Title: Pleasure Point Tours - Book Now | Expedia.com [Pleasure Point Hotels](https://expedia.com/Pleasure-Point-Hotels.0-l553248635983989103-0.Travel-Guide-Filter-Hotels)[Flights to Holliston](https://expedia.com/Cheap-Flights-To-Holliston.d3000441122.Travel-Guide-Flights)[Car Rentals in Pleasure Point](https://expedia.com/Car-Rentals-In-Pleasure-Point.d553248635983989103.Car-Rental-Guide)[Holliston Vacation Packages](https://expedia.com/Holliston.d3000441122.Destination-Travel-Guides) # Pleasure Point Tours ## Visit Pleasure Point Activities [Holliston Travel Guide](https://expedia.com/Holliston.dx3000441122) --- --- ## Plan a trip to see Pleasure Point Price found within the past 48 hours. Click for updated prices. ![Hyatt Regency Boston/Cambridge](https://images.trvl-media.com/lodging/1000000/20000/16100/16079/944dfde2_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hyatt Regency Boston/Cambridge MIT Save 100% on your flight $426 per person Apr 30 - May 3 found 1 day ago Roundtrip flight included Atlanta (ATL) to Boston (BOS) 9/10 Wonderful! (2,215 reviews) Great room, wonderful friendly customer service Reviewed on Feb 8, 2026 ![D. Hotel Suites & Spa](https://images.trvl-media.com/lodging/1000000/850000/849400/849303/5f3c4e34_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### D. Hotel Suites & Spa Save 100% on your flight $514 per person Mar 23 - Mar 29 found 8 hours ago Roundtrip flight included Chicago (CHI) to Boston (BOS) 9.4/10 Exceptional! (2,242 reviews) Great clean room that was nice and warm on the cold day. Loved the fireplace in the living area and the bed was very comfortable and cozy. Great value for the space we got! Reviewed on Feb 8, 2026 ![The Godfrey Hotel Boston](https://images.trvl-media.com/lodging/11000000/10120000/10118700/10118614/e4d256d2_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Godfrey Hotel Boston Downtown Boston Save 100% on your flight $695 per person Mar 12 - Mar 16 found 1 day ago Roundtrip flight included Atlanta (ATL) to Boston (BOS) 9.4/10 Exceptional! (4,672 reviews) Very clean room! Friendly staff! Great location! Reviewed on Feb 8, 2026 ### Popular places to visit ![Framingham City Hall and downtown aerial view panorama in downtown Framingham, Massachusetts, USA.](https://images.trvl-media.com/place/6070351/03a0975f-86c7-4361-ad5a-58f7fec97f04.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Framingham City Hall Framingham City Hall is just one of the places to see in Framingham, so why not enjoy the other things to explore during your travels? Attend a sporting event or simply enjoy the lively bars while you're in the area. [](https://expedia.com/Framingham-City-Hall-Boston.d6070351.Vacation-Attraction) #### Stoddard Park Why not spend a lazy afternoon at Stoddard Park during your trip to Holliston? Wander the lakeside and beaches while you're in the area. [](https://expedia.com/Stoddard-Park-Holliston.d553248635983992555.Vacation-Attraction) #### Pinecrest Golf Club Enjoy a round of golf in Holliston at Pinecrest Golf Club. Attend a sporting event or simply enjoy the lively bars while you're in the area. [](https://expedia.com/Pinecrest-Golf-Club-Holliston.d553248633992334149.Vacation-Attraction) #### Rocky Narrows Enjoy an outing to Rocky Narrows during your stay in Sherborn. Stroll along the riverfront or seek out the jogging trails. [](https://expedia.com/Rocky-Narrows-Boston.d553248621532667030.Vacation-Attraction) #### Bridge Island Meadows Commune with nature and explore the great outdoors at Bridge Island Meadows during your travels in Millis. Experience the area's great live music or attend a sporting event. [](https://expedia.com/Bridge-Island-Meadows-Boston.d553248621532666338.Vacation-Attraction) #### Ashland State Park You can take time to visit Ashland State Park during your travels to Ashland. While you're in the area, wander around the parks. [](https://expedia.com/Ashland-State-Park-Ashland.d553248633992331328.Vacation-Attraction) --- ## Best Lodging Options Near Pleasure Point ## Check availability on hotels close to Pleasure Point [Tonight ](https://expedia.com/Hotel-Search?rfrrid=TG.LP.CheckPrices.Package&adults=2&openPlayBack=true®ionId=553248635983989103&startDate=2026-02-10&endDate=2026-02-11)[Feb 10 - Feb 11](https://expedia.com/Hotel-Search?rfrrid=TG.LP.CheckPrices.Package&adults=2&openPlayBack=true®ionId=553248635983989103&startDate=2026-02-10&endDate=2026-02-11) [Tomorrow night ](https://expedia.com/Hotel-Search?rfrrid=TG.LP.CheckPrices.Package&adults=2&openPlayBack=true®ionId=553248635983989103&startDate=2026-02-11&endDate=2026-02-12)[Feb 11 - Feb 12](https://expedia.com/Hotel-Search?rfrrid=TG.LP.CheckPrices.Package&adults=2&openPlayBack=true®ionId=553248635983989103&startDate=2026-02-11&endDate=2026-02-12) [This weekend ](https://expedia.com/Hotel-Search?rfrrid=TG.LP.CheckPrices.Package&adults=2&openPlayBack=true®ionId=553248635983989103&startDate=2%2F13%2F2026&endDate=2%2F15%2F2026)[Feb 13 - Feb 15](https://expedia.com/Hotel-Search?rfrrid=TG.LP.CheckPrices.Package&adults=2&openPlayBack=true®ionId=553248635983989103&startDate=2%2F13%2F2026&endDate=2%2F15%2F2026) [Next weekend ](https://expedia.com/Hotel-Search?rfrrid=TG.LP.CheckPrices.Package&adults=2&openPlayBack=true®ionId=553248635983989103&startDate=2%2F20%2F2026&endDate=2%2F22%2F2026)[Feb 20 - Feb 22](https://expedia.com/Hotel-Search?rfrrid=TG.LP.CheckPrices.Package&adults=2&openPlayBack=true®ionId=553248635983989103&startDate=2%2F20%2F2026&endDate=2%2F22%2F2026) ![The Verve Hotel Boston Natick, Tapestry Collection by Hilton](https://images.trvl-media.com/lodging/1000000/20000/15300/15230/c35294bf_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### The Verve Hotel Boston Natick, Tapestry Collection by Hilton 1360 Worcester St Natick MA [](https://expedia.com/Boston-Hotels-The-Verve-Boston-Natick.h15230.Hotel-Information) ![Sheraton Boston Needham Hotel](https://images.trvl-media.com/lodging/1000000/30000/24600/24545/b24b174a_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Sheraton Boston Needham Hotel 100 Cabot St Needham MA [](https://expedia.com/Boston-Hotels-Sheraton-Boston-Needham-Hotel.h24545.Hotel-Information) ![Hampton Inn & Suites Boston/Waltham](https://images.trvl-media.com/lodging/22000000/21910000/21904300/21904239/841c68d6_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Hampton Inn & Suites Boston/Waltham 135 2nd Ave Waltham MA [](https://expedia.com/Boston-Hotels-Hampton-Inn-Suites-BostonWaltham.h21904239.Hotel-Information) ![Hilton Boston Park Plaza](https://images.trvl-media.com/lodging/1000000/10000/4300/4215/6e9f8959_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Hilton Boston Park Plaza 50 Park Plaza Boston MA [](https://expedia.com/Boston-Hotels-Boston-Park-Plaza.h4215.Hotel-Information) ![The Arcadian Hotel](https://images.trvl-media.com/lodging/32000000/31100000/31097800/31097754/f8ad7683_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### The Arcadian Hotel 1200 Beacon St Brookline MA [](https://expedia.com/Boston-Hotels-Arcadian-Hotel-Brookline.h31097754.Hotel-Information) ![DoubleTree Suites by Hilton Hotel Boston - Cambridge](https://images.trvl-media.com/lodging/1000000/10000/1000/946/e477f850_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### DoubleTree Suites by Hilton Hotel Boston - Cambridge 400 Soldiers Field Road Boston MA [](https://expedia.com/Boston-Hotels-DoubleTree-Suites-By-Hilton-Hotel-Boston-Cambridge.h946.Hotel-Information) ![The Revolution Hotel](https://images.trvl-media.com/lodging/31000000/30090000/30080300/30080227/cce5d2b3_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### The Revolution Hotel 40 Berkeley Street Boston MA [](https://expedia.com/Boston-Hotels-The-Revolution-Hotel.h30080227.Hotel-Information) ![Courtyard by Marriott Boston-Cambridge](https://images.trvl-media.com/lodging/1000000/10000/2000/1962/21d7d08c_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Courtyard by Marriott Boston-Cambridge 777 Memorial Dr Cambridge MA [](https://expedia.com/Boston-Hotels-Courtyard-By-Marriott-Boston-Cambridge.h1962.Hotel-Information) ![Hilton Boston Back Bay](https://images.trvl-media.com/lodging/1000000/10000/6000/5928/f418fbdd_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Hilton Boston Back Bay 40 Dalton St Boston MA [](https://expedia.com/Boston-Hotels-Hilton-Boston-Back-Bay.h5928.Hotel-Information) [See all 4,816 properties in Pleasure Point](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.Package®ionId=553248635983989103) Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. 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