Hillsborough Ski Chalets
Apartment
10.0(28 Reviews)
1 Bedroom
1 Bath
2 Guests
Oceanfront
Ocean View
Balcony/Terrace
View
CA $147/Night
7 Nights - CA $1,027
Villa
10.0(1 Review)
2 Bedrooms
1 Bath
5 Guests
- View
Parking
Air Conditioner
Internet
CA $259/Night
7 Nights - CA $1,811
House
10.0(2 Reviews)
1 Bedroom
1 Bath
- Balcony/Terrace
Pet Friendly
Kitchen- Parking
CA $202/Night
7 Nights - CA $1,417
House
10.0(21 Reviews)
3 Bedrooms
3 Baths
6 Guests
2200 ft²
- Ocean View
- Balcony/Terrace
- View
- Kitchen
CA $542/Night
7 Nights - CA $3,794
House
10.0(1 Review)
1 Bedroom
1 Bath
2 Guests
- View
- Parking
- Air Conditioner
- Internet
CA $183/Night
7 Nights - CA $1,284
Apartment
10.0(16 Reviews)
2 Bedrooms
1 Bath
3 Guests
- Oceanfront
- Ocean View
- View
- Kitchen
CA $163/Night
7 Nights - CA $1,140
House
9.0(1 Review)
3 Bedrooms
1 Bath
6 Guests
2152.78 ft²
- Balcony/Terrace
- View
Breakfast- Parking
CA $106/Night
7 Nights - CA $741
Apartment
10.0(13 Reviews)
2 Bedrooms
1 Bath
5 Guests
- Oceanfront
- Ocean View
- Balcony/Terrace
- View
CA $233/Night
7 Nights - CA $1,629
Apartment
9.0(1 Review)
2 Bedrooms
1 Bath
4 Guests
10763.91 ft²
- Balcony/Terrace
- View
- Breakfast
- Parking
CA $71/Night
7 Nights - CA $498
Cottage
10.0(5 Reviews)
2 Bedrooms
2 Baths
18 Guests
1400 ft²
- Oceanfront
- Ocean View
- Balcony/Terrace
- View
CA $188/Night
7 Nights - CA $1,313
House
8.3(19 Reviews)
2 Bedrooms
2 Baths
4 Guests
452.08 ft²
- Balcony/Terrace
- View
- Breakfast
- Parking
CA $82/Night
7 Nights - CA $575
Cabin
10.0(4 Reviews)
1 Bedroom
1 Bath
2 Guests
- Oceanfront
- Ocean View
- Balcony/Terrace
- View
CA $89/Night
7 Nights - CA $623
Why Choose Rent By Owner for your Hillsborough Ski Chalets?
What makes our Ski Chalets special?
Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
Diverse Options
From cozy cabins to luxurious villas, find a rental that suits your style and needs.
Weekly Weather Forecast for Hillsborough
How to Book Your Hillsborough Ski Chalets
What's our booking process?
Our platform allows you to browse a curated selection of ski chalets. Once you find the ideal property, you’ll be redirected to a trusted booking partner to complete your reservation securely.
Booking Steps
01
Search Properties
Use our filters to find the right property that fits your needs.
02
Select a Rental
Click on your preferred listing to view details, amenities, and pricing.
03
Book Online
Follow the link to finalize your reservation directly on the partner’s website.
Explore and book the perfect rental in Hillsborough
Common Ski Chalets Amenities
What amenities can you expect?
Our Ski Chalets are designed to offer all the comforts of home, often with added perks to make your stay unforgettable. Here’s some common amenities to look forward to:
Indoor Features
- Fully-equipped kitchens with modern appliances
- Comfortable living areas with flat-screen TVs
- Free Wi-Fi for staying connected
- Air conditioning and heating for year-round comfort
- In-unit washers and dryers for convenience
- Luxurious bedrooms with premium bedding
- Spa-like bathrooms with soaking tubs or walk-in showers
Other Places to Stay in Hillsborough, FL
Saint George
Saint David
Frequently Asked Questions About Hillsborough Rental Ski Chalets
1. What are the top Ski Chalets in Hillsborough?
There are a lot of options in Hillsborough. If you plan on staying in the Hillsborough area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Ski Chalets in Hillsborough:
- Petite Anse Hotel
- Petite Anse Hotel
- Mount Edgecombe Boutique Hotel
- BUTTERFLY COTTAGE Almost Paradise - 1 bed Caribbean Hideaway
- Almost Paradise Cottage Retreats
- Romantic Cottage with fabulous views over the Caribbean Sea to the islands
- Garden Cottage with sweeping lawn view to the Caribbean Sea and islands
- North Bay Inn
- Come enjoy the beauty of Bathway Beach!
- Treetops Villa Guest Suite 2
2. How many Ski Chalets are available in Hillsborough?
Currently, the total number of properties listed by RBO in 2026 is over 79 in the Hillsborough area, and still counting. By aggregating listings from multiple websites, RBO offers an immense amount of choice of the best Ski Chalets in Hillsborough.
More Rentals You May Like Near Hillsborough
House
7.7(3 Reviews)
2 Bedrooms
1 Bath
4 Guests
645.83 ft²
- View
- Pet Friendly
- Parking
- Internet
CA $123/Night
7 Nights - CA $864
Cottage
10.0(2 Reviews)
2 Bedrooms
1 Bath
4 Guests
- Ocean View
- Balcony/Terrace
- View
- Breakfast
CA $206/Night
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Cottage
10.0(2 Reviews)
1 Bedroom
1 Bath
2 Guests
420 ft²
- Ocean View
- Balcony/Terrace
- View
- Breakfast
CA $206/Night
7 Nights - CA $1,443
Apartment
10.0(2 Reviews)
1 Bedroom
1 Bath
2 Guests
- Kitchen
- Air Conditioner
- Internet
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CA $75/Night
7 Nights - CA $526
Apartment
10.0(2 Reviews)
1 Bedroom
1 Bath
4 Guests
- Ocean View
- View
- Kitchen
- Parking
CA $70/Night
7 Nights - CA $493
Villa
10.0(1 Review)
3 Bedrooms
3 Baths
6 Guests
- Air Conditioner
- Internet
- Child Friendly
Laundry
CA $306/Night
7 Nights - CA $2,139
House
10.0(1 Review)
2 Bedrooms
1 Bath
4 Guests
- Kitchen
- Parking
- Air Conditioner
- Internet
CA $151/Night
7 Nights - CA $1,054
Cottage
10.0(1 Review)
2 Bedrooms
1 Bath
4 Guests
- Balcony/Terrace
- Pet Friendly
- Kitchen
- Parking
CA $92/Night
7 Nights - CA $646
Cottage
9.8(11 Reviews)
1 Bedroom
1 Bath
3 Guests
400 ft²
- Oceanfront
- Ocean View
- Balcony/Terrace
- View
CA $159/Night
7 Nights - CA $1,111
House
9.6(8 Reviews)
3 Bedrooms
2 Baths
6 Guests
1500 ft²
- Oceanfront
- Ocean View
- Balcony/Terrace
- View
CA $184/Night
7 Nights - CA $1,287
House
9.4(3 Reviews)
1 Bedroom
1 Bath
2 Guests
- Kitchen
- Parking
- Air Conditioner
- Internet
CA $110/Night
7 Nights - CA $767
Bed & Breakfast
9.0(6 Reviews)
1 Bedroom
1 Bath
2 Guests
Pool- Balcony/Terrace
- Breakfast
- Kitchen
CA $96/Night
7 Nights - CA $672
