Title: Book the Best Hotels with POOL in Pleasant Point in 2025 | Expedia.ca [Vacation Rentals in Wellfleet](https://expedia.ca/Wellfleet-Vacation-Rentals.d6050694.Travel-Guide-VacationRentals)[Flights to Wellfleet](https://expedia.ca/Cheap-Flights-To-Wellfleet.d6050694.Travel-Guide-Flights)[Pleasant Point Car Rentals](https://expedia.ca/Car-Rentals-In-Pleasant-Point.d553248635976481213.Car-Rental-Guide)[Pleasant Point Vacations](https://expedia.ca/Pleasant-Point.d553248635976481213.Destination-Travel-Guides) ![Default HTG hotel image](https://a.travel-assets.com/travel-assets-manager/fallback-images-brand/bex_lodging_v2.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Find Hotels with a Pool in Pleasant Point, MA from CA $127 - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.svg) ### Change your mind Book hotels with free cancellation - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__deals.svg) ### Treat yourself Sign in to save 10% or more on thousands of hotels [Sign in](https://www.expedia.ca/login) - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__bed.svg) ### Be picky Search almost a million properties worldwide ## Check availability on Pleasant Point Hotels with a Pool Tonight [Nov 20 - Nov 21](https://www.expedia.ca/Hotel-Search?regionId=553248635976481213&startDate=2025-11-20&endDate=2025-11-21&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Nov 21 - Nov 22](https://www.expedia.ca/Hotel-Search?regionId=553248635976481213&startDate=2025-11-21&endDate=2025-11-22&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Nov 21 - Nov 23](https://www.expedia.ca/Hotel-Search?regionId=553248635976481213&startDate=2025-11-21&endDate=2025-11-23&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Nov 28 - Nov 30](https://www.expedia.ca/Hotel-Search?regionId=553248635976481213&startDate=2025-11-28&endDate=2025-11-30&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Pleasant Point Hotels with a Pool ![Seasonal outdoor pool, open 8:00 AM to 9:00 PM, pool umbrellas](https://images.trvl-media.com/lodging/6000000/5360000/5351000/5350999/70a957c7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Check-in/check-out kiosk](https://images.trvl-media.com/lodging/6000000/5360000/5351000/5350999/52111ada.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room, 1 King Bed](https://images.trvl-media.com/lodging/6000000/5360000/5351000/5350999/b024e5f3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/6000000/5360000/5351000/5350999/da6cb001.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cape Colony Inn Provincetown 9.2/10 Wonderful (1001) "Clean rooms, friendly staff, convenient location and nice breakfast. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Christopher CA $111 CA $127 total includes taxes & fees Nov 23 - Nov 24 [](https://www.expedia.ca/Provincetown-Hotels-Cape-Colony-Inn.h5350999.Hotel-Information) ![Seasonal outdoor pool, open 8 AM to 8 PM, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/2000000/1520000/1517300/1517204/59358146.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/2000000/1520000/1517300/1517204/f436a6d1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Breakfast, lunch, dinner served; American cuisine, garden views ](https://images.trvl-media.com/lodging/2000000/1520000/1517300/1517204/471fd6ea.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Beach nearby](https://images.trvl-media.com/lodging/2000000/1520000/1517300/1517204/1adc0002.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Chatham Wayside Inn Chatham 9.2/10 Wonderful (592) "We loved staying here! Our room was spacious, clean, quiet and very well maintained. The hotel is beautiful and a perfect location. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Beth CA $214 CA $301 total includes taxes & fees Nov 30 - Dec 1 [](https://www.expedia.ca/Chatham-Hotels-Chatham-Wayside-Inn.h1517204.Hotel-Information) ![Couples treatment rooms, sauna, hot tub, steam room, body treatments](https://images.trvl-media.com/lodging/1000000/910000/906400/906319/942f6da9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor spa tub](https://images.trvl-media.com/lodging/1000000/910000/906400/906319/b8ab45a0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Breakfast, dinner served; American cuisine, garden views ](https://images.trvl-media.com/lodging/1000000/910000/906400/906319/48285e46.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/1000000/910000/906400/906319/83efc190.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Crowne Pointe Historic Inn & Spa - Adults Only Provincetown 9.2/10 Wonderful (833) "Excellent Inn, great Spa, solid food!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) alex [](https://www.expedia.ca/Provincetown-Hotels-Crowne-Pointe-Historic-Inn-Spa-Adults-Only.h906319.Hotel-Information) ![Seasonal outdoor pool](https://images.trvl-media.com/lodging/77000000/76930000/76920700/76920689/489fb301.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Double Room | Terrace/patio](https://images.trvl-media.com/lodging/77000000/76930000/76920700/76920689/feebfa39.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/77000000/76930000/76920700/76920689/4c55d394.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/77000000/76930000/76920700/76920689/dbec4767.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Pelham on Earle West Harwich 9.4/10 Exceptional (73) "Lovely hotel with a good restaurant and walking distance to beach." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kathleen CA $264 CA $327 total includes taxes & fees Nov 21 - Nov 22 [](https://www.expedia.ca/West-Harwich-Hotels-Pelham-On-Earle.h76920689.Hotel-Information) ![Seasonal outdoor pool](https://images.trvl-media.com/lodging/2000000/1590000/1588800/1588774/5c084c88.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/2000000/1590000/1588800/1588774/78febc7a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/2000000/1590000/1588800/1588774/9fde1205.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Apartment, 1 King Bed with Sofa bed | Private kitchen](https://images.trvl-media.com/lodging/2000000/1590000/1588800/1588774/9dab64ca.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Skaket Beach Motel Orleans 9.2/10 Wonderful (448) "Clean room, great price for the offseason" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Angeline CA $140 CA $160 total includes taxes & fees Nov 23 - Nov 24 [](https://www.expedia.ca/Orleans-Hotels-Skaket-Beach-Motel.h1588774.Hotel-Information) ![Indoor pool, seasonal outdoor pool](https://images.trvl-media.com/lodging/1000000/10000/2200/2159/2bea73dd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/10000/2200/2159/bcd2c01d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Bar (on property)](https://images.trvl-media.com/lodging/1000000/10000/2200/2159/815e4372.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/10000/2200/2159/4d3d8a36.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Four Points by Sheraton Eastham Cape Cod Eastham 8.2/10 Very good (850) "Perfect overnight stay in every way!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Debra CA $165 CA $189 total includes taxes & fees Nov 25 - Nov 26 [](https://www.expedia.ca/Eastham-Hotels-Four-Points-By-Sheraton-Eastham-Cape-Cod.h2159.Hotel-Information) ![Outdoor pool, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/10000000/9600000/9591500/9591451/bc9c3e08.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Classic Room, 1 King Bed, Fireplace](https://images.trvl-media.com/lodging/10000000/9600000/9591500/9591451/9fdb8aa3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![BBQ/picnic area](https://images.trvl-media.com/lodging/10000000/9600000/9591500/9591451/e133402d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/10000000/9600000/9591500/9591451/eab34d0c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### A Beach Breeze Inn West Harwich 9.6/10 Exceptional (271) "Totally GREAT PLACE to stay." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Margaret CA $181 CA $207 total includes taxes & fees Nov 23 - Nov 24 [](https://www.expedia.ca/West-Harwich-Hotels-A-Beach-Breeze-Inn.h9591451.Hotel-Information) ![Seasonal outdoor pool](https://images.trvl-media.com/lodging/2000000/1750000/1744200/1744111/3751592d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/2000000/1750000/1744200/1744111/7285272e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Breakfast area](https://images.trvl-media.com/lodging/2000000/1750000/1744200/1744111/50cf27db.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Double Room, 2 Double Beds, Non Smoking](https://images.trvl-media.com/lodging/2000000/1750000/1744200/1744111/4627c314.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Rodeway Inn Orleans - Cape Cod Orleans 8.0/10 Very good (784) "Clean and comfortable room very enjoyable stay" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Douglas CA $147 CA $168 total includes taxes & fees Nov 30 - Dec 1 [](https://www.expedia.ca/Orleans-Hotels-Rodeway-Inn-Orleans-Cape-Cod.h1744111.Hotel-Information) ![Poolside bar](https://images.trvl-media.com/lodging/7000000/6310000/6301400/6301341/405c33ed.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room, 1 King Bed](https://images.trvl-media.com/lodging/7000000/6310000/6301400/6301341/04ea3feb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 restaurants, breakfast, lunch, dinner served; American cuisine](https://images.trvl-media.com/lodging/7000000/6310000/6301400/6301341/6a3d02f6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room, 1 King Bed | Living area](https://images.trvl-media.com/lodging/7000000/6310000/6301400/6301341/882616c1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Villages at Ocean Edge Brewster 8.4/10 Very good (1003) "We loved the room we stayed in and will return again next time we go to the Cape" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Robert A CA $177 CA $251 total includes taxes & fees Nov 25 - Nov 26 [](https://www.expedia.ca/Brewster-Hotels-The-Villages-At-Ocean-Edge.h6301341.Hotel-Information) ![Indoor pool, 2 outdoor pools, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/1000000/900000/894200/894158/e77b9952.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/1000000/900000/894200/894158/563be86c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from room](https://images.trvl-media.com/lodging/1000000/900000/894200/894158/0c3e83a4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/1000000/900000/894200/894158/2a13336a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Corsair & Cross Rip Oceanfront Resort Dennis Port 8.6/10 Excellent (221) "very peaceful, excellent staff, clean room, and close to good restaurants." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Pauline CA $172 CA $197 total includes taxes & fees Nov 27 - Nov 28 [](https://www.expedia.ca/Dennis-Port-Hotels-The-Corsair-Cross-Rip-Oceanfront-Resort.h894158.Hotel-Information) 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. [View all properties](https://expedia.ca/Hotel-Search?startDate=2025-12-04&endDate=2025-12-05®ionId=553248635976481213&adults=2&amenities=POOL&sort=RECOMMENDED&openPlayBack=true) ## Top Pleasant Point Hotel Reviews ![Edgewater Beach Resort, a VRI resort](https://images.trvl-media.com/lodging/2000000/1530000/1522300/1522228/5e9e9f5c_y.jpg) ### Edgewater Beach Resort, a VRI resort 10/10 Excellent "Room was clean and the staff was great" [](https://expedia.ca/Dennis-Port-Hotels-Edgewater-Beach-Resort.h1522228.Hotel-Information) ![Wellfleet Motel and Lodge](https://images.trvl-media.com/lodging/2000000/1180000/1173600/1173572/4c97a310_y.jpg) ### Wellfleet Motel and Lodge 10/10 Excellent "Clean room and plenty of towels. " [](https://expedia.ca/Wellfleet-Hotels-Wellfleet-Motel-And-Lodge.h1173572.Hotel-Information) ![Chatham Wayside Inn](https://images.trvl-media.com/lodging/2000000/1520000/1517300/1517204/1adc0002_y.jpg) ### Chatham Wayside Inn 10/10 Excellent "Our room was nicely appointed and an excellent layout." [](https://expedia.ca/Chatham-Hotels-Chatham-Wayside-Inn.h1517204.Hotel-Information) ![Harbor Hotel Provincetown](https://images.trvl-media.com/lodging/1000000/430000/421600/421590/e4d390ae_y.jpg) ### Harbor Hotel Provincetown 10/10 Excellent "Great place to stay friendly staff, close to shops and right across the street from the beach. " [](https://expedia.ca/Provincetown-Hotels-Harbor-Hotel-Provincetown.h421590.Hotel-Information) ![Four Points by Sheraton Eastham Cape Cod](https://images.trvl-media.com/lodging/1000000/10000/2200/2159/2bea73dd_y.jpg) ### Four Points by Sheraton Eastham Cape Cod 10/10 Excellent "Perfect overnight stay in every way!" [](https://expedia.ca/Eastham-Hotels-Four-Points-By-Sheraton-Eastham-Cape-Cod.h2159.Hotel-Information) ![Chatham Bars Inn](https://images.trvl-media.com/lodging/1000000/20000/19200/19139/w5700h3895x0y5-016d240d_y.jpg) ### Chatham Bars Inn 10/10 Excellent "Great accommodation and staff." [](https://expedia.ca/Chatham-Hotels-Chatham-Bars-Inn.h19139.Hotel-Information) ![Cape Colony Inn](https://images.trvl-media.com/lodging/6000000/5360000/5351000/5350999/70a957c7_y.jpg) ### Cape Colony Inn 10/10 Excellent "Clean rooms, friendly staff, convenient location and nice breakfast. " [](https://expedia.ca/Provincetown-Hotels-Cape-Colony-Inn.h5350999.Hotel-Information) ![The Provincetown Inn](https://images.trvl-media.com/lodging/1000000/920000/910400/910310/16b3c609_y.jpg) ### The Provincetown Inn 10/10 Excellent "Friendly and efficient staff. The view is beautiful, just a bit cold and windy too enjoy it. So definitely will return amen is Wayne" [](https://expedia.ca/Provincetown-Hotels-The-Provincetown-Inn.h910310.Hotel-Information) ![Surfside Hotel and Suites](https://images.trvl-media.com/lodging/2000000/1070000/1060700/1060693/60c7000f_y.jpg) ### Surfside Hotel and Suites 10/10 Excellent "The staff were all lovely. Our room was facing the water and that was a great perk. It’s a bit away from the downtown area but it’s one of the bike and scooter stops so we enjoyed that. We will stay here again!" [](https://expedia.ca/Provincetown-Hotels-Surfside-Hotel-And-Suites.h1060693.Hotel-Information) ## Frequently asked questions ### What are some hotels with pools in Pleasant Point? > [Chatham Bars Inn](https://www.expedia.ca/Chatham-Hotels-Chatham-Bars-Inn.h19139.Hotel-Information): Features a private beach, a seasonal outdoor pool, and a full-service spa. [Wequassett Resort and Golf Club](https://www.expedia.ca/Harwich-Hotels-Wequassett-Resort-And-Golf-Club.h3689.Hotel-Information): Offers a private beach, a seasonal outdoor pool, and 6 restaurants. [Chatham Wayside Inn](https://www.expedia.ca/Chatham-Hotels-Chatham-Wayside-Inn.h1517204.Hotel-Information): Provides daily, a seasonal outdoor pool, and free self parking. [Surfside Hotel and Suites](https://www.expedia.ca/Provincetown-Hotels-Surfside-Hotel-And-Suites.h1060693.Hotel-Information): Features a private beach, a seasonal outdoor pool, and daily. [Cape Colony Inn](https://www.expedia.ca/Provincetown-Hotels-Cape-Colony-Inn.h5350999.Hotel-Information): Offers daily, a seasonal outdoor pool, and free self parking. ### What is there to see and do in Pleasant Point? > Make a point to visit attractions like Cahoon Hollow Beach and Commercial Street. 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