Highland Vacation Rentals

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Check prices for these dates

Next weekend
Aug 22 - Aug 24
In two weeks
Aug 29 - Aug 31
In one month
Sep 12 - Sep 14
In two months
Oct 10 - Oct 12

Browse Select Highland Vacation Homes

Charming Edwardsville Home: Walk to Downtown!
Exterior detail

Charming Edwardsville Home: Walk to Downtown!

9.6 out of 10, Exceptional, (22)
"Older home but in good area convenient to restaurants and getting around. Good parking lot. "
Charming Edwardsville Home: Walk to Downtown!
Cozy Corner Mascoutah
Outdoor dining

Cozy Corner Mascoutah

9.6 out of 10, Exceptional, (67)
"Very clean and cozy"
The price is CA $144
CA $270 total
includes taxes & fees
Aug 13 - Aug 14
Cozy Corner Mascoutah
3 Bedroom Home - Lake Views on 3 Sides
Fridge, microwave, oven, stovetop

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
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, (59)
"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
Skyline - Military/Family Friendly
Interior

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
The Maple Cottage
Fridge, microwave, oven, stovetop

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
Charming 1BR Near Historic Downtown Edwardsville & SIUE
TV, fireplace

Charming 1BR Near Historic Downtown Edwardsville & SIUE

Charming 1BR Near Historic Downtown Edwardsville & SIUE
Reel 'Em Inn
3 bedrooms, iron/ironing board, free WiFi, bed sheets

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+
Property grounds

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

10.0 out of 10, Exceptional, (37)
"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+
The Aerie- Luxury Lakeside Getaway - Private Beach & Boatdock
Exterior

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
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, (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
Walking distance to Breese Legion and Main st
Exterior

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
The Beaumont Suite !
Fridge, microwave, oven, stovetop

The Beaumont Suite !

The Beaumont Suite !
Cali Coast * Small home in quiet neighborhood
Fridge, microwave, oven, stovetop

Cali Coast * Small home in quiet neighborhood

9.4 out of 10, Exceptional, (6)
"Great experience in a great location! Very attentive owners! We will definitely be booking this property again!"
Cali Coast * Small home in quiet neighborhood
The Beaumont Retreat
Fridge, microwave, oven, stovetop

The Beaumont Retreat

10.0 out of 10, Exceptional, (3)
"Place was great! "
The Beaumont Retreat
General Green is a travelers dream!
Fridge, microwave, oven, stovetop

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
Terrace/patio

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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Top Highland Hotel Reviews

Drury Inn & Suites St. Louis O'Fallon, IL

Drury Inn & Suites St. Louis O'Fallon, IL

10/10 Excellent
"The staff was very friendly and helpful. The food provided was appetizing and delicious. The staff in the food area was also friendly and very helpful. I slept very well on a very comfortable bed and hated to leave. "
Nancy 1-night trip
Posted 18 hours ago
Drury Inn & Suites St. Louis O'Fallon, IL