Photo by Joe Farmer

Highland holiday lettings

We found 152 holiday rentals — enter your dates for availability

Discover a selection of holiday rentals in Highland that are perfect for your trip. Holiday homes offer the best amenities for you and your friends, family or even pets, such as parking and a TV. At the end of the day, you'll be sure to find a property to rent for everyone's needs, including a place that's non-smoking or offers accessibility.

Holiday rentals with weekly discounts - Highland

Showing deals for:26 Dec - 2 Jan

Image gallery for Charming Miller Beach Cottage

Exterior detail
9.8 out of 10, Exceptional, (8 reviews)
Exceptional
(8 reviews)

Charming Miller Beach Cottage

Gary, IN

7% off
Price is £1,340
for 7 nights, 1 home
£191 per night
includes taxes & fees
Charming Miller Beach Cottage

Find spaces that suit your style

  • Peace of mind

    Our Book with Confidence Guarantee gives you 24/7 support

  • More quality time

    From booking to staying, the whole process is simple and enjoyable

  • All the privacy of home

    Enjoy full kitchens, pools, gardens and more

  • More for less

    More space, more privacy, more amenities — more value

Find out more about Highland

Find out more about Highland

The charming city of Highland awaits you

Enjoy the churches and other features of Highland. Travellers to this romantic city praise the ice skating, basketball games and bird watching. If you need more space to accommodate a family holiday or a trip with friends, rental homes often come with separate dining areas and spacious living rooms.

Activities and attractions in Highland

Are you hoping to find attractions to see while you're in the area? Venture out of your holiday home and experience everything that makes Highland a one-of-a-kind holiday spot. Here are some of the major attractions to see, all within 30 miles (48.2 km) of the city centre:

  • Albanese Candy Factory (11 mi / 17.8 km)
  • Ravisloe Country Club (11.3 mi / 18.1 km)
  • Deep River Water Park (13 mi / 21 km)
  • Turkey Creek Golf Course (6.5 mi / 10.4 km)
  • Lost Marsh Golf Course (7.9 mi / 12.7 km)
  • Harborside International Golf Center (12.2 mi / 19.6 km)

Exploring the natural landscape of Highland

Whether you're looking for exciting outdoor activities or just want to take in the scenery, you'll be sure to find the perfect setting for your holiday in Highland. Here are a few of the area's noteworthy features, all within 30 miles (48.2 km) of the city centre:

  • Indiana Dunes National Park (21.2 mi / 34.1 km)
  • Centennial Park (3.1 mi / 5 km)
  • Hammond Sportsplex & Community Center (3.1 mi / 5.1 km)
  • Crown Point Sports Complex (10.9 mi / 17.5 km)
  • Marquette Park (11 mi / 17.7 km)
  • Lake County Fairgrounds (11.3 mi / 18.2 km)

Transport to and around Highland

The nearest airport is in Chicago Midway Airport (MDW), located 22 mi (35.5 km) from the city centre. If you're unable to find a flight that fits your schedule, you can also fly into Chicago O'Hare International Airport (ORD), which is 37.4 mi (60.2 km) away.

Frequently asked questions

What is the best area to stay in Highland when booking a holiday rental?
When considering a holiday rental in Highland, Indiana, a popular area to stay is close to the downtown district. This vibrant neighbourhood offers a charming mix of local shops, restaurants, and parks, making it an ideal base for exploring the area. Visitors can enjoy the proximity to the beautiful Main Square Park, which is superb for leisurely strolls or picnics, and often hosts community events that can enhance your stay.

Another appealing option is the south side of Highland, where you'll find a more residential feel combined with easy access to larger shopping centres and dining options. This area is also near the popular Highland Grove Park, a lovely spot for outdoor activities and family fun. While the exact number of holiday rental properties may vary, you can generally find a good selection of options ranging from cosy apartments to spacious family homes, suiting a variety of tastes and budgets.
How much does it cost to rent a holiday home in Highland?
Prices for holiday rentals in Highland vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're traveling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in Highland to more spacious homes. To get the best value, book early and take advantage of Vrbo's free rewards program.
Are there any discounts for Highland holiday house rentals?
You can find great discounts on house rentals in Highland on Vrbo, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for Last minute bookings, and Early bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
What is the most popular type of holiday rental accomodation in Highland?
In Highland, holiday houses are the most popular type of rental accommodation, with several available throughout the area. These homes typically offer spacious interiors equipped with multiple bedrooms, fully furnished kitchens, and comfortable living spaces, making them suitable for families or larger groups. Many of these properties also feature outdoor areas, such as gardens or patios, where guests can relax and enjoy the pleasant surroundings.
Can I find long-stay holiday rentals in Highland?
A long-stay holiday rental in Highland is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your travel dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Are there pet-friendly house rentals in Highland?
In Highland, Indiana, there are several pet-friendly house rentals available, making it a welcoming destination for travellers with furry companions. Many of these rentals are situated in residential neighbourhoods that provide a comfortable and homely atmosphere. Amenities commonly found in these properties include fully equipped kitchens, spacious living areas, and outdoor spaces like gardens or patios where pets can enjoy some fresh air.
Are there any remote work holiday rentals in Highland?
In Highland, Indiana, there are several remote work holiday rentals available, making it a suitable destination for those looking to blend work and leisure. Many of these properties come equipped with dedicated workspaces, high-speed internet, and comfortable seating areas, allowing travellers to maintain productivity while enjoying their stay. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Highland holiday rentals with parking?
Vrbo offers a wide selection of holiday rentals in Highland with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details on Vrbo and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
What are popular rental amenities in Highland?
In Highland, popular holiday rental amenities include air conditioning, coffee makers, cookware, dishware, utensils, and dining tables. Many properties offer internet access as well, ensuring travellers can stay connected during their stay. These amenities contribute to a comfortable and convenient experience, making it easy for guests to relax and enjoy their time in the area.
When is the best time to visit Highland for a holiday rental?
The best time to visit Highland for a holiday rental is during the peak season from May to July. This period is particularly popular among families and outdoor enthusiasts who flock to the area to enjoy the warm weather and vibrant local events. With temperatures often reaching the high 20s Celsius, visitors can partake in a variety of outdoor activities, including hiking, biking, and enjoying the beautiful parks that Highland has to offer.

July stands out as the most popular month, where the atmosphere is lively, and various community festivals enhance the experience. Families can take advantage of numerous nearby attractions, such as the scenic trails and local playgrounds, making it an ideal time for those seeking both adventure and relaxation.

If you're looking for a more budget-friendly option, consider visiting Highland in October. During this time, you can enjoy the stunning autumn foliage, which transforms the landscape into a beautiful tapestry of colours. The cooler temperatures, typically in the low teens Celsius, provide a comfortable backdrop for leisurely strolls and exploring the charming local shops.
How early should I book a Highland holiday rental?
Book your Highland holiday rental at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your holiday rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
What are the top attractions in Highland?
In Highland, Indiana, visitors can enjoy several attractions that showcase the local charm. The downtown area features a variety of shops and eateries, great for a leisurely stroll. Nearby, the popular Wicker Memorial Park offers expansive green spaces, walking trails, and a lovely lake, making it ideal for outdoor activities and picnics.

For those interested in history, the South Shore Line train station is a gateway to nearby attractions in Chicago, allowing for easy day trips. The local Highland Historical Society provides insights into the town's heritage and often hosts events that engage the community.
Can I change or cancel my Highland home rental booking on Vrbo?
To find Highland holiday rentals with free cancellation, just use Vrbo's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Vrbo makes it easy to book with confidence.
Why should I join Vrbo as a host?
Joining Vrbo as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Vrbo makes it easy to list, manage, and succeed. Whether it's a cosy flat or a countryside retreat, you can turn your space into a standout destination—become a host and let Vrbo handle the heavy lifting to help you thrive.
Are all fees included in the Highland holiday rental prices shown on Vrbo?
Vrbo provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.

More Holiday Rentals ideas

Bright Holiday Rentals
Standard Link for Bright
Michigan City Holiday Rentals
Standard Link for Michigan City
Howe Holiday Rentals
Standard Link for Howe
Broad Ripple Holiday Rentals
Standard Link for Broad Ripple
Ruoff Home Mortgage Music Center Holiday Rentals
Standard Link for Ruoff Home Mortgage Music Center
Key West Holiday Rentals
Standard Link for Key West
Bloomington Holiday Rentals
Standard Link for Bloomington
Sarasota Holiday Rentals
Standard Link for Sarasota
Gosport Holiday Rentals
Standard Link for Gosport
Mount Vernon Holiday Rentals
Standard Link for Mount Vernon
Evansville Holiday Rentals
Standard Link for Evansville
South Bend Holiday Rentals
Standard Link for South Bend
Cambridge City Holiday Rentals
Standard Link for Cambridge City
Granger Holiday Rentals
Standard Link for Granger
Charlestown Family Activities Park Holiday Rentals
Standard Link for Charlestown Family Activities Park
MASE Clinic Monticello Holiday Rentals
Standard Link for MASE Clinic Monticello
Potato Creek State Park Holiday Rentals
Standard Link for Potato Creek State Park
Kokomo Holiday Rentals
Standard Link for Kokomo
Naples Holiday Rentals
Standard Link for Naples
Witmer Lake Holiday Rentals
Standard Link for Witmer Lake
Floyds Knobs Holiday Rentals
Standard Link for Floyds Knobs
San Diego Holiday Rentals
Standard Link for San Diego
Carmel Holiday Rentals
Standard Link for Carmel
South Haven Holiday Rentals
Standard Link for South Haven
Indianapolis Holiday Rentals
Standard Link for Indianapolis
West Harrison Holiday Rentals
Standard Link for West Harrison
Palm Springs Holiday Rentals
Standard Link for Palm Springs
Fort Wayne Holiday Rentals
Standard Link for Fort Wayne

People also search for

Nineveh Cottages
Standard Link for Nineveh
Gatlinburg Cabin Rentals
Standard Link for Gatlinburg