibly smooth and we would definitely stay here again. Highly recommend if you’re visiting Gary!

Apartment rentals with breakfast

Guest favourite
Apartment in Chicago
4.79 out of 5 average rating, 296 reviews

Cozy Garden-Subterranean Apartment

SusannaRating, 5 stars2 weeks ago
Wir hatten einen sehr schönen Aufenthalt bei Jenny. Die Wohnung hatte alles, was man braucht. Man kommt bequem mit den Öffentlichen Verkehrsmitteln in die Innenstadt und zum Flughafen. In der Nähe ist ein Supermarkt und die Gegend ist schön und ruhig.
Guest favourite
Apartment in Stickney
4.86 out of 5 average rating, 14 reviews

Near Midway Chicago- B & B

MarioRating, 5 stars2 months ago
Our stay here was an amazing experience! Would definitely stay here again! The area is very safe! The location felt like home! And so close to Chicago downtown. It was clean and met all of our standards! Alex was very friendly and always checking in on us to see if we needed anything else and made sure we were comfortable. The home had all the things we needed for a comfortable stay. Highly recommend this place for anybody that’s looking for a location close to downtown but still have that quietness away from the noisy city.
Superhost
Apartment in Chicago
5 out of 5 average rating, 7 reviews

Family-Friendly 4BR in Lincoln Park, Safe Area

CathyRating, 5 stars4 weeks ago
We had a great stay. Very safe location and in walking distance to many places. The unit was very clean and had enough room for all of us. We liked that there was a fitness center that we could use. Our host was very responsive and friendly. We would happily rent from them again.
Guest favourite
Apartment in Chicago
4.96 out of 5 average rating, 171 reviews

Decompress on a Sophisticated Chaise at a Glamorous Hideaway

JaimesonRating, 5 stars1 month ago
Enjoyed my getaway at this beautiful airbnb! Very clean and cozy. Simida was very friendly and her place made me feel right at home! Good and peaceful area, and plentiful street parking- definitely recommend!
Top Guest favourite
Apartment in Blue Island
4.94 out of 5 average rating, 294 reviews

Charming Unique 2 Bdrm Apartment in Victorian Home

DebbieRating, 5 stars6 days ago
This was our 3rd stay at this lovely Victorian apartment. The Blue Island location is perfect, whether driving into the city or to our daughter's place in a nearby suburb. My husband loves walking in this historic neighborhood. Carol is extremely responsive and flexible, when possible. The kitchen is stocked with breakfast items and a variety of snacks. We love the second story apartment, which is spacious and comfortable. Highly recommend!
Guest favourite
Apartment in Chicago
4.83 out of 5 average rating, 166 reviews

Heart of Wicker Park! Location. Walk to Everything

VictoriaRating, 5 stars1 month ago
The apartment is in a great location. There are many amazing walkable bars and restaurants. Then mostly a 15 minute Uber ride to areas like the bean, The Aquarium and so forth.
Guest favourite
Apartment in Chicago
4.92 out of 5 average rating, 37 reviews

HUGE Hyde Park Modern Duplex

LakeshaRating, 5 stars1 week ago
Bee was a great host. Home is definitely worth what I paid, it’s a home-away from home. Clean and smelled great! I would recommend this place.
Top Guest favourite
Apartment in Chicago
4.97 out of 5 average rating, 295 reviews

The Garden on Wayne

SeanRating, 5 stars1 week ago
We had a wonderful first family trip to Chicago, and staying at Erin's place made it even better. The home was spotless and exactly as described. Erin went above and beyond by baby-proofing the outlets for our toddler and thoughtfully setting out toys and books to keep him entertained—such a kind and personal touch. The location is fantastic—right in Wrigleyville and within walking distance to Wrigley Field, great restaurants, and shops. I highly recommend this spot to anyone looking for a comfortable, family-friendly stay in a super convenient area.

Bed and breakfast rentals with breakfast

Private room in Chicago
4.8 out of 5 average rating, 171 reviews

#7 Historic Chicago Home - Bunk Bedroom(Twin&Full)

DanielRating, 5 stars7 months ago
This is the best and most affordable place in Chicago. You won’t get a better deal in Airbnb. Sharing the bathroom is not a big deal when everything is clean and works properly.
Private room in Winfield
4.95 out of 5 average rating, 62 reviews

Country Retreat, 2 Block walk to Metra Train

TroyRating, 5 stars68 months ago
This country house is well located, quiet, off the beaten path, but easy to reach. The rooms are super clean and well appointed. The Hosts are very social and take great care and interest in their guests. They are great communicators, and appreciate all feedback. Best advice to potential guests....must like dogs and good conversation,( and movies). And coordinate plans closely with hosts to take advantage of their local tips and advice. and Respect for house rules will make for a smooth stay for everyone. Travelers can not go wrong choosing to stay with Laura and Mike, they were/are the best.
Private room in Chicago
4.85 out of 5 average rating, 356 reviews

Large private room w/ shared bathroom in Boystown!

GraceRating, 5 stars3 weeks ago
We enjoyed our last minute booking at The Villa Toscana! The house was a cool, eclectic space and located in Boystown, a bustling neighborhood with lots to do and see within walking distance from the house. Having a sink in the room was really nice, since the upstairs rooms all share one bathroom (as is detailed in the listing), and they provided a nice variety of breakfast items, which was above and beyond. Thanks Ashley!
Top Guest favourite
Private room in Chicago
5 out of 5 average rating, 113 reviews

Urban Oasis Pilsen - guest room in townhouse

InhyeokRating, 5 stars1 month ago
Their accommodation is definitely the best Airbnb I've ever visited. The cleanliness, facilities, host, everything was superb. From start to finish, they were always so kind to me. I will never forget them, and if I visit Chicago again, I will definitely stay at their Airbnb. 정말 감사했습니다. 하나부터 열까지 모든 것을 다 디테일하게 챙겨주었고 숙소는 말할 것도 없이 너무 최고였어요. 위치도 좋았어요. 호스트들에게 너무나도 감사하며 항상 그들이 행복했으면 좋겠어요. 언젠가 다시 방문할 날만을 기다리고 있을게요. 다시 한번 정말 최고의 시설, 최고의 호스트가 맞물러진 최고의 숙소였어요.
Superhost
Hotel room in Chicago
4.85 out of 5 average rating, 48 reviews

Queen Room w/ Balcony in Boutique Wicker Park B&B

JeanRating, 5 stars5 months ago
It was a wonderful stay with a very hospitable host. We loved the access to the beautiful kitchen with instant hot water for tea. The homemade baked goods were a delicious treat in the morning. The room was immaculate. The back rooms face the tracks for the busy Chicago Transit Blue Line, so if noise bothers you, ask for a room facing the street.
Guest favourite
Private room in Chicago
4.77 out of 5 average rating, 318 reviews

Chicago River Room near USMLE

JessicaRating, 5 stars1 month ago
Mary's place was a great location for our short trip to Chicago! It was a short Uber drive from the airport, and a short drive to the All-State Arena. We did arrive late at night due to flight delays and opted for an Uber versus the train. I am glad we did cause it seems like the train station is under construction for the side we needed and would have been a bit more of a walk departing from the other side, but definitely not a dealbreaker or anything. The house is a short walk from this breakfast place that we actually went to twice during our short stay, with other options nearby. Overall, the house felt cozy and clean, but we did struggle with getting in the bathroom first thing in the morning with the other guests in the house during our stay. Mary was very responsive and a great host to us during our stay. The bed was comfortable as well and the room had amble space for a large suitcase, a carry-on, and two large bags with space to spare for two people.
Top Guest favourite
Private room in Evanston
4.97 out of 5 average rating, 573 reviews

Classy and Cozy home in Evanston

SeanRating, 5 stars1 day ago
Fantastisk husvert som var profesjonelle, og svært hyggelige. Husen ar meget rent, med alle fasiliteter. Stilte alltid opp for å sørge for at jeg fikk det beste ut av dagen, og kom med mange gode anbefalinger. Huset var fantastisk rent, og ryddig, hadde en super beliggenhet, med gratis parkering. Husverten og mannen hennes var utrolig snille, og lagde daglig frokost og middag til meg etter eget ønske. Anbefales til alle som skal besøke Evanston, og her vil jeg leie neste anledning jeg er på reise til Evanston.
Private room in Westmont
3.33 out of 5 average rating, 3 reviews

King Bed with Jet Tub

LartezRating, 5 stars1 month ago
Nice chill spot

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