Highland Vacation Rentals & Ski-in/Ski-out Homes
House
- St. Louis
- ·
- Glen Carbon
- 1.39 mi to center
10.0Exceptional
(35 Reviews)
2 Bedrooms
1 Bath
4 Guests
1000 ft²
Parking
Balcony/Terrace
Kitchen
Air Conditioner
US $206/Night
7 Nights - US $1,443
House
- St. Louis
- ·
- Edwardsville
- 1.69 mi to center
10.0Exceptional
(2 Reviews)
3 Bedrooms
2 Baths
9 Guests
1700.7 ft²
- Parking
Internet
Pet Friendly
Sports/Activities
US $285/Night
7 Nights - US $1,993
Hotel
- Illinois
- ·
- Collinsville
- 1.64 mi to center
9.6Exceptional
(1016 Reviews)
1 Bath
Breakfast- Parking
Pool- Kitchen
US $128/Night
7 Nights - US $893
Apartment
- Collinsville
- ·
- Shiloh
- 1.33 mi to center
10.0Exceptional
(18 Reviews)
1 Bedroom
1 Bath
2 Guests
400 ft²
- Parking
- Kitchen
- Air Conditioner
- Internet
US $92/Night
7 Nights - US $641
Bed & Breakfast
- Carlyle Lake
- ·
- Breese
- 0.21 mi to center
9.8Exceptional
(9 Reviews)
4 Bedrooms
4 Baths
8 Guests
454.77 ft²
- Parking
- Balcony/Terrace
View- Air Conditioner
US $161/Night
7 Nights - US $1,127
Apartment
- Collinsville
- ·
- Shiloh
- 1.40 mi to center
10.0Exceptional
(7 Reviews)
2 Bedrooms
2 Baths
4 Guests
1100 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $208/Night
7 Nights - US $1,459
Apartment
- Carlyle Lake
- ·
- Highland
- 1.44 mi to center
10.0Exceptional
(6 Reviews)
2 Bedrooms
1 Bath
6 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
US $370/Night
7 Nights - US $2,593
House
- Collinsville
- ·
- Lebanon
- 0.31 mi to center
10.0Exceptional
(6 Reviews)
2 Bedrooms
1 Bath
4 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $222/Night
7 Nights - US $1,551
Villa
- Collinsville
- ·
- Lebanon
- 1.24 mi to center
10.0Exceptional
(5 Reviews)
2 Bedrooms
2 Baths
4 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $224/Night
7 Nights - US $1,569
Luxury Places to Stay in Highland
Over 130+ Luxury Places to Stay in or Near Highland
House
9.0Exceptional
(14 Reviews)
4 Bedrooms
4 Baths
10 Guests
6000 ft²
Hot Tub- Parking
Spa
Ocean View
US $675/Night
7 Nights - US $4,726
House
- Carlyle Lake
- ·
- Highland
- 1.23 mi to center
10.0Exceptional
(13 Reviews)
4 Bedrooms
2 Baths
11 Guests
3000 ft²
- Hot Tub
- Parking
- Balcony/Terrace
- Kitchen
US $582/Night
7 Nights - US $4,077
House
- Carlyle Lake
- ·
- Highland
- 1.58 mi to center
10.0Exceptional
(83 Reviews)
6 Bedrooms
3 Baths
14 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $538/Night
7 Nights - US $3,766
House
- St. Louis
- ·
- Glen Carbon
- 0.28 mi to center
8.6Fabulous
(8 Reviews)
5 Bedrooms
3 Baths
10 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $465/Night
7 Nights - US $3,258
House
- Illinois
- ·
- Collinsville
- 1.98 mi to center
9.6Exceptional
(99 Reviews)
3 Bedrooms
2 Baths
12 Guests
2056 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $456/Night
7 Nights - US $3,193
Hotel
7.5Very Good
(115 Reviews)
3 Baths
301.39 ft²
Private Pool- Parking
- Pool
- Kitchen
US $446/Night
7 Nights - US $3,122
Apartment
- Carlyle Lake
- ·
- Highland
- 1.54 mi to center
10.0Exceptional
(9 Reviews)
3 Bedrooms
1 Bath
6 Guests
1400 ft²
- Parking
- Kitchen
- Air Conditioner
- Internet
US $415/Night
7 Nights - US $2,908
House
- Carlyle Lake
- ·
- Highland
- 1.53 mi to center
10.0Exceptional
(2 Reviews)
2 Bedrooms
1 Bath
4 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $394/Night
7 Nights - US $2,760
House
- St. Louis
- ·
- Edwardsville
- 1.69 mi to center
9.8Exceptional
(32 Reviews)
3 Bedrooms
2 Baths
9 Guests
1700 ft²
- Parking
- Kitchen
- Air Conditioner
- Internet
US $382/Night
7 Nights - US $2,672
Top-Rated Vacation Rentals with a Pool in Highland
Over 46+ Top-Rated Vacation Rentals with a Pool in or Near Highland
Hotel
- Collinsville
- ·
- O'Fallon
- 2.03 mi to center
9.7Exceptional
(32 Reviews)
3 Baths
466.43 ft²
- Private Pool
Oceanfront- Breakfast
EV Charge Station
US $134/Night
7 Nights - US $938
Hotel
- Collinsville
- ·
- O'Fallon
- 2.28 mi to center
9.6Exceptional
(1009 Reviews)
1 Bath
- Hot Tub
- Breakfast
- Parking
- Pool
US $145/Night
7 Nights - US $1,015
Hotel
- Illinois
- ·
- Collinsville
- 1.59 mi to center
9.4Exceptional
(571 Reviews)
12 Baths
322.02 ft²
- Private Pool
- Parking
- Pool
- Kitchen
US $114/Night
7 Nights - US $796
Hotel
- St. Louis
- ·
- Edwardsville
- 3.78 mi to center
9.2Exceptional
(884 Reviews)
1 Bath
- Breakfast
- Parking
- Pool
- Kitchen
US $132/Night
7 Nights - US $924
Hotel
- Collinsville
- ·
- O'Fallon
- 1.87 mi to center
9.2Exceptional
(863 Reviews)
1 Bath
- Breakfast
- Parking
- Pool
- Kitchen
US $137/Night
7 Nights - US $956
Hotel
9.2Exceptional
(803 Reviews)
1 Bath
- Breakfast
- Parking
- Pool
- Balcony/Terrace
US $114/Night
7 Nights - US $798
Hotel
- Collinsville
- ·
- Mascoutah
- 6.38 mi to center
9.0Exceptional
(1001 Reviews)
1 Bath
- Breakfast
- Parking
- Pool
- Kitchen
US $130/Night
7 Nights - US $909
Hotel
- St. Louis
- ·
- Edwardsville
- 3.94 mi to center
9.0Exceptional
(210 Reviews)
1 Bath
- Breakfast
- Parking
- Pool
- Balcony/Terrace
US $218/Night
7 Nights - US $1,529
Hotel
- Collinsville
- ·
- O'Fallon
- 2.03 mi to center
9.0Exceptional
(151 Reviews)
1 Bath
- Breakfast
- Parking
- Pool
- Balcony/Terrace
US $358/Night
7 Nights - US $2,509
Pet-Friendly Vacation Rentals in Highland
Over 35+ Pet-Friendly Vacation Rentals in or Near Highland
House
- Collinsville
- ·
- Shiloh
- 0.85 mi to center
9.6Exceptional
(7 Reviews)
1 Bedroom
1 Bath
2 Guests
930 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $147/Night
7 Nights - US $1,031
New
House
- St. Louis
- ·
- Edwardsville
- 2.36 mi to center
1 Bedroom
2 Baths
8 Guests
1496.18 ft²
- Parking
- Air Conditioner
- Internet
- Pet Friendly
US $176/Night
7 Nights - US $1,235
Hotel
7.8Very Good
(1005 Reviews)
1 Bath
- Breakfast
- Parking
- Pool
- Kitchen
US $80/Night
7 Nights - US $559
Apartment
- Collinsville
- ·
- Caseyville
- 1.49 mi to center
9.4Exceptional
(51 Reviews)
1 Bedroom
1 Bath
4 Guests
700 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $228/Night
7 Nights - US $1,596
Hotel
- Collinsville
- ·
- Mascoutah
- 6.37 mi to center
8.8Fabulous
(378 Reviews)
1 Bath
365.97 ft²
- Private Pool
- Oceanfront
- Breakfast
- Parking
US $129/Night
7 Nights - US $900
House
- Collinsville
- ·
- Caseyville
- 1.06 mi to center
10.0Exceptional
(2 Reviews)
2 Bedrooms
1 Bath
5 Guests
1000 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $106/Night
7 Nights - US $744
Cottage
- St. Louis
- ·
- Glen Carbon
- 1.89 mi to center
2 Bedrooms
1 Bath
3 Guests
788 ft²
- Air Conditioner
- Internet
- Pet Friendly
Child Friendly
US $169/Night
7 Nights - US $1,185
House
- St. Louis
- ·
- Edwardsville
- 1.60 mi to center
10.0Exceptional
(26 Reviews)
3 Bedrooms
3 Baths
6 Guests
2050 ft²
- Hot Tub
- Parking
- Balcony/Terrace
- Kitchen
US $469/Night
7 Nights - US $3,280
House
- Collinsville
- ·
- Shiloh
- 1.13 mi to center
10.0Exceptional
(2 Reviews)
3 Bedrooms
3 Baths
6 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $238/Night
7 Nights - US $1,666
Large Vacation Homes & Villas in Highland
Over 5+ Large Vacation Homes & Villas in or Near Highland
New
Other
- Litchfield
- ·
- Staunton
- 2.29 mi to center
3 Bedrooms
2 Baths
13 Guests
- Internet
Laundry
Bedding/Linens
Wellness Facilities
US $284/Night
7 Nights - US $1,988
House
- Carlyle Lake
- ·
- Greenville
- 1.41 mi to center
3 Bedrooms
2 Baths
10 Guests
- Parking
- Air Conditioner
- Internet
- Laundry
US $215/Night
7 Nights - US $1,502
House
- Collinsville
- ·
- New Baden
- 3.62 mi to center
7.0Very Good
(8 Reviews)
5 Bedrooms
4 Baths
10 Guests
- Hot Tub
- Air Conditioner
- Internet
- Pet Friendly
US $329/Night
7 Nights - US $2,303
Bed & Breakfast
- Illinois
- ·
- Clinton County
- 5.78 mi to center
10.0Exceptional
(1 Review)
4 Bedrooms
2 Baths
12 Guests
- Child Friendly
US $275/Night
7 Nights - US $1,925
US $400/Night
7 Nights - US $2,800
Wheelchair Accessible Vacation Homes in Highland
Over 30+ Wheelchair Accessible Vacation Homes in or Near Highland
Condo
- Collinsville
- ·
- O'Fallon
- 2.69 mi to center
4.5Average
(2 Reviews)
2 Bedrooms
2 Baths
- View
- Kitchen
- Air Conditioner
- Internet
US $175/Night
7 Nights - US $1,225
Hotel
8.8Fabulous
(113 Reviews)
14 Baths
519.74 ft²
- Private Pool
- Oceanfront
- Breakfast
- EV Charge Station
US $224/Night
7 Nights - US $1,568
Hotel
- St. Louis
- ·
- Edwardsville
- 3.90 mi to center
8.6Fabulous
(723 Reviews)
1 Bath
- Breakfast
- Parking
- Balcony/Terrace
- Kitchen
US $114/Night
7 Nights - US $797
Hotel
- St. Louis
- ·
- Edwardsville
- 3.81 mi to center
8.7Fabulous
(145 Reviews)
10 Baths
328.3 ft²
- Private Pool
- Oceanfront
- Breakfast
- Parking
US $141/Night
7 Nights - US $984
Hotel
- Carlyle Lake
- ·
- Greenville
- 2.90 mi to center
8.4Excellent
(455 Reviews)
1 Bath
- Breakfast
- Parking
- Pool
- Kitchen
US $114/Night
7 Nights - US $797
Hotel
- Collinsville
- ·
- O'Fallon
- 1.87 mi to center
8.6Fabulous
(201 Reviews)
1 Bath
301.39 ft²
- Private Pool
- EV Charge Station
- Parking
- Pool
US $150/Night
7 Nights - US $1,048
Hotel
8.2Excellent
(1003 Reviews)
1 Bath
- Breakfast
- Parking
- Pool
- Kitchen
US $80/Night
7 Nights - US $559
Hotel
- St. Louis
- ·
- Edwardsville
- 3.90 mi to center
8.5Fabulous
(204 Reviews)
1 Bath
283.45 ft²
- Parking
- Balcony/Terrace
- Air Conditioner
- Internet
US $166/Night
7 Nights - US $1,160
Hotel
8.2Excellent
(150 Reviews)
12 Baths
301.39 ft²
- Private Pool
- Oceanfront
- Breakfast
- Parking
US $134/Night
7 Nights - US $938
Highland Resorts and Airbnb Homes Under $200
Over 74+ Highland Resorts and Airbnb Homes Under $200
House
- Collinsville
- ·
- Lebanon
- 0.25 mi to center
9.8Exceptional
(21 Reviews)
2 Bedrooms
2 Baths
4 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
US $194/Night
7 Nights - US $1,361
House
- St. Louis
- ·
- Glen Carbon
- 1.39 mi to center
2 Bedrooms
1 Bath
4 Guests
1001.04 ft²
- Parking
- Air Conditioner
- Internet
- Laundry
US $160/Night
7 Nights - US $1,123
Hotel
- Carlyle Lake
- ·
- Pocahontas
- 0.88 mi to center
8.8Fabulous
(28 Reviews)
1 Bath
- Parking
- Internet
- Child Friendly
- Laundry
US $92/Night
7 Nights - US $644
Apartment
- Collinsville
- ·
- Shiloh
- 1.19 mi to center
9.8Exceptional
(8 Reviews)
1 Bedroom
1 Bath
2 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $101/Night
7 Nights - US $706
Hotel
- St. Louis
- ·
- Edwardsville
- 1.97 mi to center
8.5Fabulous
(20 Reviews)
8 Baths
309.46 ft²
- Parking
- Air Conditioner
- Internet
- Child Friendly
US $180/Night
7 Nights - US $1,262
Apartment
- St. Louis
- ·
- Edwardsville
- 2.80 mi to center
1 Bedroom
1 Bath
2 Guests
700 ft²
- Kitchen
- Air Conditioner
- Internet
- Laundry
US $97/Night
7 Nights - US $681
Apartment
- St. Louis
- ·
- Edwardsville
- 2.80 mi to center
1 Bedroom
1 Bath
2 Guests
700 ft²
- Kitchen
- Air Conditioner
- Internet
- Child Friendly
US $85/Night
7 Nights - US $593
New
Apartment
- St. Louis
- ·
- Edwardsville
- 2.80 mi to center
1 Bedroom
1 Bath
2 Guests
700 ft²
- Kitchen
- Air Conditioner
- Internet
- Laundry
US $81/Night
7 Nights - US $566
House
- Collinsville
- ·
- Shiloh
- 1.32 mi to center
9.8Exceptional
(18 Reviews)
3 Bedrooms
1 Bath
6 Guests
1100 ft²
- Parking
- Kitchen
- Air Conditioner
- Internet
US $178/Night
7 Nights - US $1,244
Instantly Bookable Vacation Homes in Highland
Over 28+ Instantly Bookable Vacation Homes in or Near Highland
Apartment
- Carlyle Lake
- ·
- Highland
- 1.35 mi to center
10.0Exceptional
(4 Reviews)
2 Bedrooms
1 Bath
6 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
US $359/Night
7 Nights - US $2,515
House
- St. Louis
- ·
- Edwardsville
- 1.78 mi to center
9.6Exceptional
(39 Reviews)
3 Bedrooms
2 Baths
8 Guests
2800 ft²
- Parking
- Ocean View
- Balcony/Terrace
- View
US $286/Night
7 Nights - US $2,005
Apartment
- St. Louis
- ·
- Edwardsville
- 1.62 mi to center
9.6Exceptional
(21 Reviews)
3 Bedrooms
1 Bath
6 Guests
- Child Friendly
Security/Safety
US $209/Night
7 Nights - US $1,464
House
- Carlyle Lake
- ·
- Greenville
- 1.41 mi to center
10.0Exceptional
(3 Reviews)
2 Bedrooms
1 Bath
6 Guests
1860 ft²
- Parking
- Kitchen
- Air Conditioner
- Internet
US $303/Night
7 Nights - US $2,118
House
- Carlyle Lake
- ·
- Greenville
- 1.41 mi to center
10.0Exceptional
(2 Reviews)
1 Bedroom
1 Bath
4 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
US $249/Night
7 Nights - US $1,745
House
- Collinsville
- ·
- Lebanon
- 0.33 mi to center
10.0Exceptional
(42 Reviews)
2 Bedrooms
2 Baths
4 Guests
870 ft²
- Parking
- Kitchen
- Air Conditioner
- Internet
US $159/Night
7 Nights - US $1,110
House
- St. Louis
- ·
- Edwardsville
- 2.35 mi to center
6.0Good
(2 Reviews)
1 Bedroom
1 Bath
2 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
US $86/Night
7 Nights - US $600
Apartment
- St. Louis
- ·
- Edwardsville
- 3.41 mi to center
2 Bedrooms
2 Baths
6 Guests
- Air Conditioner
- Internet
- Laundry
- Bedding/Linens
US $260/Night
7 Nights - US $1,820
Apartment
- St. Louis
- ·
- Edwardsville
- 2.80 mi to center
1 Bedroom
1 Bath
2 Guests
667 ft²
- Kitchen
- Air Conditioner
- Internet
- Laundry
US $116/Night
7 Nights - US $809
Book a Last Minute Place to Stay in Highland
About Highland Vacation Rentals
Explore over 139 vacation rentals in Highland with SunSki Resorts. These accommodations, comprising vacation homes, cottages, cabins, and condos, boast excellent amenities at great value, ensuring comfort and luxury. Enhance your stay with SunSki Resorts in Highland for more space and value.
In search of last-minute deals or the best bargains on vacation rentals? With SunSki Resorts, you can conveniently compare various options and deals in Highland. Discover rentals with desirable amenities like swimming pools, hot tubs, and pet-friendly options. Find the ideal vacation rental in Highland tailored to your preferences. On average, these rentals offer 431.61 ft² of space, and are priced at an average of US $173 per night.
SunSki Resorts simplifies and secures the process of finding and comparing vacation rentals in Highland at prices typically 30-40% lower than hotels. Discover your perfect vacation rental and book now.
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Top Types of Ski Accommodations in Highland
| Type | Count |
|---|---|
| Vacation Homes | 35 |
| Holiday Apartments | 22 |
| B&B | 3 |
| Cabin Rentals | 3 |
| Others | 2 |
| Cottages | 1 |
| Villas | 1 |
Use these Quick Filters to Find a Vacation Rental in Highland
★ Pro Tip: Discover Your Ideal Vacation Rental in Highland with SunSki Resorts™. Compare a diverse array of properties, including RBO homes, vacation rentals, cottages, cabins, and more. Utilize our advanced filters to search by location, amenities, and price. Book with confidence and enjoy savings of up to 40-60% compared to a hotel stay. Create unforgettable memories with SunSki Resorts™.
Weather in Highland, IL
View the weather forecast for Highland before booking your Highland Vacation Rentals to confirm your best time to go.
December - February
High 60°F Low 26°F
March - May
High 77°F Low 40°F
June - August
High 91°F Low 64°F
September - November
High 84°F Low 38°F
Top Attractions Around Highland, IL
Sunski offers a large selection of top attractions around Highland . Research things to do on your vacation before you visit Highland.
Other Places to Stay in Highland, IL
Frequently Asked Questions About Highland?
What are the top vacation rentals in Highland?
When organizing your trip to Highland, don't miss the chance to explore the top-rated vacation rentals in the vicinity. With a plethora of options available, you're bound to discover the ideal accommodation for your stay in Highland. Peruse our collection of highly-rated properties and secure your reservation today.
- Craftsman styled home in the heart of downtown Highland
- Sunset Cottage - 2 King beds! Downtown Glen Carbon
- The Hangar - Healthcare/Military friendly!
- LARGE 3000 sq. ft Newly Renovated Upstairs Loft - Ideal Families & Friend
- The Loft on the Square
- The PanAm Flat - 2bed/2bath next to hospitals & Scott AFB
- The Swiss Post Apartment B
- Close to McKendree, Scott AFB & St. Louis
- Beautiful Historic Lebanon Illinois 2 Bedroom Villa
- The Swiss Post Apartment A
How many vacation rentals have private pools in Highland?
Uncover 12 vacation rentals boasting private pools near Highland. Explore top-rated RBO homes offering access to a swimming pool:
- Hilton Garden Inn St. Louis Shiloh/O'Fallon IL
- TownePlace Suites by Marriott St. Louis Edwardsville, IL
- Super 8 by Wyndham Troy IL/St. Louis Area
- Comfort Inn & Suites Greenville I-70
Which vacation homes or resorts in Highland are best for families?
Choose SunSki for a wide variety of vacation rentals, including family-friendly homes, ski cabins, cottages, and more in Highland. Enjoy great views, locations and save money with SunSki Resorts.™
- Patriot on Old Route 66, fire ring and camping available in 2 acre pasture
- Brick B&B - 3Bed 2Full Bath! Downtown Edwardsville
- Powhatan Motel
How many SunSkiResorts vacation rentals or resorts are available in Highland?
Discover the ideal vacation rental in Highland with SunSki Resorts™. We provide an extensive selection of over 139 properties, encompassing vacation homes, private villas, cottages, and more. Explore our listings to find the perfect place to stay for your upcoming trip to Highland.
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