Holiday rentals in Wolf Lake

Aviation Getaway with Private Runway Access!

Dreaming of an exclusive aviation escape? This stunning new construction is designed for pilots, aviation enthusiasts, and families looking for a truly unique experience. Fly your airplane right in and park in the luxury showroom-style hangar – perfect for multiple planes! This custom-built retreat features three spacious bedrooms and 3.5 bathrooms, a full bar, pool table, poker table, and an inviting outdoor fire pit. It's the perfect weekend escape for families, couples, or groups of friends.

The Spa of Downtown Whiting

so close to Chicago but so far away. NEWLY REMODELED AND COMPLETELY FURNISHED. There's so much to enjoy in this incredible converted 2 flat, now a single unit. WE COMPLETELY RIPPED ON AND REDID THE ENTIRE INTERIOR. 1ST Flr-spa w/ 2 person jacuzzi, shower, continuous hot water, family room, kitchen 2nd flr, sitting room w/ TV and surround sound, 2 bedrooms, w/ bathroom and bath/shower. -FRONT BALCONY, -SPEAKERS THROUGHOUT -BLOCKS FROM THE BEACH & WOLFE LAKE -PERFECT LOCATION FOR PIEROGIFEST

Frank Lloyd Wright's The Meyer House

Seize this opportunity to stay in a Frank Lloyd Wright treasure! Mahogany accents have been meticulously restored, and the gardens are in full bloom throughout the season. Awarded the Seth Peterson Cottage Conservancy's 2019 Visser Award for Outstanding Restoration of a FLW House and the 2021 Wright Spirit Award in the private category. Once your reservation is confirmed you will need to provide your email in order to receive the house manual and contact information for the house manager.

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.

Exquisite Modern A-frame all WithInnReach

An amazing space that truly caters to the guest experience. We've built this art piece to have our guests immerse themselves in all the amenities, from heated floors to in-ceiling speakers - all whilst losing yourself in the wood burning fireplace. At WithInnReach the attention to detail was paramount - with an emphasis of what we enjoy...amazing food through a well balanced kitchen, beautiful sound through Klipsch speakers and relaxation with floor to ceiling showers...enjoy to the fullest.

Enchanted Garden Treehouse (Amenity*)

Summer's here, the treehouse air conditioned and cozy, and the hot tub ready! Relax in our luxurious, 420 friendly, very private, 4' deep cedar hot tub nestled in the evergreens, while the moon and stars swirl overhead, the waterfall tumbles into the koi pond, and the fire table and torches blaze. The stream makes this a wildlife refuge, with many birds, squirrels, rabbit & fox. Come experience the magic and make a special memory! See why Chgo Magazine rates us top 3 staycations in Chgo!

Sunset Cove LakeHouse-Paddle Boat-HotTub-Billiards

Enjoy the spacious lakefront retreat in Rockford designed for unforgettable family vacations, group getaways, and relaxing weekends on the water. Nestled on a stocked 10-acre lake, this home offers the perfect mix of comfort, entertainment, and outdoor fun-all just minutes from I-90 Whether you're fishing off the dock at sunset, soaking in the hot tub, grilling on the deck, or putzing in the paddle boat, Sunset Cove is the perfect place to relax, reconnect, and enjoy lake life together!

TheGlassCabin @ HackmatackRetreat

The Pond House, a vintage glass cabin filled with art, water views & eclectic vibes privately perched on the sacred grounds of Hackmatack Retreat Center. Native prairie, a winding slow river, two ponds, 200+ year old oaks & big sky- Countless places to curl up, gathering, focus-- nooks and crannies indoors and out, we offer “time out for time in” amidst this noisy world. Minutes from 2 small towns, all amenities, we're all about peace & ease-- let us custom curate your experience !

Stunning Secluded Luxury Escape w/Hot Tub & Gaming

Sticks & Stones Rustic Retreat is a spacious luxury log home on the west edge of Bloomington, IL. Secluded in peaceful wooded acreage, yet just 10-15 minutes from a vibrant scene of local restaurants, landmarks & activities! 🎱 Two awesome game rooms! 🏒⛳️🏀 🫧 Jacuzzi & sauna! 🔥 Fire pit & grill 🥘 Fully stocked kitchen 👑 Comfy lounge furniture throughout 🛌 Super comfortable mattresses 💤 🎮 HD TVs & Xbox 🕊️ Beautiful Porches 🌳 Swings & large yard

Malaya Dunes | Walk to Laketown Beach!

10 minutes from downtown Saugatuck, yet private and secluded, Malaya Dunes sits on 12 acres of wooded coastal sand dunes. Take a 10-minute hike through the dunes to the beach and soak in the Pure Michigan coast, one of the most highly sought-after landscapes on earth. Inside, you’ll find four luxurious bedrooms, a modern kitchen, an open entertaining space and huge picture windows to look out on the serene and peaceful landscape.

Cabin off 39 - Peaceful, private one bedroom cabin

Kick back and relax in this calm, stylish space. Nestled among the trees, it provides a quiet getaway from the chaos of life allowing you to recharge and renew. The main residence is approximately 400 feet from the cabin. The cabin is secluded and yet close to local attractions, restaurants, biking and nature trails. The Cabin has a total of 420 sq ft living space with 280 sq ft on the ground floor and a 140 sq ft bedroom loft.

The Cabin on the water!

Relax with the whole family at this peaceful place to stay. The main bedroom has a queen size bed, smart tv with a barn door that overlooks the water. The double bunk rooms mirror each other and both have closets,drawers and USB charging port’s ..very fun and unique! The entire cabin has been masterfully crafted with barn wood and materials from years gone bye. It’s definitely one of a kind!