Highland Holiday Rentals

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Holiday Rentals in Highland

The Swiss Post Apartment B

2.0 star property
Highland
10.0 out of 10, Exceptional, (3)
"Tricia was a wonderful host, everything was spotless, well equipped easy and comfortable. A perfect stay."
United States
Joy C.
The Swiss Post Apartment B

Craftsman styled home in the heart of downtown Highland

Highland
10.0 out of 10, Exceptional, (66)
"We had a 12 person wedding party and this place was the perfect mix of single beds and king/queen beds. Awesome host was very helpful and couldn’t have asked for a better place to stay!"
United States
Austin S.
Craftsman styled home in the heart of downtown Highland

The Swiss Post Apartment A

2.0 star property
Highland
10.0 out of 10, Exceptional, (2)
"Everything was great! Nice stay in a quiet and friendly area"
United States
Jason S.
The Swiss Post Apartment A

The Loft on the Square

Highland
10.0 out of 10, Exceptional, (4)
"Clean, perfect for wedding at olde wicks factory"
United States
Dylan M.
The Loft on the Square

3 Bedroom Loft overlooking water

Caseyville
9.6 out of 10, Exceptional, (113)
"My family and I had a great stay here. Beautiful location, super easy to navigate to the Metro Stl area. The place is nice and clean. Great value, good communication, clean, safe place to stay."
United States
Gary C.
3 Bedroom Loft overlooking water

Cozy Corner Mascoutah

Mascoutah
9.6 out of 10, Exceptional, (72)
"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. "
United States
Ann G.
The price is NZ$346
includes taxes & fees
16 Nov - 17 Nov
Cozy Corner Mascoutah

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

Greenville
10.0 out of 10, Exceptional, (38)
"We wanted a house large enough for 20 with easy access to the lake. We got it. Loved the private beach in the cove, great for little children."
United States
John S.
THE NEST getaways&gatherings, beach/lake sleeps 20+

Spacious 5-bedroom house in gorgeous Glen Carbon with AC

2.0 star property
Glen Carbon
10.0 out of 10, Exceptional, (1)
"Great place to stay "
United States
Karl W.
The price is NZ$959
includes taxes & fees
15 Nov - 16 Nov
Spacious 5-bedroom house in gorgeous Glen Carbon with AC

Skyline - Military/Family Friendly

Shiloh
10.0 out of 10, Exceptional, (16)
"The home was very clean and comfortable. Minutes from everything."
United States
Mark V.
Skyline - Military/Family Friendly

The Maple Cottage

Caseyville
10.0 out of 10, Exceptional, (2)
"The house was perfect for us and our three adult children. Incredibly clean, and decor was perfect. We accidentally left something behind and Brandon, our host, told us before we even knew it. Made sure we got everything back safely."
United States
James P.
The Maple Cottage

3 Bedroom Home - Lake Views on 3 Sides

Caseyville
9.6 out of 10, Exceptional, (95)
"The lake did it for all. Everyone learned to fish even my 2 year old great grand. Could not have picked a better place"
United States
Carol S.
3 Bedroom Home - Lake Views on 3 Sides

The Aerie- Luxury Lakeside Getaway - Private Beach & Boatdock

Greenville
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."
United States
Diane S.
The Aerie- Luxury Lakeside Getaway - Private Beach & Boatdock

Private 4 Bedroom Home with a hot tub

Caseyville
9.4 out of 10, Exceptional, (51)
"Good choice for a sizeable group."
United States
Brad H.
Private 4 Bedroom Home with a hot tub

Reel 'Em Inn

Carlyle
9.0 out of 10, Wonderful, (6)
"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!"
United States
Ronald R.
Reel 'Em Inn

3-Bedroom Downtown apartment with Game Room

2.0 star property
Carlyle
10.0 out of 10, Exceptional, (1)
"The property was great! Very clean, appropriately stocked, and everything the owner had described. We truly enjoyed our family gathering at this location. "
United States
Kara H.
3-Bedroom Downtown apartment with Game Room

The Beaumont Retreat

Greenville
10.0 out of 10, Exceptional, (3)
"Family get together "
United Kingdom
DAVID J.
The Beaumont Retreat

Carlyle lake home!

Carlyle
9.0 out of 10, Wonderful, (2)
"It was a pleasant place, handy to everything and certainly had everything needed. The king bed was very comfortable. We enjoyed our stay. I do recommend that just once price be indicated instead of all the extra charges on top of the basic price of the place."
United States
Richard B.
Carlyle lake home!

Cozy Historic Downtown Edwardsville Charmer

Edwardsville
9.4 out of 10, Exceptional, (14)
"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."
United States
Desera G.
Cozy Historic Downtown Edwardsville Charmer

The Hangar - Healthcare/Military friendly!

Shiloh
10.0 out of 10, Exceptional, (17)
"Close to family and Scott AFB"
United States
Jamie S.
The Hangar - Healthcare/Military friendly!

Charming 1BR Near Historic Downtown Edwardsville & SIUE

Edwardsville
10.0 out of 10, Exceptional, (1)
"Charles is a very conscientious VRBO member who was available when I had difficulty entering. This home has been recently updated and the interior decor is quite attractive and comfortable. The bathroom even has an in floor heating system. The house is located in an older section of town but the entire street of homes are well maintained. The location is super convenient to the university and all the activities in downtown Edwardsville."
United States
Joseph K.
Charming 1BR Near Historic Downtown Edwardsville & SIUE
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

Find out more about Highland

Everything you need to know about Highland holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Highland holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Highland holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Highland holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Highland. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Highland holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Highland holiday rentals we have selected for you start as low as NZ$346 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Highland rentals

At Expedia, we put the best Highland holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Highland rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Highland holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Highland. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Frequently asked questions

Are there holiday rentals in Highland?

Yes, there are holiday rentals close to the most popular sights in Highland, or you can select a more secluded option if you're looking for a relaxing stay. Our travellers 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 are some of the best holiday rentals that Highland has to offer?

Craftsman styled home in the heart of downtown Highland: This highly rated holiday home rental in Highland is located in the city centre, and has a garden, a BBQ 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 that 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 wider area, you’ll find Korte Recreation Center and Copper Dock Winery.

What are holiday rentals like in Highland?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Highland. Holiday rentals feature amenities such as WiFi and washers and dryers so you'll feel just like you're at home. If you're concerned about a sanitised environment, a holiday rental can offer a sense of privacy away from public hotel lifts and busy concierge desks while still allowing you the excitement and enjoyment of travel. You'll also have more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is a popular option for small groups.