Holiday rentals in Winfield

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Top-rated holiday rentals in Winfield

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Top guest favourite
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.
Guest house in Valparaiso
4.98 out of 5 average rating, 114 reviews

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.

Top guest favourite
A cozy bedroom space features a queen-sized bed adorned with a colorful patterned blanket. Two bedside lamps provide soft lighting. A large window offers views of the outdoors, while wooden walls enhance the rustic charm of the loft.
Farm stay in De Motte
4.96 out of 5 average rating, 211 reviews

Cozy barn loft on organic vegetable farm

Find peace and restoration in this beautiful barn loft at Perkins' Good Earth Farm. The loft has a bedroom, separate shower and toilet spaces, work area, sitting room, kitchen space, and heating/cooling fresh air system. Located above our farm store, the loft provides privacy for you while giving you access to fresh fruits & veggies, locally sourced meats, homemade soups & salads from our farm kitchen, and so much more. You can also walk our farm trails, visit the veggies, or enjoy a campfire.

Guest favourite
A welcoming living area is brightened by natural light streaming through a large window. A comfortable gray daybed is adorned with decorative pillows, complemented by a cozy blue couch. A round coffee table sits on a textured rug, with a potted orchid as a centerpiece.
Flat in Valparaiso
4.98 out of 5 average rating, 121 reviews

Cozy Casa: Downtown Digs!

Located in the heart of downtown Valparaiso, guests will love this updated, historic charmer! Walk to fabulous restaurants, local shops, or breweries & wineries in minutes. This unit has been fully updated and fully stocked with room to sleep 6. You'll be 25 minutes from the beaches of Lake Michigan/Indiana Dunes National Park, an hour from Chicago, and close to quaint towns and apple/berry picking orchards. This space is perfect for families & friends who want to relax or adventure outdoors!

Top guest favourite
The cottage exterior showcases a single-story structure with a light grey facade and a newly roofed design. Large windows allow natural light to enter, framed by a lush green landscape. A welcoming entryway leads to the home, complemented by garden pots and a gentle pathway.
Cottage in Gary
4.95 out of 5 average rating, 207 reviews

Neon Dunes Vista Beachfront Cottage

Neon Dunes Cottage is a one bedroom romantic getaway. A newly renovated cottage with new kitchen, modern appliances and new bathroom all in a bright airy home. It is located in Indiana Dunes National Park/Miller Beach. Only 1.5 blocks to the beach, you can hike trails nearby and come back to relax in a unique, comfortable setting with ambiance and charm. It's perfect for summer/holidays. Wifi, onsite parking and self check in, allow you to enjoy our wonderful home in privacy and peace.

Superhost
An aerial view captures the inviting pool area surrounded by lush greenery. The sparkling blue pool is framed by several lounge chairs, with a shaded patio leading to a well-maintained RV parked near the entrance. Colorful landscaping adds to the serene outdoor setting.
Campervan/Motorhome in Porter
4.82 out of 5 average rating, 749 reviews

'Pool Barn Camper' w/Hot Tub near Indiana Dunes

Hot tub open all year! Pool will reopen May 1. Fully equipped RV sleeps 5, has bathroom w/shower, stove, microwave, TV, heat & A/C, & running water all year. Located on the bike trail & only minutes from the sand beaches of Indiana Dunes on Lake Michigan. Hike in the Indiana Dunes National Park along the Little Calumet River & the historic Bailley homestead, only 1 block from the RV. Enjoy our large pool, hot tub, grill, campfire, & playground too. Schedule your visit today!

Guest favourite
The exterior of a two-story duplex is shown, featuring large windows and a welcoming porch. Well-maintained shrubs line the walkway, leading to the entrance. A grassy yard surrounds the home, with trees lining the background under a partly cloudy sky.
Flat in Crown Point
4.93 out of 5 average rating, 122 reviews

Lovely 2 bedroom just a few blocks from the square

6 Minute's walk from The Square! Shopping, dining, and sightseeing in the historical Crown Point Courthouse Square. Your family will be close to everything when you stay at this centrally-located place. Welcome to this amazing Century old freshly redone duplex home. You will be so very relaxed as you walk through the large shared front porch with 2 cozy reading nooks and upstairs into your private snug spot to lay your head while you're in Crown Point.

Top guest favourite
A cozy living area is illuminated by natural light streaming through the windows. A sofa is paired with an armchair beside a small table, creating a welcoming space. Soft textures are present in the area rug and decorative pillows, enhancing the comfort of the room.
Home in De Motte
4.96 out of 5 average rating, 277 reviews

Country Cottage

Looking for week-end get away? Traveling through Northwest Indiana on I-65 and looking for a quiet place to stay for the night? Situated on 6 acres and with convenient (2 mile) access to I-65, our cozy Country Cottage is a great choice! Enjoy the cottage feel of this recently renovated (new cabinets, flooring, appliances) and charmingly decorated home, located in close proximity to local attractions! Our 650 square foot cottage is ideal for 1 - 4 guests.

Guest favourite
A cozy living space features a dark blue sectional sofa, illuminated by a nearby table lamp. A colorful artwork hangs on the wall, complementing the light-colored walls. An open entryway leads to a dining area, where a wooden table and chairs are visible.
Home in De Motte
4.94 out of 5 average rating, 158 reviews

Home of 1888

Conveniently located 6 1/2 miles from I-65 between the Lowell and Roselawn exits and 6 miles from Sandy Pines Golf course & The Pavilion. This fully updated place has everything to feel right at home. The kitchen is provided with everything you need to prepare a meal. Plenty of places to eat out are just down the street. A 43" Samsung smart TV with Sling TV and Paramount Plus. When it's time to rest you'll do so on a brand new Nectar memory foam beds.

Guest favourite
A cozy seating area features a dark blue couch and a wooden side table. A welcoming sign is placed atop the table. Open shelves hold kitchen items, while a doorway leads to the bedroom. Natural light illuminates the space, enhancing its inviting appearance.
Flat in Valparaiso
4.86 out of 5 average rating, 125 reviews

Cute Skylar: Valparaiso University ShortTerm Stay

Welcome to Skylar's Relaxing Spot! This cozy one-bedroom on the second level features a queen-size bed, its own entrance, deck space, and building laundry facilities. Perfect for accessing downtown and Valpo University. Enjoy strong WiFi for remote work and relaxing movie nights on the TV. Located near Route 30 and I-49, it’s an hour from Chicago and 15 minutes from Indiana Dunes, close to malls, ice cream parlors, and great restaurants! ☺️

Top guest favourite
The exterior of a private guest house is shown, featuring a detached two-story structure. A driveway leads to a garage with a white door, while a wooden staircase ascends to the entryway. The surrounding area includes greenery and paved walkways.
Guest suite in Crown Point
4.94 out of 5 average rating, 255 reviews

IT'S THE WRIGHT PLACE

Private guest house newly remodeled. One bedroom queen bed, bath w/shower, full kitchen stocked, including microwave and Keurig coffee maker pods included, family room TV, and WIFI. No matter if you are in town for work, sport competition, family or just vacationing we offer all the comforts of home. Air Mattress available upon request. Please treat as your own home, follow all house rules. No party or gatherings. This is a no smoking home.

Guest favourite
Cottage in Valparaiso
4.88 out of 5 average rating, 585 reviews

Flint Lake Cottage.

This is a rustic cottage with old world charm. There are 2 fireplaces,. The home sits on a hill overlooking the channel that leads to Flint Lake. - Pet free -May not be appropriate for people with mobility issues. - Earth friendly cleaning products - Private beach & park access - Easy access to city center & university - One hour from downtown Chicago - National Lakeshore and Dunes State Park nearby - Wood fireplaces (winter only!)

Guest favourite
A well-maintained exterior view of the cottage is displayed, featuring a neatly manicured lawn and bordered by trees. A private driveway leads to the entrance. The structure showcases a front porch area, and a fire pit is visible in the yard, inviting outdoor enjoyment.
Cottage in Merrillville
4.88 out of 5 average rating, 269 reviews

The Hideaway-An experience getaway!

NEW: Sauna & Jacuzzi! Welcome to your cozy cottage ESCAPE, a modern sanctuary 30 minutes from Chicago. This secluded private, detached cottage on a 3-acre property features a NEW SAUNA with Bluetooth & light therapy & JACUZZI (outdoor w/ privacy walls, a king-size bed, and a full kitchen. Enjoy your own yard, fire pit, and covered parking. A perfect blend of comfort and convenience. Single, or couples only.

Popular amenities for Winfield holiday rentals

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