Guesthouse holiday rentals in Northwest Indiana

Make Lasting Memories at Beautiful Lake Chapin

Beautiful self contained private guest house right on shore of Lake Chapin. Big Bedroom overlooking the lake. Extra sleeping space for 6 people. Large bathroom. Updated 2021 new carpet & kitchen with granite, stainless stove, & Sink. Lake Chapin is all sport lake with good fishing, bring the boat and water toys or forget bringing anything and enjoy the lakeside fire pit, paddle boat and kayaks that we provide. Stocked with linens, towels, kitchenware, charcoal grill. Pets welcome for small fee

“Treetops” Charming Country Coach House

Second-floor comfortably furnished coach house. Stylish and airy space with full kitchen. Great views. Private in-ground 20' x 40' swimming pool reserved exclusively for you and your guests. Basketball half-court. Softball diamond. Bocce court. Great for bicyclists. 20 acres of woods. Hiking trails on property and pond with wildlife. Centrally located between New Buffalo, MI, and Michigan City, IN. Close to the Indiana Dunes, and Lake Michigan. 70 minutes to Chicago, 45 minutes to South Bend.

Sunlit Sanctuary w/Country View. Tranquil & Clean.

Retreat to the country with this newly renovated guest house. Located just 8 minutes away, this modern space offers a tranquil, country setting with quick, easy access to Kokomo. A lovely space to unwind and relax after a busy day at work or play, this quiet setting ensures you rest peacefully. In the morning, after drawing back the blackout curtains, take in the serene views of the countryside and perhaps catch a glance of the local wildlife as rabbits, squirrels and birds are abundant.

Guesthouse Suites (C)

For business or pleasure, you will experience lovely Winona Lake staying in our newly constructed GuestHouse Suites. Next to the heart of The Village at Winona, a short walk up to Grace College or a short walk over to visit the shops and restaurants; Spring Fountain Park graces your view. Winona Lake Limitless Park, public beach, splash pad, tennis, pickleball and basketball courts, paved walking/bike trails, mountain bike trails, and an ice skating pavillion, are all within walking distance

"myhathouse" detached studio downtown Chesterton

Vaulted skylights allow natural light. Ksize bed. Couch opens into a full size bed. (DEEP cleaned to AirBnb COVID-19 disinfectant standards) Fully stocked kitchen, sm. bathroom w/ shower. Parking ft. of house, 1.5 M from Lake Michigan Shoreline, 2 blocks to 15th St. entry to Prairie-Dune Trail. European Market (May -Oct) each Saturday downtown. Fall season drives along U.S. HW 12 & 20 for foliage Winter day hikes, x-county skis trail, shopping trips to the Michigan City Outlet mall.

"Tiny House" Guest House - No Cleaning Fee

"Tiny House" guest house located under large oak trees near the beach, and not far from I-94 and the Michigan state line. Vaulted ceiling, open feeling. Light and bright décor. Full bathroom, comfy couch, and other amenities. Polished concrete floor, whitewashed shiplap ceiling, hand-crafted oak furniture, suspended shelving. High ceilings, windows with southern exposure, front porch with siting chairs and a grill. Convenient charger for electric cars. Never a cleaning fee.

Modern Webster Lake cottage

This home has a great floor plan for 2-4 people with a small loft bed for a youngster. It has high end kitchen accessories and in-unit washer and dryer. Water softener for great water, maple hardwood floors and a front deck for outdoor barbecuing. Parking for 3 cars and a shed with lots of amenities including bikes and hammock for recreation and relaxing. New in 2024, new rug, blackout curtains and solar panels! EV charger free for guests!

Romantic Getaway Guesthouse/ Jacuzzi/Sauna/Pool

Romantic Getaway | Private Suite w/ Jacuzzi, Sauna, Pool & Gym Indulge in a luxurious, private retreat designed for couples! This beautifully styled guesthouse/in-law suite offers ultimate relaxation with a private entrance, spa-like jacuzzi, sauna, pool access, and a fully equipped gym. Perfect for honeymoons, anniversaries, or weekend escapes, our space blends comfort, privacy, and elegance for an unforgettable stay.

Red Barn Lodge

The Red Barn Lodge is a few minutes from orchards, beaches and vineyards. The converted barn combines the convenience of modern kitchen and bathroom within a spacious loft. Air-conditioned and private huge fenced backyard with shady and sunny areas and fire pit. There is a woodburning fireplace inside for cozy fall and winter evenings and a charcoal grill in the yard.