Highland Vacation Rentals

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Vacation Rentals in Highland

Craftsman styled home in the heart of downtown Highland

10.0 out of 10, Exceptional, (48)
"It was a perfect space for us during my wedding weekend. The home was open and nice and easy to gather in "
Craftsman styled home in the heart of downtown Highland

The Swiss Post Apartment B

2.0 star property
The Swiss Post Apartment B

The Swiss Post Apartment A

2.0 star property
The Swiss Post Apartment A

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

Historic Lebanon, quiet 2 Bedroom 2 Bath home!

10.0 out of 10, Exceptional, (40)
"This is our second time staying here. It was perfect once again! The home is in a safe neighborhood that is centrally located between Staunton, Belleville and Fairview. We moved away from the area and this is the perfect place to come back when visiting family. "
Historic Lebanon, quiet 2 Bedroom 2 Bath home!

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

Cozy Corner Mascoutah

9.6 out of 10, Exceptional, (56)
"Very clean and cozy"
The price is CA $149
CA $272 total
includes taxes & fees
Feb 24 - Feb 25
Cozy Corner Mascoutah

Charming Edwardsville Home: Walk to Downtown!

10.0 out of 10, Exceptional, (12)
"We had an amazing time! The house was wonderful and we couldn’t have been happier. Location was great! We were able to so wedding prep on Friday and have a nice place to hang out and relax between events. Flawless transaction!! "
Charming Edwardsville Home: Walk to Downtown!

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

Cozy Historic Downtown Edwardsville Charmer

10.0 out of 10, Exceptional, (4)
"N/A"
Cozy Historic Downtown Edwardsville Charmer

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

The Maple Cottage

The price is CA $139
CA $267 total
includes taxes & fees
Mar 10 - Mar 11
The Maple Cottage

Skyline - Military/Family Friendly

10.0 out of 10, Exceptional, (14)
"Everything was advertised. Clean. No issues"
Skyline - Military/Family Friendly

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+

Downtown Midcentury Home- Walk to Everything!

10.0 out of 10, Exceptional, (22)
"We liked that the home was clean and the beds were very comfortable. "
Downtown Midcentury Home- Walk to Everything!

Walking distance to Breese Legion and Main st

10.0 out of 10, Exceptional, (11)
"Love this property. Highly recommend. The owners are great to work with and very responsive. We appreciate them sharing their home with us. "
Walking distance to Breese Legion and Main st

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

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

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

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
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

2.5 star property
8.2 out of 10, Very good, (552)
"room was clean and comfortable, property was under remodel so there was areas that was cluttered but that is expected all in all good value for the price "
The price is CA $128
CA $142 total
includes taxes & fees
Feb 23 - Feb 24
Seasons Inn & Suites Highland

Craftsman styled home in the heart of downtown Highland

10.0 out of 10, Exceptional, (48)
"It was a perfect space for us during my wedding weekend. The home was open and nice and easy to gather in "
Craftsman styled home in the heart of downtown Highland

The Swiss Post Apartment B

2.0 star property
The Swiss Post Apartment B
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.