139+ Vacation Home Rentals in Highland |
Highland Vacation Rentals & Ski-in/Ski-out Homes
House
- St. Louis
- ·
- Glen Carbon
- 1.39 mi to center
10.0Exceptional
(33 Reviews)
2 Bedrooms
1 Bath
4 Guests
1000 ft²
Fireplace/Heating
Balcony/Terrace
Kitchen
Parking
US $216/Night
7 Nights - US $1,511
House
- St. Louis
- ·
- Edwardsville
- 1.69 mi to center
10.0Exceptional
(2 Reviews)
3 Bedrooms
2 Baths
9 Guests
1700.7 ft²
- Fireplace/Heating
Pet Friendly- Parking
Internet
US $285/Night
7 Nights - US $1,993
Hotel
- St. Louis
- ·
- Edwardsville
- 3.94 mi to center
9.0Exceptional
(207 Reviews)
1 Bath
Pool- Balcony/Terrace
Breakfast- Pet Friendly
US $292/Night
7 Nights - US $2,044
Apartment
- Collinsville
- ·
- Shiloh
- 1.33 mi to center
10.0Exceptional
(18 Reviews)
1 Bedroom
1 Bath
2 Guests
400 ft²
- Fireplace/Heating
- Kitchen
- Parking
Air Conditioner
US $90/Night
7 Nights - US $629
Bed & Breakfast
- Carlyle Lake
- ·
- Breese
- 0.21 mi to center
9.8Exceptional
(9 Reviews)
4 Bedrooms
4 Baths
8 Guests
454.77 ft²
- Fireplace/Heating
- Balcony/Terrace
View- Parking
US $161/Night
7 Nights - US $1,127
Apartment
- Collinsville
- ·
- Shiloh
- 1.40 mi to center
10.0Exceptional
(6 Reviews)
2 Bedrooms
2 Baths
4 Guests
1100 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $149/Night
7 Nights - US $1,043
Apartment
- Carlyle Lake
- ·
- Highland
- 1.44 mi to center
10.0Exceptional
(5 Reviews)
2 Bedrooms
1 Bath
6 Guests
- Fireplace/Heating
- Kitchen
- Parking
- Air Conditioner
US $314/Night
7 Nights - US $2,195
House
- Collinsville
- ·
- Lebanon
- 0.31 mi to center
10.0Exceptional
(5 Reviews)
2 Bedrooms
1 Bath
4 Guests
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $161/Night
7 Nights - US $1,125
Apartment
- Carlyle Lake
- ·
- Highland
- 1.35 mi to center
10.0Exceptional
(3 Reviews)
2 Bedrooms
1 Bath
6 Guests
- Fireplace/Heating
- Kitchen
- Parking
- Air Conditioner
US $305/Night
7 Nights - US $2,135
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
Spa- Fireplace/Heating
Ocean View
US $645/Night
7 Nights - US $4,514
Hotel
- St. Louis
- ·
- Edwardsville
- 3.90 mi to center
8.5Fabulous
(204 Reviews)
1 Bath
283.45 ft²
- Fireplace/Heating
- Balcony/Terrace
- Parking
- Air Conditioner
US $495/Night
7 Nights - US $3,465
House
- St. Louis
- ·
- Glen Carbon
- 0.28 mi to center
9.4Exceptional
(6 Reviews)
5 Bedrooms
3 Baths
10 Guests
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $487/Night
7 Nights - US $3,406
House
- Illinois
- ·
- Collinsville
- 1.98 mi to center
9.6Exceptional
(98 Reviews)
4 Bedrooms
2 Baths
12 Guests
2056 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $453/Night
7 Nights - US $3,171
Hotel
7.5Very Good
(115 Reviews)
3 Baths
301.39 ft²
Private Pool- Fireplace/Heating
- Pool
- Kitchen
US $446/Night
7 Nights - US $3,122
House
- Carlyle Lake
- ·
- Highland
- 1.23 mi to center
10.0Exceptional
(12 Reviews)
4 Bedrooms
2 Baths
11 Guests
3000 ft²
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $444/Night
7 Nights - US $3,107
Hotel
7.1Very Good
(187 Reviews)
4 Baths
290.63 ft²
- Private Pool
- Fireplace/Heating
- Pool
- Pet Friendly
US $377/Night
7 Nights - US $2,639
House
- Carlyle Lake
- ·
- Highland
- 1.58 mi to center
10.0Exceptional
(77 Reviews)
7 Bedrooms
3 Baths
14 Guests
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $375/Night
7 Nights - US $2,625
Apartment
- Carlyle Lake
- ·
- Highland
- 1.54 mi to center
10.0Exceptional
(7 Reviews)
3 Bedrooms
1 Bath
6 Guests
1400 ft²
- Fireplace/Heating
- Pet Friendly
- Kitchen
- Parking
US $351/Night
7 Nights - US $2,457
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
9.6Exceptional
(32 Reviews)
3 Baths
466.43 ft²
- Private Pool
Oceanfront- Fireplace/Heating
- Pool
US $158/Night
7 Nights - US $1,106
Hotel
- Illinois
- ·
- Collinsville
- 1.59 mi to center
9.4Exceptional
(571 Reviews)
12 Baths
322.02 ft²
- Private Pool
- Fireplace/Heating
- Pool
- Pet Friendly
US $158/Night
7 Nights - US $1,106
Hotel
- Collinsville
- ·
- Mascoutah
- 6.37 mi to center
8.8Fabulous
(393 Reviews)
1 Bath
365.97 ft²
- Private Pool
- Oceanfront
- Fireplace/Heating
- Pool
US $119/Night
7 Nights - US $830
Hotel
- St. Louis
- ·
- Edwardsville
- 3.81 mi to center
8.7Fabulous
(145 Reviews)
10 Baths
328.3 ft²
- Private Pool
- Oceanfront
- Fireplace/Heating
- Pool
US $169/Night
7 Nights - US $1,185
Hotel
8.7Fabulous
(111 Reviews)
14 Baths
519.74 ft²
- Private Pool
- Oceanfront
- Fireplace/Heating
- Pool
US $224/Night
7 Nights - US $1,568
Hotel
- Collinsville
- ·
- O'Fallon
- 1.87 mi to center
8.6Fabulous
(201 Reviews)
1 Bath
301.39 ft²
- Private Pool
- Pool
- Pet Friendly
- Parking
US $139/Night
7 Nights - US $973
Hotel
8.2Excellent
(150 Reviews)
12 Baths
301.39 ft²
- Private Pool
- Oceanfront
- Spa
- Fireplace/Heating
US $134/Night
7 Nights - US $938
Hotel
- Collinsville
- ·
- O'Fallon
- 1.92 mi to center
7.8Very Good
(106 Reviews)
1 Bath
383.59 ft²
- Private Pool
- Oceanfront
- Fireplace/Heating
- Pool
US $211/Night
7 Nights - US $1,474
Hotel
7.6Very Good
(224 Reviews)
3 Baths
290.63 ft²
- Private Pool
- Fireplace/Heating
- Pool
- Parking
US $319/Night
7 Nights - US $2,233
Pet-Friendly Vacation Rentals in Highland
Over 31+ 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
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $113/Night
7 Nights - US $790
Hotel
- Litchfield
- ·
- Staunton
- 2.13 mi to center
8.3Excellent
(228 Reviews)
4 Baths
363.28 ft²
- Fireplace/Heating
- Pet Friendly
- Parking
- Air Conditioner
US $88/Night
7 Nights - US $618
Hotel
7.8Very Good
(1001 Reviews)
1 Bath
- Fireplace/Heating
- Pool
- Breakfast
- Pet Friendly
US $89/Night
7 Nights - US $621
Apartment
- Collinsville
- ·
- Caseyville
- 1.49 mi to center
9.4Exceptional
(51 Reviews)
2 Bedrooms
1 Bath
4 Guests
700 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $187/Night
7 Nights - US $1,306
Hotel
- Carlyle Lake
- ·
- Greenville
- 2.83 mi to center
7.6Very Good
(97 Reviews)
1 Bath
- Private Pool
- Oceanfront
- Hot Tub
- Pool
US $95/Night
7 Nights - US $665
House
- St. Louis
- ·
- Edwardsville
- 1.69 mi to center
9.8Exceptional
(31 Reviews)
3 Bedrooms
2 Baths
9 Guests
1700 ft²
- Fireplace/Heating
- Pet Friendly
- Kitchen
- Parking
US $280/Night
7 Nights - US $1,961
Apartment
- Illinois
- ·
- Collinsville
- 1.98 mi to center
9.6Exceptional
(113 Reviews)
3 Bedrooms
1 Bath
9 Guests
1100 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $252/Night
7 Nights - US $1,767
House
- Collinsville
- ·
- Caseyville
- 1.06 mi to center
10.0Exceptional
(2 Reviews)
2 Bedrooms
1 Bath
5 Guests
1000 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
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
- Pet Friendly
- Air Conditioner
- Internet
Child Friendly
US $169/Night
7 Nights - US $1,185
Large Vacation Homes & Villas in Highland
Over 7+ Large Vacation Homes & Villas in or Near Highland
Villa
- Collinsville
- ·
- Lebanon
- 1.24 mi to center
10.0Exceptional
(3 Reviews)
2 Bedrooms
2 Baths
4 Guests
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $176/Night
7 Nights - US $1,235
House
- Carlyle Lake
- ·
- Greenville
- 1.41 mi to center
3 Bedrooms
2 Baths
10 Guests
- Fireplace/Heating
- Parking
- Air Conditioner
- Internet
US $188/Night
7 Nights - US $1,316
Villa
- Collinsville
- ·
- Lebanon
- 0.36 mi to center
10.0Exceptional
(177 Reviews)
3 Bedrooms
1 Bath
6 Guests
- Fireplace/Heating
- Kitchen
- Parking
- Air Conditioner
US $143/Night
7 Nights - US $1,001
House
- Collinsville
- ·
- New Baden
- 3.62 mi to center
7.0Very Good
(8 Reviews)
5 Bedrooms
4 Baths
10 Guests
- Hot Tub
- Fireplace/Heating
- Pet Friendly
- Air Conditioner
US $329/Night
7 Nights - US $2,303
House
- Carlyle Lake
- ·
- Breese
- 0.22 mi to center
10.0Exceptional
(19 Reviews)
5 Bedrooms
2 Baths
8 Guests
3000 ft²
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
- View
US $331/Night
7 Nights - US $2,318
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 28+ 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
- Carlyle Lake
- ·
- Greenville
- 2.21 mi to center
7.2Very Good
(132 Reviews)
5 Baths
297.08 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Parking
US $63/Night
7 Nights - US $441
Hotel
- Illinois
- ·
- Collinsville
- 1.64 mi to center
9.6Exceptional
(1010 Reviews)
1 Bath
- Pool
- Breakfast
- Kitchen
- Parking
US $130/Night
7 Nights - US $909
Hotel
- Collinsville
- ·
- O'Fallon
- 2.19 mi to center
7.0Very Good
(68 Reviews)
8 Baths
322.92 ft²
- Private Pool
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $125/Night
7 Nights - US $877
Hotel
- Collinsville
- ·
- O'Fallon
- 2.28 mi to center
9.6Exceptional
(1003 Reviews)
1 Bath
- Hot Tub
- Pool
- Breakfast
- Kitchen
US $143/Night
7 Nights - US $998
Hotel
- Carlyle Lake
- ·
- Greenville
- 2.20 mi to center
6.7Good
(171 Reviews)
1 Bath
301.39 ft²
- Private Pool
- Oceanfront
- Fireplace/Heating
- Pool
US $76/Night
7 Nights - US $532
Hotel
- Collinsville
- ·
- O'Fallon
- 1.87 mi to center
9.2Exceptional
(852 Reviews)
1 Bath
- Fireplace/Heating
- Pool
- Breakfast
- Kitchen
US $154/Night
7 Nights - US $1,075
Hotel
- St. Louis
- ·
- Glen Carbon
- 2.48 mi to center
6.7Good
(78 Reviews)
1 Bath
204.51 ft²
- Private Pool
- Oceanfront
- Fireplace/Heating
- Pool
US $148/Night
7 Nights - US $1,039
Hotel
- Illinois
- ·
- Collinsville
- 1.51 mi to center
6.6Good
(140 Reviews)
4 Baths
247.57 ft²
- Fireplace/Heating
- Kitchen
- Parking
- Air Conditioner
US $330/Night
7 Nights - US $2,310
Highland Resorts and Airbnb Homes Under $200
Over 73+ Highland Resorts and Airbnb Homes Under $200
Apartment
- Collinsville
- ·
- Shiloh
- 1.19 mi to center
9.8Exceptional
(8 Reviews)
1 Bedroom
1 Bath
2 Guests
1 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $87/Night
7 Nights - US $609
Hotel
- Carlyle Lake
- ·
- Greenville
- 2.16 mi to center
7.6Very Good
(72 Reviews)
3 Baths
150.69 ft²
- Parking
- Air Conditioner
- Internet
- Child Friendly
US $50/Night
7 Nights - US $347
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
- St. Louis
- ·
- Edwardsville
- 2.80 mi to center
1 Bedroom
1 Bath
2 Guests
700 ft²
- Fireplace/Heating
- Kitchen
- Air Conditioner
- Internet
US $102/Night
7 Nights - US $711
Hotel
- St. Louis
- ·
- Edwardsville
- 3.96 mi to center
7.5Very Good
(35 Reviews)
6 Baths
426.97 ft²
- Private Pool
- Pool
- Pet Friendly
- Parking
US $181/Night
7 Nights - US $1,269
Apartment
- St. Louis
- ·
- Edwardsville
- 2.80 mi to center
1 Bedroom
1 Bath
2 Guests
700 ft²
- Fireplace/Heating
- Kitchen
- Air Conditioner
- Internet
US $100/Night
7 Nights - US $702
House
- Collinsville
- ·
- Shiloh
- 1.32 mi to center
10.0Exceptional
(16 Reviews)
3 Bedrooms
1 Bath
6 Guests
1100 ft²
- Fireplace/Heating
- Kitchen
- Parking
- Air Conditioner
US $135/Night
7 Nights - US $946
Apartment
- St. Louis
- ·
- Edwardsville
- 1.62 mi to center
9.6Exceptional
(17 Reviews)
3 Bedrooms
1 Bath
6 Guests
- Child Friendly
Security/Safety
US $165/Night
7 Nights - US $1,152
House
- Carlyle Lake
- ·
- Greenville
- 1.41 mi to center
10.0Exceptional
(2 Reviews)
1 Bedroom
1 Bath
4 Guests
- Fireplace/Heating
- Kitchen
- Parking
- Air Conditioner
US $190/Night
7 Nights - US $1,333
Instantly Bookable Vacation Homes in Highland
Over 28+ Instantly Bookable Vacation Homes in or Near Highland
House
- St. Louis
- ·
- Edwardsville
- 1.78 mi to center
9.6Exceptional
(34 Reviews)
3 Bedrooms
2 Baths
8 Guests
2800 ft²
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
- View
US $264/Night
7 Nights - US $1,850
House
- St. Louis
- ·
- Glen Carbon
- 0.33 mi to center
8.0Excellent
(5 Reviews)
4 Bedrooms
2 Baths
8 Guests
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $274/Night
7 Nights - US $1,917
House
- Carlyle Lake
- ·
- Greenville
- 1.41 mi to center
10.0Exceptional
(3 Reviews)
2 Bedrooms
1 Bath
6 Guests
1860 ft²
- Fireplace/Heating
- Kitchen
- Parking
- Air Conditioner
US $215/Night
7 Nights - US $1,505
Hotel
- Carlyle Lake
- ·
- Greenville
- 2.16 mi to center
6.0Good
(1 Review)
1 Bath
- Fireplace/Heating
- Pool
- Kitchen
- Parking
US $114/Night
7 Nights - US $800
US $316/Night
7 Nights - US $2,211
US $316/Night
7 Nights - US $2,211
US $211/Night
7 Nights - US $1,474
US $211/Night
7 Nights - US $1,474
US $114/Night
7 Nights - US $800
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 419.8 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 | 33 |
| Holiday Apartments | 23 |
| B&B | 3 |
| Cabin Rentals | 3 |
| Villas | 2 |
| Cottages | 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!
- Skyline - Military/Family 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
- The Swiss Post Apartment A
How many vacation rentals have private pools in Highland?
Uncover 4 vacation rentals boasting private pools near Highland. Explore top-rated RBO homes offering access to a swimming pool:
- Seasons Inn & Suites Highland
- Sleep Inn O'Fallon near I-64
- Comfort Inn & Suites O'Fallon - St Louis Area
- La Quinta by Wyndham O'Fallon, IL - St. Louis
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.™
- Stay in the heart of downtown Highland in this spacious luxury loft!
- Urban Collective Boutique Hotel
- 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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