Holiday rentals in Valparaiso

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Top-rated holiday rentals in Valparaiso

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

Guest favourite
Guest house 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. 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.
17–24 Feb
$74 SGD per night
4.96 out of 5 average rating, 161 reviews
Guest favourite
Home in Portage
Newly Renovated with Finished Basement
This beautiful house is located near Lake Michigan in Northwest Indiana, less than 10 minutes from the expressway and toll road. There is a stainless steel kitchen, spa bathroom, finished basement and bar with sleeping capacity to accommodate two families. This is a smart home with Ring db, lights and thermostat controlled by your voice. We are less than an hour drive from downtown Chicago, and there are many great beaches nearby. Shopping and great dining options are also within a close drive.
7–14 Feb
$186 SGD per night
4.92 out of 5 average rating, 142 reviews
Guest favourite
Flat in Valparaiso
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!
23–30 Jun
$221 SGD per night
5.0 out of 5 average rating, 111 reviews

Popular amenities for Valparaiso holiday rentals

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 holiday rentals in Valparaiso

Guest favourite
Home in Chesterton
Hotel Whiskey
6–13 Apr
$188 SGD per night
4.98 out of 5 average rating, 123 reviews
Guest favourite
Flat in Valparaiso
Studio Apt. Near Downtown Valpo! (.2 mile walk)
1–8 Jun
$118 SGD per night
4.79 out of 5 average rating, 56 reviews
Guest favourite
Flat in Valparaiso
Downtown Apartment on Lincolnway
8–15 Aug
$168 SGD per night
4.92 out of 5 average rating, 50 reviews
Guest favourite
Home in Valparaiso
Cozy Luxe Downtown Valparaiso Stay
26 Jul – 2 Aug
$188 SGD per night
4.96 out of 5 average rating, 76 reviews
Guest favourite
Home in Valparaiso
Backyard Park Access and Walking Distance Downtown
4–11 Apr
$168 SGD per night
4.94 out of 5 average rating, 66 reviews
Guest favourite
Home in Valparaiso
Cheerful three bedroom home in Downtown Valparaiso
28 Apr – 5 May
$153 SGD per night
4.89 out of 5 average rating, 64 reviews
Guest favourite
Cottage in Valparaiso
Cozy 2 Bedroom Valparaiso Cottage
12–19 May
$128 SGD per night
4.95 out of 5 average rating, 44 reviews
Guest favourite
Flat in Valparaiso
Lovely Downtown Historic Apartment in Valparaiso
25 Jan – 1 Feb
$126 SGD per night
4.87 out of 5 average rating, 69 reviews
Guest favourite
Home in Valparaiso
Entire Home in Downtown Valparaiso!
15–22 Sep
$194 SGD per night
4.98 out of 5 average rating, 47 reviews
Guest favourite
Flat in Valparaiso
Modern 2 BR Apt Downtown Valpo
29 Nov – 6 Dec
$217 SGD per night
4.97 out of 5 average rating, 33 reviews
Guest favourite
Cabin in Valparaiso
Cabin on the Lake
31 May – 7 Jun
$422 SGD per night
5.0 out of 5 average rating, 41 reviews
Guest favourite
Home in Valparaiso
Secluded 3400sq ft home jet tub close to amenities
16–23 Apr
$189 SGD per night
4.95 out of 5 average rating, 38 reviews

Quick stats about holiday rentals in Valparaiso

Total rentals

60 properties

Rentals with dedicated workspaces

30 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

3.3K reviews

Nightly prices starting at

$54 SGD before taxes and fees

Destinations to explore

  1. Airbnb
  2. United States
  3. Indiana
  4. Porter County
  5. Valparaiso