Title: Book the Best BOUTIQUE Hotels 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://media.expedia.com/media/content/shared/images/travelguides/sem-hotels-tablet.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Find Boutique Hotels in Pleasant Point, MA from CA $325 ![calendar shield illustration](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.svg) ### Change your mind Book hotels with free cancellation ![deals illustration](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) ![bed illustration](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 Boutique Hotels Tonight [Oct 8 - Oct 9](https://www.expedia.ca/Hotel-Search?regionId=553248635976481213&startDate=2025-10-08&endDate=2025-10-09&adults=2&propertyStyle=BOUTIQUE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Oct 9 - Oct 10](https://www.expedia.ca/Hotel-Search?regionId=553248635976481213&startDate=2025-10-09&endDate=2025-10-10&adults=2&propertyStyle=BOUTIQUE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Oct 10 - Oct 12](https://www.expedia.ca/Hotel-Search?regionId=553248635976481213&startDate=2025-10-10&endDate=2025-10-12&adults=2&propertyStyle=BOUTIQUE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Oct 17 - Oct 19](https://www.expedia.ca/Hotel-Search?regionId=553248635976481213&startDate=2025-10-17&endDate=2025-10-19&adults=2&propertyStyle=BOUTIQUE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Pleasant Point Boutique Hotels ![Lobby](https://images.trvl-media.com/lodging/17000000/16060000/16054000/16053950/ae314726.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Luxury Double Room](https://images.trvl-media.com/lodging/17000000/16060000/16054000/16053950/6b723d26.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/17000000/16060000/16054000/16053950/52ca6854.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Single Room | View from room](https://images.trvl-media.com/lodging/17000000/16060000/16054000/16053950/dae82b2e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Ellery Hotel Provincetown Provincetown 9.4/10 Exceptional (371) "Great location lovely staff " CA $261 CA $325 total includes taxes & fees Oct 27 - Oct 28 [](https://www.expedia.ca/Provincetown-Hotels-Carpe-Diem-Guesthouse-And-SPA.h16053950.Hotel-Information) ![Seasonal outdoor pool](https://images.trvl-media.com/lodging/1000000/20000/19200/19139/w5700h3895x0y5-016d240d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Couples treatment rooms, body treatments, aromatherapy](https://images.trvl-media.com/lodging/1000000/20000/19200/19139/w5695h3900x5y0-3649fa2f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/1000000/20000/19200/19139/0e2de95d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/1000000/20000/19200/19139/f7ed55d6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Chatham Bars Inn Chatham 9.2/10 Wonderful (791) "Beautiful property. Great service!" CA $528 CA $634 total includes taxes & fees Oct 30 - Oct 31 [](https://www.expedia.ca/Chatham-Hotels-Chatham-Bars-Inn.h19139.Hotel-Information) ![Beach bar](https://images.trvl-media.com/lodging/1000000/10000/3700/3689/9873e07e.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) ![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) ![Round Cove Suite](https://images.trvl-media.com/lodging/1000000/10000/3700/3689/ce420299.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Wequassett Resort and Golf Club Harwich 9.4/10 Exceptional (240) "Beautiful property!! Excellent service!! Room was amazing!! " CA $905 CA $1,109 total includes taxes & fees Nov 8 - Nov 9 [](https://www.expedia.ca/Harwich-Hotels-Wequassett-Resort-And-Golf-Club.h3689.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/12000000/11630000/11620900/11620830/4fedb51c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily continental breakfast](https://images.trvl-media.com/lodging/12000000/11630000/11620900/11620830/3f14083d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Garden](https://images.trvl-media.com/lodging/12000000/11630000/11620900/11620830/7eb65101.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Room, 1 King Bed](https://images.trvl-media.com/lodging/12000000/11630000/11620900/11620830/52e061c1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Salt House Inn Provincetown 9.6/10 Exceptional (277) "Awesome staff, comfiest, cleanest room perfect for 2, amazing location and delicious daily breakfast" CA $446 CA $511 total includes taxes & fees Oct 9 - Oct 10 [](https://www.expedia.ca/Provincetown-Hotels-Salt-House-Inn.h11620830.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=2025-10-22&endDate=2025-10-23®ionId=553248635976481213&adults=2&specialized_stays_group_explore=boutique_property&sort=RECOMMENDED&openPlayBack=true) ## Top Pleasant Point Hotel Reviews ![Chatham Bars Inn](//images.trvl-media.com/lodging/1000000/20000/19200/19139/w5700h3895x0y5-016d240d_y.jpg) ### Chatham Bars Inn 10/10 Excellent "Beautiful property. Great service!" [](https://expedia.ca/Chatham-Hotels-Chatham-Bars-Inn.h19139.Hotel-Information) ![Wequassett Resort and Golf Club](//images.trvl-media.com/lodging/1000000/10000/3700/3689/36170a91_y.jpg) ### Wequassett Resort and Golf Club 10/10 Excellent "Lovely " [](https://expedia.ca/Harwich-Hotels-Wequassett-Resort-And-Golf-Club.h3689.Hotel-Information) ## Frequently asked questions ### What's there to see and do in Pleasant Point? > After you've decided where to stay, figure out some fun things to do on your trip. Activities and attractions to experience around Pleasant Point include Wellfleet Harbor Actors Theater, Provincetown Theater, and Pilgrim Monument. You might also like to explore more of the area and take in additional sights like Cape Cod National Seashore, Cahoon Hollow Beach, and Edward Penniman House and Barn while you're here. ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rental - More ways to book - [Adults Only Resorts & in Boston](https://www.expedia.ca/Boston-Hotels-Adults-Only-Resorts.0-0-d178239-tAdultsOnlyResorts.Travel-Guide-Filter-Hotels) - [Business Hotels in Boston](https://www.expedia.ca/Boston-Hotels-Business-Hotel.0-0-d178239-tBusinessHotel.Travel-Guide-Filter-Hotels) - [Hotels & Resorts for Couples in Boston](https://www.expedia.ca/Boston-Hotels-Couples-Resorts-Hotels.0-0-d178239-tCouplesResortsHotels.Travel-Guide-Filter-Hotels) - [Golf Hotels in Boston](https://www.expedia.ca/Boston-Hotels-Golf-Hotel.0-0-d178239-tGolfHotel.Travel-Guide-Filter-Hotels) - [Green Hotels in Boston](https://www.expedia.ca/Boston-Hotels-Green-Sustainable.0-0-d178239-tGreenSustainable.Travel-Guide-Filter-Hotels) - 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