Highland Holiday Rentals

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Check prices for these dates

Tonight
24 Jul - 25 Jul
Tomorrow
25 Jul - 26 Jul
This weekend
25 Jul - 27 Jul
Next weekend
1 Aug - 3 Aug

Holiday Rentals in Highland

Craftsman styled home in the heart of downtown Highland
Enjoy cooking in this well-equipped kitchen with a central island, stove, and ample counter space.

Craftsman styled home in the heart of downtown Highland

10.0 out of 10, Exceptional, (58)
"We had a wonderful stay! Plenty of room and Jennifer did a fantastic job of communicating with us! "
Craftsman styled home in the heart of downtown Highland
The Loft on the Square
Classic bedroom with a large bed, chandelier, and black radiator.

The Loft on the Square

10.0 out of 10, Exceptional, (2)
"Family stay over holidays. Place was decorated and made us feel at home. Love the historical touches, would stay here again. "
The Loft on the Square
The Swiss Post Apartment A
Enjoy meals in this dining area with a round table and six chairs, surrounded by a brick wall and a large window with an outdoor view.

The Swiss Post Apartment A

2.0 star property
The Swiss Post Apartment A
The Swiss Post Apartment B
Enjoy cooking in this well-equipped kitchen with a dishwasher, microwave, oven, and sink.

The Swiss Post Apartment B

2.0 star property
10.0 out of 10, Exceptional, (1)
"Very nice apartment in a great location! Really enjoyed our stay!"
The Swiss Post Apartment B
3 Bedroom Loft overlooking water
Enjoy a serene lakeside retreat with a deck offering a glass-top table and comfortable seating for four.

3 Bedroom Loft overlooking water

9.6 out of 10, Exceptional, (108)
"We really enjoyed staying at this property; it was fantastic!"
3 Bedroom Loft overlooking water
3 Bedroom Home - Lake Views on 3 Sides
Enjoy cooking in this well-equipped kitchen with a central island, refrigerator, and dishwasher.

3 Bedroom Home - Lake Views on 3 Sides

9.6 out of 10, Exceptional, (94)
"The pictures match the property very well. House was clean stocked with everything that you would need for a family. There was good fishing on the lake."
3 Bedroom Home - Lake Views on 3 Sides
Charming Edwardsville Home: Walk to Downtown!
Welcome to Rollo, a charming home with a cozy porch and lush garden.

Charming Edwardsville Home: Walk to Downtown!

9.8 out of 10, Exceptional, (19)
"We very much enjoyed our stay at this adorable property. Very well furnished everything you need and we even had a special treat of delicious cinnamon rolls left for us on the kitchen counter. If we are ever in the area again we would definitely stay here. "
Charming Edwardsville Home: Walk to Downtown!
Cozy Historic Downtown Edwardsville Charmer
Kitchen features a double sink, stainless steel oven, and microwave.

Cozy Historic Downtown Edwardsville Charmer

9.8 out of 10, Exceptional, (8)
"We really enjoyed all the little extras this host thought of. We appreciated the comfortable beds, ample outdoor space, and the speedy responses from the host, We would certainly highly recommend this to anyone looking for a great vacation rental!"
Cozy Historic Downtown Edwardsville Charmer
The Beaumont Retreat
Enjoy cooking in this well-equipped kitchen with a refrigerator, oven, microwave, and ample storage.

The Beaumont Retreat

10.0 out of 10, Exceptional, (3)
"Place was great! "
The Beaumont Retreat
The Maple Cottage
Enjoy meals in a well-equipped kitchen with a dining area.

The Maple Cottage

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!!"
The Maple Cottage
Skyline - Military/Family Friendly
Enjoy cooking in this kitchen with a stainless steel sink, wooden cabinets, and a wall-mounted utensil rack.

Skyline - Military/Family Friendly

10.0 out of 10, Exceptional, (16)
"The location was perfect! Alex was a great host and responded immediately when we had any questions. Would recommend. "
Skyline - Military/Family Friendly
Reel 'Em Inn
Restful retreat with a neatly made bed, two nightstands, and soft lighting.

Reel 'Em Inn

9.6 out of 10, Exceptional, (4)
"The overll booking porcess. Bokked through Expedia and then they wnet trough VRBO. Did not like the overall way it was handled. Property itself suited outr purpose."
Reel 'Em Inn
THE NEST getaways&gatherings, beach/lake sleeps 20+
Relax on the elevated deck with benches, taking in the serene views of the surrounding trees and water.

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

10.0 out of 10, Exceptional, (36)
"The house was wonderful and the beach a lot of fun. It was the perfect family vacation spot!"
THE NEST getaways&gatherings, beach/lake sleeps 20+
Private 4 Bedroom Home with a hot tub
Prepare meals and dine in comfort at this kitchen with a central island, refrigerator, microwave, and ample counter space.

Private 4 Bedroom Home with a hot tub

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"
Private 4 Bedroom Home with a hot tub
Cozy Corner Mascoutah
Attached garage and patio area with outdoor seating.

Cozy Corner Mascoutah

9.4 out of 10, Exceptional, (65)
"Very clean and cozy"
The price is NZ$322
includes taxes & fees
19 Aug - 20 Aug
Cozy Corner Mascoutah
The Aerie- Luxury Lakeside Getaway - Private Beach & Boatdock
Experience the charm of this two-story building with a gabled roof and brick facade, surrounded by a serene landscape and a spacious outdoor area perfect for relaxation and socializing.

The Aerie- Luxury Lakeside Getaway - Private Beach & Boatdock

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."
The Aerie- Luxury Lakeside Getaway - Private Beach & Boatdock
Walking distance to Breese Legion and Main st
Stylish single-story home with a brick facade, gabled roof, and a welcoming front porch.

Walking distance to Breese Legion and Main st

10.0 out of 10, Exceptional, (16)
"The house is in a great location, well kept, and worked perfectly for our group. We will be staying there again!"
Walking distance to Breese Legion and Main st
Everwood Cottage ^ Trees, Birds, and Quiet! Military Friendly
Enjoy cooking in this well-lit kitchen with a stainless steel sink, microwave, and wooden countertop.

Everwood Cottage ^ Trees, Birds, and Quiet! Military Friendly

10.0 out of 10, Exceptional, (34)
"Perfect place! Enjoyed the stay."
Everwood Cottage ^ Trees, Birds, and Quiet! Military Friendly
The Hangar - Healthcare/Military friendly!
Welcome to this charming home with a cozy front entrance featuring a circular window and a beautifully landscaped garden.

The Hangar - Healthcare/Military friendly!

10.0 out of 10, Exceptional, (16)
"This place was awesome, very clean and had everything we needed, would definitely consider staying again!"
The Hangar - Healthcare/Military friendly!
The Beaumont Suite !
Kitchen features a refrigerator, microwave, stove, sink, and dining area with a table for two.

The Beaumont Suite !

The Beaumont Suite !
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

Days Inn by Wyndham Collinsville/St. Louis

Days Inn by Wyndham Collinsville/St. Louis

10/10 Excellent
"Convenient to highway. Location to the venue was within walking distance. Many restaurant options. The staff was very friendly. The only negative was pool not being opened, but things happen."
Sandra 4-night trip
Posted 2 days ago
Days Inn by Wyndham Collinsville/St. Louis

Frequently asked questions

Are there holiday rentals in Highland?

Yes, there are holiday rentals close to the most popular sights in Highland, or you can select a more secluded option if you're looking for a relaxing stay. Our travellers 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 are some of the best holiday rentals that Highland has to offer?

Craftsman styled home in the heart of downtown Highland: This highly rated holiday home rental in Highland is located in the city centre, and has a garden, a BBQ 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 that you can cook with friends or family.

How many holiday rentals are there in Highland?

Expedia has 3 holiday 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 wider area, you’ll find Korte Recreation Center and Copper Dock Winery.

What are holiday rentals like in Highland?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Highland. Holiday rentals feature amenities such as WiFi and washers and dryers so you'll feel just like you're at home. If you're concerned about a sanitised environment, a holiday rental can offer a sense of privacy away from public hotel lifts and busy concierge desks while still allowing you the excitement and enjoyment of travel. You'll also have more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is a popular option for small groups.