Vacation rentals in Winfield

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Top-rated vacation rentals in Winfield

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

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Guest favorite

A living room is presented with a soft grey sofa adorned with yellow cushions. A round wooden coffee table sits on a patterned rug, while two cream-colored armchairs are positioned for conversation. Natural light floods the space through numerous windows, highlighting the fireplace against a blue accent wall.

Home in Crown Point

Small Town Gem - Crown Point

This 1940's charming midwestern home will take you back to your roots.The home is equipped with all of the necessities.The 3 bedrooms are surrounded with windows for enjoying the bright sunny days or gazing at the snow, relax in front of the living room fireplace or the 3 seasons room overlooking the yard.A garden oasis awaits you on summer days-perfect for a BBQ or reading a book.Whether you are in town for business or vacay, this little gem will have you living the dream of small town America.

FamilyLocationBackyard

4.95 out of 5 average rating, 37 reviews

Top guest favorite

A comfortably arranged living area features a large, sectional sofa complemented by a circular coffee table. The space is illuminated by soft lighting from a nearby lamp. A television is mounted on the wall, and a decorative plant adds a touch of greenery.

Home in Merrillville

Creekside Getaway

Take it easy at this unique and tranquil getaway. Located in a wooded cul-de-sac, privacy and nature abound. The home is also situated on a deer path. Watch families of deer migrate to the east in the morning and return West in the early evening. Blue Heron fish in the backyard creek. The creek is also used for kayaking to Lake George in Hobart. Try your hand at fishing. Blue gill, crappy and carp have been caught from those waters. Service dogs will be charged $ 75.00 cleaning fee.

FamilyValueBathroom

4.94 out of 5 average rating, 69 reviews

Top guest favorite

Home in Whiting

The Ashlin House.

Stay at our family-friendly home on a quiet, cobblestone street on vacation or business. We've recently repainted the exterior and painted the master BR. Walking distance to quaint Downtown Whiting , Lake Michigan, Whihala Beach & Lakefront trails. The Horseshoe Casino, Wolf Lake & Pavilion, Hammond Sportsplex, Calumet College, PNW, IUN, U of Chicago, BP, & golf courses are a short drive. See Chicago's Skyline at Lakefront Park. Chicago's attractions & Hard Rock Casino are < 30 mins away.

FamilyValueCheckout

4.92 out of 5 average rating, 143 reviews

Top guest favorite

A modern farmhouse is showcased, featuring a covered front porch with comfortable seating. Lush greenery surrounds the entrance and a small outdoor seating area with a table and chairs is visible. The structure is complemented by large windows that invite natural light.

Home in Crown Point

Quiet Farmhouse Retreat

Looking for a tranquil farmhouse destination? Get away at Wadsworth Acres- a Scottish Highland hobby farm! This modern farmhouse is the perfect space to relax. Complete with a very spacious primary suite, large eat-in kitchen, exercise room, and space to play outside- you’ll never have to leave! Enjoy your morning coffee with breathtaking farm sunrises on the patio and evenings in the hammocks.Peaceful escape just 5 minutes from the highway, 10 from historical downtown, 35 from the Dunes!

FamilyLocationGetting around

4.96 out of 5 average rating, 140 reviews

Superhost

Farm stay in Crown Point

Country vibe at Pomme Place - 3 bedroom apartment

Wind down and enjoy the country. Pomme Place, our private three bedroom apartment at Apple Blossom Trails, has a private entrance and the amenities of home. We have an apple orchard to roam, animals to watch, an adjacent playground and a great spot for bird watching. A large private deck extends from the apartment providing the perfect place to enjoy an evening. We live on site, adjacent to the apartment. We also have Paul, our musical security person, on site living in a mobile home.

LocationValueView

4.87 out of 5 average rating, 160 reviews

Guest favorite

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.

Apartment in Crown Point

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.

FamilyLocationAir conditioning

4.94 out of 5 average rating, 148 reviews

Guest favorite

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

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.

ValueFamilyOutdoor spaces

4.94 out of 5 average rating, 196 reviews

Superhost

Home in Cedar Lake

New! Cedar Lake 4br Home for 8 W/ Lake Views

Welcome to your Cedar Lake getaway! Located within walking distance of Cedar Lake, one of the largest natural lakes in Northwest Indiana, this spacious 4-bedroom home offers the perfect blend of comfort, convenience, and lakeside adventure. Whether you're planning a family vacation, fishing trip, boating weekend, or relaxing getaway with friends, you'll enjoy easy access to the lake while having plenty of space to unwind after a day of exploring.

FamilyLocationGetting around

4.8 out of 5 average rating, 5 reviews

Top guest favorite

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

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.

LocationFamilyNearby

4.94 out of 5 average rating, 291 reviews

Top guest favorite

A rustic cottage is nestled among lush greenery, featuring a stone path that leads to the entrance. The home, with blue shutters and a welcoming porch, is framed by a flowering tree and various plants, creating a peaceful setting.

Cottage in Valparaiso

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!)

LocationFamilyView

4.89 out of 5 average rating, 634 reviews

Guest favorite

Home in Valparaiso

Secluded Lakefront A-frame House.

Take it easy at this unique and tranquil private getaway. Enjoy a full kitchen, grilling out, sitting on the deck taking in lake views, relaxing in the hot tub, napping in a queen or king bed, or warming up around a camp fire with a cup of hot chocolate. At the same time take advantage of this new house build modern amenities.

LocationFamilyCheck-in

4.97 out of 5 average rating, 62 reviews

Guest favorite

Home in Schererville

Comfy 3BR 2BA, Liv+Fam Rm, Prime, 3-Car Parking

Welcome to your home away from home! Whether you're visiting for business, a family vacation, or a weekend getaway, this home offers the perfect blend of comfort, convenience, and relaxation. Everything is thoughtfully set up to ensure a smooth and enjoyable stay. Book your stay today and make yourself at home!

ValueLocationSleep quality

4.91 out of 5 average rating, 102 reviews