Compare HOTELS, RESORTS, AND RENTALS in Pleasure Point, Holliston, Massachusetts, USA
About Pleasure Point Vacation Rentals
There are more than 47 places to stay in Pleasure Point that are available. These options include hotels, resorts, rentals as well as short-term private accommodations (i.e. RVs, Condos, Cabins, Chalets, etc.). The places can provide you with a great option on your next holiday. Compare many places to stay in Pleasure Point.
Are you seeking a last-minute hotel deal, or are you wanting to find the best deals available for hotels, resorts, cottages, condos, private villas, chalets, or a large vacation homes? With Hotala Pleasure Point, you can quickly compare different options to find the hottest deals with a single click. Looking for a resort with an infinity pool, hot tub, is pet-friendly, or features a large master suite bedrooms or has a fireplace? You can find hotels, resorts, or other popular Airbnb-style properties in or near Pleasure Point. Places to stay near Pleasure Point are 230.94 ft² on average, with prices averaging US $300 a night.
Hotala makes it easy to find and compare hotels, resorts, and holiday rentals in Pleasure Point with prices often listed at a 30-40% off the rack rate. Just enter your destination and secure your reservation today.
Frequently Asked Questions About Pleasure Point?
What are the top hotels or resorts in Pleasure Point?
You have a lot of choices in or near Pleasure Point. If you need a hotel in the Pleasure Point area, consider making a reservation for a few nights at one of our suggested properties as these have been known to be the Top Vacation Rentals and Places to Stay in Pleasure Point:
- Warren Conference Center and Inn
- Holiday Inn Express Boston - Milford by IHG
- DoubleTree by Hilton Boston - Milford
- Sonesta Select 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
- DoubleTree by Hilton Boston-Milford
- Comfort Inn Boston Milford
- Fairfield Inn & Suites by Marriott Boston Milford
How many hotels, resorts, or rentals are available in Pleasure Point?
At present, the total number of properties listed by Hotala -- including hotels, resorts, and rentals -- as of 2025 is over 47 in the Pleasure Point area, and still growing. By combining listings from multiple websites, Hotala provides a huge selection of the best hotels, resorts, and vacation properties in Pleasure Point.
Nearby Neighborhood (3)
| Neighborhood | Property Count |
|---|---|
| Babson Park Hotel & Resort Deals in Holliston, Massachusetts | 45 |
| Wellesley Hills Hotel & Resort Deals in Holliston, Massachusetts | 36 |
| Lake Pearl Hotel & Resort Deals in Holliston, Massachusetts | 27 |
