Holiday rentals with breakfast in Illinois

When 6 guests ranging from 13-79 all love the place, it’s a win!! It was so peaceful and we felt right at home! We had a blast with the arcade, pool table, & the hot tub! We highly recommend! Thanks to the host for going above expectations!

Exactly as described. Was a very welcoming experience and we felt very comfortable during our stay.

Renee was a great host with quick response time and provided added resources for what shelbyville had to offer. The house exceeded our expectations and we appreciated all the amenities that the house had to offer- will be recommending to other organizations to use for retreats!

This was our 3rd or 4th stay at Jared's spacious and well equipped place, so that says a lot right there! They are always quickly responsive and accomodating hosts ahead of time and their house ( that is a whole house in a nice neighborhood not next to the hosts) and they always leave us lots of sweet and savory snacks, sweets, and fruit. We highly recommend Jared's place and plan to return again whenever visiting family in the area.

Amy’s place is amazing. Has everything family needs!

Michelle’s home was wonderful. The location is very serene and the house was exceptionally clean and well equipped for a relaxing stay. The house has bedrooms and bathrooms on all three levels, along with a screened in porch, multiple decks, and two fireplaces, with easy access (no stairs) to the main entry. Seating throughout the home is invitingly cozy and comfortable. There was a welcome basket of treats in the kitchen, such a nice touch. We really enjoyed our time at this lovely home.

This was our second stay here. We will always reach out to Sandra for future stays. She is always very accommodating and goes above & beyond to make everything quick & easy.

The house was great for what we needed. Small house in a very quiet and neat neighborhood. Thanks for allowing us to stay.

We had a wonderful stay at Jay's place. He met us in person to check in and personally showed us through the house and made us feel so welcome. The house was very homey and had everything we needed. It's also in a great location in a very walkable neighborhood close to the Frank Lloyd Wright Studio. Oh, and morning coffee on the sun porch was delightful. Thanks for a great stay, Jay.

We loved our stay in the Pink House, which felt truly like a home away from home with everything we could possibly need. You can tell how thoughtful Niki and Sean are about their space and that they care about their guests having a lovely time - especially appreciated the comfy linens and snacks! Perfect location too with an easy walk to the L and plenty to discover just by wandering around the immediate neighborhood. Niki has all the recs.

Staying at Jenny's place was fantastic! She was always responsive and helpful. The apartment itself was cozy and pretty quiet, especially for a Chicago unit. I hope to stay there again in the future!

Location is in a great place! Home was super clean as well with a comfy bed! Only downfall is the 4 sets of stairs to make it up to the 3rd floor with our suitcases. Other than that absolutely loved! Thanks again!

Carol’s place was very comfortable for our family of 4! Amenities were all as listed and everything was clean and inviting. We hope to stay here again the next time we visit family in Blue Island!

Perfect spot for 2, more spacious than expected for a 3rd floor apt. Easy, clear instructions when viewing the listing and inside the apt

Well equipped and clean Instructions are very clear

The house was comfortable and spacious

Great stay, incredibly kind and welcoming hosts

My friend and I enjoyed staying with them. They are a very nice couple. Very helpful. We would definitely recommend staying there to anyone in the future.

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.

Cal's place is a beautiful home and holds so much history. The place was clean and perfect to rest after a long trip. He is a great host!

Loved the carriage house! The hosts were very accommodating as we had family coming and leaving on slightly different schedules and they were able to meet all of us and meet our needs. My partner has specific dietary requirements and they met them quite cheerfully, making him a special plate with just what he needed. Overall an excellent experience.

Patricia offered us unparalleled hospitality with a unique balance between privacy and availability, with tasty and varied breakfasts. Friendliness and kindness did the rest making our stay extremely pleasant.

Jan and Rich have an absolute gem here and they are great hosts. I happily give Walnut Grove Farmhouse my highest recommendation.

I cannot say enough good things about Miss Murphy’s Bed and Breakfast. From the moment I arrived, I felt like I had stepped into a storybook. The house is charming, cozy, and full of character—every detail thoughtfully curated to make you feel right at home. My room was spotless, beautifully decorated, and incredibly comfortable. The location is also perfect—tucked away just enough for peace and quiet, yet still a short stroll from the heart of downtown Galena with all its cute shops and historic charm. If you’re headed to Galena, do yourself a favor and stay here! It’s the kind of place that stays with you long after you leave. Can’t wait to come back!