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Compare 19 Vacation Homes in Highland with updated reviews, rates, and availability.

Walking distance to Breese Legion and Main st
curb appeal

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
Cozy Corner Mascoutah
kitchen

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 AED 386
AED 705 total
includes taxes & fees
2 Jan - 3 January 2025
Cozy Corner Mascoutah
Craftsman styled home in the heart of downtown Highland
Exterior

Craftsman styled home in the heart of downtown Highland

10.0 out of 10, Exceptional, (45)
"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
Historic Lebanon, quiet 2 Bedroom 2 Bath home!
Living area

Historic Lebanon, quiet 2 Bedroom 2 Bath home!

10.0 out of 10, Exceptional, (37)
"Lovely place. The Christmas tree was special. "
Historic Lebanon, quiet 2 Bedroom 2 Bath home!
3 Bedroom Home - Lake Views on 3 Sides
Lake View from the deck

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
Private 4 Bedroom Home with a hot tub
Living Room

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 NEST getaways&gatherings, beach/lake sleeps 20+
The Private Beach. The Nest is to the right

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!
Formerly a church rectory, this midcentury home has been repurposed as the nicest place to stay in Edwardsville!

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
Aerie with boat dock and sun/swim deck. Doesn’t include beach on right.

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
Reel 'Em Inn
Living area

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
Exterior

5 bedrooms near SAFB

7.0 out of 10, Good, (8)
"We loved our stay"
5 bedrooms near SAFB
Charming Edwardsville Home: Walk to Downtown!
Edwardsville Vacation Rental | 3BR | 2BA | 1,700 Sq Ft | Step-Free Access

Charming Edwardsville Home: Walk to Downtown!

10.0 out of 10, Exceptional, (11)
"What a cozy home. Christmas decor made it even more cheerful and inviting. Clean and roomy, Perfect location. We truly enjoyed our stay and definitely plan to be back. Thank you to our wonderful hosts."
Charming Edwardsville Home: Walk to Downtown!
Skyline - Military/Family Friendly
Room

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
Cali Coast * Small home in quiet neighborhood
Living area

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
Interior

Main Stay on Market -Military/Healthcare Friendly

10.0 out of 10, Exceptional, (1)
Main Stay on Market -Military/Healthcare Friendly
The Beaumont Retreat
8

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 !
10

The Beaumont Suite !

The Beaumont Suite !
General Green is a travelers dream!
Exterior

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
Property grounds

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

Craftsman styled home in the heart of downtown Highland
Exterior

Craftsman styled home in the heart of downtown Highland

10.0 out of 10, Exceptional, (45)
"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 Swiss Post Apartment A
Interior

The Swiss Post Apartment A

2.0 star property
The Swiss Post Apartment A
The Loft on the Square
Parking

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.