48+ Rental Villas and Private Getaways in Highland Park |
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Highland Park Vacation Rentals & One Degree Stays Homes

About Highland Park Vacation Rentals

There are more than 48 vacation rentals that are available in Highland Park. 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 Highland Park.

Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With OneDegreeStays Highland Park, 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 Highland Park. Places to stay near Highland Park are 384.26 ft² on average, with prices averaging US $415 a night.

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

Type Count
Vacation Homes 24
Holiday Apartments 21

Use these Quick Filters to Find a Vacation Rental in Highland Park

★ 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 Highland Park.

Weather in Highland Park, MA

View the weather forecast for Highland Park before booking your Highland Park 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 Highland Park?

What are the top vacation rentals in Highland Park?

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

Which vacation homes in Highland Park are best for families?

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

How many onedegreestays vacation rentals are available in Highland Park?

Currently, the total number of properties listed by One Degree Stays in 2025 is over 48 in the Highland Park 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 Highland Park. 

Nearby Neighborhood (5) 
Neighborhood Property Count
Roxbury Vacation Rentals in Boston, Massachusetts 81
Jamaica Plain Vacation Rentals in Boston, Massachusetts 48
Washington Park Vacation Rentals in Boston, Massachusetts 25
Egleston Square Vacation Rentals in Boston, Massachusetts 2141
Mission Hill Vacation Rentals in Boston, Massachusetts 3216

People Also Ask

There are 48 Highland Park, MA Vacation Rentals

Recently Booked Vacation Rentals in Highland Park