121+ Rental Villas and Private Getaways in Highlands |
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Highlands Vacation Rentals & One Degree Stays Homes

About Highlands Vacation Rentals

There are more than 121 vacation rentals that are available in Highlands. 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 Highlands.

Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With OneDegreeStays Highlands, 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 Highlands. Places to stay near Highlands are 585.56 ft² on average, with prices averaging US $296 a night.

OneDegreeStays makes it easy and safe to find and compare vacation rentals in Highlands 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 Highlands

Type Count
Holiday Apartments 48
Vacation Homes 33
Villas 1

Use these Quick Filters to Find a Vacation Rental in Highlands

★ 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 Highlands.

Weather in Highlands, MA

View the weather forecast for Highlands before booking your Highlands 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

Frequently Asked Questions About Highlands?

What are the top vacation rentals in Highlands?

There are a lot of options in Highlands. If you plan on staying in the Highlands area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Highlands:

How many vacation rentals have private pools in Highlands?

There are 2 vacation rentals with private pools near Highlands. Top-rated ODS homes that have access to a swimming pool include:

Which vacation homes in Highlands are best for families?

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

How many onedegreestays vacation rentals are available in Highlands?

Currently, the total number of properties listed by One Degree Stays in 2025 is over 121 in the Highlands 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 Highlands. 

Nearby Neighborhood (3) 
Neighborhood Property Count
The Lanes Vacation Rentals in Boston, Massachusetts 50
Piety Corner Vacation Rentals in Boston, Massachusetts 50
Banks Square Vacation Rentals in Boston, Massachusetts 141

People Also Ask

There are 121 Highlands, MA Vacation Rentals

Recently Booked Vacation Rentals in Highlands