Title: Book the Best Hotels with POOL in Lion Head Beach in 2026 | Expedia.ca

[Lion Head Beach Travel Guide](https://expedia.ca/Lion-Head-Beach.dx553248635976395221)[Hotels in Lion Head Beach](https://expedia.ca/Lion-Head-Beach-Hotels.d553248635976395221.Travel-Guide-Hotels)[Vacation Rentals in Lion Head Beach](https://expedia.ca/Lion-Head-Beach-Vacation-Rentals.d553248635976395221.Travel-Guide-VacationRentals)[Lion Head Beach Car Rentals](https://expedia.ca/Car-Rentals-In-Lion-Head-Beach.d553248635976395221.Car-Rental-Guide)[Lion Head Beach Vacation Packages](https://expedia.ca/Lion-Head-Beach.d553248635976395221.Destination-Travel-Guides)

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## Check availability on Lion Head Beach Hotels with a Pool

Tonight

[Jan 17 - Jan 18](https://www.expedia.ca/Hotel-Search?regionId=553248635976395221&startDate=2026-01-17&endDate=2026-01-18&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

Tomorrow

[Jan 18 - Jan 19](https://www.expedia.ca/Hotel-Search?regionId=553248635976395221&startDate=2026-01-18&endDate=2026-01-19&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

Next weekend

[Jan 23 - Jan 25](https://www.expedia.ca/Hotel-Search?regionId=553248635976395221&startDate=2026-01-23&endDate=2026-01-25&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two weeks

[Jan 30 - Feb 1](https://www.expedia.ca/Hotel-Search?regionId=553248635976395221&startDate=2026-01-30&endDate=2026-02-01&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

## Our top choices for Lion Head Beach hotels with a pool

![Exterior](https://images.trvl-media.com/lodging/13000000/12700000/12694100/12694044/d18d0d4f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Aerial view](https://images.trvl-media.com/lodging/13000000/12700000/12694100/12694044/aa464430.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/13000000/12700000/12694100/12694044/4be91ce8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior detail](https://images.trvl-media.com/lodging/13000000/12700000/12694100/12694044/ec2516ce.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Montauk Manor

[](https://www.expedia.ca/Montauk-Hotels-Montauk-Manor.h12694044.Hotel-Information)

Montauk

9.2/10

Wonderful

(1,281 reviews)

"Very beautiful place, staff are amazing. Thank you"

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

Frank

CA $193

CA $247 total

includes taxes & fees

Jan 20 - Jan 21

[](https://www.expedia.ca/Montauk-Hotels-Montauk-Manor.h12694044.Hotel-Information)

![Seasonal outdoor pool, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/16000000/15280000/15273200/15273178/83c7bce7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Resort view](https://images.trvl-media.com/lodging/16000000/15280000/15273200/15273178/7aeccb7c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/16000000/15280000/15273200/15273178/8a4a605e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lunch, dinner, brunch served; American cuisine, beach views ](https://images.trvl-media.com/lodging/16000000/15280000/15273200/15273178/55b708b5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Sound View Greenport

[](https://www.expedia.ca/Greenport-Hotels-Sound-View-Greenport.h15273178.Hotel-Information)

Greenport

8.6/10

Excellent

(606 reviews)

"Nice place"

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

Mateusz

CA $187

CA $253 total

includes taxes & fees

Jan 21 - Jan 22

[](https://www.expedia.ca/Greenport-Hotels-Sound-View-Greenport.h15273178.Hotel-Information)

![Seasonal outdoor pool, open 8:00 AM to 7:00 PM, sun loungers](https://images.trvl-media.com/lodging/44000000/43540000/43532300/43532300/1345db22.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby lounge](https://images.trvl-media.com/lodging/44000000/43540000/43532300/43532300/2c9cc7e9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![View from room](https://images.trvl-media.com/lodging/44000000/43540000/43532300/43532300/7ebc6d88.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![One Bedroom Harbor View Terrace Suite | View from room](https://images.trvl-media.com/lodging/44000000/43540000/43532300/43532300/46cd22ca.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Harbor Front Inn

[](https://www.expedia.ca/Greenport-Hotels-The-Harborfront-Inn.h43532300.Hotel-Information)

Greenport

8.8/10

Excellent

(562 reviews)

"Everything was Great Immaculate hotel very good location sraff was great"

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

latoya

CA $164

CA $228 total

includes taxes & fees

Jan 19 - Jan 20

[](https://www.expedia.ca/Greenport-Hotels-The-Harborfront-Inn.h43532300.Hotel-Information)

![Outdoor pool](https://images.trvl-media.com/lodging/114000000/113580000/113578500/113578409/7a155d22.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![View from room](https://images.trvl-media.com/lodging/114000000/113580000/113578500/113578409/69b11154.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/114000000/113580000/113578500/113578409/c614d2a2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Ocean View 2 Queens](https://images.trvl-media.com/lodging/114000000/113580000/113578500/113578409/6944012d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Offshore Montauk

[](https://www.expedia.ca/Montauk-Hotels-The-Offshore.h113578409.Hotel-Information)

Montauk

9.4/10

Exceptional

(93 reviews)

"Hotel was beautiful !!"

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

Erica

CA $161

CA $264 total

includes taxes & fees

Feb 4 - Feb 5

[](https://www.expedia.ca/Montauk-Hotels-The-Offshore.h113578409.Hotel-Information)

![Seasonal outdoor pool, open 8:00 AM to 8:00 PM, pool umbrellas](https://images.trvl-media.com/lodging/54000000/53970000/53963000/53962986/4bbf34cb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, premium bedding, down comforters, in-room safe](https://images.trvl-media.com/lodging/54000000/53970000/53963000/53962986/b432d22f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Reception](https://images.trvl-media.com/lodging/54000000/53970000/53963000/53962986/cc53a2c2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, premium bedding, down comforters, in-room safe](https://images.trvl-media.com/lodging/54000000/53970000/53963000/53962986/1bfd9996.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Bentley Hotel Southampton

[](https://www.expedia.ca/Southampton-Hotels-Bentley-Southampton.h53962986.Hotel-Information)

Southampton

9.6/10

Exceptional

(424 reviews)

"Adorable boutique hotel with charming unique touches. "

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

Mary

CA $169

CA $194 total

includes taxes & fees

Jan 29 - Jan 30

[](https://www.expedia.ca/Southampton-Hotels-Bentley-Southampton.h53962986.Hotel-Information)

![Seasonal outdoor pool, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/9000000/8480000/8475000/8474914/4e86636a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/9000000/8480000/8475000/8474914/89358591.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/9000000/8480000/8475000/8474914/dc79a27f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Apartment, 1 Bedroom | Living area](https://images.trvl-media.com/lodging/9000000/8480000/8475000/8474914/78e3666a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Kenny's Tipperary Inn

[](https://www.expedia.ca/Montauk-Hotels-Kennys-Tipperary-Inn.h8474914.Hotel-Information)

Culloden Shores

8.4/10

Very good

(882 reviews)

"Really clean and nice location"

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

Tiara

[](https://www.expedia.ca/Montauk-Hotels-Kennys-Tipperary-Inn.h8474914.Hotel-Information)

![Outdoor pool](https://images.trvl-media.com/lodging/27000000/26500000/26497900/26497858/14a9b9bf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby lounge](https://images.trvl-media.com/lodging/27000000/26500000/26497900/26497858/6037fc82.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Building design](https://images.trvl-media.com/lodging/27000000/26500000/26497900/26497858/1c345cd0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/27000000/26500000/26497900/26497858/f95ca887.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Sag Harbor Inn

[](https://www.expedia.ca/Sag-Harbor-Hotels-Sag-Harbor-Inn.h26497858.Hotel-Information)

Sag Harbor

9.4/10

Exceptional

(581 reviews)

"Lovely hotel, very clean and friendly! Definitely going back!"

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

Hollie

CA $285

CA $325 total

includes taxes & fees

Feb 15 - Feb 16

[](https://www.expedia.ca/Sag-Harbor-Hotels-Sag-Harbor-Inn.h26497858.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/10000000/9510000/9501200/9501176/b41b085d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Yoga](https://images.trvl-media.com/lodging/10000000/9510000/9501200/9501176/6f482e8a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Basic Suite, 2 Bedrooms](https://images.trvl-media.com/lodging/10000000/9510000/9501200/9501176/ea7d9e1c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Room](https://images.trvl-media.com/lodging/10000000/9510000/9501200/9501176/f1b58415.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Daunt's Albatross Motel

[](https://www.expedia.ca/Montauk-Hotels-Daunts-Albatross-Motel.h9501176.Hotel-Information)

Downtown Montauk

9.0/10

Wonderful

(298 reviews)

"Very clean room, nice staff. Will definitely come back . "

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

Kosuke

[](https://www.expedia.ca/Montauk-Hotels-Daunts-Albatross-Motel.h9501176.Hotel-Information)

![Aerial view](https://images.trvl-media.com/lodging/1000000/120000/117200/117135/7d31a3c7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property entrance](https://images.trvl-media.com/lodging/1000000/120000/117200/117135/51a7b673.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/1000000/120000/117200/117135/6bba5430.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Breakfast, lunch, brunch served; local cuisine ](https://images.trvl-media.com/lodging/1000000/120000/117200/117135/27675de4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Southampton Inn

[](https://www.expedia.ca/Southampton-Hotels-Southampton-Inn.h117135.Hotel-Information)

Southampton

8.6/10

Excellent

(554 reviews)

"Beautiful small hotel with lots of parking , beautiful area "

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

David

CA $278

CA $340 total

includes taxes & fees

Jan 20 - Jan 21

[](https://www.expedia.ca/Southampton-Hotels-Southampton-Inn.h117135.Hotel-Information)

![Seasonal outdoor pool, open 10:00 AM to 8:00 PM, pool umbrellas](https://images.trvl-media.com/lodging/2000000/1220000/1210400/1210398/15a14a38.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby lounge](https://images.trvl-media.com/lodging/2000000/1220000/1210400/1210398/d096a355.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Double Room | Terrace/patio](https://images.trvl-media.com/lodging/2000000/1220000/1210400/1210398/302ae081.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Seasonal outdoor pool, open 10:00 AM to 8:00 PM, pool umbrellas](https://images.trvl-media.com/lodging/2000000/1220000/1210400/1210398/4c4718fb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Hamlet Inn

[](https://www.expedia.ca/Southampton-Hotels-Hamlet-Inn.h1210398.Hotel-Information)

Southampton

8.6/10

Excellent

(448 reviews)

"Room was in good condition however I found the shower to be extremely small despite having great water pressure and extremely nice temperature."

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

gail

CA $121

CA $157 total

includes taxes & fees

Jan 20 - Jan 21

[](https://www.expedia.ca/Southampton-Hotels-Hamlet-Inn.h1210398.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=2026-01-31&endDate=2026-02-01&regionId=553248635976395221&adults=2&amenities=POOL&sort=RECOMMENDED&openPlayBack=true)

## Top Lion Head Beach Hotel Reviews

![Gurney's Montauk Resort & Seawater Spa](https://images.trvl-media.com/lodging/8000000/7040000/7033800/7033726/895004c9_y.jpg)

### Gurney's Montauk Resort & Seawater Spa

10/10 Excellent

"Staying at Gurney's after their many renovations was surprising !! The rooms don't look outdated anymore including the Spa / Pool area - for the price you're paying per night, I appreciated the face lift. Oceanviews from any angle of this hotel site will always be incredible ! "

[](https://expedia.ca/Montauk-Hotels-Gurneys-Montauk-Resort-Seawater-Spa.h7033726.Hotel-Information)

![The Atlantic Hotel](https://images.trvl-media.com/lodging/1000000/450000/447900/447803/0c137ed2_y.jpg)

### The Atlantic Hotel

10/10 Excellent

"Staff was very friendly room was clean and comfortable "

[](https://expedia.ca/Southampton-Hotels-The-Atlantic-Hotel.h447803.Hotel-Information)

![Sound View Greenport](https://images.trvl-media.com/lodging/16000000/15280000/15273200/15273178/b52e0fa4_y.jpg)

### Sound View Greenport

10/10 Excellent

"Amazing room and view from the room was perfect! "

[](https://expedia.ca/Greenport-Hotels-Sound-View-Greenport.h15273178.Hotel-Information)

![Daunt's Albatross Motel](https://images.trvl-media.com/lodging/10000000/9510000/9501200/9501176/a3cd59ff_y.jpg)

### Daunt's Albatross Motel

10/10 Excellent

"Very clean room, nice staff. Will definitely come back . "

[](https://expedia.ca/Montauk-Hotels-Daunts-Albatross-Motel.h9501176.Hotel-Information)

![Hamlet Inn](https://images.trvl-media.com/lodging/2000000/1220000/1210400/1210398/15a14a38_y.jpg)

### Hamlet Inn

10/10 Excellent

"Nice getaway spot in Southampton. Friendly staff. Well situated to may local points of interest. "

[](https://expedia.ca/Southampton-Hotels-Hamlet-Inn.h1210398.Hotel-Information)

![Kenny's Tipperary Inn](https://images.trvl-media.com/lodging/9000000/8480000/8475000/8474914/4e86636a_y.jpg)

### Kenny's Tipperary Inn

10/10 Excellent

"Perfect"

[](https://expedia.ca/Montauk-Hotels-Kennys-Tipperary-Inn.h8474914.Hotel-Information)

![Marram](https://images.trvl-media.com/lodging/16000000/15410000/15408300/15408228/619dc6c0_y.jpg)

### Marram

10/10 Excellent

"Wonderful stay! Spacious and elegant room, friendly staff, breathtaking view. Memorable birthday weekend. "

[](https://expedia.ca/Montauk-Hotels-Marram.h15408228.Hotel-Information)

![Harborside Motel](https://images.trvl-media.com/lodging/20000000/19190000/19185200/19185143/cfcf412a_y.jpg)

### Harborside Motel

10/10 Excellent

"Merle is the best"

[](https://expedia.ca/Montauk-Hotels-Harborside-Motel.h19185143.Hotel-Information)

## Frequently asked questions

### What are some accommodations with pools in Lion Head Beach?

### What is there to see and do in Lion Head Beach?

### When is the best time to book a hotel with a pool in Lion Head Beach?

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