Title: Book the Best Hotels with BARS 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 Hotels with Bar in Pleasant Point, MA from CA $143 ![](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 Bar ## Top Pleasant Point Hotels with Bar ![Indoor pool, seasonal outdoor pool](https://images.trvl-media.com/lodging/2000000/1180000/1173600/1173572/4c97a310.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Room, 2 Queen Beds](https://images.trvl-media.com/lodging/2000000/1180000/1173600/1173572/2c3e374d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property amenity](https://images.trvl-media.com/lodging/2000000/1180000/1173600/1173572/438fdc4c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Breakfast served, American cuisine](https://images.trvl-media.com/lodging/2000000/1180000/1173600/1173572/e8e7c2c5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Wellfleet Motel and Lodge Wellfleet 9.4/10 Exceptional (1006) "The room was so nice and breakfast was delicious " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Michele CA $125 CA $143 total includes taxes & fees Oct 20 - Oct 21 [](https://www.expedia.ca/Wellfleet-Hotels-Wellfleet-Motel-And-Lodge.h1173572.Hotel-Information) ![Beach nearby](https://images.trvl-media.com/lodging/2000000/1520000/1517300/1517204/1adc0002.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) ![Exterior](https://images.trvl-media.com/lodging/2000000/1520000/1517300/1517204/e74c9a7c.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) ### Chatham Wayside Inn Chatham 9.2/10 Wonderful (575) "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) ![Lighthouse Waterfront Suite](https://images.trvl-media.com/lodging/2000000/1070000/1060700/1060693/921621aa.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) ![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) ### Surfside Hotel and Suites Provincetown 8.6/10 Excellent (1003) "Great place" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Anna CA $150 CA $228 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Provincetown-Hotels-Surfside-Hotel-And-Suites.h1060693.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 (1010) "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 $127 CA $194 total includes taxes & fees Oct 20 - Oct 21 [](https://www.expedia.ca/Brewster-Hotels-The-Villages-At-Ocean-Edge.h6301341.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) ![Lobby](https://images.trvl-media.com/lodging/1000000/10000/2200/2159/4d3d8a36.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 26 - Oct 27 [](https://www.expedia.ca/Eastham-Hotels-Four-Points-By-Sheraton-Eastham-Cape-Cod.h2159.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/1000000/10000/8000/7948/5d8fbc52.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![In-room safe, desk, iron/ironing board, free cribs/infant beds](https://images.trvl-media.com/lodging/1000000/10000/8000/7948/96ca76a7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 indoor pools, 3 outdoor pools, sun loungers](https://images.trvl-media.com/lodging/1000000/10000/8000/7948/3c08c6f0.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 $271 CA $360 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Brewster-Hotels-The-Mansion-At-Ocean-Edge.h7948.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/6000000/5560000/5559400/5559336/76ad4134.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Loft, Beach View](https://images.trvl-media.com/lodging/6000000/5560000/5559400/5559336/13c7da6a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Suite | Private kitchen](https://images.trvl-media.com/lodging/6000000/5560000/5559400/5559336/d6ab9d47.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Loft, Ocean View | Beach/ocean view](https://images.trvl-media.com/lodging/6000000/5560000/5559400/5559336/53ae7bc4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Lotus Provincetown Provincetown 8.8/10 Excellent (346) "Great location! Beautiful beach view~" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Nara CA $125 CA $154 total includes taxes & fees Oct 22 - Oct 23 [](https://www.expedia.ca/Provincetown-Hotels-Lotus-Guest-House.h5559336.Hotel-Information) ![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) ![Premium Double Room | Room amenity](https://images.trvl-media.com/lodging/77000000/76930000/76920700/76920689/c746d678.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) ![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) ### 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 $238 CA $295 total includes taxes & fees Oct 26 - Oct 27 [](https://www.expedia.ca/West-Harwich-Hotels-Pelham-On-Earle.h76920689.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/120000000/119420000/119416800/119416782/d636494a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Manner House 2nd Floor - Deluxe King Sunroom | Street view](https://images.trvl-media.com/lodging/120000000/119420000/119416800/119416782/w951h635x0y1-4f20f225.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/120000000/119420000/119416800/119416782/f66d13c5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Manner House 2nd Floor - 1 Queen](https://images.trvl-media.com/lodging/120000000/119420000/119416800/119416782/c51baf10.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Charm on Main Sea Pines 10/10 Exceptional (1) "Cute place. Love the decor in the main house and room. Nice that they had water and snacks available at any time. Loved spending time on the big porch and in the rocking chairs. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Beth CA $352 CA $403 total includes taxes & fees Nov 5 - Nov 6 [](https://www.expedia.ca/Brewster-Hotels-Charm-On-Main.h119416782.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) ![Terrace/patio](https://images.trvl-media.com/lodging/1000000/900000/894200/894158/2cac1643.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) ### The Corsair & Cross Rip Oceanfront Resort Dennis Port 8.6/10 Excellent (214) "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 $197 CA $225 total includes taxes & fees Oct 20 - Oct 21 [](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=2025-11-02&endDate=2025-11-03®ionId=553248635976481213&adults=2&amenities=BAR&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) ![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) ![Chatham Wayside Inn](//images.trvl-media.com/lodging/2000000/1520000/1517300/1517204/1adc0002_y.jpg) ### Chatham Wayside Inn 10/10 Excellent "The location could not be beat! You are right on Main St in Chatham. We really appreciated the free parking, while tourists were fighting for spots on the street. Breakfast was VERY nice. Especially considering what you normally get for free at a hotel. My only small complaint was the bathroom. There was some peeling paint on the ceiling. The tub floor felt squishy when you stepped on it, implying either improper installation or rot underneath. Otherwise, it was clean and very functional. I would stay here again. However, it is very pricey. But if a super convenient location is important for you, it's worth it. " [](https://expedia.ca/Chatham-Hotels-Chatham-Wayside-Inn.h1517204.Hotel-Information) ![Cape Colony Inn](//images.trvl-media.com/lodging/6000000/5360000/5351000/5350999/70a957c7_y.jpg) ### Cape Colony Inn 10/10 Excellent "Loved everything about staying at Cape Colony Inn; affordable, comfortable, great staff and perfect continental breakfast!!!!" [](https://expedia.ca/Provincetown-Hotels-Cape-Colony-Inn.h5350999.Hotel-Information) ![Crowne Pointe Historic Inn & Spa - Adults Only](//images.trvl-media.com/lodging/1000000/910000/906400/906319/b8ab45a0_y.jpg) ### Crowne Pointe Historic Inn & Spa - Adults Only 10/10 Excellent "Room and staff were amazing! Highly recommend!" [](https://expedia.ca/Provincetown-Hotels-Crowne-Pointe-Historic-Inn-Spa-Adults-Only.h906319.Hotel-Information) ![The Villages at Ocean Edge](//images.trvl-media.com/lodging/7000000/6310000/6301400/6301341/405c33ed_y.jpg) ### The Villages at Ocean Edge 10/10 Excellent "Nice room with a kitchen. Bed was large and comfy for two. Room cleaned daily. Coffee was replenished daily as well. The “campus” was beautiful. We were there in early October so the town was pretty much getting ready to close up" [](https://expedia.ca/Brewster-Hotels-The-Villages-At-Ocean-Edge.h6301341.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) ![Top Mast Resort](//images.trvl-media.com/lodging/12000000/11740000/11737100/11737053/d022d597_y.jpg) ### Top Mast Resort 10/10 Excellent "Absolutely! Looking forward to our next stay!" [](https://expedia.ca/North-Truro-Hotels-Top-Mast-Resort.h11737053.Hotel-Information) ## Frequently asked questions ### Searching for hotels with bars in Pleasant Point? > Though you might not find a hotel in Pleasant Point well-known for its bar, you will find 11 properties to choose from, some of which will have an onsite bar where you can unwind with a late-night cocktail after a day out and about. While you're in the area, consider a visit to Wellfleet Harbor Actors Theater and Cape Cod National Seashore. ### What are the best hotels with bars in Pleasant Point? > Here are some favorite hotels with bars in and around Pleasant Point: [Sandcastle Resort and Club](https://www.expedia.ca/Provincetown-Hotels-Sandcastle-Resort-And-Club.h1870586.Hotel-Information): Resort with 3 restaurants. Enjoy the 3 poolside bars, beach bar, and 3 outdoor pools. [Captains Quarters Motel & Conference Center](https://www.expedia.ca/Eastham-Hotels-Captains-Quarters-Motel-Conference-Center.h1080509.Hotel-Information): Resort with restaurant. Enjoy the bar, free WiFi, and free parking. [The Villages at Ocean Edge](https://www.expedia.ca/Brewster-Hotels-The-Villages-At-Ocean-Edge.h6301341.Hotel-Information): Hotel with 3 restaurants. Enjoy the 2 bars, seasonal outdoor pool, and beach locale. [Chatham Bars Inn](https://www.expedia.ca/Chatham-Hotels-Chatham-Bars-Inn.h19139.Hotel-Information): Enjoy the bar, free WiFi, and free parking. [The Provincetown Inn](https://www.expedia.ca/Provincetown-Hotels-The-Provincetown-Inn.h910310.Hotel-Information): Resort with 6 restaurants. Enjoy the 2 poolside bars, beach bar, and free WiFi. ### What is there to do in Pleasant Point? > Consider a visit to Wellfleet Harbor Actors Theater, Cape Cod National Seashore, and Cahoon Hollow Beach, and then find a cozy spot for a nightcap. Other places to see in the area include Mayo Beach and Wellfleet Preservation Hall. ### How can I get to Pleasant Point and around the area? > You might want to make the most of these transportation options in and around Pleasant Point: Fly into Provincetown, MA (PVC-Provincetown Municipal), which is located 15.8 mi (25.4 km) away. Otherwise, you can search for flights to Hyannis, MA (HYA-Barnstable Municipal), which is 22.3 mi (35.9 km) away. ## 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) - [Hotels with Wifi in Boston](https://www.expedia.ca/Boston-Hotels-Hotel-With-Wifi.0-0-d178239-tHotelwithwifi.Travel-Guide-Filter-Hotels) - 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