
Guesthouse holiday rentals in Northwest Indiana
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Top-rated Guesthouses in Northwest Indiana
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Polk Street Coach House Apartment, Little Italy/Medical Dist
Cook in a kitchen with everything from a KitchenAir convection range and Kitchen Aid food processor to Calphalon pots and pans. The mid-century look includes a comfy American Leather sofa, Gansgo Mobler dining table, and Frem Rolje teak chairs. Welcome to Polk Street Guest House: a well-appointed, completely private, 2-bedroom carriage house in Little Italy near the Medical District. Decorated with mid-century antiques and paintings, our 2nd floor coach house apartment is perfect for guests looking for a home-away-from-home. It has a fully-equipped kitchen, teak furnishings, comfortable queen size beds, and a private entrance accessible though a side gate from the street. For folks with kids, please note there is no child gate near the top of the stairs. Enjoy quiet parks and have easy access to all of Chicago. Major hospitals at Rush, University of Illinois, Hines, VA and Stroger are within 3 to 6 blocks. Chicago's elevated pink line train is 2 blocks away; the Blue line is 3 blocks. Take a quick cab ride to “the loop" downtown for $10, or take a Divvy bike. Chicago's famed Little Italy restaurants on Taylor Street are a block South. Free street parking with 24-hour zoned pass. Your hosts: Ken & Curt Want privacy? You have privacy! Use an entry code to access the coach house through the side gate to the left of our main house. Your private entrance, which also has keypad entry, is on the left side of the vine-covered brick building in back. The main living area is upstairs. There will be a 24-hour zoned parking pass waiting for you on a shelf as you enter the Coach with instructions on how to fill out the parking pass. We regret that the Coach House is not ADA/wheelchair accessible. For those arriving early than check-in, or who are staying later than check-out, we have an area beneath the coach house where you may leave your luggage. Just ask. Our space is your space. The coach house is entirely separate from our main house where we live. The coach house has a separate entrance and full amenities. You’re welcome to use the seating area in the courtyard, and the Weber grill. We're happy to provide any tips about the city, or to help show you how to use anything in the apartment. Just call our cell phones (they are listed in the apartment), or step across the yard and say hello. Three blocks to the Medical District and major hospitals, walk from this tree-lined Little Italy neighborhood to restaurants of all kinds. Host recommendations include Rosebud for classic Italian, and Indian cuisine on Taylor Street. Stroll in Garibaldi Park on the doorstep, with Arrigo Park a block away. We are conveniently located for transit, bike, car and Uber. Public Transportation: -Pink Line, Polk Station, CTA: 3 blocks west of us, this rail line gets you downtown in 10 minutes (plan 30 minutes total time with walking for most destinations) and is useful for most site-seeing. -Blue Line, Racine Station, CTA: 4 blocks east or west of us, this rail line gets you to O'Hare airport in less than an hour, or downtown in about 10 minutes (it's a bit longer walk to the Blue Line than to the Pink Line) . -#157 Bus (Streeterville): This super convenient bus 1 block south of us on Taylor Street runs during the daytime only and takes you to the Magnificent Mile for upscale shopping on North Michigan Avenue in 25 minutes. -#12 Bus (Roosevelt): This is about 3-4 blocks south of us, runs east-west, and takes you to the Soldier Field stadium and the Roosevelt Road shopping area with Whole Foods, Nordstrom Rack, Best Buy, Core Power Yoga, and much more. Bicycle: You bike? We bike. There is a DIVVY bike share station a block east in Arrigo Park. Get at DIVVY bike-share 24-hour pass with unlimited half-hour rides. Switch out bikes for longer distances. If you have your own bike, you can park it safely on the ground floor of your coach house apartment. It takes 15 to 20 minutes to bike to most downtown locations. Car: Our home is 3 blocks south of I-290 (the Eisenhower), and near I-55 (the Stevenson), I-90 and I-94 (the Dan Ryan and Kennedy). Parking: We provide parking passes for free zoned street parking available on a small shelf as you enter the Coach House along with instructions. Please be very careful about filling out the pass, as City workers seem motivated to issue tickets if the pass is not filled out correctly. We travel a lot and know what it's like to be away from home. That's why we've furnished the apartment with appealing furniture, comfortable beds, plenty of towels (and more towels), soaps, shampoos, and a kitchen outfitted with all the basics plus a few more: Kitchen Aid food processor, toaster, microwave, baking and cooking tools, Calphalon pots & pans. Please note there is no dishwasher. Enjoy complimentary Nespresso coffee, Bigelow teas, bottle water, and snacks. Three blocks to the Medical District. Walk the tree-lined streets of the Little Italy to restaurants of all kinds. Host recommendations include Rosebud for classic Italian, and Asian cuisine on Taylor Street. Stroll in Garibaldi Park steps away, or Arrigo Park a block away.

Romantic Spa Getaway -Private 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 suite is attached to the main house but completely private—you’ll have your own private entrance for total seclusion. Enjoy spa-like relaxation with a 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.

Unique Dome Retreat by Indiana Dunes w/ Lake View
Escape to our Valparaiso Lakeside Retreat with king bed, lake views, unique dome experience, fire pit, grill & hot tub, all near Indiana Dunes National Park, Valparaiso University & 4 local parks! Experience a nature getaway at our newly renovated lake guest house on the ground level of our home with keyless entry & unique outdoor amenities, ideal for friend groups, small families, business travelers & couples. 10 min - downtown Valparaiso. Book now to experience this unique tranquil retreat.

Cottage in a Garden
Enjoy the serenity of our secret garden from your private guest house. Enjoy privacy on the covered sun porch. Watch butterflies float by in the pollinator garden. Listen to evening quiet on the patio overlooking the garden. Spin some records from the eclectic collection. Stroll the leafy neighborhood. Stop for a beer at award-winning Temperance Brewery. 5 minute walk to Divvy bike station gives you access to all of Chicago and CTA/Metra train. Short ride to lakefront, Northwestern, downtown.

Farm Cottage
Sweet cottage on our farm: Fully equipped kitchen and furnished living/sleeping area 14’x15' approx., washer/dryer. Sleeps 4: queen bed and queen sofa bed. Lots of privacy and next to organic garden, fields, stable and fruit orchards. All utilities, TV and WI-FI included. Well water with new water softener and water heater. Pet friendly; no pet fee. Lots of farm paths to walk your pet. Encourage off leash if trained. Horses have moved to another farm while pasture and stable rehabbed.

Private Cottage in Gated Nudist Community
We offer a private cottage on the grounds of Lake O the Woods Club. Cottage has Queen size bed, air conditioning, heater, refrigerator, microwave, TV, coffee maker, work/dining area, private deck and porta-potty. Payment of club daily grounds fee ($30-$60) is mandatory. Pricing on club website. There is no running water in the cottage. Bathrooms, showers, hot tub, sauna and swimming pool are available at the clubhouse and pool area . The cottage is sanitized after every rental.

Bro’s Place 6 mile drive to Indiana Dune’s
Welcome if you like country life Bro’s place is the place to be...watching the sheep, chickens and wildlife on you back deck making dinner on the grill with a full kitchen. Pick your own veggies outside the back door when in season. You will find a welcome basket with snacks, wine and homemade soap in bathroom fresh eggs from our chickens when available if your planning to visit our Beautiful Indiana Dunes you’ll find everything you need..chairs, towels, cooler Queen size sofa sleeper

"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.

South Bend Fully Restored Cottage Built in 1912
South Bend historic cottage in the National Historic District of Chapin Park. Minutes from Notre Dame and downtown. There is a queen sized bed and a sofa, not sofa bed in the sitting room. This cottage built in 1912. Private and cozy, the cottage has a big screen TV, wifi and a gourmet kitchen. The owner lives almost directly behind and is available and happy to assist. Chapin Park's tree-lined, brick streets and diverse historic architecture are charming. No smoking.

'Pool Barn' w/Games & Hot Tub near Indiana Dunes
Heated pool open until mid October!Hot tub open all year! The Pool Barn is only 1 hour from Chicago & less than 10 minutes from large sand beaches & hiking trails of Indiana Dunes National Park & Indiana Dunes State Park. Outside enjoy our Pool, hot tub, grill, firepit, playground, & we are on the hike/bike trail. Inside is billiards, ping pong, air hockey, darts, popashot, foosball, board games, large smart tv, 5 beds, couch, & full kitchen. No cleaning fee. Book today!

Heron's Rest Hideaway, nature lovers' dream
Privacy on 11 acres of conservancy-protected land including two small lakes, river access , woods. Rowboat available. Minutes from Michigan’s most popular beach, breweries, wineries, antique malls, farm-to-table restaurants. Fully equipped kitchen, gas fireplace. Private fire pit, deck, and gas grill. Kayak, bike, hike nearby. Separated from our home by a breezeway. Private entrance, quiet road, dark nights. Daytime woodworking noise possible. Limit of 4 guests.
Popular amenities for Northwest Indiana guesthouses
Family-Friendly guesthouses

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The Rectory

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The Sturdy Loft
Guesthouses with a patio

Solar Victorian MCM Coach House

Cozy Guest House with Pool near National Park

Between South Bend & New Carlisle, IN Comfy!

Blue Laguna Cottage I Private Beach I Riverfront

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Private Studio in Bridgeport, Chicago

Cozy Cottage Minutes from Downtown Chicago

Eclectic Coach House Apartment
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- Lincoln Park
- Wrigley Field
- Millennium Park
- United Center
- Navy Pier
- Shedd Aquarium
- 875 North Michigan Avenue
- Humboldt Park
- Guaranteed Rate Field
- Frank Lloyd Wright Home and Studio
- Oak Street Beach
- The Field Museum
- Wicker Park
- Garfield Park Conservatory
- Lincoln Park Zoo
- Brookfield Zoo
- Museum of Science and Industry
- Washington Park Zoo
- Willis Tower
- The Beverly Country Club
- Raging Waves Waterpark
- The 606
- Olympia Fields Country Club
- DuSable Museum of African American History