Holiday houses in Valparaiso

4.99 out of 5 average rating, 494 reviews

Farm stay in La Porte

Cabin on Swede Hill

Welcome to "Cabin on Swede Hill". Our family has farmed this land since 1871. My great grandparents, Swan and Johanna Johnson immigrated to America in the 1860's, found this land which was similar to Sweden. They raised their family here. Approximately 65 Swedish families settled in this community, became to be know as the "Swede Hills". We just received the Hoosier Homestead Award from Indiana celebrating the Sesquicentennial Award. We invite you to come...... and experience country life.

4.88 out of 5 average rating, 548 reviews

Cottage 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

4.93 out of 5 average rating, 120 reviews

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!

4.93 out of 5 average rating, 29 reviews

Modern Studio Apt w/ Separate Bedroom Area

Newly renovated studio garden/basement level apartment with separate bedroom area in the heart of downtown Valparaiso. Onsite parking!! Centrally located, everything 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 more! Just a 25 minute drive north and you’re at the stunning Indiana Dunes/Lake Michigan lakeshore. You’re sure to enjoy this modern apartment in a 100 year old building!

5 out of 5 average rating, 154 reviews

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!

5 out of 5 average rating, 180 reviews

Barn in Valparaiso

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.

4.95 out of 5 average rating, 131 reviews

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

4.95 out of 5 average rating, 201 reviews

Guesthouse in Valparaiso

Private Cottage in Gated Nudist Community

We offer a private cottage on the grounds of Lake O the Woods Club. Cottage has Queen size bed, air conditioning, heater, refrigerator, microwave, TV, coffee maker, work/dining area, private deck and porta-potty. Payment of club daily grounds fee ($30-$60) is mandatory. Pricing on club website. There is no running water in the cottage. Bathrooms, showers, hot tub, sauna and swimming pool are available at the clubhouse and pool area . The cottage is sanitized after every rental.

4.97 out of 5 average rating, 31 reviews

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. Enjoy the tranquility of the yard and 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!

Superhost

5 out of 5 average rating, 9 reviews

Serene Retreat in Beauty Creek

Enjoy our cozy yet spacious retreat located in the peaceful Beauty Creek Subdivision of Valparaiso, Indiana! This brand new stylish 3-bedroom home offers modern comforts and a relaxing living space perfect for families or small groups. Nestled in a quiet neighborhood, you're just minutes away from Valpo's vibrant downtown area, 5 minutes from Butterfly Meadows Park, and just 20 minutes from the Dunes! Book your stay and experience all that Valpo has to offer today!

4.96 out of 5 average rating, 406 reviews

Guesthouse in Valparaiso

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.

4.86 out of 5 average rating, 152 reviews

Charming Valpo University 2 BDR ShortTerm Stay

Stay comfortably in this 2-bedroom apartment, ideally located for extended stays. It features two queen-size beds and is within walking distance of Valpo University and downtown Valparaiso. Equipped with strong WiFi for remote work and a TV for leisure, the apartment provides easy access to Route 30 and I-49. Conveniently located, it’s just an hour from Chicago and 15 minutes from the Indiana Dunes, with nearby malls and dining options.!☺️

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Other great holiday rentals in Valparaiso

5 out of 5 average rating, 7 reviews

Downtown 2 BR Cottage w/ King Bed

GabrielRating, 5 stars1 day ago

It was a Great place to stay at. Me and my girlfriend enjoyed the area as well there was lots to do and the places we went to were fun. The house was amazing especially the living room and kitchen. The morning view in the kitchen was amazing and the living room was also amazing at night. Hayley was a great host as well as she responded quick to any questions we had. Overall me and my girlfriend loved the place and area and would 10/10 recommend this place to stay at.

5 out of 5 average rating, 9 reviews

Farm stay in Valparaiso

Good Acres

IzzyRating, 5 stars1 month ago

Had an awesome time at the barn! Met some friends for dinner at stacks and ended the night in the cozy loft! Gym was filled with activities that kept us entertained the evening. Host was very quick with responses. Would recommend again.

4.71 out of 5 average rating, 7 reviews

Sweet home

AlaneRating, 5 stars1 month ago

Enjoyed our brief stay. The downstairs space was clean and modern; seems that it was just recently finished, with everything new. Leticia responded immediately to a couple questions we had about entry, supplies and made us feel very welcomed. It's a great location, close to downtown -- and very close to our favorite spot: Journeyman's! Thanks for sharing your home!

5 out of 5 average rating, 3 reviews

Creekside Cozy 3BD • Near Dunes

SaulRating, 5 stars1 month ago

Place looks like the pictures. Located in a nice neighborhood with stores nearby.

Campervan/RV in Chesterton

4.88 out of 5 average rating, 60 reviews

South Shore RV National Park.

OliviaRating, 5 stars1 week ago

We had an awesome last minute stay with Robert. His family and dogs were extremely friendly. We utilized the pond and fishing poles and had a blast, Mike the dog is an avid fisher pup and came to sit with us while we fished. It’s a very quiet and peaceful area. We forgot a few things and Robert was more than happy to assist us and was extremely quick with responses and communication. We would love to come back and stay again. I highly highly recommend this spot. It looks just like the photos and the fire pit was a relaxing way to calm down at the end of the night. Thanks Robert! :-)

4.92 out of 5 average rating, 13 reviews

Home in Valparaiso

KenRating, 5 stars1 week ago

I can't say enough about Carol. When I reached out to her and asked if we could check-in early due to driving all night, she gave us permission so we could get in, get some rest and tend to my father's affairs (the main reason for the visit). Because of Carol's understanding and willingness to be flexible, we were able to get our rest and then tend to our family matters. We offered to give her extra and she wouldn't accept it. That shows me the true character of Carol and hope that anyone wanting to stay here understands how important it is to find people like that these days. The home had EVERYTHING we needed and then some and we'll reach out to her again for our next trip to the area! The foosball table and games on the enclosed back porch were a bonus (didn't see that when we signed up to stay) and my daughters loved having the chairs back there to sit and read their books while it was raining outside. THANK YOU AGAIN CAROL, for everything!!! :) Ken

4.6 out of 5 average rating, 148 reviews

MODERN GEM, CLOSE TO DOWNTOWN VALPO AND VU

JoanaRating, 5 stars3 weeks ago

We needed a place last minute & thankful Mike’s place was available. Location close to Valpo Univ! Can’t wait to return!