69+ Rental Villas and Private Getaways in Winter Hill |
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Winter Hill Vacation Rentals & One Degree Stays Homes

About Winter Hill Vacation Rentals

There are more than 69 vacation rentals that are available in Winter Hill. These rentals, including vacation rentals, One Degree Stays Homes (ODSs) and other short-term private accommodations, have top-notch amenities with the best value, providing you with comfort and luxury at the same time. Get more value and more room when you stay at an ODS property in Winter Hill.

Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With OneDegreeStays Winter Hill, you have the flexibility of comparing different options of various deals with a single click. Looking for an ODS with the best swimming pools, hot tubs, allows pets, or even those with huge master suite bedrooms and have large screen televisions? You can find vacation rentals by owner (ODSs), and other popular Airbnb-style properties in Winter Hill. Places to stay near Winter Hill are 618.99 ft² on average, with prices averaging US $515 a night.

OneDegreeStays makes it easy and safe to find and compare vacation rentals in Winter Hill with prices often at a 30-40% discount versus the price of a hotel. Just search for your destination and secure your reservation today.

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Top Rental Accommodation Types in Winter Hill

Type Count
Holiday Apartments 52
Vacation Homes 9

Use these Quick Filters to Find a Vacation Rental in Winter Hill

★ Pro Tip: OneDegreeStays makes it easy to compare the best listings on ODS homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between ODS homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals availability, eco-friendly properties, property type, cancellation policies, prices, and several different options. All these make it easier to find the perfect accommodation for your next vacation in Winter Hill.

Weather in Winter Hill, MA

View the weather forecast for Winter Hill before booking your Winter Hill 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

Other Places to Stay in Winter Hill, MA


Somerville 167 Properties

Frequently Asked Questions About Winter Hill?

What are the top vacation rentals 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 Vacation Rentals in Winter Hill:

Which vacation homes in Winter Hill are best for families?

If you are looking for a family-friendly vacation home in Winter Hill, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Winter Hill:

How many onedegreestays vacation rentals are available in Winter Hill?

Currently, the total number of properties listed by One Degree Stays in 2025 is over 69 in the Winter Hill area, and still counting. By aggregating listings from multiple websites, One Degree Stays offers an immense amount of choice of the best ODS properties in Winter Hill. 

Nearby Neighborhood (5) 
Neighborhood Property Count
East Somerville Vacation Rentals in Boston, Massachusetts 37
South Medford Vacation Rentals in Boston, Massachusetts 893
Spring Hill Vacation Rentals in Boston, Massachusetts 1758
Prospect Hill Vacation Rentals in Boston, Massachusetts 3011
Magoun Square Vacation Rentals in Boston, Massachusetts 1112

People Also Ask

There are 69 Winter Hill, MA Vacation Rentals

Recently Booked Vacation Rentals in Winter Hill