Winter Hill Ski Chalets
Apartment
7 Bedrooms
7 Baths
17 Guests
Fireplace/Heating
Balcony/Terrace
Kitchen
Parking
US $1,577/Night
7 Nights - US $11,038
Apartment
10.0(3 Reviews)
2 Bedrooms
2 Baths
6 Guests
1097.92 ft²
- Fireplace/Heating
- Parking
Air Conditioner
Internet
US $556/Night
7 Nights - US $3,894
Apartment
4 Bedrooms
3 Baths
12 Guests
- Fireplace/Heating
Pet Friendly- Kitchen
- Parking
US $694/Night
7 Nights - US $4,859
New
House
4 Bedrooms
4 Baths
8 Guests
- Fireplace/Heating
- Air Conditioner
- Internet
Child Friendly
US $1,181/Night
7 Nights - US $8,265
Apartment
10.0(1 Review)
3 Bedrooms
3 Baths
8 Guests
2002.09 ft²
- Fireplace/Heating
- Balcony/Terrace
- Parking
- Air Conditioner
US $565/Night
7 Nights - US $3,953
New
Apartment
4 Bedrooms
2 Baths
12 Guests
- Fireplace/Heating
- Air Conditioner
- Internet
- Child Friendly
US $577/Night
7 Nights - US $4,036
Apartment
10.0(1 Review)
4 Bedrooms
4 Baths
12 Guests
2002.09 ft²
- Fireplace/Heating
- Parking
- Air Conditioner
- Internet
US $437/Night
7 Nights - US $3,059
Condo
10.0(2 Reviews)
1 Bedroom
4 Baths
16 Guests
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $1,041/Night
7 Nights - US $7,287
Bed & Breakfast
9.1(490 Reviews)
6 Bedrooms
3 Baths
7 Guests
186.57 ft²
- Fireplace/Heating
- Parking
- Air Conditioner
- Internet
US $212/Night
7 Nights - US $1,481
Apartment
10.0(2 Reviews)
2 Bedrooms
2 Baths
8 Guests
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $817/Night
7 Nights - US $5,720
Bed & Breakfast
9.0(84 Reviews)
6 Bedrooms
6 Baths
15 Guests
177.6 ft²
- Fireplace/Heating
- Balcony/Terrace
View- Parking
US $322/Night
7 Nights - US $2,254
New
Apartment
10.0(1 Review)
2 Bedrooms
1 Bath
4 Guests
- Fireplace/Heating
- Pet Friendly
- Kitchen
- Parking
US $349/Night
7 Nights - US $2,443
Why Choose Rent By Owner for your Winter Hill 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 Winter Hill
How to Book Your Winter Hill 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 Winter Hill
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 Winter Hill, MA
Somerville
Winter Hill Ski Chalets Frequently Asked Questions
1. What are the top Ski Chalets in Winter Hill?
There are a lot of options in Winter Hill. If you plan on staying in the Winter Hill area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Ski Chalets in Winter Hill:
- Somerville 4BR: 2 Parking/Yard/Game Rm—Near Boston
- LUX Retreat Home with Yard & Parking
- 5BR3Bath + Yard in Somerville LUX Retreat Home
- 3BR2BATH Lux Home in Somerville
- SkyDeck Stylish Stay
- 3BR3Bth Penthouse 2 Parking Spaces/TD/MIT/Harvard
- CLEAN Apt Near Boston/Cambridge, Harvard, MIT with Parking - Great Reviews!
- Spacious 3BDR near Harvard/5-Min Walk to Train - Davis Sq/Free Parking!
- Property on Broadway Somerville
- Spacious 3BR Family Flat Near Encore Assembly Row
2. How many Ski Chalets are available in Winter Hill?
Currently, the total number of properties listed by RBO in 2026 is over 88 in the Winter Hill area, and still counting. By aggregating listings from multiple websites, RBO offers an immense amount of choice of the best Ski Chalets in Winter Hill.
More Rentals You May Like Near Winter Hill
Bed & Breakfast
9.0(74 Reviews)
7 Bedrooms
7 Baths
17 Guests
197.34 ft²
- Fireplace/Heating
- Balcony/Terrace
- View
- Kitchen
US $170/Night
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Condo
9.8(22 Reviews)
1 Bedroom
3 Baths
10 Guests
- Fireplace/Heating
- Balcony/Terrace
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- Parking
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Apartment
9.6(47 Reviews)
2 Bedrooms
1 Bath
3 Guests
450 ft²
- Fireplace/Heating
- Kitchen
- Parking
- Air Conditioner
US $195/Night
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Condo
9.6(7 Reviews)
2 Bedrooms
1 Bath
10 Guests
1000 ft²
- Fireplace/Heating
- Pet Friendly
- Kitchen
- Air Conditioner
US $335/Night
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Condo
9.4(17 Reviews)
1 Bedroom
1 Bath
6 Guests
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $450/Night
7 Nights - US $3,151
Apartment
2 Bedrooms
2 Baths
6 Guests
1000 ft²
- Fireplace/Heating
- Pet Friendly
- Kitchen
- Parking
US $588/Night
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New
Apartment
2 Bedrooms
2 Baths
6 Guests
- Fireplace/Heating
- Kitchen
- Parking
- Air Conditioner
US $560/Night
7 Nights - US $3,920
Apartment
2 Bedrooms
1 Bath
10 Guests
- Fireplace/Heating
- Kitchen
- Parking
- Air Conditioner
US $401/Night
7 Nights - US $2,804
New
House
2 Bedrooms
2 Baths
4 Guests
- Fireplace/Heating
- Pet Friendly
- Kitchen
- Parking
US $389/Night
7 Nights - US $2,725
Apartment
1 Bedroom
1 Bath
3 Guests
- Fireplace/Heating
- Pet Friendly
- Kitchen
- Parking
US $290/Night
7 Nights - US $2,029
Apartment
10.0(3 Reviews)
4 Bedrooms
3 Baths
12 Guests
2000 ft²
- Fireplace/Heating
- Pet Friendly
- Kitchen
- Parking
US $846/Night
7 Nights - US $5,919
Apartment
10.0(3 Reviews)
3 Bedrooms
2 Baths
9 Guests
- Fireplace/Heating
- Kitchen
- Parking
- Air Conditioner
US $598/Night
7 Nights - US $4,183
