Title: Book the Best Pleasant Point WINERY Hotels in 2026 | Expedia.ca

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## Check availability on Pleasant Point Winery Hotels

Tonight

[Feb 6 - Feb 7](https://www.expedia.ca/Hotel-Search?regionId=553248635976481213&startDate=2026-02-06&endDate=2026-02-07&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

Tomorrow

[Feb 7 - Feb 8](https://www.expedia.ca/Hotel-Search?regionId=553248635976481213&startDate=2026-02-07&endDate=2026-02-08&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

This weekend

[Feb 6 - Feb 8](https://www.expedia.ca/Hotel-Search?regionId=553248635976481213&startDate=2026-02-06&endDate=2026-02-08&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

Next weekend

[Feb 13 - Feb 15](https://www.expedia.ca/Hotel-Search?regionId=553248635976481213&startDate=2026-02-13&endDate=2026-02-15&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

## Our top choices for Pleasant Point hotels with winery

![Beach nearby](https://images.trvl-media.com/lodging/2000000/1520000/1517300/1517204/1adc0002.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)

![Breakfast, lunch, dinner served; American cuisine, garden views ](https://images.trvl-media.com/lodging/2000000/1520000/1517300/1517204/97707902.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/2000000/1520000/1517300/1517204/0ed95706.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Chatham Wayside Inn

[](https://www.expedia.ca/Chatham-Hotels-Chatham-Wayside-Inn.h1517204.Hotel-Information)

Chatham

9.2/10

Wonderful

(629 reviews)

"Yes, lovely place to stay."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Angela

[](https://www.expedia.ca/Chatham-Hotels-Chatham-Wayside-Inn.h1517204.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=2026-02-20&endDate=2026-02-21&regionId=553248635976481213&adults=2&location_highlights_explore=winery&sort=RECOMMENDED&openPlayBack=true)

## Top Pleasant Point Hotel Reviews

![Mercury Hotel Provincetown](https://images.trvl-media.com/lodging/2000000/1510000/1501600/1501547/917d85d9_y.jpg)

### Mercury Hotel Provincetown

10/10 Excellent

"Amazing. As always! <3"

[](https://expedia.ca/Provincetown-Hotels-The-BeaconLight-Guest-House.h1501547.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

"Beautiful property "

[](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

"We had this place to our selves. Since our stay was the last one till spring. Luis the manager was phenomenal extremely friendly and made sure we were all set. The breakfast was truly great. Had a great conversation with Luis at Breakfast It was a wonderful stay a will be back soon "

[](https://expedia.ca/Provincetown-Hotels-Cape-Colony-Inn.h5350999.Hotel-Information)

![Crowne Pointe Historic Inn & Spa - Adults Only](https://images.trvl-media.com/lodging/1000000/910000/906400/906319/b8ab45a0_y.jpg)

### Crowne Pointe Historic Inn & Spa - Adults Only

10/10 Excellent

"We had a great room (king superior) that was spacious, clean and quiet. The bed was comfortable and the staff and management were incredibly friendly and welcoming. Would definitely stay here again!"

[](https://expedia.ca/Provincetown-Hotels-Crowne-Pointe-Historic-Inn-Spa-Adults-Only.h906319.Hotel-Information)

![Harbor Hotel Provincetown](https://images.trvl-media.com/lodging/1000000/430000/421600/421590/e4d390ae_y.jpg)

### Harbor Hotel Provincetown

10/10 Excellent

"Clean "

[](https://expedia.ca/Provincetown-Hotels-Harbor-Hotel-Provincetown.h421590.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)

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