Holiday rentals in Wolf Lake

Stunning XL Rustic Modern Escape w/ Gaming & Spa!

Sticks & Stones Rustic Recreation Retreat is a 16+ guest luxury log cabin on the west edge of Bloomington, IL. Secluded in peaceful wooded acreage, yet just minutes from TONS of restaurants, bars, sports & activities! 🧩 HUGE GAMING LEVEL! 🎱🎲⛳️🏀 🫧 Jacuzzi & Sauna 🔥 Fire pit & gas grill 🥘 Fully stocked kitchen ❤️ Comfy lounge furniture 🤩 6 sleeping areas, 3 full baths 🛌 Deep hybrid mattresses 🚿 Endless hot water 🎮 6 TVs & Xbox w/ Game Pass 🕊️ 4 Beautiful Porches 🌳 Swings & huge yard!

Handicap accessible apartment w/Level-2 EV Charger

Just 12.5 miles from downtown in the extremely quiet Chicago neighborhood of Hegewisch. Walking distance to the South Shore train line, which can easily get you to Chicago museums and entertainment, or attractions in NW Indiana. Private parking in back also gives you the option of driving anywhere and then walking directly to your door, and outside cameras are present for security. Banks, restaurants, grocery, convenience, and liquor stores are all 1 block of the apartment for all your needs.

Lakefront House, Pontoon, Deck, Fire Pit & More!

Pontoon INCLUDED in all rentals May 2026-Sept 2026! No extra fees for unlimited use of private pontoon, pier, paddle boards and more!! Rental price of our lakefront house includes the pontoon, deck, yard and endless activities!! Take the pontoon for a cruise, fish, swim, paddle board, kayak, watch the wildlife or have a bonfire!! Travel 15 minutes to the Indiana Dunes or 10 minutes to downtown Valpo. You will also be able to cook delicious meals on the propane grill & fully stocked kitchen

Luxury Cabin Getaway •2 min to Beach• 1hr Chicago

Luxury meets nature: forest cabin steps from the beach, 1 hour from Chicago. Book your escape to our designer log cabin on Lake Michigan just steps from the beach and nestled in a peaceful forest, it’s the perfect retreat. Built in 1932, our charming cabin sleeps 8 in 4 bedrooms. Enjoy 2 living areas, a stone fireplace, fire pit, games, puzzles & books. Featured in Country Living and the NYT, it’s perfect for families, friends, or retreats. Book now and create lasting memories in Michiana.

Your second home in Chicago

Why settle for a hotel when you can immerse yourself in our vacation rental that boasts of three spacious bedrooms and 1.5 bathrooms, all designed with a relaxing, modern touch. The open-concept space is adorned with contemporary furnishings, creating a serene environment perfect for unwinding after a day of city exploration. The location of our home offers ample parking, a rare find in the city. Plus, you're just a five-minute drive from the beautiful shores of Lake Michigan. Come Enjoy.

MiniGolfHouse-Chicago Close Beach & Indoor Fun!

*REQUIRED* ✅ Will you bring a pet? ✅ Have you read and agree to all rules? 🌆 30min drive to downtown Chicago ⭐️ Near Horseshoe Casino, Lake Michigan, Whihala Beach, Whoa Zone ⛳️ Heated basement with mini golf, arcade games and big TV ⭐️ Close To: Wolf Lake, Indiana Dunes, HardRock 🏠 cots, air mattress, futon sofa 🍼 pack & play, high chair avail ❤️ Guests love: -short drive into Chicago -comfortable beds -indoor mini golf -nearby shops & food -heated bidet toilets

Beach Bird Cottage- 5min walk to the lake! 3BR/1BA

Dear friends, Welcome to Beach Bird Cottage, situated on a quiet street with other vintage cottages in the heart of Union Pier. It is an easy 5-minute walk to an association beach. The cottage has many updates, including a new kitchen, bathroom, washer/dryer, outdoor shower and a wood stove. The master and second bedroom each have queen-size beds and the children's bedroom has two twin beds. Enjoy an early swim before breakfast or have an evening beach picnic under the sunset.

Blackbird…On the Drive

SEE OUR SPRING DISCOUNTS Fully renovated home with breathtaking views of downtown lights and Peoria Lake - two full king ensuites, custom gourmet kitchen, cozy den w/ fireplace, lounge with walkout access to an amazing second story deck for cocktails, coffee or just relaxing and watching beautiful sunsets. The recently added third story is 600 sq ft suite, complete with king size bed, fireplace, walk-in closet and full bath with double walk-in shower. Pamper yourself

A Family Rowhouse by UChicago

Our three level rowhouse includes a main floor with an open concept living space and kitchen making it the perfect gathering space. Basement in-law suite with kitchenette allows for max privacy for a large group. Located on University Ave. steps from UChicago and easy access to the lakefront trail and beaches as well as to downtown via Metra or express bus. A short walk to downtown Hyde Park. NOTE: Registered guests only. No parties. Thanks!

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!)

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.

Whiting Getaway

Nicely situated in the quiet and safe city of Whiting IN, near the bustling Whihala Beach on Lake Michigan, just down the street from Wolfe Lake and the Wolfe Lake Pavilion, within 2 miles of The Horseshoe Casino and just 20 minutes (17.5 miles) from downtown Chicago, this house offers a perfect location for a complete vacation. Come and enjoy all that the 'region' has to offer