Best Vacation Homes in Highland
Cottage
10.0(29 Reviews)
2 Bedrooms
1 Bath
4 Guests
Fireplace/Heating
Balcony/Terrace
Kitchen
Parking
AU $298/Night
7 Nights - AU $2,088
House
10.0(2 Reviews)
3 Bedrooms
2 Baths
9 Guests
1700.7 ft²
- Fireplace/Heating
Pet Friendly- Parking
Internet
AU $399/Night
7 Nights - AU $2,793
Hotel
9.6(1003 Reviews)
1 Bath
Hot Tub
Pool
Breakfast- Kitchen
AU $172/Night
7 Nights - AU $1,207
Apartment
10.0(18 Reviews)
1 Bedroom
1 Bath
2 Guests
400 ft²
- Fireplace/Heating
- Kitchen
- Parking
Air Conditioner
AU $126/Night
7 Nights - AU $881
Bed & Breakfast
9.6(11 Reviews)
4 Bedrooms
4 Baths
8 Guests
454.77 ft²
- Fireplace/Heating
- Balcony/Terrace
View- Parking
AU $226/Night
7 Nights - AU $1,579
Apartment
10.0(6 Reviews)
2 Bedrooms
2 Baths
4 Guests
1100 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
AU $209/Night
7 Nights - AU $1,462
Apartment
10.0(5 Reviews)
2 Bedrooms
1 Bath
6 Guests
- Fireplace/Heating
- Kitchen
- Parking
- Air Conditioner
AU $439/Night
7 Nights - AU $3,076
House
10.0(5 Reviews)
2 Bedrooms
1 Bath
4 Guests
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
AU $219/Night
7 Nights - AU $1,533
Highland Luxury Rentals
Hotel
6.7(78 Reviews)
1 Bath
204.51 ft²
Private Pool
Oceanfront- Fireplace/Heating
- Pool
AU $768/Night
7 Nights - AU $5,376
House
9.6(97 Reviews)
4 Bedrooms
2 Baths
12 Guests
22131 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
AU $734/Night
7 Nights - AU $5,136
House
9.0(14 Reviews)
4 Bedrooms
4 Baths
10 Guests
6000 ft²
- Hot Tub
Spa- Fireplace/Heating
Ocean View
AU $704/Night
7 Nights - AU $4,927
Hotel
8.5(204 Reviews)
1 Bath
283.45 ft²
- Fireplace/Heating
- Balcony/Terrace
- Parking
- Air Conditioner
AU $694/Night
7 Nights - AU $4,856
House
9.4(6 Reviews)
5 Bedrooms
3 Baths
10 Guests
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
AU $682/Night
7 Nights - AU $4,773
Hotel
7.5(115 Reviews)
3 Baths
301.39 ft²
- Private Pool
- Fireplace/Heating
- Pool
- Kitchen
AU $625/Night
7 Nights - AU $4,375
House
10.0(11 Reviews)
4 Bedrooms
2 Baths
11 Guests
3000 ft²
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
AU $601/Night
7 Nights - AU $4,211
Hotel
7.1(187 Reviews)
4 Baths
290.63 ft²
- Private Pool
- Fireplace/Heating
- Pool
- Pet Friendly
AU $528/Night
7 Nights - AU $3,698
Highland Pet Friendly Vacation Rentals
House
9.6(7 Reviews)
1 Bedroom
1 Bath
2 Guests
930 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
AU $151/Night
7 Nights - AU $1,058
Hotel
9.5(32 Reviews)
3 Baths
466.43 ft²
- Private Pool
- Oceanfront
- Fireplace/Heating
- Pool
AU $221/Night
7 Nights - AU $1,550
Hotel
9.0(203 Reviews)
1 Bath
- Pool
- Balcony/Terrace
- Breakfast
- Pet Friendly
AU $346/Night
7 Nights - AU $2,424
Apartment
9.4(51 Reviews)
2 Bedrooms
1 Bath
4 Guests
700 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
AU $258/Night
7 Nights - AU $1,808
Hotel
9.4(571 Reviews)
12 Baths
322.02 ft²
- Private Pool
- Fireplace/Heating
- Pool
- Pet Friendly
AU $221/Night
7 Nights - AU $1,550
Apartment
10.0(7 Reviews)
3 Bedrooms
1 Bath
6 Guests
1400 ft²
- Fireplace/Heating
- Pet Friendly
- Kitchen
- Parking
AU $492/Night
7 Nights - AU $3,443
House
9.8(27 Reviews)
3 Bedrooms
2 Baths
9 Guests
1700 ft²
- Fireplace/Heating
- Pet Friendly
- Kitchen
- Parking
AU $431/Night
7 Nights - AU $3,017
Apartment
9.6(113 Reviews)
3 Bedrooms
1 Bath
9 Guests
1100 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
AU $314/Night
7 Nights - AU $2,199
Highland Large Vacation Homes
Villa
10.0(3 Reviews)
2 Bedrooms
2 Baths
4 Guests
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
AU $247/Night
7 Nights - AU $1,731
House
3 Bedrooms
2 Baths
10 Guests
- Fireplace/Heating
- Parking
- Air Conditioner
- Internet
AU $264/Night
7 Nights - AU $1,844
Villa
10.0(177 Reviews)
3 Bedrooms
1 Bath
6 Guests
- Fireplace/Heating
- Kitchen
- Parking
- Air Conditioner
AU $200/Night
7 Nights - AU $1,403
House
10.0(75 Reviews)
7 Bedrooms
3 Baths
14 Guests
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
AU $514/Night
7 Nights - AU $3,596
House
10.0(19 Reviews)
5 Bedrooms
2 Baths
8 Guests
3000 ft²
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
- View
AU $417/Night
7 Nights - AU $2,919
House
7.0(8 Reviews)
5 Bedrooms
4 Baths
10 Guests
- Hot Tub
- Fireplace/Heating
- Pet Friendly
- Air Conditioner
AU $461/Night
7 Nights - AU $3,227
Bed & Breakfast
10.0(1 Review)
4 Bedrooms
2 Baths
12 Guests
Child Friendly
AU $385/Night
7 Nights - AU $2,698
House
6 Bedrooms
3 Baths
12 Guests
- Child Friendly
AU $561/Night
7 Nights - AU $3,924
Why Choose Rent By Owner for your Highland Vacation Rental Homes?
What makes our Vacation Rentals special?
Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
Diverse Options
From cozy cabins to luxurious villas, find a rental that suits your style and needs.
Best Times to Visit Highland
When should you plan your Vacation Rentals stay?
Choosing the optimal time to visit here can enhance your experience, as seasonal variations in the region offer different opportunities for enjoying your stay in Highland, Illinois.
Peak Season Highlights
Late Spring to Early Summer (May to June)
During this time, you'll enjoy warm weather that makes outdoor activities and exploring the area more enjoyable. The region experiences a pleasant climate ideal for outdoor pursuits, attracting visitors seeking a lively yet comfortable atmosphere.
Average Temperature Daytime: 75°F - Nighttime: 55°F
Early Fall (September to October)
This season offers mild temperatures and vibrant fall foliage, making it an excellent choice for scenic drives and outdoor adventures. The area's natural beauty peaks during these months, drawing travelers looking for picturesque surroundings and comfortable weather.
Average Temperature Daytime: 70°F - Nighttime: 50°F
Off-Season Highlights
Mid Winter (January to February)
The cold winter months bring cooler temperatures, offering a quieter experience away from the crowds. If you prefer solitude and are prepared for colder weather, this is a peaceful time to visit and enjoy cozy accommodations.
Average Temperature Daytime: 35°F - Nighttime: 20°F
Late Fall (November to December)
As the region transitions into winter, temperatures drop and the landscape prepares for snowfall. This off-peak period provides a calm ambiance, ideal for those seeking a relaxed retreat before the holiday rush.
Average Temperature Daytime: 45°F - Nighttime: 30°F
Weekly Weather Forecast for Highland
How to Book Your Highland Vacation Rental Home
What's our booking process?
Our platform allows you to browse a curated selection of vacation rentals. Once you find the ideal property, you’ll be redirected to a trusted booking partner to complete your reservation securely.
Booking Steps
01
Search Properties
Use our filters to find the right property that fits your needs.
02
Select a Rental
Click on your preferred listing to view details, amenities, and pricing.
03
Book Online
Follow the link to finalize your reservation directly on the partner’s website.
Explore and book the perfect rental in Highland
Common Vacation Rentals Amenities
What amenities can you expect?
Our Vacation Rentals are designed to offer all the comforts of home, often with added perks to make your stay unforgettable. Here’s some common amenities to look forward to:
Indoor Features
- Fully-equipped kitchens with modern appliances
- Comfortable living areas with flat-screen TVs
- Free Wi-Fi for staying connected
- Air conditioning and heating for year-round comfort
- In-unit washers and dryers for convenience
- Luxurious bedrooms with premium bedding
- Spa-like bathrooms with soaking tubs or walk-in showers
Outdoor Amenities
- Enjoy a private outdoor space with a well-maintained patio or deck for relaxing and entertaining.
- Take advantage of spacious yards perfect for outdoor games, picnics, or simply soaking up the sunshine.
- Look for properties with access to scenic walking or biking trails in the surrounding region.
- Relish the convenience of outdoor grilling facilities, ideal for preparing meals during your stay.
- Discover options that include a refreshing swimming pool to cool off during warm days here.
- Find properties with outdoor furniture to enjoy meals or unwind while taking in the views of this destination's natural beauty.
- Check for outdoor fire pits or fireplaces, creating cozy spots for evening gatherings under the stars.
Top Attractions Around Highland
What attractions are nearby?
Nearby, you can enjoy a variety of outdoor activities and local attractions that showcase the charm and natural beauty of the Highland region, making your stay both relaxing and memorable.
Family Activities
- Highland Community Park: Spend quality time outdoors with your family at this scenic park, offering playgrounds, walking trails, and picnic areas perfect for a relaxing day.
- St. Jacob Historical Museum: Discover the local history of the area through engaging exhibits and exhibits that are ideal for educating and entertaining children and adults alike.
- Local Family-Friendly Restaurants: Enjoy delicious meals at family-oriented eateries within the region, making dining out convenient and enjoyable during your stay.
- Nearby Nature Trails: Explore the region's picturesque nature trails where you can hike, bike, or take leisurely strolls amidst the area's natural beauty with your loved ones.
Adult Activities
- Historical Museum Tour: Explore the local history through engaging exhibits that showcase Highland's rich cultural heritage.
- Scenic Nature Walks: Enjoy peaceful strolls along picturesque trails, offering a perfect escape into the natural beauty surrounding here.
- Craft Beverage Experiences: Visit local breweries and wineries to sample regional brews and wines, immersing yourself in the area's vibrant craft scene.
- Community Events and Festivals: Participate in lively local festivals and gatherings that highlight the region’s unique traditions and friendly atmosphere.
Other Places to Stay in Highland, IL
Korte Recreation Center
Silver Lake Park
Highland Travel Tips
How Can You Make the Most of Your Stay?
- Explore Local Dining and Shops: Take advantage of the area's charming eateries and boutique shops to experience the local culture and enhance your stay.
- Plan Outdoor Activities: Discover nearby parks and outdoor spaces that offer opportunities for relaxing walks or active adventures during your visit.
- Book Early for Popular Dates: Secure your preferred vacation rentals well in advance, especially during peak seasons, to ensure availability in this sought-after destination.
- Check for Local Events: Stay informed about community happenings or seasonal festivals that can add a memorable touch to your trip here.
Transportation Options
- Highland Amtrak Station: This station offers convenient rail connections to major cities, making it easy for you to arrive and depart using regional train services.
- Local Bus Services: Public bus options serve the area, providing an affordable and accessible way to explore Highland and its surroundings.
- Private Car Rentals: Numerous car rental agencies are available here, giving you flexible transportation options during your stay.
- Taxi and Ride-Sharing Services: Taxis and ride-sharing options like Uber and Lyft operate in the region, ensuring quick and reliable transportation when needed.
Local Customs Options
- Southern Hospitality: You’ll notice a warm welcome and friendly interactions that reflect the region’s tradition of Southern hospitality in Highland, Illinois.
- Local Craftsmanship: Appreciating handcrafted goods and artisanal products is part of the area's cultural fabric, offering you authentic souvenirs during your stay.
- Community Celebrations: Participating in local festivals and events provides insight into Highland’s close-knit community spirit and cherished traditions.
- Respect for Nature: Environmental consciousness and outdoor etiquette are valued here, encouraging responsible exploration of the region’s parks and natural spaces.
Frequently Asked Questions About Highland?
1. What are the top vacation rentals in Highland?
There are a lot of options in Highland. If you plan on staying in the Highland area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Highland:
- Quiet villa located one block from McKendree University in Lebanon Illinois.
- Craftsman styled home in the heart of downtown Highland
- Sunset Cottage - Entire home downtown Glen Carbon
- Walking distance to Breese Legion and Main st
- The Hangar - Healthcare/Military friendly!
- Skyline - Military/Family Friendly
- LARGE 3000 sq. ft Newly Renovated Upstairs Loft - Ideal Families & Friend
- The Loft on the Square
- The PanAm Flat - 2bed/2bath next to hospitals & Scott AFB
- The Swiss Post Apartment B
2. How many vacation rentals have private pools in Highland?
There are 12 vacation rentals with private pools near Highland. Top-rated RBO homes that have access to a swimming pool include:
3. Which vacation homes in Highland are best for families?
If you are looking for a family-friendly vacation home in Highland, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Highland:
4. How many Rentbyowner vacation rentals are available in Highland?
Currently, the total number of properties listed by Rent By Owner in 2026 is over 143 in the Highland area, and still counting. By aggregating listings from multiple websites, Rent By Owner offers an immense amount of choice of the best RBO properties in Highland.
5. What is the cancellation policy for booking a vacation rental in Highland, Illinois?
Cancellation policies can vary depending on the specific property owner. You should review the details listed on the rental's page or contact the host directly to understand the terms related to cancellations and refunds.
6. Are there any additional fees I should be aware of when booking in this area?
Additional fees such as cleaning fees, service charges, or taxes are typically detailed during the booking process. It's recommended to read the listing information carefully or reach out to the host for clarity on any extra costs.
7. How do I ensure the vacation rental I choose has the amenities I need?
All listings include a comprehensive description of amenities. You can filter search results based on your preferred amenities or contact the property owner directly to confirm availability before finalizing your reservation.
8. What is the check-in and check-out process for properties here?
Check-in and check-out procedures are specified in each listing. Many hosts offer flexible times, but it’s best to verify these details with the host prior to arrival to ensure a smooth stay.
9. How can I find the most suitable vacation rental in this destination?
Use the search filters and read reviews from previous guests to identify a property that matches your preferences. If you have specific questions, contacting the host can also help ensure the rental meets your expectations.
Highland Top Rated Vacation Rentals
Hotel
9.6(1001 Reviews)
1 Bath
- Pool
- Breakfast
- Kitchen
- Parking
AU $179/Night
7 Nights - AU $1,251
Hotel
9.2(849 Reviews)
1 Bath
- Pool
- Breakfast
- Kitchen
- Parking
AU $251/Night
7 Nights - AU $1,760
AU $199/Night
7 Nights - AU $1,390
Hotel
9.2(772 Reviews)
1 Bath
- Pool
- Balcony/Terrace
- Breakfast
- Kitchen
AU $190/Night
7 Nights - AU $1,328
Hotel
9.0(1005 Reviews)
1 Bath
- Fireplace/Heating
- Pool
- Breakfast
- Kitchen
AU $182/Night
7 Nights - AU $1,274
Hotel
9.0(145 Reviews)
1 Bath
- Pool
- Balcony/Terrace
- Breakfast
- Kitchen
AU $328/Night
7 Nights - AU $2,298
Hotel
8.8(391 Reviews)
1 Bath
365.97 ft²
- Private Pool
- Oceanfront
- Fireplace/Heating
- Pool
AU $166/Night
7 Nights - AU $1,163
Hotel
8.7(145 Reviews)
10 Baths
328.3 ft²
- Private Pool
- Oceanfront
- Fireplace/Heating
- Pool
AU $237/Night
7 Nights - AU $1,661
