40 properties  

$150-900/night

Abodes on Oak: Fully stocked, side-by-side homes!

4 Bedrooms • 3 Baths • Sleeps 1-12
Internet
The ultimate family-friendly vacation for up to 12 people! This listing includes TWO houses on the same property; the main house sleeps up to 9 people, and the small studio sleeps up to 3. Enjoy foosball, board games, & even a coin operated bubblegum machine...Stay home and make yourself coffee or a cocktail at the kitchen bar, or venture out to the nearby national park, casino, wineries, zoo, & outlet mall. Fully updated & stocked with kitchenware, appliances, & smart TVs; we've got it all!

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$99-1,558/night

Big Blue

5 Bedrooms • 2 Baths • Sleeps 8-12
Internet Beach
The ultimate friend/family vacation house! Fully updated & stocked with new kitchenware, appliances, beach toys/towels, & smart TVs; this rental has everything you need! Less than 2 miles from the beach & casino, & a short drive from tree-lined hiking trails in the nation's newest national park. Enjoy wineries, boat rentals, cafes, Michigan City zoo, splash pad & park, outlet malls, & antique shops. The perfect getaway for up to 12 people! (Futon for a 13th person for an additional fee)

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$113-1,133/night

Big Brick Bungalow - Lower Unit

4 Bedrooms • 2 Baths • Sleeps 6-10
Internet Fireplace Beach
She's a brick...Duplex! This is the lower level unit of a home where guests can enjoy arcade games, 2 smart TVs, and an outdoor firepit. Recently renovated and decorated, and only 2 miles from sandy beaches. Near tree-lined hiking trails in the national park, casino, wineries, boat rentals, cafes, Michigan City Zoo, splash pad and park, outlet malls, & antique shops; the perfect getaway for up to 10 people who want to relax or adventure!

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$67-580/night

Brick Bungalow Upper Unit: Close to Beach, Casino, & Wineries

1 Bedroom • 1 Bath • Sleeps 2-4
Internet Beach
She's a brick..Duplex! This is the upper level, totally separate unit, with it's own entrance, where guests can enjoy their own cozy apartment with smart TV and an outdoor firepit. Recently renovated and decorated, and only 2 miles from sandy beaches. Near tree-lined hiking trails in the national park, casino, wineries, boat rentals, cafes, Michigan City Zoo, splash pad and park, outlet malls, & antique shops; the perfect getaway for up to 4 people who want to relax or adventure!

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$159-1,447/night

Chesterton Charmer

5 Bedrooms • 2 Baths • Sleeps 1-12
Internet Beach
The perfect solution for 2 traveling families: Two separate units in the same house, conveniently located in the heart of downtown Chesterton. These have been recently updated and fully stocked with room to sleep 12. Just a 15-minute drive from the Indiana Dunes/Lake Michigan, & a 2-minute walk to downtown! Lay low and relax in your stylish surroundings, cook a meal in a stocked kitchen, or head out to explore nearby attractions. No matter what your plans are, this home has you covered!

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$82-546/night

Chesterton Charmer: Lower Unit

3 Bedrooms • 1 Bath • Sleeps 1-6
Internet Beach
Just a 15-minute drive from the Indiana Dunes/Lake Michigan, & a two-minute walk to downtown Chesterton! Guests will love this upper unit in a historic home. The prime location and fully stocked kitchen allow you to walk downtown for a meal or dine in. Watch a movie in the spacious living room, enjoy a cup of coffee on the cozy porch, or venture out to explore nearby attractions. Whether you want to lay low & relax, or explore all the area has to offer, this rental has you covered!

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$78-523/night

Chesterton Charmer: Upper Unit

2 Bedrooms • 1 Bath • Sleeps 1-6
Internet Beach
Just a 15-minute drive from the Indiana Dunes/Lake Michigan, & a two-minute walk to downtown Chesterton! Guests will love this upper unit in a historic home. The prime location and fully stocked kitchen allow you to walk downtown for a meal or dine in. Watch a movie in the spacious living room, enjoy a cup of coffee on the cozy back porch, or venture out to explore nearby attractions. Whether you want to lay low & relax, or explore all the area has to offer, this rental has you covered!

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$90-539/night

Cozy Casa

2 Bedrooms • 1 Bath • Sleeps 1-6
Internet Beach
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!

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$79-602/night

Cozy House near Beach, Casino, Outlets, & Hiking

3 Bedrooms • 1 Bath • Sleeps 5-7
Internet Beach
Escape with family or friends near the dunes of Lake Michigan! Recently renovated and decorated, you won't find a better rental! Guests will love this cozy home located near a variety of attractions. Just 2 miles from the sandy beaches, near tree-lined hiking trails in the nation's newest national park, casino, wineries, boat rentals, cafes, Michigan City Zoo, splash pad and park, outlet malls, & antique shops. This is the perfect little getaway for up to 6 people who want to relax or adventure!

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$173-1,035/night

Downtown Duplex

4 Bedrooms • 2 Baths • Sleeps 1-12
Internet Beach
The perfect solution for 2 traveling families: Two separate units in the same house, conveniently located in the heart of downtown Valparaiso. Walk to fabulous restaurants, local shops, breweries & wineries in minutes. These units have been recently updated and fully stocked with room to sleep 12. Just 25 minutes from Lake Michigan/Indiana Dunes National Park, an hour from Chicago, and close to quaint towns and apple/berry picking: perfect for families & friends who want to relax or adventure!

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$149-1,103/night

Dunes Duplex - 2 units in 1 - close to everything!

4 Bedrooms • 2 Baths • Sleeps 7-12
Internet Beach
The perfect solution for 2 traveling families: 2 separate units in the same house, conveniently located near a variety of attractions! Fully renovated and tastefully decorated! Two miles from the sandy beaches, near tree-lined hiking trails in the nation's newest national park, casino, wineries, boat rentals, cafes, Michigan City Zoo, splash pad and park, outlet malls, & antique shops. This is the perfect little getaway for up to 12 people who want to relax or adventure!

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$88-839/night

Game On Getaway!

2 Bedrooms • 2 Baths • Sleeps 4-10
Internet Beach Downtown
The Perfect Getaway Awaits! “Game On” Getaway is a charming second-floor unit in the House Wins duplex with fun decor and modern amenities. Enjoy endless entertainment in the game room, comfy beds, and a shared outdoor fire pit. Just a short walk to shops, restaurants, parks, and beautiful beaches. The fully equipped kitchen is perfect for meals with family, or explore nearby dining options to experience the best of downtown Michigan City!

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