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Dunes Homestead - Near Dunes + Lake + Dog Friendly

Welcome to "The Dunes Homestead". Where all pets are welcome! Right in-between The Dunes National Park and downtown Chesterton, you will be close to everything when you stay at this centrally located home. Artfully crafted, this charismatic, dog themed home greets you with all new furniture, a front porch, big yard, and focuses the design around your "man's best friend"! Less than 10 minutes to the Dunes and beaches or head 5 minutes to downtown for food, drinks and plenty of small-town fun. 😁

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!

-The District 5 Schoolhouse-

The District 5 Schoolhouse was historically built "with not a single nail in the structure" in the 1800's. It still stands as a symbol of dedication to craftsmanship and community. Lovingly restored, preserving as much of the original soul as possible, it promises to be a luxury stay in understated sophistication with 100% linen sheets, beautiful kitchen/dining, lovely private outdoor space, tranquil idyllic work/recharge areas, and enough space to make your own history. You won't want to leave.

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!

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

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!

Modern House, Sleeps 10, Near Downtown, 2000 sqft

Your family will enjoy this centrally-located home a mile from downtown and the new Journeyman Distillery, close to VU as well as 20 min to the beach. Our home is perfect for a large family or wedding party, it has 5 beds and can comfortably sleep to 10 guests. The home includes stainless steel appliances, a ping pong and Foosball table. With two bathrooms featuring double vanities, as well as a half bath, there's room for everyone to get ready. We hope you enjoy your journey to Valpo!

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!

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! ☺️

The Lake Escape -Cozy Lakefront Cottage Valparaiso

Escape the everyday with a relaxing stay at this cozy cottage located on Flint Lake! Hot tub, pontoon boat, fire pit, gas fireplace, tv, lake front, canoe, kayak, sauna, grill and more. This charming property is lake front with a small 50ft beach area and dock. Use of 2018 Sylvan pontoon boat, canoe, and kayak are included. You will love the lake life. Please note the pontoon boat is only available in season from May 1st to October 1st.

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!)

Cozy Luxe Downtown Valparaiso Stay

Welcome to “Chalet Valpo”! A historic carriage house located minutes from the heart of Valpo that we have had completely gutted and made new for you! This home is a carriage house, it is located on our personal property. You have complete privacy during your stay in a private fenced in area. Do not hesitate to reach out with any questions. Walkable to downtown Valparaiso! NO CLEANING FEE!