Holiday rentals in Highland

Cabin on Swede Hill

Welcome to "Cabin on Swede Hill". Our family has farmed this land since 1871. My great grandparents, Swan and Johanna Johnson immigrated to America in the 1860's, found this land which was similar to Sweden. They raised their family here. Approximately 65 Swedish families settled in this community, became to be know as the "Swede Hills". We just received the Hoosier Homestead Award from Indiana celebrating the Sesquicentennial Award. We invite you to come...... and experience country life.

Lakeside Dome Retreat w Hot Tub Near Indiana Dunes

Welcome to Valparaiso Lakeside Retreat a private getaway on Long Lake featuring a one-of-a-kind outdoor geodesic dome (11 feet), hot tub, fire pit, & kayaks. 20 minutes from Indiana Dunes National Park. Perfect for couples, remote workers & nature lovers seeking a tranquil escape. Enjoy stunning Long Lake views from your private backyard & dome. Long Lake public beach access is just around the corner. Perfect for kayaking, swimming, or a morning walk to the water. Book this unique stay today!

Couples Getaway, Jacuzzi, Sauna, Pool

Couples 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.

Spacious home 28 miles from Downtown Chicago

This lovely 4B/2B home features an open concept floor plan. Property features a living/dining room and kitchen with a Keurig for your morning coffee. This home is located close to I80-94 making it convenient for guests to explore the area! Our guests have access to the entire home. This property is located less than 30 minutes from downtown Chicago and Schererville, IN and less than an hour from Orland Park and Oak Brook Mall where there are plenty of restaurants and stores for shopping.

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!

Lockports Famous Hideaway ~ 2bdrm Guest House Flat

A history buff’s dream filled with antiques & artifacts relating to Chicago, Joliet, Lockport, the I & M Canal & "Route 66"! *Note: Pricing is based on "Double Occupancy". Extra charges per person apply after 2 guests. Can accommodate up to 6 guests. Family & Business Friendly. The entire upstairs 1,500 sq ft vintage 2-bedroom house apartment is all your own space. The flat is NOT shared with other guests/host. Private-entrance/self-check-in. Have a 'historic' stay at the "Hideaway"!

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.

Hot tub open year round in modern/rustic cottage!

Kick back and relax in this rustic & stylish cottage that is surrounded by gorgeous landscaping on almost 2 acres in Harbert. Cherry Beach a 5 min drive, 15 mins to New Buffalo, & minutes to Greenbush, Infusco, Susan's & the new Out There wine bar! Perfect place if you seek peace & quiet - play a record, hit the hot tub, read a book in screened in porch or hammock, hang out by the firepit or jump on one of the 4 bikes! So close to boutiques, coffee shops and cute restaurants!

The Hideaway-New Sauna & Jacuzzi

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. No children or pets with exceptions to nursing infants.

Rainbows End 🌈 Plensa

Escape to a tranquil countryside cottage on a 20-acre farm. Enjoy breathtaking sunrises from the picture window, relax in lounge chairs, and gather around the fire pit and grill or take a trail walk down to the south branch of the Galien River. Just 10 minutes from Lake Michigan, and within 5 miles of a casino and a golf course, it's the perfect retreat for nature lovers and entertainment seekers. Book now and experience rural bliss with nearby attractions!

Cozy three bedroom home in Munster , Indiana.

Plan your next escape to Indiana or Illinois and stay in this beautifully renovated and thoughtfully appointed 3 bedroom and 1 bath home. Located in the quiet and safe suburb of Munster, Indiana, the property is just a 3 minute, easy access to the I-94 Highway. Exciting Downtown Chicago is just 30 minutes away! Walk to Riverside Park and take in the scenic view while enjoying a morning croissant and coffee from one of the quaint neighbourhood cafés.

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.