
Guesthouse vacation rentals in Northwest Indiana
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Top-rated guesthouses in Northwest Indiana
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Vacation rentals for every style
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Popular amenities for Northwest Indiana guesthouses
Family-friendly guesthouses

Coachhouse in central OP 4 blk to L
Place was fantastic. Everything as advertised. Niles was a pleasure to deal with and even leaves some nice extras for you too. One of the most comfortable beds in any B&B I’ve stayed in. Perfect for business or pleasure. Five stars all the way. Definitely using again!! Parking too!!!!

Cozy Green Cottage with Private Beach
We stayed at the Cozy Green Cottage over the Thanksgiving holiday week. We were looking for a quiet, peaceful cabin to get away to and this spot was perfect. I worked remote for the first half of the week and had no problem with her internet connection. We were able to do Zoom calls as well as stream movies. The cottage is super charming. It's over 100 years old and has many hand crafted details. Kitchen is small but totally functional for 2 people. Bathroom has a claw-foot tub with hand-held shower head. The grounds around the cabin are serene. This cabin is behind private homes but since this was off-season, no one was around. It is a short walk to the stairs that take you to Lake Michigan. We opted to drive down the road to a public access area right on the lake. Also very convenient. If you are looking to get away from the everyday buzz of life or need a no-distractions, quiet space to get a project finished, I recommend this cottage!

The Rectory
Loved our stay at The Rectory! The location was great; walkable to DePaul and close to restaurants, shopping, DePaul and Lincoln Park Zoo. The unit looks exactly like the photos. Instructions were clear for check-in and check-out. Will definitely come back. We enjoyed our stay!

Come relax near beautiful Lake Webster
2nd time staying. Very quiet location. Really love the living room space. Very comfortable.

Coach House Art Studio, By Downtown & Northwestern
Great host, great location easy walking distance into downtown Evanston and the Northwestern campus, very clean and tidy studio. I was very happy with my stay and would recommend for others.

The Shire
It felt great staying at this place. I think the water boiler was not quite functional during our stay, but they immediately offered a solution. We personally felt that we were okay with semi warm shower and did not want the owner to come in to fix the issue, but that's just us. Can't blame the owner for a broken water boiler. Overall, a great place for a great price.

Serenity by the Sea! With Hot Tub
Bobs place is in a great location. It is ideal for a group, offering lots of gathering space, and plenty of beds. The driveway was an added bonus.

Riverfront guesthouse; 15 min to ND
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.
Guesthouses with a patio

Romantic Getaway Guesthouse/ Jacuzzi/Sauna/Pool
This was a great little guest house! Loved the decor, and the lighting in the living room! Bathroom was clean! Loved the hot tub! The are seems pretty nice. Great shopping! Wanted something close to Chicago but not directly in the city and it's only an house drive away! I definitely enjoyed my time at this Airbnb! Agna is pretty quick with responding if you have a question. Would definitely book this one again!

Cozy Guest House with Pool in Chesterton
The guest house was very comfortable and peaceful. It was as listed and matched the pictures well. probably one of the most comfortable beds we have slept in. would definately recommend to others.

Guesthouse Adjacent to Wheaton College
The location was perfect. Jury steps from Wheaton college. We stayed here during the Wheaton College Christmas Festival which we were able to walk to. Angel’s place was clean, had a Keurig with different choices, and filtered water. We had everything we needed for a short overnight stay. Thank you for a great stay!

Cozy Luxe Downtown Valparaiso Stay
My partner and I had such a lovely stay! The home was beautiful and gave off such a calming atmosphere. Check in was very simple and we felt right as home as soon as we entered! Kelly and George were also very communicative, friendly, and quick to respond. We will definitely be back!!

Secluded Country Cabin
Linda and Doug were exceptional hosts. Very warm and welcoming, gave great suggestions for to-do’s/food in the area. The cabin was the perfect size for two people and the bed was comfy! We hiked through the woods and had a fire - perfect overnight getaway. The place felt isolated which is exactly what we wanted. We would definitely revisit! Thank you both so much for such a warm welcome.

Lake retreat w/ unique dome near Indiana Dunes
Elena’s home is a wonderful getaway with beautiful views of a gorgeous lake. We were looking for a place close to Chicago where we could unplug from our busy weekdays and enjoy a relaxing weekend of hiking and this spot was perfect. It didn’t feel like we were only an hour outside the city. Waking up to the view and the sound of birds in the morning, along with the temperature-controlled dome, was truly special. We had a cozy night in playing games, grilling, and sitting around the fire pit. The kitchen was well-stocked, clean, and free of unnecessary clutter, which made cooking easy and enjoyable. The bathroom and linens were pristine, with all-white towels and bedding—a detail we really appreciated. The no-shoes policy added to the cozy, clean atmosphere of the home. The location was also ideal—just a 15-minute drive from the dunes, and the included seasonal parking pass was a great bonus. Overall, our stay was comfortable, relaxing, and exactly what we were hoping for!

Bird’s Nest Air BnB
Lovely accommodations in a bucolic setting. Karen was a very kind, and gracious hostess. Definitely would try to book this again if our travels take us this way!

2 person cottage with hot tub!
Our stay was perfect! We were in a super private area with beautiful surroundings, the sweetest outdoor cats, and awesome hot tub, and a lamb was even born the weekend of our arrival! I would absolutely recommend this stay to anybody wanting a relaxing weekend
Guesthouse rentals with a washer and dryer

South Bend Fully Restored Cottage Built in 1912
Joan's cottage was perfectly cozy and quiet for my short stay. I especially loved the charming kitchen and overall layout of the space. I only wish I could've stayed longer. I'll definitely book again next time I'm in South Bend!

Cozy Guesthouse near NU - next to Lee Street Beach
I was so excited to visit family and stay at this property. Lisa was a great communicator both leading up to my stay and during my stay. The residential location, parking, and access to groceries, restaurants, and the lakefront make this home an ideal location. I did have to contact my host on my first day to report that the home had not been cleaned from what I could tell. She immediately offered to have the property recleaned. I really appreciated Lisa taking my concern seriously and remediating the situation.

Polk Street Coach House Apartment, Little Italy/Medical Dist
Great place to stay for a visit of Chicago. Beautifully furnished house with public transport at a stone’s throw. Would recommend!!

Bro’s Place 6 mile drive to Indiana Dunes
Bro’s Place was a great place to stay! I enjoyed being out on the country, but it was nice to be close to the owners property. I ended up traveling alone and felt safe and comfortable. I definitely highly recommend this Air Bnb!

Farm Cottage
I had such a lovely and memorable stay here! One of the highlights for me was when the host encouraged me to let my dogs run off-leash — it absolutely melted my heart to watch them run free and have the time of their lives exploring the farm. That experience was so unique and meant a lot to me. The whole place was incredibly peaceful, which made for a perfect escape. Everything was very clean, and the bed was super comfy — I slept so well. Highly recommend to anyone looking for a tranquil, dog-friendly getaway!

Stylish Coachhouse in lovely Oak Park!
We absolutely loved our stay! We really enjoyed the quick walk to the train that would take us anywhere into Chicago. The location and neighborhood was beautiful, and the Coachhouse itself was beautifully decorated, private, and comfortable. Highly recommend!

The Green Door - safe and calm with walkability
Would stay again in a heartbeat. Was everything I needed for a 5-night stay and nothing more (no clutter.) The space was extremely well laid-out. Kitchen had all necessities. It felt private despite being attached to owners home. Met both owners, lovely and interesting people. Bed was comfortable, bath had space for all my products. Had snow during my stay and the drive and walk were shoveled super early. Five star stay!

Eclectic Coach House Apartment
Great little place to stay. Know that there are some tight places and stairs but has everything you need.
Destinations to explore
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- Millennium Park
- Wrigley Field
- United Center
- Navy Pier
- Oak Street Beach
- Shedd Aquarium
- Guaranteed Rate Field
- Humboldt Park
- Frank Lloyd Wright Home and Studio
- 875 North Michigan Avenue
- The Field Museum
- Lincoln Park Zoo
- Flossmoor Golf Club
- Museum of Science and Industry
- Willis Tower
- Lincoln Park
- Wicker Park
- Chicago History Museum
- Skokie Country Club
- Washington Park Zoo
- Promontory Point
- Brookfield Zoo
- Garfield Park Conservatory
- Chicago Cultural Center