Valparaiso vacation rentals

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Top-rated vacation rentals in Valparaiso

Guests agree: these vacation rentals are highly rated for location, cleanliness, and more.

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Guest favorite

Guesthouse in Valparaiso

4.96 out of 5 average rating, 161 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. Bathrooms, showers, hot tub, sauna and swimming pool are available at the clubhouse and pool area . The cottage is sanitized after every rental. Fresh baked muffins are available in the morning.

Sep 2 – 9

R1,199 ZAR per night

Guest favorite

Farm stay in De Motte

4.94 out of 5 average rating, 113 reviews

Cozy barn loft on organic vegetable farm

Find peace and restoration in this beautiful barn loft at Perkins' Good Earth Farm. The loft has a bedroom, separate shower and toilet spaces, work area, sitting room, kitchen space, and heating/cooling fresh air system. Located above our farm store, the loft provides privacy for you while giving you access to fresh fruits & veggies, locally sourced meats, homemade soups & salads from our farm kitchen, and so much more. You can also walk our farm trails, visit the veggies, or enjoy a campfire.

Mar 5 – 12

R1,601 ZAR per night

Guest favorite

Apartment in Valparaiso

5.0 out of 5 average rating, 111 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!

Sep 17 – 24

R3,781 ZAR per night

Guest favorite

Home in Valparaiso

4.95 out of 5 average rating, 112 reviews

Lakefront House, Pontoon, Deck, Fire Pit & More!

Pontoon included in all rentals April 15, 2024-September 30, 2024 Are you ready to plan an unforgettable summer vacation? How does the relaxing scenery of a lakefront house with pontoon, deck, yard and endless activities sound? 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.

May 9 – 16

R8,445 ZAR per night

Guest favorite

Barn in Valparaiso

5.0 out of 5 average rating, 119 reviews

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.

Oct 27 – Nov 3

R4,024 ZAR per night

Guest favorite

Cottage in Valparaiso

4.88 out of 5 average rating, 495 reviews

Flint Lake Cottage.

This is a rustic cottage with old world charm. There are 2 fireplaces,. The home sits on a hill overlooking a lake. The lake can be accessed from the back yard. - 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

Oct 24 – 31

R2,435 ZAR per night

Guest favorite

Farm stay in Crown Point

4.91 out of 5 average rating, 106 reviews

Country vibe at Pomme Place - 3 bedroom apartment

Wind down and enjoy the country. Pomme Place, our private three bedroom apartment at Apple Blossom Trails, has a private entrance and the amenities of home. We have an apple orchard to roam, animals to watch, an adjacent playground and a great spot for bird watching. A large private deck extends from the apartment providing the perfect place to enjoy an evening. We live on site, adjacent to the apartment. We also have Paul, our musical security person, on site living in a mobile home.

Mar 24 – 31

R2,576 ZAR per night

Guest favorite

Guesthouse in Chesterton

4.96 out of 5 average rating, 114 reviews

Bro’s Place

Welcome if you like country life Bro’s place is the place to be...watching the sheep, chickens and wildlife on you back deck making dinner on the grill with a full kitchen. Pick your own veggies outside the back door when in season. You will find a welcome basket with snacks, wine and homemade soap in bathroom fresh eggs from our chickens when available if your planning to visit our Beautiful Indiana Dunes you’ll find everything you need..chairs, towels, cooler Queen size sofa sleeper

Dec 26 – Jan 2

R1,958 ZAR per night

Guest favorite

Guesthouse in Chesterton

4.91 out of 5 average rating, 313 reviews

"myhathouse" detached studio downtown Chesterton

Vaulted skylights allow natural light. Ksize bed. Futon opens into a bed. (DEEP cleaned to AirBnb COVID-19 disinfectant standards) Fully stocked kitchen, sm. bathroom w/ shower. Parking ft. of house, 1.5 M from Lake Michigan Shoreline, 2 blocks to 15th St. entry to Prairie-Dune Trail. European Market (May -Oct) each Saturday downtown. Fall season drives along U.S. HW 12 & 20 for foliage Winter day hikes, x-county skis trail, shopping trips to the Michigan City Outlet mall

Jan 1 – 8

R1,919 ZAR per night

Guest favorite

Home in De Motte

4.96 out of 5 average rating, 206 reviews

Country Cottage

Looking for week-end get away? Traveling through Northwest Indiana on I-65 and looking for a quiet place to stay for the night? Situated on 6 acres and with convenient (2 mile) access to I-65, our cozy Country Cottage is a great choice! Enjoy the cottage feel of this recently renovated (new cabinets, flooring, appliances) and charmingly decorated home, located in close proximity to local attractions! Our 650 square foot cottage is ideal for 1 - 4 guests.

Nov 20 – 27

R2,065 ZAR per night

Guest favorite

Guesthouse in Valparaiso

4.95 out of 5 average rating, 371 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.

May 7 – 14

R2,343 ZAR per night

Guest favorite

Cottage in Merrillville

4.89 out of 5 average rating, 183 reviews

The Hideaway

This cozy cottage (lodging only, renters only) located 30 minutes from Chicago is located on a private 3 acre property. It’s a private detached cottage that sleeps four. One king size bedroom (sheets supplied), large full bathroom with deep tub (towels supplied), full kitchen (dishes, pots and pans ect supplied) and private parking. Also has its own fire pit for enjoyment.

Jul 28 – Aug 4

R2,449 ZAR per night

Vacation rentals for every style

Get the amount of space that is right for you

Popular amenities for Valparaiso vacation rentals

Gym

BBQ grill

Laptop-friendly workspace

Wifi

Air conditioning

Stay near Valparaiso's top sights

Walmart Supercenter4 locals recommend

Industrial Revolution Eatery & Grille7 locals recommend

Glenrose Park North - ValPLAYso5 locals recommend

Stacks Bar and Grill24 locals recommend

Zao Island22 locals recommend

Kelsey's Steak & Seafood8 locals recommend

Other great vacation rentals in Valparaiso

Guest favorite

Guesthouse in New Buffalo

4.98 out of 5 average rating, 692 reviews

"Tiny House" Guest House Under the Oak Trees

Apr 30 – May 7

R1,980 ZAR per night

Guest favorite

Barn in Michigan City

4.96 out of 5 average rating, 342 reviews

The Black Pearl Great Escape Spa & Art Shop

Feb 15 – 22

R2,359 ZAR per night

Guest favorite

Cabin in Grovertown

4.93 out of 5 average rating, 200 reviews

Cozy Cabin at Coppertop Barn

Sep 10 – 17

R2,701 ZAR per night

Guest favorite

Home in Michigan City

4.89 out of 5 average rating, 442 reviews

Beautiful beach bungalow with hiking and hot tub!

Feb 23 – Mar 2

R1,805 ZAR per night

Guest favorite

Guesthouse in New Buffalo

4.99 out of 5 average rating, 270 reviews

Rainbows End 🌈 Bourgeois

Nov 21 – 28

R2,883 ZAR per night

Guest favorite

Guest suite in Crown Point

4.93 out of 5 average rating, 208 reviews

IT'S THE WRIGHT PLACE

Jun 27 – Jul 4

R1,487 ZAR per night

Guest favorite

Home in Portage

4.92 out of 5 average rating, 148 reviews

Newly Renovated with Finished Basement

Nov 4 – 11

R3,056 ZAR per night

Guest favorite

Home in Valparaiso

4.96 out of 5 average rating, 85 reviews

Cozy Luxe Downtown Valparaiso Stay

Aug 29 – Sep 5

R2,539 ZAR per night

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Other great vacation rentals in Valparaiso

Guest favorite

Apartment in Valparaiso

4.91 out of 5 average rating, 53 reviews

Downtown Apartment on Lincolnway

Sep 22 – 29

R3,449 ZAR per night

Guest favorite

Home in Valparaiso

4.95 out of 5 average rating, 39 reviews

Secluded 3400sq ft home jet tub close to amenities

Dec 29 – Jan 5

R2,967 ZAR per night

Guest favorite

Camper/RV in Valparaiso

4.97 out of 5 average rating, 59 reviews

New trailer in gated nudist community

Mar 29 – Apr 5

R1,432 ZAR per night

Guest favorite

Apartment in Valparaiso

4.87 out of 5 average rating, 70 reviews

Lovely Downtown Historic Apartment in Valparaiso

Mar 29 – Apr 5

R2,432 ZAR per night

Guest favorite

Home in Valparaiso

4.93 out of 5 average rating, 68 reviews

Backyard Park Access and Walking Distance Downtown

May 30 – Jun 6

R3,719 ZAR per night

Guest favorite

Home in Trail Creek

4.98 out of 5 average rating, 65 reviews

Leo Lodge

Dec 2 – 9

R2,001 ZAR per night

Guest favorite

Cabin in Valparaiso

5.0 out of 5 average rating, 46 reviews

Cabin on the Lake

Jul 5 – 12

R6,833 ZAR per night

Guest favorite

Apartment in Valparaiso

4.97 out of 5 average rating, 33 reviews

Modern 2 BR Apt Downtown Valpo

Mar 13 – 20

R3,676 ZAR per night

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Quick stats about vacation rentals in Valparaiso

Total rentals
60 properties
Rentals with dedicated workspaces
40 properties have a dedicated workspace
Pet-friendly rentals
20 properties allow pets
Family-friendly rentals
30 properties are a good fit for families
Total number of reviews
3.1K reviews
Nightly prices starting at
R760 ZAR before taxes and fees

Frequently Asked Questions

Are there pet-friendly vacation rentals in Valparaiso?
Four-legged friends are welcome in Valparaiso. Choose from more than 20 vacation rentals for guests traveling with pets.
Are there vacation rentals with a dedicated workspace in Valparaiso?
Yes! Work meets play with ease at over 40 vacation rentals in Valparaiso featuring dedicated workspaces. Stay connected and productive in your home away from home.
Do apartment rentals in Valparaiso have air conditioning?
Absolutely! We offer over 10 apartment rentals with air conditioning in Valparaiso. Enjoy a tailored experience with all the comforts you desire.
How much does it cost to stay in apartment rentals in Valparaiso?
Experience the best of Valparaiso with our apartment rentals, starting at about $80 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Are there family-friendly house rentals in Valparaiso?
Valparaiso has more than 20 family-friendly house rentals. Amenities on the property may include high chairs, travel cribs, or strollers.
Do house rentals in Valparaiso have wireless internet?
Absolutely! We offer over 30 house rentals with wireless internet in Valparaiso. Enjoy a tailored experience with all the comforts you desire.

Valparaiso vacation rentals

Top-rated vacation rentals in Valparaiso

Vacation rentals for every style

Houses

Apartments

Hotels

Popular amenities for Valparaiso vacation rentals

Stay near Valparaiso's top sights

Other great vacation rentals in Valparaiso

Guesthouse in New Buffalo

Barn in Michigan City

Cabin in Grovertown

Home in Michigan City

Guesthouse in New Buffalo

Guest suite in Crown Point

Home in Portage

Home in Valparaiso

Other great vacation rentals in Valparaiso

Apartment in Valparaiso

Home in Valparaiso

Camper/RV in Valparaiso

Apartment in Valparaiso

Home in Valparaiso

Home in Trail Creek

Cabin in Valparaiso

Apartment in Valparaiso

Quick stats about vacation rentals in Valparaiso

Total rentals

Rentals with dedicated workspaces

Pet-friendly rentals

Family-friendly rentals

Total number of reviews

Nightly prices starting at

Frequently Asked Questions

Are there pet-friendly vacation rentals in Valparaiso?

Are there vacation rentals with a dedicated workspace in Valparaiso?

Do apartment rentals in Valparaiso have air conditioning?

How much does it cost to stay in apartment rentals in Valparaiso?

Are there family-friendly house rentals in Valparaiso?

Do house rentals in Valparaiso have wireless internet?

Destinations to explore