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Trailside Retreat

Welcome to Trailside Retreat, your ideal getaway. Our spacious, open-concept 1,000 square ft. apartment located behind the main house has complete privacy. It has two bedrooms—one with a king-size bed and another with two full beds, plus a full-size hide-a-bed in the living room. It includes a fully equipped kitchen with open dining area. And the living room area is perfect for game nights, movie marathons or a romantic dinner for two. Enjoy your private patio and beautifully landscaped yard.

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!

NEW* Blend of Glam and Vintage Charm

Newly Updated Unit. The whole group will enjoy easy access to everything from this centrally located place. Just 2 blocks from quaint downtown Valpo square featuring shops, restaurants, outdoor pavilion and ice rink for winter fun. This unit has a perfect set up for groups and families with two private queen bed rooms, and one room w/ triple bunk beds: queen, full and twin. An oversized couch in a spacious living room & dining table is great for game night, dinners or hanging out together.

Contemporary Downtown 1-Bedroom Apartment

Welcome to your ideal getaway in the heart of downtown Valparaiso! This sought-after one-bedroom unit is perfectly situated near a new parking garage, making it convenient for travelers. Features: Ethan Allen Furniture: Enjoy the sophisticated decor that adds a touch of luxury. 43-Inch Smart TV Circulon Cookware: Equipped with high-quality pans, perfect for preparing delicious meals on the quartz countertops. Prime Location: Just steps away from vibrant local attractions & delicious dining.

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 Compass Retreat

The Compass Retreat — Spacious 3BR, 2BA fully furnished guest suite at Compass Pointe Apartments in Valparaiso. This second-floor home features a modern open layout, fully equipped kitchen, full-size washer/dryer, and private balcony. Sleeps up to 6 with linens and housewares provided. Located in the heart of Valparaiso—just 2 minutes from downtown, near Valparaiso University, and only 30 minutes to Lake Michigan and the Indiana Dunes. Enjoy access to pools, fitness centers, and more.

Modern 2 BR Apt Downtown Valpo - EV Charging

Cozy 2 bd/1 bath garden/basement level apartment in the heart of downtown Valparaiso—just 1.5 miles from Valparaiso University! Onsite parking!! Everything within walking distance... coffee shops, restaurants, and boutiques. Central Park Plaza is a block away and offers a summer market, concerts in the park, ice skating, and other exciting events. The stunning Indiana Dunes/Lake Michigan lakeshore is just a 25 minute drive away. A modern apartment in a 100 year old building.

Studio Apt. Near Downtown Valpo! (.2 mile walk)

Beautiful Studio Apartment that is not only a short walk from downtown Valparaiso but also less than a mile away from the University!! Perfectly located for anyone wanting to enjoy the culture and cuisine that make downtown Valparaiso a growing travel destination or for anyone looking to enjoy a weekend sporting event at Valparaiso University. The studio apartment is around 600 sq feet and has new, modern furniture that will make your stay both comfortable and relaxing!

Private Downtown Apartment

Downtown Chesterton private apartment. Walk to parks, dining, shopping, taverns, winery, European market, and more. Only 3 miles from sand beaches & hiking trails at Indiana Dunes State Park and Indiana dunes National Park. Apt has living, dining, full kitchen, large bedroom w/King bed, large jet bath & fireplace, and bathroom. Living room has 58" smart tv and an L shaped couch. Glider and gas grill outside too. No cleaning fee. Instant book with us now!

Cozy Corner, Apartment 2S. Steps to shops & Dining

Welcome to Cozy Corner 2S, a charming second-floor apartment in our fully restored historic home—just steps from downtown Valparaiso! Perfect for up to 4 guests, this updated unit blends old-world character with modern amenities. Cook in the kitchen, stream a movie on the Smart TV, or head outdoors to the shared firepit, picnic tables, and cornhole game. With restaurants, shops, breweries, and cafes just minutes away, you’ll never run out of things to do.

Cute Skylar: Valparaiso University ShortTerms

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! ☺️

Creekside Cozy 3BD • Near Dunes or Corporate Stay

The perfect mix of work and play! Relax or recharge at this peaceful retreat just 16 mins from Indiana Dunes State Park! Ideal for families or business travelers—close to local industries, hiking, and beaches. Sleeps 6 with a cozy creekside view, full kitchen, comfy beds, and open-concept living. Nestled in a quiet, nature-filled neighborhood with fast Wi-Fi and free parking.