Holiday rentals 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, 549 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!

Superhost

Home in Chesterton

4.8 out of 5 average rating, 298 reviews

South Shore Studio Apartment {National Park}

I have to warn you definitely not a hook up spot or party house!!! typically rise with rooster on this 5 acre country setting with a small fishing pond. 420 friendly .. Quiet hours are 11 -8 generally some music playing, musicians are welcome !! if you happen to book on a Sunday i host an Open Mic in my Barn every Sunday ..... pretty relaxed. Upon arriving, turn into the driveway, and then right into the yard. Apartment is upstairs, the door is open with the keys inside. ✌️

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.

Superhost

Cottage in Merrillville

4.87 out of 5 average rating, 247 reviews

The Hideaway

This Christian friendly cozy cottage, located 30 minutes from Chicago is located on a private 3 acre property. It’s a private detached cottage from main house that sleeps four. One king size bedroom (2 air mattresses) (sheets supplied), large full bathroom with deep tub w/ handle (towels supplied), full kitchen (dishes, pots and pans ect supplied) private covered parking and yard (directly in front of cottage) w/ its own fire pit for enjoyment. No plug for electric cars (station 2 m away).

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

Guest house in Valparaiso

4.95 out of 5 average rating, 201 reviews

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.

Guest house in Valparaiso

4.96 out of 5 average rating, 408 reviews

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.

4.85 out of 5 average rating, 117 reviews

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! ☺️

Guest house in Valparaiso

4.98 out of 5 average rating, 163 reviews

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!

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Other great holiday rentals in Valparaiso

4.93 out of 5 average rating, 59 reviews

Campsite in La Porte

Peaceful Campsite with Creekside Fire Pit

TiaRating, 5 stars2 weeks ago

Justin was a fantastic host! Campsite is exactly as described, private and very peaceful. Bathroom was accessible and clean. Would definitely recommend ⭐️⭐️⭐️⭐️⭐️

5 out of 5 average rating, 7 reviews

Downtown 2 BR Cottage w/ King Bed

GabrielRating, 5 stars3 days 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.

4.91 out of 5 average rating, 70 reviews

The Cottage at Twin Creeks Farm

BernadetteRating, 5 stars5 months ago

Second time staying. Wonderful place to stay and great host. Highly recommend.

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

The Jefferson House

ThomasRating, 5 stars2 weeks ago

We stayed at the Jefferson House for 14 days and what an amazing place. The moment we arrived, we just knew that our stay would be great. Walking into the beautiful garden, with nice chairs around a fireplace in the middle and going up to the back porch with all the cozy furnitures could make for some great outdoor time and it sure did. Going in to the house from the back entrance is perfect, so that you can drop all your stuff there and continue to the kitchen and living room. All the bedrooms are on the top floor and were perfect for the 7 of us. They had nice and clean beds, with bathrobes and towels for everyone and you could really feel that Shana had put time and effort into all the rooms with details that made it comfortable and nice to stay there. From booking the house, through our stay and after, Shana the host has been so nice and helpful, we would definitely stay there again. Also remember to read Shana tips about restaurants and stuff to do in the area, they are so good 😀

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.

4.82 out of 5 average rating, 17 reviews

Clover Haven * Modern 3-Br Home Near Lake & Dunes

RameshRating, 5 stars5 months ago

My stay at this Airbnb was a delightful experience! The space was impeccably clean, comfortable, and had everything needed for a relaxing stay. The peaceful setting made it a perfect getaway, while still being conveniently located near local spots. Thoughtful details throughout the property added to the charm. I’d gladly book again and highly recommend it to anyone visiting Valparaiso!