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. ![The Cove At Yarmouth](https://images.trvl-media.com/lodging/1000000/10000/4400/4331/4eacbec7_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Cove At Yarmouth Save 100% on your flight $579 per person May 1 - May 8 found 1 day ago Roundtrip flight included Chicago (CHI) to Boston (BOS) 9.2/10 Wonderful! (243 reviews) Room was not easy to get to and it was 0 degrees out …1st they put me out in a building where the property was a sheet of ice so I asked to be moved to the main building since I was by myself. Fortunately, they moved me, but the room was confusing to get to. :-( The pool was closed for maintenance, and I was planning to swim. :-( The room was great, clean and a comfortable bed, so I would stay again, but I would request staying closer to the lobby next time. Reviewed on Jan 31, 2026 ![The Colonnade Hotel Back Bay](https://images.trvl-media.com/lodging/1000000/20000/12700/12660/f43e7537_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Colonnade Hotel Back Bay Back Bay Save 100% on your flight $737 per person Mar 25 - Mar 30 found 1 day ago Roundtrip flight included Atlanta (ATL) to Boston (BOS) 9.2/10 Wonderful! (2,268 reviews) Easy check in, courteous staff, clean rm and great view. Prudential mall across Huntington Ave.. Reviewed on Feb 2, 2026 ![Eurostars The Boxer](https://images.trvl-media.com/lodging/2000000/1120000/1118900/1118893/db81308e_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Eurostars The Boxer West End Save 100% on your flight $798 per person May 5 - May 10 found 1 day ago Roundtrip flight included Atlanta (ATL) to Boston (BOS) 8.6/10 Excellent! (1,337 reviews) 2nd time staying, great location, nice hotel. Reviewed on Feb 11, 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=2026-02-14&endDate=2026-02-15)[Feb 14 - Feb 15](https://expedia.com/Hotel-Search?rfrrid=TG.LP.CheckPrices.Package&adults=2&openPlayBack=true®ionId=553248635983989103&startDate=2026-02-14&endDate=2026-02-15) [Tomorrow night ](https://expedia.com/Hotel-Search?rfrrid=TG.LP.CheckPrices.Package&adults=2&openPlayBack=true®ionId=553248635983989103&startDate=2026-02-15&endDate=2026-02-16)[Feb 15 - Feb 16](https://expedia.com/Hotel-Search?rfrrid=TG.LP.CheckPrices.Package&adults=2&openPlayBack=true®ionId=553248635983989103&startDate=2026-02-15&endDate=2026-02-16) [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) ![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) ![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) ![Hyatt Regency Boston/Cambridge](https://images.trvl-media.com/lodging/1000000/20000/16100/16079/944dfde2_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Hyatt Regency Boston/Cambridge 575 Memorial Drive Cambridge MA [](https://expedia.com/Boston-Hotels-Hyatt-Regency-BostonCambridge.h16079.Hotel-Information) ![citizenM Boston Back Bay](https://images.trvl-media.com/lodging/97000000/97000000/96998900/96998829/90056141_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### citizenM Boston Back Bay 408 Newbury street Boston MA [](https://expedia.com/Boston-Hotels-CitizenM-Boston-Back-Bay.h96998829.Hotel-Information) [See all 4,769 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. Prices and availability subject to change. Additional terms may apply. ![](https://forever.travel-assets.com/flex/flexmanager/images/2026/02/06/expedia-sale-2026-desktop-us-ca.jpg?impolicy=fcrop&w=1400&h=600&q=mediumHigh) ## The Annual Vacation Sale Members save up to 40% on hotels and homes. Plan this year’s big trip and save. [Book now](https://expedia.com/deals?rfrr=DX_POI_Spring_PROMO_553248635983989103)