Highland Vacation Rentals

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Nov 22 - Nov 23
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Nov 23 - Nov 24
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Vacation Rentals in Highland

Microwave, oven, stovetop, dishwasher
The Swiss Post Apartment B

The Swiss Post Apartment B

2.0 star property
Highland
10.0 out of 10, Exceptional, (3)
"Very nice apartment in a great location! Really enjoyed our stay!"
United States
Machelle H.
The Swiss Post Apartment B
Dining
The Swiss Post Apartment A

The Swiss Post Apartment A

2.0 star property
Highland
10.0 out of 10, Exceptional, (2)
"Everything was great! Nice stay in a quiet and friendly area"
United States
Jason S.
The Swiss Post Apartment A
Fridge, microwave, oven, stovetop
Craftsman styled home in the heart of downtown Highland

Craftsman styled home in the heart of downtown Highland

Highland
10.0 out of 10, Exceptional, (67)
"Clean and spacious home perfect for several family members. Checkin was a breeze and parking plenty. Home close to downtown square. "
United States
Deb S.
Craftsman styled home in the heart of downtown Highland
3 bedrooms, iron/ironing board, travel crib, WiFi
The Loft on the Square

The Loft on the Square

Highland
10.0 out of 10, Exceptional, (4)
"Cutest VRBO in the cutest area of the cutest little town. Thanks for renovating everything so thoughtfully and with so many special touches. Such a lovely and relaxing place to stay while visiting Highland."
United States
Alanna B.
The Loft on the Square
Exterior
Stay in the heart of downtown Highland in this spacious luxury loft!

Stay in the heart of downtown Highland in this spacious luxury loft!

2.0 star property
Highland
Stay in the heart of downtown Highland in this spacious luxury loft!
Outdoor dining
3 Bedroom Loft overlooking water

3 Bedroom Loft overlooking water

Caseyville
9.6 out of 10, Exceptional, (113)
"Loved sitting on the patio overlooking the lake. "
United States
Mark
3 Bedroom Loft overlooking water
TV, fireplace
Spacious 5-bedroom house in gorgeous Glen Carbon with AC

Spacious 5-bedroom house in gorgeous Glen Carbon with AC

2.0 star property
Glen Carbon
10.0 out of 10, Exceptional, (1)
"Great place to stay "
United States
Karl W.
The price is ￥22,398
￥66,836 total
includes taxes & fees
Nov 23 - Nov 24
Spacious 5-bedroom house in gorgeous Glen Carbon with AC
Private kitchen
3-Bedroom Downtown apartment with Game Room

3-Bedroom Downtown apartment with Game Room

2.0 star property
Carlyle
10.0 out of 10, Exceptional, (1)
"The property was great! Very clean, appropriately stocked, and everything the owner had described. We truly enjoyed our family gathering at this location. "
United States
Kara H.
3-Bedroom Downtown apartment with Game Room
Outdoor dining
Cozy Corner Mascoutah

Cozy Corner Mascoutah

Mascoutah
9.6 out of 10, Exceptional, (74)
"Very clean, accessible, and great communication! Happy with our experience. "
United States
Katherine P.
The price is ￥16,423
￥30,667 total
includes taxes & fees
Nov 29 - Nov 30
Cozy Corner Mascoutah
Property grounds
Historic 4-bedroom house in Glen Carbon with AC

Historic 4-bedroom house in Glen Carbon with AC

2.0 star property
Glen Carbon
10.0 out of 10, Exceptional, (1)
"Room was clean and very affordable for 5 people"
United States
jamison l.
Historic 4-bedroom house in Glen Carbon with AC
Fridge, microwave, oven, stovetop
3 Bedroom Home - Lake Views on 3 Sides

3 Bedroom Home - Lake Views on 3 Sides

Caseyville
9.6 out of 10, Exceptional, (95)
"Very responsive host, beautiful home to stay in with plenty of space for a group. We will definitely be staying again. "
United States
Venessa O.
3 Bedroom Home - Lake Views on 3 Sides
Fridge, microwave, oven, stovetop
The Maple Cottage

The Maple Cottage

Caseyville
10.0 out of 10, Exceptional, (2)
"Amazing place to stay! Very clean and nice inside. Everything you needed was provided, a yard and carport as well! The owners are super friendly and sweet. Everything you need is 5 minutes down the road. The house was extremely pretty and roomy! Our family loved staying here and would absolutely do it again next time! Thank you for everything!!"
United States
Kelia S.
The Maple Cottage
Exterior
The Aerie- Luxury Lakeside Getaway - Private Beach & Boatdock

The Aerie- Luxury Lakeside Getaway - Private Beach & Boatdock

Greenville
10.0 out of 10, Exceptional, (19)
"Plenty of private space, gathering space, eating area and food prep supplies. Lots to do as well. There was even a rainbow over the lake the last day."
United States
Diane S.
The Aerie- Luxury Lakeside Getaway - Private Beach & Boatdock
Fridge, microwave, oven, stovetop
Private 4 Bedroom Home with a hot tub

Private 4 Bedroom Home with a hot tub

Caseyville
9.4 out of 10, Exceptional, (51)
"Great space for big family or 2. Communication with owner was quick and easy. Quick to resolve questions. We really enjoyed our stay. thanks"
United States
Becky T.
Private 4 Bedroom Home with a hot tub
Property grounds
THE NEST getaways&gatherings, beach/lake sleeps 20+

THE NEST getaways&gatherings, beach/lake sleeps 20+

Greenville
10.0 out of 10, Exceptional, (38)
"We stayed at the Nest for a week and thoroughly enjoyed our stay. The property is secluded and quiet for a relaxing time at the lake. The house is well stocked with items you would need for a vacation as well as having ample outdoor activities on site available for use. The lake is very calm and, during our stay, was not very trafficked. Coach was prompt as the property manager with any questions or needs. "
United States
Aaron V.
THE NEST getaways&gatherings, beach/lake sleeps 20+
3 bedrooms, iron/ironing board, free WiFi, bed sheets
Reel 'Em Inn

Reel 'Em Inn

Carlyle
9.0 out of 10, Wonderful, (6)
"The game room was the highlight of the house. Lots of room for the whole group and the bedrooms were very spacious! We really enjoyed our stay and we’re impressed with how nice the house was! Would definitely recommend to stay here!"
United States
Ronald R.
Reel 'Em Inn
Fridge, microwave, oven, stovetop
The Beaumont Retreat

The Beaumont Retreat

Greenville
10.0 out of 10, Exceptional, (3)
"Place was great! "
United States
Lawrence S.
The Beaumont Retreat
Terrace/patio
Carlyle lake home!

Carlyle lake home!

Carlyle
9.0 out of 10, Wonderful, (2)
"This was a very clean home with lots of amenities and was pet friendly as well! Would definitely come here again!"
United States
Patricia W.
Carlyle lake home!
Private kitchen
Cozy Historic Downtown Edwardsville Charmer

Cozy Historic Downtown Edwardsville Charmer

Edwardsville
9.4 out of 10, Exceptional, (15)
"Wonderful location for what we needed! Comfortable beds and great amenities. Lots of little touches and extras."
United States
Lori H.
Cozy Historic Downtown Edwardsville Charmer
Exterior detail
The Hangar - Healthcare/Military friendly!

The Hangar - Healthcare/Military friendly!

Shiloh
10.0 out of 10, Exceptional, (17)
"We had a great time. Room was clean and spacious. Very secure location."
United States
Dorcas K.
The Hangar - Healthcare/Military friendly!
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Highland Hotel Reviews

Drury Inn & Suites St. Louis O'Fallon, IL

Drury Inn & Suites St. Louis O'Fallon, IL

10/10 Excellent
"Employees are super friendly & nice. The room & bathroom was clean & the bed comfortable. The breakfast had plenty of options & the food at happy hour was unexpected & nice variety. "
Jenifer 3-night trip
Posted 20 hours ago
Drury Inn & Suites St. Louis O'Fallon, IL

Find out more about Highland

Search for holiday rentals in Highland on Expedia! You can easily find your home rentals, villas, holiday apartments in Highland using one of the methods below:

  • View our selection of featured holiday rentals in Highland
  • Use the map to find apartments and other holiday homes in the Highland neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Highland while they last

Look no further and take a look at our great range of rental properties in Highland!

Frequently asked questions

Are there vacation rentals in Highland?

Yes, we have vacation rentals near the most popular points of interest in Highland, or you can go with a secluded option if you want a relaxing place to stay. Our travelers say Highland has a good selection of restaurants. Make sure you have time to check out the architecture and lake views during your trip.

What's the top vacation rental that Highland has to offer?

Craftsman styled home in the heart of downtown Highland: This Highland vacation home rental is located in the city center and has a garden, a barbecue grill, and air-conditioning to put you at ease in your new surroundings. It has 6 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family.

How many vacation rentals are there in Highland?

Expedia has 3 vacation rentals for your stay in Highland.

What can I see and do in Highland?

While you're exploring the area, Silver Lake Park and O'Fallon Family Sports Park are a couple of picturesque spots to get outside and enjoy nature. In the larger area, you’ll find Korte Recreation Center and McKendree University.

What are vacation rentals like in Highland?

Vacation rentals are privately owned accommodations you can book for a couple days or more in Highland. Vacation rentals provide amenities like laundry facilities and kitchens so you'll have all the conveniences of home. If you're concerned about a sanitized environment, a vacation rental can offer a sense of privacy away from public hotel elevators and lobbies bustling with people while still allowing you a great travel experience. You'll also find more space in a vacation rental than in a standard hotel, which is another reason why a vacation rental is a great option for a family getaway.