Holiday houses in Lakes of the Four Seasons

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Top-rated holiday rentals in Lakes of the Four Seasons

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

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Top Guest favourite

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!

4.96 out of 5 average rating, 140 reviews

Guest favourite

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.

4.89 out of 5 average rating, 159 reviews

Guest favourite

A spacious wooden deck descends to a fenced backyard featuring a well-maintained lawn. The outdoor seating area includes a large table set for meals, with views of the lake and surrounding greenery visible beyond the yard.

Home in Cedar Lake

Lakeside Loft

Escape the noise and unwind at our cozy lakeside getaway, just a 40 minute drive from downtown Chicago. Nestled in a peaceful, rural area, this charming property is perfect for families seeking a refreshing retreat. With five spacious bedrooms, three indoor lounges, three outdoor seating areas including a fire pit, and a fully equipped kitchen, our home comfortably accommodates the whole family. Featuring direct access to the beautiful Cedar Lake right in your backyard.

5.0 out of 5 average rating, 52 reviews

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.

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.

4.94 out of 5 average rating, 148 reviews

Guest favourite

Guesthouse in Valparaiso

The Ambrose Suite - Guesthouse in Valparaiso

Stay at the historic Elmer Wolf House, also known as the Wolf Manor, built in 1890. This luxe suite features pristine antique furnishings with refined elegance on 4.8 peaceful acres with gardens, birdwatching, and multiple outdoor spaces. Enjoy hammocks, fire pit, and a stone picnic area. Just 6 miles to downtown Valparaiso and 15 minutes to the Dunes National Park. Private entrance, carriage house parking, full kitchen, queen bedroom, bath, and laundry.

4.94 out of 5 average rating, 32 reviews

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

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.

4.94 out of 5 average rating, 196 reviews

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

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.

4.94 out of 5 average rating, 291 reviews

Top Guest favourite

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!)

4.89 out of 5 average rating, 633 reviews

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 suite in Valparaiso

Lakeside Dome Retreat w Hot Tub Near Indiana Dunes

Cozy up under the twinkling lights of your own geodesic dome, then soak away the day in the hot tub just steps away. This lakeside retreat is made for couples craving a slow, quiet escape: private dome, hot tub, fire pit, kayaks, and a 20 minute drive to Indiana Dunes National Park. Your private backyard opens onto Long Lake, with public access for kayaking and swimming a short walk away (the dock next door belongs to our neighbors).

4.98 out of 5 average rating, 179 reviews

Top Guest favourite

Barn in Valparaiso

The Good Farm: Barn BnB on 44 acres near Lake Mich

Escape to BarnBnB, a charming barn apartment on 44 acres just 15 minutes from Lake Michigan beaches and Indiana Dunes National Park. 🐓🌳 Perfect for families or groups (up to 6 guests), this peaceful retreat blends modern comforts with farm life—free-range chickens, firepit evenings, and trails included. Relax in nature or explore nearby Valparaiso, Chesterton, and Michigan City for the perfect mix of adventure and tranquility.

5.0 out of 5 average rating, 245 reviews

Superhost

Home in Crown Point

SummerTree Estates Home

Forget your worries in this spacious and serene space. 45 Mins from Chicago IL, 20 Mins from Indiana Dunes Beaches, State Park, This beautiful 4 Bedroom, 2 and a Half Bath Home is the best choice to come spend quality time with family. 3 King Size Beds, 1 Queen Size Bed, 2 Living Rooms, 2 Dining Rooms, Office space and with beautiful size bathroom is your perfect get away for vacation.

5.0 out of 5 average rating, 4 reviews

Top Guest favourite

The exterior of the home showcases a white siding and large windows, surrounded by lush greenery. A wooden deck with seating is visible, complemented by stone steps leading to the yard. The fenced area offers a private outdoor space for relaxation.

Cottage in Valparaiso

Cozy 2 Bedroom Valparaiso Cottage

This quiet, centrally located north side home offers a perfect place to relax. Only minutes away from downtown Valparaiso and the Indiana Dunes National Park. Conveniently situated for day and evening adventures and activities. Such as, local lakes, parks, and festivals. Enjoy hiking, bird watching, swimming, fishing, fine dining, local breweries and wineries, and so much more.

4.97 out of 5 average rating, 140 reviews