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 $240 ![](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 Boutique Hotels Tonight [Oct 23 - Oct 24](https://www.expedia.ca/Hotel-Search?regionId=553248635976481213&startDate=2025-10-23&endDate=2025-10-24&adults=2&propertyStyle=BOUTIQUE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Oct 24 - Oct 25](https://www.expedia.ca/Hotel-Search?regionId=553248635976481213&startDate=2025-10-24&endDate=2025-10-25&adults=2&propertyStyle=BOUTIQUE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Oct 24 - Oct 26](https://www.expedia.ca/Hotel-Search?regionId=553248635976481213&startDate=2025-10-24&endDate=2025-10-26&adults=2&propertyStyle=BOUTIQUE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Oct 31 - Nov 2](https://www.expedia.ca/Hotel-Search?regionId=553248635976481213&startDate=2025-10-31&endDate=2025-11-02&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) ![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) ![Exterior](https://images.trvl-media.com/lodging/17000000/16060000/16054000/16053950/eb749b04.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) ### Ellery Hotel Provincetown Provincetown 9.4/10 Exceptional (376) "Great location lovely staff " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kathleen CA $193 CA $240 total includes taxes & fees Nov 12 - Nov 13 [](https://www.expedia.ca/Provincetown-Hotels-Carpe-Diem-Guesthouse-And-SPA.h16053950.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 (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) ![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) ![Restaurant](https://images.trvl-media.com/lodging/1000000/20000/19200/19139/07d625ad.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) ![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) ### Chatham Bars Inn Chatham 9.2/10 Wonderful (792) "Excellent experience all around Gorgeous location and beautiful hotel Lively lobby " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Montana CA $529 CA $636 total includes taxes & fees Oct 30 - Oct 31 [](https://www.expedia.ca/Chatham-Hotels-Chatham-Bars-Inn.h19139.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) ![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) ![Standard Room, 1 Queen Bed](https://images.trvl-media.com/lodging/12000000/11630000/11620900/11620830/b420d63e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Salt House Inn Provincetown 9.6/10 Exceptional (280) "Great stay" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Maureen CA $448 CA $512 total includes taxes & fees Oct 26 - Oct 27 [](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=2025-11-06&endDate=2025-11-07®ionId=553248635976481213&adults=2&specialized_stays_group_explore=boutique_property&sort=RECOMMENDED&openPlayBack=true) ## Top Pleasant Point Hotel Reviews ![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) ![Chatham Bars Inn](//images.trvl-media.com/lodging/1000000/20000/19200/19139/w5700h3895x0y5-016d240d_y.jpg) ### Chatham Bars Inn 10/10 Excellent "Excellent experience all around Gorgeous location and beautiful hotel Lively lobby " [](https://expedia.ca/Chatham-Hotels-Chatham-Bars-Inn.h19139.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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