Compare Vacation Rentals & Rent By Owner Homes in Pleasure Point, Holliston, Massachusetts, USA
About Pleasure Point Vacation Rentals
With more than 47 Pleasure Point vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Rent By Owner Homes (RBOs) 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 RBO property in Pleasure Point.
Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With RentByOwner Pleasure Point, you have the flexibility of comparing different options of various deals with a single click. Looking for an RBO 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 (RBOs), and other popular Airbnb-style properties in Pleasure Point. Places to stay near Pleasure Point are 230.94 ft² on average, with prices averaging US $327 a night.
RentByOwner makes it easy and safe to find and compare vacation rentals in Pleasure Point with prices often at a 30-40% discount versus the price of a hotel. Just search for your destination and secure your reservation today.
Pleasure Point Vacation Rental Frequently Asked Questions
What are the top vacation rentals in Pleasure Point?
- Infant-friendly Luxurious 7 Beds, 6 Room Home with BONUS Loft! A Dream Getaway!
- Spacious 3-bedroom apartment in lovely Millis with AC, WiFi
- Spacious Cozy Cabin Style house.
- Warren Conference Center and Inn
- Holiday Inn Express Boston - Milford by IHG
- Sonesta Select Boston Milford
- DoubleTree by Hilton Boston - Milford
- Fairfield Inn & Suites by Marriott Boston Milford
- Milford Inn
- Vacation Day Is Always A Great Idea! w/Indoor Pool, Pets are Allowed Here
How many Rentbyowner vacation rentals are available in Pleasure Point?
Currently, the total number of properties listed by Rent By Owner in 2025 is over 47 in the Pleasure Point area, and still counting. By aggregating listings from multiple websites, Rent By Owner offers an immense amount of choice of the best RBO properties in Pleasure Point.
Nearby Neighborhood (3)
| Neighborhood | Property Count |
|---|---|
| Babson Park Vacation Rentals in Holliston, Massachusetts | 45 |
| Wellesley Hills Vacation Rentals in Holliston, Massachusetts | 36 |
| Lake Pearl Vacation Rentals in Holliston, Massachusetts | 27 |
