Highland Vacation Rentals

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Check prices for these dates

Tonight
Apr 20 - Apr 21
Tomorrow
Apr 21 - Apr 22
Next weekend
Apr 25 - Apr 27
In two weeks
May 2 - May 4

Vacation Rentals in Highland

Craftsman styled home in the heart of downtown Highland
Fridge, microwave, oven, stovetop

Craftsman styled home in the heart of downtown Highland

10.0 out of 10, Exceptional, (50)
"Our family stayed here for a funeral.for a second time.. The house was perfect for our big family"
Craftsman styled home in the heart of downtown Highland
The Loft on the Square
3 bedrooms, iron/ironing board, travel crib, WiFi

The Loft on the Square

10.0 out of 10, Exceptional, (1)
"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 B
Private kitchen

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
The Swiss Post Apartment A
Interior

The Swiss Post Apartment A

2.0 star property
The Swiss Post Apartment A
Historic Lebanon, quiet 2 Bedroom 2 Bath home!
Fridge, microwave, oven, stovetop

Historic Lebanon, quiet 2 Bedroom 2 Bath home!

10.0 out of 10, Exceptional, (42)
"It was a very pleasant stay. We ended up staying a tornado watch and warning even losing power for a short time. Our host was extremely attentive, checking on us during the power outage to be sure we were ok and if we needed anything. Would definitely stay here again. "
Historic Lebanon, quiet 2 Bedroom 2 Bath home!
Charming Edwardsville Home: Walk to Downtown!
Exterior detail

Charming Edwardsville Home: Walk to Downtown!

9.8 out of 10, Exceptional, (16)
"The location of the house was perfect for our stay. It's a cute house that's nicely decorated and very clean. I had great communication with the host, and they went out of their way to ensure our safety during a really stormy and potentially dangerous night. We would definitely recommend staying here!"
Charming Edwardsville Home: Walk to Downtown!
3 Bedroom Home - Lake Views on 3 Sides
Fridge, microwave, oven, stovetop

3 Bedroom Home - Lake Views on 3 Sides

9.4 out of 10, Exceptional, (91)
"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
3 Bedroom Loft overlooking water
Outdoor dining

3 Bedroom Loft overlooking water

9.6 out of 10, Exceptional, (105)
"15 minutes from gateway center in Collinsville, IL. Very nice neighborhood with a beautiful lake that is filled with fish, turtles, and ducks that our kids loved. We enjoyed the comfortable beds."
3 Bedroom Loft overlooking water
Private 4 Bedroom Home with a hot tub
Fridge, microwave, oven, stovetop

Private 4 Bedroom Home with a hot tub

9.4 out of 10, Exceptional, (50)
"Great house. Unique location in the country. Great access to St Louis and horse track in Collinsville, Illinois."
Private 4 Bedroom Home with a hot tub
The Maple Cottage
Fridge, microwave, oven, stovetop

The Maple Cottage

10.0 out of 10, Exceptional, (1)
"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 price is CA $96
CA $220 total
includes taxes & fees
Apr 23 - Apr 24
The Maple Cottage
Cozy Corner Mascoutah
Fridge, microwave, oven, stovetop

Cozy Corner Mascoutah

9.6 out of 10, Exceptional, (58)
"The Cozy Corner is a true gem! The home is super comfortable, exceptionally clean, and located in a quiet neighborhood. The house is stocked with everything you could need and the property manager, Susan, was very responsive. The house is down the street from a school and park which provided a nice place to walk the dogs. This home was just what we needed to recharge during a long, cross-country drive. "
The price is CA $145
CA $267 total
includes taxes & fees
Apr 27 - Apr 28
Cozy Corner Mascoutah
Downtown Midcentury Home- Walk to Everything!
Fridge, microwave, oven, stovetop

Downtown Midcentury Home- Walk to Everything!

10.0 out of 10, Exceptional, (24)
"Our family highly enjoyed our stay this week. The location in downtown Edwardsville made walking our dogs easy and walking to local restaurants fun. This house was very comfortable for our family of 4, providing quality, comfortable beds and plenty of space for all. Communication with the owners was great and very friendly neighbors. The backyard was great for dogs and kids to play and parents to sit and relax on the back patio. We will definitely stay here again! "
Downtown Midcentury Home- Walk to Everything!
THE NEST getaways&gatherings, beach/lake sleeps 20+
Property grounds

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

10.0 out of 10, Exceptional, (36)
"This is our second stay at the Nest. We love everything about it. House, Beach, Shade, Outdoor Play Area. The property managers are easy to reach and responsive. Highly recommend a stay here. "
THE NEST getaways&gatherings, beach/lake sleeps 20+
Reel 'Em Inn
3 bedrooms, iron/ironing board, free WiFi, bed sheets

Reel 'Em Inn

9.6 out of 10, Exceptional, (4)
"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!"
Reel 'Em Inn
Skyline - Military/Family Friendly
Interior

Skyline - Military/Family Friendly

10.0 out of 10, Exceptional, (17)
"The location was perfect! Alex was a great host and responded immediately when we had any questions. Would recommend. "
Skyline - Military/Family Friendly
Cozy Historic Downtown Edwardsville Charmer
Private kitchen

Cozy Historic Downtown Edwardsville Charmer

9.8 out of 10, Exceptional, (6)
"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 Hangar - Healthcare/Military friendly!
1 bedroom, desk, free WiFi, bed sheets

The Hangar - Healthcare/Military friendly!

10.0 out of 10, Exceptional, (14)
"This property was perfect for what I needed. The location is great whether you want to go into St. Louis (there’s a metro station pretty close) or stay around the Belleville/O’Fallon area. I’ll highly consider staying here again!"
The Hangar - Healthcare/Military friendly!
Everwood Cottage ^ Trees, Birds, and Quiet! Military Friendly
Fridge, microwave, oven, stovetop

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

10.0 out of 10, Exceptional, (33)
"Great place to stay near McKendree Univ. Kitchen was better equipped than some house VRBO’a we have stayed in. Beautifully decorated and exactly as the pictures show. We will be back! Thank you for sharing your cottage with us. "
Everwood Cottage ^ Trees, Birds, and Quiet! Military Friendly
The Aerie- Luxury Lakeside Getaway - Private Beach & Boatdock
Exterior

The Aerie- Luxury Lakeside Getaway - Private Beach & Boatdock

10.0 out of 10, Exceptional, (19)
"We rented the Nest too. We had 8 people there and 11 at the Aerie. Each couple was able to have their own space this way. Adults didn't have to give up their privacy. At the Aerie, the living space, kitchen and rec room were spacious. We were fortunate to have perfect weather so we were outside all day and into the night. The outdoor space was fabulous for outdoor eating and "playing". We all give this venue A thumbs up!"
The Aerie- Luxury Lakeside Getaway - Private Beach & Boatdock
The PanAm Flat - 2bed/2bath next to hospitals & Scott AFB
Fridge, microwave, oven, stovetop

The PanAm Flat - 2bed/2bath next to hospitals & Scott AFB

10.0 out of 10, Exceptional, (3)
"Everything was great "
The PanAm Flat - 2bed/2bath next to hospitals & Scott AFB
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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Other types of properties in Highland you may be interested in

Seasons Inn & Suites Highland
In-room safe, desk, iron/ironing board, free WiFi

Seasons Inn & Suites Highland

2.5 star property
8.2 out of 10, Very good, (563)
"Clean, good showers, decent breakfast, reasonable price. No complaints."
The price is CA $151
CA $168 total
includes taxes & fees
Apr 22 - Apr 23
Seasons Inn & Suites Highland
Craftsman styled home in the heart of downtown Highland
Fridge, microwave, oven, stovetop

Craftsman styled home in the heart of downtown Highland

10.0 out of 10, Exceptional, (50)
"Our family stayed here for a funeral.for a second time.. The house was perfect for our big family"
Craftsman styled home in the heart of downtown Highland
The Loft on the Square
3 bedrooms, iron/ironing board, travel crib, WiFi

The Loft on the Square

10.0 out of 10, Exceptional, (1)
"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
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.

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 Copper Dock Winery.

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.