Holiday Homes in Highland

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Featured Holiday Homes in Highland

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

Historic Lebanon, quiet 2 Bedroom 2 Bath home!

10.0 out of 10, Exceptional, (34)
"The property was inviting and had everything we needed for a comfortable stay. The neighborhood was quiet and we felt safe. We plan to stay here again when we visit family in the area. "
Historic Lebanon, quiet 2 Bedroom 2 Bath home!

Charming Edwardsville Home: Walk to Downtown!

9.8 out of 10, Exceptional, (10)
"We really enjoyed our stay at the Seedling. It is impeccably clean and in a great location. It is within walking distance of downtown and very close to the major shopping and entertainment of Edwardsville. The communications from the property manager are awesome. We loved the decorations and the peacefulness of the area."
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

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+

Cozy Corner Mascoutah

9.6 out of 10, Exceptional, (54)
"Perfect night for a quick in and out of town stay. There is a little bar within walking distance that my husband and son went to for a quick beer before bed. Hotels can be hard for a dog so this was exactly what we needed to keep our girl happy. "
The price is AU$298
includes taxes & fees
3 Dec - 4 Dec
Cozy Corner Mascoutah

Downtown Midcentury Home- Walk to Everything!

10.0 out of 10, Exceptional, (21)
"Nice set up and spacious "
Downtown Midcentury Home- Walk to Everything!

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

Craftsman styled home in the heart of downtown Highland

10.0 out of 10, Exceptional, (44)
"This is gem! Lots of room for multiple families and people. We were there for a wedding and it was the perfect spot for everyone to get ready. Bathrooms are great size and the extra amenities thru out the home are great. (Coffee, soap, shampoo, lotion, etc). Back porch and parking was perfect for all the guests. Highly recommend and will be back! "
Craftsman styled home in the heart of downtown Highland

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

5 bedrooms near SAFB

7.0 out of 10, Good, (8)
"We loved our stay"
5 bedrooms near SAFB

Skyline - Military/Family Friendly

10.0 out of 10, Exceptional, (12)
"We had the greatest time! Never been to that area and we loved it! Your property was perfect in a perfect location!! We loved it! tMcKendree,Shiloh"
Skyline - Military/Family Friendly

Walking distance to Breese Legion and Main st

10.0 out of 10, Exceptional, (10)
"thanks again for the use of your home. Everything worked out great."
Walking distance to Breese Legion and Main st

Cali Coast * Small home in quiet neighborhood

9.4 out of 10, Exceptional, (6)
"Smooth in every aspect,super quiet and comfortable small accom,great response from owner,def stay again when I visit as in a good location"
Cali Coast * Small home in quiet neighborhood

Main Stay on Market -Military/Healthcare Friendly

Main Stay on Market -Military/Healthcare Friendly

The Beaumont Retreat

10.0 out of 10, Exceptional, (1)
"Wonderful experience! The host is SO accommodating and kind, and really has thought of absolutely everything. This house is so well stocked and comfortable that it feels like you are staying at a friend or family members house! The host is super responsive and goes above and beyond to make you feel welcome. Great central location. We will be back!"
The Beaumont Retreat

The Beaumont Suite !

The Beaumont Suite !

General Green is a travelers dream!

10.0 out of 10, Exceptional, (1)
"Everything about this rental was perfect from the initial booking, to communication, to the wonderful little extra touches around the house. It was perfect for my family of 5 to enjoy our trip to IL together. I would absolutely return to this house if I am back in that area again. I have stayed in many VRBOs but this was one of the most pleasant overall experiences that I have had. Thanks so much!"
General Green is a travelers dream!

HannLeveling Vacation House Illinois

HannLeveling Vacation House Illinois
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 property types in Highland

The Swiss Post Apartment A

2.0 star property
The Swiss Post Apartment A

Craftsman styled home in the heart of downtown Highland

10.0 out of 10, Exceptional, (44)
"This is gem! Lots of room for multiple families and people. We were there for a wedding and it was the perfect spot for everyone to get ready. Bathrooms are great size and the extra amenities thru out the home are great. (Coffee, soap, shampoo, lotion, etc). Back porch and parking was perfect for all the guests. Highly recommend and will be back! "
Craftsman styled home in the heart of downtown Highland

The Loft on the Square

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.
Beautiful view of the beach with palm trees

Black Friday: Members save 30%+

Members save 30%+ on selected hotels until 4 Dec (property time) with our Black Friday deals. Stay by 15 Dec 2025.