Highland Vacation Rentals

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Check prices for these dates

In two weeks
Sep 12 - Sep 14
In one month
Sep 26 - Sep 28
In two months
Oct 24 - Oct 26
In three months
Nov 21 - Nov 23

Vacation Rentals in Highland

Our top choices for Highland vacation rentals

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, (61)
"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
The Swiss Post Apartment B
Microwave, oven, stovetop, dishwasher

The Swiss Post Apartment B

2.0 star property
10.0 out of 10, Exceptional, (2)
"Very nice apartment in a great location! Really enjoyed our stay!"
The Swiss Post Apartment B
The Swiss Post Apartment A
Dining

The Swiss Post Apartment A

2.0 star property
10.0 out of 10, Exceptional, (1)
"Beautifully decorated, clean, and perfect location for my work trip to Highland. Safe neighborhood, food very close, farmers market in the square. Easy check in and out. Second story location with staircase to enter."
The Swiss Post Apartment A
The Loft on the Square
3 bedrooms, iron/ironing board, travel crib, WiFi

The Loft on the Square

10.0 out of 10, Exceptional, (2)
"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
3 Bedroom Loft overlooking water
Outdoor dining

3 Bedroom Loft overlooking water

9.6 out of 10, Exceptional, (110)
"We really enjoyed staying at this property; it was fantastic!"
3 Bedroom Loft overlooking water
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
Charming 1BR Near Historic Downtown Edwardsville & SIUE
TV, fireplace

Charming 1BR Near Historic Downtown Edwardsville & SIUE

Charming 1BR Near Historic Downtown Edwardsville & SIUE
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)
"I was looking for a quiet, relaxing place to stay while visiting family in a nearby town. This was just what I wanted. Would definitely stay again next time I’m in the area. "
The price is CA $145
CA $270 total
includes taxes & fees
Sep 2 - Sep 3
Cozy Corner Mascoutah
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
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 NEST getaways&gatherings, beach/lake sleeps 20+
Property grounds

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

10.0 out of 10, Exceptional, (38)
"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
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
Cozy Historic Downtown Edwardsville Charmer
Private kitchen

Cozy Historic Downtown Edwardsville Charmer

9.6 out of 10, Exceptional, (10)
"This was such a nice home, perfect for my family's stay in the area. We appreciated having access to the full kitchen, dining room and living room to make our stay comfortable."
Cozy Historic Downtown Edwardsville Charmer
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
The Hangar - Healthcare/Military friendly!
Exterior detail

The Hangar - Healthcare/Military friendly!

10.0 out of 10, Exceptional, (17)
"This place was awesome, very clean and had everything we needed, would definitely consider staying again!"
The Hangar - Healthcare/Military friendly!
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 Retreat
Fridge, microwave, oven, stovetop

The Beaumont Retreat

10.0 out of 10, Exceptional, (3)
"Place was great! "
The Beaumont Retreat
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, (35)
"Perfect place! Enjoyed the stay."
Everwood Cottage ^ Trees, Birds, and Quiet! Military Friendly
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

La Quinta Inn & Suites by Wyndham O'Fallon, IL - St. Louis

La Quinta Inn & Suites by Wyndham O'Fallon, IL - St. Louis

10/10 Excellent
"For the price this is a great hotel. I’ve read through some other reviews where people complain and the cleanliness and the breakfast? Like really? This is not a 5 star hotel. Its a good affordable hotel that is cleaner than a lot of hotels in the area and costs way less, the breakfast buffet is pretty much what I would refer to as a continental breakfast plus, not to mention that the staff are very friendly and efficient, the rooms are about one and a half the size of the average hotel rooms with plenty of space to unload your baggage and the overall area is very clean and welcoming. I would highly recommend this place for anyone who is looking for a hotel that has ample room and won’t bankrupt you. The indoor pool is also a plus along with the laundry room and gym. "
Linda 1-night trip
Posted 1 day ago
La Quinta Inn & Suites by Wyndham O'Fallon, IL - St. Louis

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.

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.