Guesthouse holiday rentals in Northwest Indiana

this is a gem. the place to book if you want to sleep near Chicago, outside of the city center rush, but at only 30 mins from downtown with the green line. The apartment is very well furnished (especially the kitchen !). Niles is an experienced host that provided us with recommandations and guidance for our stay. parking is free. Everything was super clean. check in and check out were smooth and independent. the quality/price ratio is good.

Absolutely recommend this place! It is warm and cozy, with a massive backyard which was great for our dogs to play in and for us to relax in! It feels very private and has such a unique vibe! Ann was amazing, she was kind, friendly, and gave incredible recommendations! Mason Jar Cafe is a MUST! Highly recommend and hope to return soon!

A lovely spot! Our family of 4 had plenty of space and great sleeping arrangements (crucial for traveling with preschoolers!) and lots of space for kids to play. David was responsive and helpful. This is a very quiet home in such a great location! We would love to come back again, it was the perfect set up for our family vacation. And bonus, a beautiful restoration of the rectory and obviously very well kept property.

We had such a nice stay here. Elise's place was spacious and comfortable. Her list of local recommendations was wonderful. We're planning another trip back just to try more restaurants on her list! Do yourself a favor and stay here!

We loved our stay at the Shire! The place was perfect for our family. Our kids adored the pond and waterfall and enjoyed feeding the fish. The location was the perfect relaxing base for exploring southwest Michigan! We can’t wait to come back!

Matthew saw us into the apartment and immediately inflated the extra bed that we needed. Wine and drinks were available. Place was quiet and clean. Walkable to Northwestern and downtown Evanston.

For this trip, it was my husband and I and our 2 kids (18 & 21). Kyle's airbnb is in a perfect location right on the St. Joseph's River. It is beautiful and peaceful. The in-ground pool is a lovely perk and he has a dock to hang out on or go fishing. My husband and son loved fishing and hanging out on the dock. Kyle and his wife are friendly and so are the neighbors. The second floor apartment is above a garage and is 1 bedroom with beds all in the same room. There is a second bathroom with a shower as well as a sitting room with a larger TV and kitchen space downstairs which is nice if you need more space. We had problems while there with the internet. Kyle did check into it and tried to fix it, however it didn't work well the entire stay. We would definitely stay here again if in the area.

Very clean and as advertised. You can get to the beach either through the scenic route, which is walking over some dunes (hills) or via a sidewalk on a street, with no hills. They have an app that provides a lot of information about the area.

We had a lovely stay at this quiet little oasis in Wicker Park. The Coach House is charming, comfy, spotless, and stocked with everything you need. There is great food and transit just steps away. Joe and Shannon are fantastic hosts—friendly, responsive, and full of great local tips. You can tell they really love their city, and it shows in the way they host. Can’t wait to come back!

Me and my friend stayed here since we were going to be visiting the Indiana Dunes, and it was lovely! As soon as we walked in we both said wow because of how open and clean it felt. It’s a beautiful place with everything you would need. They had so many cool extras that really added to our experience. Perfect quiet place to hang out at. And their Koi pond was beautiful and peaceful. I’ve suggested their place to others!

Very nice home and surrounding area, and very active community. The loft is fun for kids. The host reached out daily. Easy walk to the beach with our dog. The boat rental w/ captain was fun, and got a little tour of the shoreline. Awesome quality of food at the local restaurants!

Super clean and adorable Airbnb! Linda was very responsive and flexible. The tiny home was stocked with lots of goodies. The land is clean and peaceful. They have space for a bonfire, outdoor seating and grill. So sad we only needed somewhere to sleep for the night - would have loved to hangout there for a few extra days! Definitely plan on staying here again when we come back to the area!

Beautiful stay with a very responsive and helpful host.

The cottage was clean and easy to find. It had everything we needed. Had snacks and water for us. Clear instructions on how to get into the cottage. Will definitely be back. Close to downtown could walk.

Our stay with Karen was exactly what we were looking for. She was hospitable, friendly, and responsive. The accommodations were lovely and clean. We look forward to returning. Thank you for your hospitality.

very nice place for a short weekend vacation!

This little cottage was the perfect retreat while I was attending a conference at Notre Dame. It was clean, quiet, private, and comfortable, and Joan has done an exceptional job with the interior. There were also special touches--like snacks in the kitchen and toiletries in the bathroom (I forgot a few things, but it wasn't a problem). The cottage is located in a historic neighborhood, and I enjoyed my walks to campus. Joan was responsive to my questions and all-in-all an excellent host. I definitely recommend this place!

the airbnb was so lovely and spacious for our party of 4! we had 0 trouble finding the home and had the best weekend in chicago reuniting with our friends from college. would def recommend - it is a quieter part of chicago. the walk to little italy is quite lovely and is a quick uber from the west loop

Jim's place was a great spot to stay in North Webster-- right off of the lake, very comfortable, and everything you needed for a quiet, cozy weekend away. The area is very beautiful. Jim was also very helpful, provided good directions to the cottage, and responsive to any needs we had during the course of our stay.

We really enjoyed staying here. It’s close to many things, and very peaceful and quiet. A beautiful and relaxing place to stay.

Very comfortable and convenient. We have stayed many times and look forward to another visit soon! Five star rating.

The location was quiet and as described. The place was clean and cozy. Amenities were available in the kitchen, bathroom, and bedroom (extra blankets, towels, toiletries, iron, pots, plates etc.) I was able to come and go easily. Park in front of the garage as suggested, I parked under the tree and ended up needing a car wash due to the birds. Overall, good communication, quiet space, and nice location to many things in the Chicagoland area.

A great place to stay for a couple of nights! cozy!

Beautiful cottage and garden! All was lovely. Eclectic decor, responsive hosts. Well stocked kitchen and bathroom. Had everything we needed. Highly recommend!!