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Guesthouse vacation rentals in Northwest Indiana

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Top-rated guesthouse rentals in Northwest Indiana

Guests agree: these guesthouse rentals are highly rated for location, cleanliness, and more.

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A charming green cottage is nestled among trees, surrounded by well-kept landscaping and flower pots. A red umbrella shades a picnic table nearby, creating a welcoming outdoor space. The gravel path leads to the cottage entrance, framed by large windows for natural light.

Guesthouse in Benton Harbor

4.94 out of 5 average rating, 181 reviews

Cozy Green Cottage with Private Beach

Cozy cottage hidden away in a quiet neighborhood 1.5 blocks from Lake Michigan, featuring a screened back porch perfect for morning coffee. Near the Benton Harbor Arts District, downtown St Joe, this cottage is surrounded by local restaurants, breweries, wineries, golf courses and shops. The beach is a year round destination, each season has its own wonders. Note: no TV, and WiFi can be spotty due to hills. Expect 90+ tiered steps to the sandy beach below. AC upstairs, original claw footed tub.

A private in-ground swimming pool is surrounded by lush greenery. Several white lounge chairs are positioned around the pool's edge, with a shaded dining area featuring a table and umbrella nearby. The clear water reflects sunlight under a bright blue sky.

Guesthouse in Michigan City

4.99 out of 5 average rating, 117 reviews

“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.

Top guest favorite

A well-lit bedroom features two spacious beds dressed in white linens. Two bedside lamps with blue bases provide soft lighting, while framed artwork adorns the walls. A mirror reflects the tranquil setting, and a small table offers a cozy touch.

Guesthouse in Winona Lake

5 out of 5 average rating, 235 reviews

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

A private cottage is surrounded by lush greenery and features a wooden deck adorned with several blue planters. Steps lead up to the entrance, which is framed by large windows allowing natural light to fill the interior.

Guesthouse in Valparaiso

4.95 out of 5 average rating, 206 reviews

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.

Top guest favorite

A serene sunset casts warm hues of orange and gold over a calm body of water, with a distant city skyline silhouetted against the horizon. The smooth water surface reflects the colors of the sky, creating a tranquil atmosphere.

Guesthouse in Chesterton

4.96 out of 5 average rating, 179 reviews

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

A quaint cottage is nestled among towering pine trees on a spacious, lush lawn. A stone pathway leads to the entrance, framed by a serene natural setting filled with greenery and shaded by the surrounding trees.

Guesthouse in Sawyer

4.89 out of 5 average rating, 132 reviews

Lola's Pine Tree Cottage

Lola's Pine Tree Cottage is a uniquely perfect old-school Michigan Beach cottage, with modern amenities! Enjoy the quiet of 1.5 acre of combined yard and forest (with friendly deer and wills turkeys!); walk to the beach; snuggle in front of the fire! A perfect hideaway, fall, winter, spring, or summer! Close to all the charms and amenities of Sawyer, Three Oaks, Union Pier, New Buffalo, and St. Joes. Excellent writing retreat, we’ve been told, and a sweet spot for a romantic getaway!

Top guest favorite

An outdoor space is presented with a patio featuring a round table and four chairs under a red umbrella. A fire pit is positioned nearby, with a pile of branches placed in the foreground. The area is enclosed by a wooden fence with decorative artwork visible.

Guesthouse in Chesterton

4.92 out of 5 average rating, 377 reviews

"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.

Top guest favorite

The front porch of the cottage features a welcoming entrance with a red door. Two seating areas are situated on the porch, complemented by colorful flower pots. The porch is framed by green columns, and a gravel pathway leads towards the entrance.

Guesthouse in South Bend

4.96 out of 5 average rating, 281 reviews

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. This cottage built in 1912 has been lovingly restored. 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 protected historic architecture make this location exquisitely charming. No smoking.

Top guest favorite

A charming cabin is nestled among tall trees, with a deck visible on one side. Surrounding areas feature mowed grass and fallen leaves, creating a tranquil rural setting. Additional structures, including a shed, can be seen in the background, adding to the serene atmosphere of the property.

Guesthouse in Sawyer

4.93 out of 5 average rating, 183 reviews

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.

The guest house is nestled among lush greenery, featuring a spacious wooden deck adorned with an umbrella. A well-manicured lawn leads to the entrance, while the house showcases large glass doors that invite natural light into the interior.

Guesthouse in Valparaiso

4.94 out of 5 average rating, 415 reviews

Private Guest House, in Gated Nudist Resort.

Book your get away today. Make it a few days or a week. If you've ever thought of trying social nudity. This is the place to do it. Very private 200+ acre property. You can also USE GUESTHOUSE AS BASE FOR SHORT DAY TRIPS, to Indiana Dunes State Park, Michigan Wine Country, or Chicago. You won't find a more beautiful, cost effective setting for a get away. This listing is for Guest house only (see guest access below)...where NUDITY IS NOT REQUIRED.

Top guest favorite

A grey house with solar panels is seen alongside a driveway, featuring a parked white SUV. Lush orange flowers bloom prominently in the foreground, while multiple trees provide greenery in the background under a blue sky.

Guesthouse in North Webster

4.98 out of 5 average rating, 244 reviews

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!

Top guest favorite

A cozy cottage interior features a warm-toned wooden structure with a spacious bed adorned with a patterned coverlet. A microwave is placed on a cart near a door painted in a muted tone, while books are neatly arranged on a dark shelf. Natural light enters through a window with light curtains.

Guesthouse in New Buffalo

4.96 out of 5 average rating, 434 reviews

Rainbows End 🌈 Puryear

Discover the tranquility of a charming cottage nestled on a 20-acre farm, surrounded by nature with walking trails that end up at the South Branch of the Galien River. Unwind on the patio with a cozy fire pit and enjoy all the amenities you'll need for a perfect getaway. Just 10 minutes away from the beautiful shores of Lake Michigan and only 3 miles from Four Winds Casino. Experience the peaceful countryside retreat—book now!

Vacation rentals for every style

Get the amount of space that is right for you

Apartments

Convenient locations with everyday essentials

Cabins

Kick off your hiking boots at these rustic lodgings

Cottages

Quaint homes, peaceful surroundings

Popular amenities for Northwest Indiana guesthouse rentals

Free parking on premises

Air conditioning

Family-friendly guest house rentals

An inviting living area features a white couch paired with a dark coffee table, facing a flat-screen TV. The modern kitchen showcases sleek cabinetry, a stainless steel refrigerator, and a central island with bar seating, lit by overhead lighting.

Guesthouse in Oak Park

4.89 out of 5 average rating, 511 reviews

Coachhouse in central OP 4 blk to L

Top guest favorite

The exterior of the converted barn is shown, featuring a rustic red facade with multiple windows on the upper level. Lush green grass and large decorative plants frame the building, while a charcoal grill is positioned on a patio area, providing space for outdoor gatherings.

Guesthouse in Stevensville

4.98 out of 5 average rating, 315 reviews

Red Barn Lodge

A dining area features a wooden table set with glassware, surrounded by four wooden chairs with decorative fabric. Large windows are draped with light curtains, allowing natural light to fill the space. A stylish staircase is visible in the background, leading to the upper level.

Guesthouse in Chicago

4.88 out of 5 average rating, 296 reviews

The Rectory

The image showcases a spacious kitchen area with a granite countertop extending into the dining space. A well-lit dining table is surrounded by wooden chairs, while a living area featuring a sectional sofa is visible in the background. Natural light streams through the windows, enhancing the open feel.

Guesthouse in North Webster

4.9 out of 5 average rating, 172 reviews

Come relax near beautiful Lake Webster

Top guest favorite

An inviting kitchen features wooden cabinetry and granite countertops. A black 'welcome' sign is placed on the countertop next to a vase of fresh flowers. Kitchen appliances, including a coffee maker, are neatly arranged, creating a functional and welcoming space.

Guesthouse in Stevensville

5 out of 5 average rating, 220 reviews

The Shire

An aerial view showcases a well-maintained property with a brown roof. The surrounding neighborhood features a mix of houses and green spaces. A swimming pool can be seen in the backyard, along with trees and a fence creating a private outdoor area.

Guesthouse in New Buffalo

4.33 out of 5 average rating, 6 reviews

Serenity by the Sea! With Hot Tub

A serene view of the St. Joseph River at sunset, reflecting a colorful sky and the surrounding trees. The calm water mirrors the soft hues of orange and purple, with a bridge visible in the distance, enhancing the tranquil atmosphere.

Guesthouse in Mishawaka

4.84 out of 5 average rating, 43 reviews

Riverfront guesthouse; 15 min to ND

An open floor plan featuring a Great Room with vaulted ceilings and skylights. A wooden dining table seats six, with a comfortable sofa and armchairs nearby. Modern kitchen amenities are visible, alongside light-colored cabinetry and warm wooden flooring, creating a welcoming ambiance.

Guesthouse in Miller Beach

4.2 out of 5 average rating, 30 reviews

Coach House, Dunes Nat’l Park, 10min hike to Beach

Guest house rentals with a patio

Top guest favorite

A landscaped garden patio is illuminated by soft lighting, highlighting a central tree and neatly arranged plants. An outdoor dining table with several chairs stands on stone paving, creating a welcoming space for relaxation. The brick facade of the coach house is visible in the background.

Guesthouse in Chicago

4.98 out of 5 average rating, 47 reviews

Solar Victorian MCM Coach House

Top guest favorite

A well-maintained garden area features vibrant flowers and greenery surrounding a gated patio. Potted plants and colorful blooms add a touch of nature, while a green umbrella provides shade over the outdoor seating area visible behind the gate.

Guesthouse in Chesterton

4.98 out of 5 average rating, 56 reviews

Cozy Guest House with Pool in Chesterton

A modern two-story cottage features a clean white exterior complemented by dark window frames and garage doors. Large windows allow natural light to enter, while two exterior lights enhance functionality at night. The building is surrounded by greenery, providing a sense of privacy.

Guesthouse in New Buffalo

4.8 out of 5 average rating, 25 reviews

Blue Laguna Cottage I Private Beach I Riverfront

An outdoor patio area features a concrete surface with seating arrangements and a large umbrella for shade. A charcoal grill is positioned nearby, surrounded by decorative planters with sunflowers, creating a relaxing space for outdoor enjoyment.

Guesthouse in Berrien Springs

4.97 out of 5 average rating, 118 reviews

Secluded Country Cabin

Top guest favorite

A clear, geodesic dome is set on a paved patio surrounded by a grassy area and decorative plants. The backdrop features a tranquil lake and lush trees, illuminated by a colorful sunset sky.

Guesthouse in Valparaiso

4.98 out of 5 average rating, 92 reviews

Lake retreat w/ unique dome near Indiana Dunes

A bright living space showcases a comfortable grey sofa positioned on a light area rug. A white entertainment unit holds decorative baskets while a flat-screen television is mounted on the wall. Large windows invite natural light and provide views of the outdoor greenery.

Guesthouse in Chesterton

5 out of 5 average rating, 14 reviews

Charming Hidden Cottage

Top guest favorite

A fenced-in pool area features a clear water pool surrounded by a concrete deck. Lounge chairs and a dining set are positioned nearby, while a red umbrella offers shade. A slide is visible in the pool, with cornfields extending in the background under a cloudy sky.

Guesthouse in Cassopolis

4.98 out of 5 average rating, 159 reviews

Quiet cottage with pool and hot tub!

Howard Park is illustrated at night, featuring illuminated structures and festive lights. A pathway winds through grassy areas, leading to the park entrance, where 'Howard Park' is displayed prominently. In the backdrop, city lights twinkle from surrounding buildings, creating a vibrant atmosphere.

Guesthouse in South Bend

5 out of 5 average rating, 48 reviews

Newly finished studio unit minutes from Notre Dame

Guest house rentals with a washer and dryer

The kitchen features light wooden cabinets and a stainless steel refrigerator. A modern stove is accompanied by a microwave and various kitchen utensils. The spacious counter is topped with granite, and soft light illuminates the space from a stylish fixture above.

Guesthouse in Berrien Springs

4.92 out of 5 average rating, 248 reviews

Make Lasting Memories at Beautiful Lake Chapin

Top guest favorite

A spacious living area features a comfortable black leather sofa and a distinctive black chair. Natural light filters through large windows, illuminating the mid-century cabinetry and vibrant area rug. Light-colored curtains frame the windows, and a circular coffee table sits at the center.

Guesthouse in Chicago

4.99 out of 5 average rating, 867 reviews

Polk Street Coach House Apartment, Little Italy/Medical Dist

A spacious outdoor view is presented from a deck, overlooking expansive green fields and wooden fencing. In the distance, a large barn is visible, along with a few horses grazing nearby. A tree branch frames the scene, creating a peaceful country atmosphere.

Guesthouse in Sodus Township

4.78 out of 5 average rating, 263 reviews

Farm Cottage

Top guest favorite

An open living area is highlighted by a spacious dark sofa adorned with decorative cushions, complemented by a wood coffee table. A large, comfortable bed occupies one side, while a dining area with a glass table and chairs is visible. Art pieces are displayed on the walls.

Guesthouse in Oak Park

4.99 out of 5 average rating, 117 reviews

Stylish Coachhouse in lovely Oak Park!

A private backyard space is visible, featuring a green lawn and paved path surrounded by various potted plants. Outdoor seating is arranged around a table shaded by a tree, while a grill stands ready for use against the wall of the guesthouse.

Guesthouse in Chicago

4.91 out of 5 average rating, 351 reviews

Private Studio in Bridgeport, Chicago

Top guest favorite

A charming cottage is surrounded by lush greenery and colorful autumn foliage. A small patio area with blue chairs offers a welcoming space. The exterior features a blend of wood and stone, while a shaded entryway provides shelter from the elements.

Guesthouse in Countryside

4.94 out of 5 average rating, 493 reviews

Cozy Cottage Minutes from Downtown Chicago

Top guest favorite

The airy living room features a spiral staircase leading to the upper level. A wooden coffee table lies in front of a comfortable sofa. A vibrant vinyl record player sits atop a wooden crate, with bookshelves filled with various titles in the background. Natural light streams through multiple windows.

Guesthouse in Evanston

4.99 out of 5 average rating, 278 reviews

Cottage in a Garden

The exterior of the vintage garage apartment is shown, featuring a bright yellow facade with two white garage doors. A large window is positioned above the doors, with greenery surrounding the property, contributing to the charming appearance.

Guesthouse in Villa Park

4.92 out of 5 average rating, 128 reviews

Eclectic Coach House Apartment

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