Vacation rentals 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 a that leads to Flint lLake.The lake can be acce - Pet free - 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 - Local breweries & award winning restaurants - Biking & hiking trails near by - Wood fire places to enjoy in cold weather only

Downtown Apartment on Lincolnway

Convenience at its best meets historic charm! Located in the center of downtown Valparaiso (literally), The Lincoln is in a prime location that puts you within minutes to enjoy all that downtown Valparaiso and the surrounding areas have to offer. Walk to fabulous restaurants, local boutique shops, bars, breweries, wineries, and distillery in minutes. Downtown Valpo offers numerous exciting events throughout the year. The Lincoln is perfect for families & friends who want to relax or adventure!

The Hazel Irene | ModernVintage Cottage

Welcome to the Hazel Irene! This charming 1942 cottage offers a perfect blend of modern comfort and vintage charm with thoughtfully curated details, a peaceful and private yard with mature manicured gardens. Located in a quiet neighborhood 3 mins from downtown Valparaiso and 5 mins to Valparaiso University. The Hazel Irene is perfectly located for adventures within Indiana and or exploring Illinois and Michigan, making this an ideal 3 state getaway! As they say...location, location, location!

ValpoVilla: Location, location, location!

Located in the heart of downtown Valparaiso, guests will love this updated, historic charmer! Walk to fabulous restaurants, local shops, or breweries & wineries in minutes. This unit has been fully updated and fully stocked with room to sleep 6. You'll be 25 minutes from the beaches of Lake Michigan/Indiana Dunes National Park, an hour from Chicago, and close to quaint towns and apple/berry picking orchards. This space is perfect for families & friends who want to relax or adventure outdoors!

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

Enjoy 44 acres just 15 minutes from the beaches of Lake Michigan! With room to sleep 6, guests will enjoy this fully stocked barn apartment with gorgeous views! You'll be near Indiana Dunes National Park, tree-lined hiking/biking trails, wineries, cafes, outlet malls, & antique shops. Roast s'mores in the fire pit, watch chickens free range through the yard or grab a bite to eat downtown Valpo/Chesterton/MC—the perfect getaway for families or friends who want to relax or adventure in nature.

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

Pontoon INCLUDED in all rentals thru Sept 2025! 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

Tiny Home on Organic Veggie Farm

Place yourself right in the beauty of the land and nature in this cozy tiny home at Perkins' Good Earth Farm. The tiny home has a loft bedroom, bathroom with shower and composting toilet, kitchen, sitting area, and deck. You'll be surrounded by organic vegetable fields, 11 acres of woods, walking trails--and within perfect view of both the sunrise and sunset. You'll also have easy access to our farm store where you'll find fresh fruits & veggies, homemade soups & salads and so much more.

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.

Cute Skylar: Valparaiso University ShortTerm Stay

Welcome to Skylar's Relaxing Spot! This cozy one-bedroom on the second level features a queen-size bed, its own entrance, deck space, and building laundry facilities. Perfect for accessing downtown and Valpo University. Enjoy strong WiFi for remote work and relaxing movie nights on the TV. Located near Route 30 and I-49, it’s an hour from Chicago and 15 minutes from Indiana Dunes, close to malls, ice cream parlors, and great restaurants! ☺️