Title: Book the Best Pleasant Point FAMILY FRIENDLY Hotels from CA $157 - Kid-Friendly Hotels in Pleasant Point, Wellfleet | 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/bex-affinities/family_friendly.jpeg?impolicy=fcrop&w=1200&h=500&q=medium) # Find Family Hotels in Pleasant Point, Wellfleet from CA $157 ![](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 Family Hotels Tonight [Oct 23 - Oct 24](https://www.expedia.ca/Hotel-Search?regionId=553248635976481213&startDate=2025-10-23&endDate=2025-10-24&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=family_friendly) Tomorrow [Oct 24 - Oct 25](https://www.expedia.ca/Hotel-Search?regionId=553248635976481213&startDate=2025-10-24&endDate=2025-10-25&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=family_friendly) This weekend [Oct 24 - Oct 26](https://www.expedia.ca/Hotel-Search?regionId=553248635976481213&startDate=2025-10-24&endDate=2025-10-26&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=family_friendly) Next weekend [Oct 31 - Nov 2](https://www.expedia.ca/Hotel-Search?regionId=553248635976481213&startDate=2025-10-31&endDate=2025-11-02&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=family_friendly) ## Top Pleasant Point Family Hotels ![Beach nearby](https://images.trvl-media.com/lodging/2000000/1520000/1517300/1517204/1adc0002.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Junior Suite, 1 King Bed](https://images.trvl-media.com/lodging/2000000/1520000/1517300/1517204/9874775f.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) ![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) ### Chatham Wayside Inn Chatham 9.2/10 Wonderful (577) "Great hotel, great locatiion" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Susan CA $213 CA $300 total includes taxes & fees Oct 26 - Oct 27 [](https://www.expedia.ca/Chatham-Hotels-Chatham-Wayside-Inn.h1517204.Hotel-Information) ![Private beach, sun loungers, beach umbrellas, beach towels](https://images.trvl-media.com/lodging/2000000/1070000/1060700/1060693/60c7000f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Apartment, 2 Bedrooms, Beach View | Private kitchen](https://images.trvl-media.com/lodging/2000000/1070000/1060700/1060693/8c6b2415.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Apartment, Beach View | Living area](https://images.trvl-media.com/lodging/2000000/1070000/1060700/1060693/11727ca7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Bayview Suite | Living area](https://images.trvl-media.com/lodging/2000000/1070000/1060700/1060693/db5a2ef0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Surfside Hotel and Suites Provincetown 8.6/10 Excellent (1002) "Great place" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Anna CA $213 CA $300 total includes taxes & fees Oct 26 - Oct 27 [](https://www.expedia.ca/Provincetown-Hotels-Surfside-Hotel-And-Suites.h1060693.Hotel-Information) ![Oceanfront Efficiency, 1 King Bed](https://images.trvl-media.com/lodging/16000000/15370000/15369000/15368979/13f44770.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Mini-fridge, microwave, coffee/tea maker, cookware/dishes/utensils](https://images.trvl-media.com/lodging/16000000/15370000/15369000/15368979/7ca6ffc1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/16000000/15370000/15369000/15368979/b27fc938.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/16000000/15370000/15369000/15368979/9c379e8d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Chatham Tides South Chatham 9.4/10 Exceptional (641) "Love the proximity to the beach" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Debra CA $225 CA $258 total includes taxes & fees Nov 3 - Nov 4 [](https://www.expedia.ca/South-Chatham-Hotels-Chatham-Tides.h15368979.Hotel-Information) ![Seasonal outdoor pool, sun loungers](https://images.trvl-media.com/lodging/8000000/7470000/7461700/7461681/8190ce86.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/8000000/7470000/7461700/7461681/e981387d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Two Queen Beds](https://images.trvl-media.com/lodging/8000000/7470000/7461700/7461681/44c4b987.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/8000000/7470000/7461700/7461681/550a87c5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Greyfinch Chatham Inn Chatham 8.8/10 Excellent (251) "Wonderful place to stay" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) John CA $200 CA $277 total includes taxes & fees Oct 27 - Oct 28 [](https://www.expedia.ca/Chatham-Hotels-Chatham-Highlander-Village-Inn.h7461681.Hotel-Information) ![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) ![Property grounds](https://images.trvl-media.com/lodging/2000000/1750000/1744200/1744111/7285272e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/2000000/1750000/1744200/1744111/0e60c73b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![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) ### Rodeway Inn Orleans - Cape Cod Orleans 8.0/10 Very good (782) "Love this place. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Christine CA $147 CA $168 total includes taxes & fees Oct 26 - Oct 27 [](https://www.expedia.ca/Orleans-Hotels-Rodeway-Inn-Orleans-Cape-Cod.h1744111.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) ![Desk, iron/ironing board, free cribs/infant beds, free WiFi](https://images.trvl-media.com/lodging/1000000/10000/2200/2159/1fa0a070.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) ### Four Points by Sheraton Eastham Cape Cod Eastham 8.2/10 Very good (842) "Very close to great beaches and restaurants" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Carmen CA $165 CA $189 total includes taxes & fees Oct 28 - Oct 29 [](https://www.expedia.ca/Eastham-Hotels-Four-Points-By-Sheraton-Eastham-Cape-Cod.h2159.Hotel-Information) ![2 indoor pools, 3 outdoor pools, sun loungers](https://images.trvl-media.com/lodging/1000000/10000/8000/7948/bdbb5eef.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Bar (on property)](https://images.trvl-media.com/lodging/1000000/10000/8000/7948/51991eef.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/10000/8000/7948/669edd67.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Private beach, sun loungers, beach umbrellas, beach towels](https://images.trvl-media.com/lodging/1000000/10000/8000/7948/cb01c753.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Mansion at Ocean Edge Brewster 8.2/10 Very good (1001) "Amazing stay and location! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Joanne CA $227 CA $308 total includes taxes & fees Nov 6 - Nov 7 [](https://www.expedia.ca/Brewster-Hotels-The-Mansion-At-Ocean-Edge.h7948.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/2000000/1880000/1870600/1870586/a05a2668.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Balcony](https://images.trvl-media.com/lodging/2000000/1880000/1870600/1870586/a9a84e22.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Small Suite with Balcony | Private kitchen](https://images.trvl-media.com/lodging/2000000/1880000/1870600/1870586/cc2cc84b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Aerial view](https://images.trvl-media.com/lodging/2000000/1880000/1870600/1870586/6b25a20a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Sandcastle Resort and Club Provincetown 7.4/10 Good (1127) "Right on the beach, outstanding room/views" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kris CA $137 CA $157 total includes taxes & fees Oct 26 - Oct 27 [](https://www.expedia.ca/Provincetown-Hotels-Sandcastle-Resort-And-Club.h1870586.Hotel-Information) ![Outdoor pool, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/7000000/6510000/6501900/6501879/233ffbf0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free continental breakfast](https://images.trvl-media.com/lodging/7000000/6510000/6501900/6501879/464447e1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Comfort Apartment, 2 Bedrooms | Balcony](https://images.trvl-media.com/lodging/7000000/6510000/6501900/6501879/b35403de.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Check-in/check-out kiosk](https://images.trvl-media.com/lodging/7000000/6510000/6501900/6501879/7883c644.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Seaglass Inn & Spa Provincetown 9.6/10 Exceptional (767) "Farther away from the action but it's a great place and it has a great saltwater pool." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Maureen CA $235 CA $270 total includes taxes & fees Nov 7 - Nov 8 [](https://www.expedia.ca/Provincetown-Hotels-Seaglass-Inn-Spa.h6501879.Hotel-Information) ![Children's play area - outdoor](https://images.trvl-media.com/lodging/1000000/10000/3700/3689/7ae2a959.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Frette Italian sheets, premium bedding, down comforters, minibar](https://images.trvl-media.com/lodging/1000000/10000/3700/3689/994ac272.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/10000/3700/3689/d5db7da1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Frette Italian sheets, premium bedding, down comforters, minibar](https://images.trvl-media.com/lodging/1000000/10000/3700/3689/2c23c623.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Wequassett Resort and Golf Club Harwich 9.4/10 Exceptional (241) "Our Room looked over the beautiful gardens and out to the cove where small boats were bouyed. Very nicely appointed Room and superb weather during our stay. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Charles CA $454 CA $557 total includes taxes & fees Nov 3 - Nov 4 [](https://www.expedia.ca/Harwich-Hotels-Wequassett-Resort-And-Golf-Club.h3689.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=2025-11-07&endDate=2025-11-08®ionId=553248635976481213&adults=2&travelerType=family_friendly&sort=RECOMMENDED&openPlayBack=true) ## Top Pleasant Point Hotel Reviews ![Chatham Tides](//images.trvl-media.com/lodging/16000000/15370000/15369000/15368979/13f44770_y.jpg) ### Chatham Tides 10/10 Excellent "It was everything as advertised!!" [](https://expedia.ca/South-Chatham-Hotels-Chatham-Tides.h15368979.Hotel-Information) ![Sandcastle Resort and Club](//images.trvl-media.com/lodging/2000000/1880000/1870600/1870586/a05a2668_y.jpg) ### Sandcastle Resort and Club 10/10 Excellent "Great staff. It was exactly what we needed! " [](https://expedia.ca/Provincetown-Hotels-Sandcastle-Resort-And-Club.h1870586.Hotel-Information) ![Wellfleet Motel and Lodge](//images.trvl-media.com/lodging/2000000/1180000/1173600/1173572/4c97a310_y.jpg) ### Wellfleet Motel and Lodge 10/10 Excellent "Comfortable bed new bathroom breakfast on site good location " [](https://expedia.ca/Wellfleet-Hotels-Wellfleet-Motel-And-Lodge.h1173572.Hotel-Information) ![Top Mast Resort](//images.trvl-media.com/lodging/12000000/11740000/11737100/11737053/d022d597_y.jpg) ### Top Mast Resort 10/10 Excellent "Kerine was exceptional! I chatted with her on the phone about our reservation and she was amazing. Her customer service was outstanding. " [](https://expedia.ca/North-Truro-Hotels-Top-Mast-Resort.h11737053.Hotel-Information) ![Edgewater Beach Resort, a VRI resort](//images.trvl-media.com/lodging/2000000/1530000/1522300/1522228/5e9e9f5c_y.jpg) ### Edgewater Beach Resort, a VRI resort 10/10 Excellent "Good views and great grounds " [](https://expedia.ca/Dennis-Port-Hotels-Edgewater-Beach-Resort.h1522228.Hotel-Information) ![Captains Quarters Motel & Conference Center](//images.trvl-media.com/lodging/2000000/1090000/1080600/1080509/7b4bf26e_y.jpg) ### Captains Quarters Motel & Conference Center 10/10 Excellent "Everything was comfortable, very nice front desk person " [](https://expedia.ca/Eastham-Hotels-Captains-Quarters-Motel-Conference-Center.h1080509.Hotel-Information) ![Wequassett Resort and Golf Club](//images.trvl-media.com/lodging/1000000/10000/3700/3689/9873e07e_y.jpg) ### Wequassett Resort and Golf Club 10/10 Excellent "There is no finer place. Everything is tastefully appointed. Food is phenomenal. Staff could not be more helpful and they are always smiling- extremely professional. The food is over the top designed and tasteful. If you love luxury and a great night’s sleep in a most comfortable bed- this is the place for you. " [](https://expedia.ca/Harwich-Hotels-Wequassett-Resort-And-Golf-Club.h3689.Hotel-Information) ![Surfside Hotel and Suites](//images.trvl-media.com/lodging/2000000/1070000/1060700/1060693/60c7000f_y.jpg) ### Surfside Hotel and Suites 10/10 Excellent "It was a very nice room right on the water. Everyone was very nice. " [](https://expedia.ca/Provincetown-Hotels-Surfside-Hotel-And-Suites.h1060693.Hotel-Information) ![Harbor Hotel Provincetown](//images.trvl-media.com/lodging/1000000/430000/421600/421590/e4d390ae_y.jpg) ### Harbor Hotel Provincetown 10/10 Excellent "The vista out my window was spectacular....and so quiet! The staff was so kind, and welcoming!!! Great place to get away!" [](https://expedia.ca/Provincetown-Hotels-Harbor-Hotel-Provincetown.h421590.Hotel-Information) ## Frequently asked questions ### What's Pleasant Point like for family-friendly vacations? > The destination of Pleasant Point is a great choice if you've been thinking about a vacation with your kids. There are some interesting activities the entire family might enjoy. Take to the air and fly into Provincetown, MA (PVC-Provincetown Municipal), which is located 15.8 mi (25.4 km) from the center of Pleasant Point. ### What's there to see and do with your family in Pleasant Point? > Wellfleet Harbor Actors Theater, Rail Trail Bike Shop, and Commercial Street are interesting attractions you and your family will enjoy exploring while you are staying in Pleasant Point. 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