941+ Rental Villas and Private Getaways in Oak Square |
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Oak Square Vacation Rentals & One Degree Stays Homes

About Oak Square Vacation Rentals

There are more than 941 vacation rentals that are available in Oak Square. 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 Oak Square.

Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With OneDegreeStays Oak Square, 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 Oak Square. Places to stay near Oak Square are 610.65 ft² on average, with prices averaging US $362 a night.

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

Type Count
Holiday Apartments 594
Vacation Homes 184
Cottages 1

Use these Quick Filters to Find a Vacation Rental in Oak Square

★ 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 Oak Square.

Weather in Oak Square, MA

View the weather forecast for Oak Square before booking your Oak Square 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 Oak Square?

What are the top vacation rentals in Oak Square?

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

How many vacation rentals have private pools in Oak Square?

There are 10 vacation rentals with private pools near Oak Square. Top-rated ODS homes that have access to a swimming pool include:

Which vacation homes in Oak Square are best for families?

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

How many onedegreestays vacation rentals are available in Oak Square?

Currently, the total number of properties listed by One Degree Stays in 2025 is over 941 in the Oak Square 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 Oak Square. 

Nearby Neighborhood (7) 
Neighborhood Property Count
Brighton Vacation Rentals in Boston, Massachusetts 87
Cleveland Circle Vacation Rentals in Boston, Massachusetts 71
Allston Vacation Rentals in Boston, Massachusetts 54
St. Elizabeth's Vacation Rentals in Boston, Massachusetts 44
Commonwealth Vacation Rentals in Boston, Massachusetts 28
Newton Corner Vacation Rentals in Boston, Massachusetts 497
Hunnewell Hill Vacation Rentals in Boston, Massachusetts 609

People Also Ask

There are 941 Oak Square, MA Vacation Rentals

Recently Booked Vacation Rentals in Oak Square