Title: Book The Best Hotels in Wainscott Woods, NY for 2026 from CA $210 - Fully Refundable Options - Expedia.ca

[Wainscott Woods Travel Guide](https://expedia.ca/Wainscott-Woods.dx553248635976471516)[Vacation Rentals in Wainscott Woods](https://expedia.ca/Wainscott-Woods-Vacation-Rentals.d553248635976471516.Travel-Guide-VacationRentals)[Wainscott Woods Car Rentals](https://expedia.ca/Car-Rentals-In-Wainscott-Woods.d553248635976471516.Car-Rental-Guide)[Wainscott Woods Vacation Packages](https://expedia.ca/Wainscott-Woods.d553248635976471516.Destination-Travel-Guides)

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## Go beyond your typical stay in Wainscott Woods

Family friendly

[](https://www.expedia.ca/Hotel-Search?destination=Wainscott+Woods%2C+New+York%2C+United+States+of+America&regionId=553248635976471516&latLong=40.951743%2C-72.251062&adults=2&startDate=2026-03-16&d1=2026-03-16&endDate=2026-03-18&d2=2026-03-18&travelerType=family_friendly)

Spa

[](https://www.expedia.ca/Hotel-Search?destination=Wainscott+Woods%2C+New+York%2C+United+States+of+America&regionId=553248635976471516&latLong=40.951743%2C-72.251062&adults=2&startDate=2026-03-16&d1=2026-03-16&endDate=2026-03-18&d2=2026-03-18&amenities=SPA_ON_SITE)

Pool

[](https://www.expedia.ca/Hotel-Search?destination=Wainscott+Woods%2C+New+York%2C+United+States+of+America&regionId=553248635976471516&latLong=40.951743%2C-72.251062&adults=2&startDate=2026-03-16&d1=2026-03-16&endDate=2026-03-18&d2=2026-03-18&amenities=POOL)

Pet friendly

[](https://www.expedia.ca/Hotel-Search?destination=Wainscott+Woods%2C+New+York%2C+United+States+of+America&regionId=553248635976471516&latLong=40.951743%2C-72.251062&adults=2&startDate=2026-03-16&d1=2026-03-16&endDate=2026-03-18&d2=2026-03-18&amenities=PETS)

Hot tub

[](https://www.expedia.ca/Hotel-Search?destination=Wainscott+Woods%2C+New+York%2C+United+States+of+America&regionId=553248635976471516&latLong=40.951743%2C-72.251062&adults=2&startDate=2026-03-16&d1=2026-03-16&endDate=2026-03-18&d2=2026-03-18&amenities=HOT_TUB)

Apart­ment

[](https://www.expedia.ca/Hotel-Search?destination=Wainscott+Woods%2C+New+York%2C+United+States+of+America&regionId=553248635976471516&latLong=40.951743%2C-72.251062&adults=2&startDate=2026-03-16&d1=2026-03-16&endDate=2026-03-18&d2=2026-03-18&lodging=APARTMENT)

Condo

[](https://www.expedia.ca/Hotel-Search?destination=Wainscott+Woods%2C+New+York%2C+United+States+of+America&regionId=553248635976471516&latLong=40.951743%2C-72.251062&adults=2&startDate=2026-03-16&d1=2026-03-16&endDate=2026-03-18&d2=2026-03-18&lodging=CONDO)

Cottage

[](https://www.expedia.ca/Hotel-Search?destination=Wainscott+Woods%2C+New+York%2C+United+States+of+America&regionId=553248635976471516&latLong=40.951743%2C-72.251062&adults=2&startDate=2026-03-16&d1=2026-03-16&endDate=2026-03-18&d2=2026-03-18&lodging=COTTAGE)

## Check prices for these dates

Tonight

[Mar 2 - Mar 3](https://www.expedia.ca/Hotel-Search?regionId=553248635976471516&startDate=2026-03-02&endDate=2026-03-03&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

Tomorrow

[Mar 3 - Mar 4](https://www.expedia.ca/Hotel-Search?regionId=553248635976471516&startDate=2026-03-03&endDate=2026-03-04&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

This weekend

[Mar 6 - Mar 8](https://www.expedia.ca/Hotel-Search?regionId=553248635976471516&startDate=2026-03-06&endDate=2026-03-08&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

Next weekend

[Mar 13 - Mar 15](https://www.expedia.ca/Hotel-Search?regionId=553248635976471516&startDate=2026-03-13&endDate=2026-03-15&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

## Our top choices for Wainscott Woods hotels

![Exterior](https://images.trvl-media.com/lodging/16000000/15250000/15241400/15241380/147e40ed.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Breakfast area](https://images.trvl-media.com/lodging/16000000/15250000/15241400/15241380/ee8b7737.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/16000000/15250000/15241400/15241380/1bb00541.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/16000000/15250000/15241400/15241380/cfee764e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Shorewood Inn

[](https://www.expedia.ca/Riverhead-Hotels-Shorewood-Inn.h15241380.Hotel-Information)

Riverhead

8.4/10

Very good

(724 reviews)

"ROOM WAS CLEAN, WARM, GOOD PARKING"

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

JOSEPH

CA $125

CA $143 total

includes taxes & fees

Mar 3 - Mar 4

[](https://www.expedia.ca/Riverhead-Hotels-Shorewood-Inn.h15241380.Hotel-Information)

![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/54000000/53970000/53963000/53962986/88fef67d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Seasonal outdoor pool, open 8:00 AM to 8:00 PM, pool umbrellas](https://images.trvl-media.com/lodging/54000000/53970000/53963000/53962986/c5b3ea42.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

(441 reviews)

"Adorable room"

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

Martin

CA $183

CA $210 total

includes taxes & fees

Mar 8 - Mar 9

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

![Restaurant](https://images.trvl-media.com/lodging/2000000/1220000/1210400/1210398/85851742.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)

![Property grounds](https://images.trvl-media.com/lodging/2000000/1220000/1210400/1210398/8ac37006.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Private beach nearby, beach towels](https://images.trvl-media.com/lodging/2000000/1220000/1210400/1210398/8a104c05.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

(454 reviews)

"Great weekend stay! staff was super kind and property was beautiful! "

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

Chyanne

CA $134

CA $173 total

includes taxes & fees

Mar 3 - Mar 4

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

![Bar (on property)](https://images.trvl-media.com/lodging/20000000/19720000/19716000/19715959/7fc14e3a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior detail](https://images.trvl-media.com/lodging/20000000/19720000/19716000/19715959/9f64cb2a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/20000000/19720000/19716000/19715959/e820e996.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Standard Room, 1 King Bed](https://images.trvl-media.com/lodging/20000000/19720000/19716000/19715959/9f1bca91.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Hampton Maid

[](https://www.expedia.ca/Hampton-Bays-Hotels-Hampton-Maid-Motel.h19715959.Hotel-Information)

Hampton Bays

9.0/10

Wonderful

(688 reviews)

"Great place to stay"

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

Mitchell

[](https://www.expedia.ca/Hampton-Bays-Hotels-Hampton-Maid-Motel.h19715959.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/16000000/15630000/15622100/15622089/f2951978.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Garden Suite, Wheelchair Accessible, Ground Floor, 2 Queen Beds, Non-Smoking](https://images.trvl-media.com/lodging/16000000/15630000/15622100/15622089/8dd4e80f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Restaurant](https://images.trvl-media.com/lodging/16000000/15630000/15622100/15622089/942c49f5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Bar (on property)](https://images.trvl-media.com/lodging/16000000/15630000/15622100/15622089/a9a67717.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Zey Hotel

[](https://www.expedia.ca/Greenport-Hotels-The-Gallery-Hotel.h15622089.Hotel-Information)

Greenport

9.2/10

Wonderful

(298 reviews)

"Quiet yet situated right in the heart of Greenport."

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

Andrew

CA $442

CA $505 total

includes taxes & fees

Mar 3 - Mar 4

[](https://www.expedia.ca/Greenport-Hotels-The-Gallery-Hotel.h15622089.Hotel-Information)

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

![Free daily continental breakfast](https://images.trvl-media.com/lodging/27000000/26500000/26497900/26497858/5688a130.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![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)

### Sag Harbor Inn

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

Sag Harbor

9.4/10

Exceptional

(584 reviews)

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

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

Hollie

CA $280

CA $319 total

includes taxes & fees

Mar 3 - Mar 4

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

![Outdoor pool](https://images.trvl-media.com/lodging/6000000/5590000/5581400/5581380/8b4b1f10.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Bar (on property)](https://images.trvl-media.com/lodging/6000000/5590000/5581400/5581380/db3d6717.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Cottage, 2 Single Beds | View from room](https://images.trvl-media.com/lodging/6000000/5590000/5581400/5581380/9125969a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/6000000/5590000/5581400/5581380/9423d3da.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Topping Rose House

[](https://www.expedia.ca/Bridgehampton-Hotels-Topping-Rose-House.h5581380.Hotel-Information)

Bridgehampton

9.2/10

Wonderful

(143 reviews)

"Our second home :)"

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

olivia

CA $730

CA $839 total

includes taxes & fees

Mar 3 - Mar 4

[](https://www.expedia.ca/Bridgehampton-Hotels-Topping-Rose-House.h5581380.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/8000000/7040000/7033800/7033726/b29cbb53.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Ocean View One Bedroom Suite](https://images.trvl-media.com/lodging/8000000/7040000/7033800/7033726/d3ce4464.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/8000000/7040000/7033800/7033726/0272b9dd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Ocean View King](https://images.trvl-media.com/lodging/8000000/7040000/7033800/7033726/9241bd8b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Gurney's Montauk Resort & Seawater Spa

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

Montauk

8.4/10

Very good

(735 reviews)

"Room was spotless, staff were great and the resort is top notch!!"

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

Carrie

CA $480

CA $659 total

includes taxes & fees

Apr 2 - Apr 3

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

![Studio](https://images.trvl-media.com/lodging/11000000/10450000/10449600/10449505/859942ac.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Studio | Terrace/patio](https://images.trvl-media.com/lodging/11000000/10450000/10449600/10449505/bf9e4083.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Studio](https://images.trvl-media.com/lodging/11000000/10450000/10449600/10449505/bbfe6924.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Studio | Living area](https://images.trvl-media.com/lodging/11000000/10450000/10449600/10449505/bc345330.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Beach Plum Resort

[](https://www.expedia.ca/Montauk-Hotels-Beach-Plum-Resort.h10449505.Hotel-Information)

Montauk

9.0/10

Wonderful

(159 reviews)

"Nice place to stay."

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

Mark

CA $250

CA $315 total

includes taxes & fees

Apr 1 - Apr 2

[](https://www.expedia.ca/Montauk-Hotels-Beach-Plum-Resort.h10449505.Hotel-Information)

![Deluxe Double Room, 1 King Bed, City View](https://images.trvl-media.com/lodging/107000000/106840000/106830300/106830297/96395fe6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/107000000/106840000/106830300/106830297/a206dde5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Comfort Double Room | Private kitchenette](https://images.trvl-media.com/lodging/107000000/106840000/106830300/106830297/b36c7eba.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/107000000/106840000/106830300/106830297/f08791bb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Hampton Bays Hotel on Main

[](https://www.expedia.ca/Hampton-Bays-Hotels-Hampton-Bays-Hotel-On-Main.h106830297.Hotel-Information)

Hampton Bays

7.2/10

Good

(71 reviews)

"Loved the 2 bar options on the property."

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

Jennifer

CA $193

CA $220 total

includes taxes & fees

Mar 6 - Mar 7

[](https://www.expedia.ca/Hampton-Bays-Hotels-Hampton-Bays-Hotel-On-Main.h106830297.Hotel-Information)

![One Bedroom Condo King with Ocean view | Living area](https://images.trvl-media.com/lodging/119000000/118950000/118940400/118940366/fd0f941b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![One Bedroom Condo King with Steam Shower | Living area](https://images.trvl-media.com/lodging/119000000/118950000/118940400/118940366/a9bb02b2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![In-room dining](https://images.trvl-media.com/lodging/119000000/118950000/118940400/118940366/0ca01820.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![One Bedroom Condo King with Ocean view | Beach/ocean view](https://images.trvl-media.com/lodging/119000000/118950000/118940400/118940366/173765ea.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Offshore Residences

[](https://www.expedia.ca/Montauk-Hotels-Offshore-Residences.h118940366.Hotel-Information)

Downtown Montauk

CA $653

CA $902 total

includes taxes & fees

Mar 3 - Mar 4

[](https://www.expedia.ca/Montauk-Hotels-Offshore-Residences.h118940366.Hotel-Information)

![Exterior detail](https://images.trvl-media.com/lodging/8000000/7880000/7874100/7874046/2bfbb5cd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/8000000/7880000/7874100/7874046/w3438h2272x6y0-ee61100c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior detail](https://images.trvl-media.com/lodging/8000000/7880000/7874100/7874046/885537fe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Deluxe Room | Living area](https://images.trvl-media.com/lodging/8000000/7880000/7874100/7874046/0fc29bdf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Southampton Long Island Hotel

[](https://www.expedia.ca/Southampton-Hotels-Southampton-Long-Island-Hotel.h7874046.Hotel-Information)

Southampton

8.6/10

Excellent

(207 reviews)

"Staff was amazing. The room was very clean. I've stayed here numerous times, even on the night before my wedding as I was married in the Hamptons and I highly recommend! "

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

Martine

CA $162

CA $193 total

includes taxes & fees

Mar 31 - Apr 1

[](https://www.expedia.ca/Southampton-Hotels-Southampton-Long-Island-Hotel.h7874046.Hotel-Information)

![Beach nearby](https://images.trvl-media.com/lodging/36000000/35380000/35373800/35373712/e5f6999f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Free continental breakfast on weekends](https://images.trvl-media.com/lodging/36000000/35380000/35373800/35373712/062f5fd3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior detail](https://images.trvl-media.com/lodging/36000000/35380000/35373800/35373712/553f589d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Garden](https://images.trvl-media.com/lodging/36000000/35380000/35373800/35373712/98e9a1b4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Huntting Inn

[](https://www.expedia.ca/East-Hampton-Hotels-The-Huntting-Inn.h35373712.Hotel-Information)

Egypt Lane Historic District

9.0/10

Wonderful

(105 reviews)

"Inn has been newly renovated. Room was spotless. Staff were wonderful. Had an excellent stay. Highly recommend! "

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

Valerie

CA $488

CA $572 total

includes taxes & fees

Mar 16 - Mar 17

[](https://www.expedia.ca/East-Hampton-Hotels-The-Huntting-Inn.h35373712.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/90000000/89990000/89981800/89981758/7b5c5b88.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Reception](https://images.trvl-media.com/lodging/90000000/89990000/89981800/89981758/w1170h1164x0y1-82df79df.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/90000000/89990000/89981800/89981758/w1169h650x0y0-3f68a3a3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Restaurant](https://images.trvl-media.com/lodging/90000000/89990000/89981800/89981758/w1170h1461x0y0-bc75bc71.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Rams Head Inn

[](https://www.expedia.ca/Shelter-Island-Heights-Hotels-The-Rams-Head-Inn.h89981758.Hotel-Information)

Shelter Island Heights

7.6/10

Good

(18 reviews)

"Beautiful views and lovely service "

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

Lana

CA $539

CA $616 total

includes taxes & fees

Mar 6 - Mar 7

[](https://www.expedia.ca/Shelter-Island-Heights-Hotels-The-Rams-Head-Inn.h89981758.Hotel-Information)

![Sundeck](https://images.trvl-media.com/lodging/36000000/35230000/35229400/35229370/dc6eb455.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/36000000/35230000/35229400/35229370/22af8e56.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Meeting facility](https://images.trvl-media.com/lodging/36000000/35230000/35229400/35229370/f0f56ac7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Breakfast served](https://images.trvl-media.com/lodging/36000000/35230000/35229400/35229370/29d9fdab.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Menhaden

[](https://www.expedia.ca/Greenport-Hotels-The-Menhaden.h35229370.Hotel-Information)

Greenport

9.6/10

Exceptional

(177 reviews)

"Wonderful stay in a quaint hotel..The small town was amazing and had such cozy welcoming atmosphere! "

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

Cory

CA $330

CA $432 total

includes taxes & fees

Mar 3 - Mar 4

[](https://www.expedia.ca/Greenport-Hotels-The-Menhaden.h35229370.Hotel-Information)

![Individually decorated, individually furnished, iron/ironing board](https://images.trvl-media.com/lodging/5000000/4210000/4207200/4207136/3dd02542.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Oceanfront 2BD Queen and 2 Twins | Terrace/patio](https://images.trvl-media.com/lodging/5000000/4210000/4207200/4207136/2b9ce1d1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![West Studio Queen and Full | Living area](https://images.trvl-media.com/lodging/5000000/4210000/4207200/4207136/fcfe3def.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/5000000/4210000/4207200/4207136/9b931aba.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Windward Shores Ocean Resort

[](https://www.expedia.ca/Amagansett-Hotels-Windward-Shores-Ocean-Resort.h4207136.Hotel-Information)

Napeague

8.8/10

Excellent

(308 reviews)

"Quiet place, went off season, cooked all meals in the room, good home base to explore the area."

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

Jerry

CA $195

CA $260 total

includes taxes & fees

Mar 3 - Mar 4

[](https://www.expedia.ca/Amagansett-Hotels-Windward-Shores-Ocean-Resort.h4207136.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/77000000/76720000/76716300/76716269/5a27472c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace King](https://images.trvl-media.com/lodging/77000000/76720000/76716300/76716269/efe41897.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace King | Living area](https://images.trvl-media.com/lodging/77000000/76720000/76716300/76716269/582203a3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Restaurant](https://images.trvl-media.com/lodging/77000000/76720000/76716300/76716269/7f5c2322.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Shoals Suites and Slips

[](https://www.expedia.ca/Southold-Hotels-The-Shoals-Suites-And-Slips.h76716269.Hotel-Information)

Southold

9.4/10

Exceptional

(243 reviews)

"Great stay, will definitely go again"

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

ANTONIO J

CA $215

CA $246 total

includes taxes & fees

Mar 15 - Mar 16

[](https://www.expedia.ca/Southold-Hotels-The-Shoals-Suites-And-Slips.h76716269.Hotel-Information)

![Interior detail](https://images.trvl-media.com/lodging/37000000/36880000/36879900/36879849/565c8d39.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Superior Room, 1 King Bed](https://images.trvl-media.com/lodging/37000000/36880000/36879900/36879849/51619c0b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Bathrobes, slippers, towels](https://images.trvl-media.com/lodging/37000000/36880000/36879900/36879849/383870b7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/37000000/36880000/36879900/36879849/2ac0e6c9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Harpoon House

[](https://www.expedia.ca/Southampton-Hotels-Harpoon-House.h36879849.Hotel-Information)

Southampton

8.4/10

Very good

(149 reviews)

"Great spot!"

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

Keith

[](https://www.expedia.ca/Southampton-Hotels-Harpoon-House.h36879849.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/97000000/96720000/96718100/96718085/242d28e0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior detail](https://images.trvl-media.com/lodging/97000000/96720000/96718100/96718085/bb62973a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby sitting area](https://images.trvl-media.com/lodging/97000000/96720000/96718100/96718085/70895a0f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Seasonal outdoor pool](https://images.trvl-media.com/lodging/97000000/96720000/96718100/96718085/59bbc572.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vine & Sand

[](https://www.expedia.ca/Southold-Hotels-Vine-Sand.h96718085.Hotel-Information)

Southold

9.6/10

Exceptional

(15 reviews)

"Wonderful stay"

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

Judy

[](https://www.expedia.ca/Southold-Hotels-Vine-Sand.h96718085.Hotel-Information)

![Front of property](https://images.trvl-media.com/lodging/10000000/9510000/9501200/9501176/a4afa9ce.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)

![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)

![Yoga](https://images.trvl-media.com/lodging/10000000/9510000/9501200/9501176/6f482e8a.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

(303 reviews)

"Clean room, courteous staff and great location "

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

James

[](https://www.expedia.ca/Montauk-Hotels-Daunts-Albatross-Motel.h9501176.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=2026-03-16&endDate=2026-03-17&regionId=553248635976471516&adults=2&sort=RECOMMENDED&openPlayBack=true)

![](https://forever.travel-assets.com/flex/flexmanager/images/2026/02/06/expedia-sale-2026-desktop-us-ca.jpg?impolicy=fcrop&w=1400&h=600&q=mediumHigh)

## 

The Annual Vacation Sale 

Members save up to 40% on hotels and homes. Plan this year’s big trip and save. 

[Book now](https://expedia.ca/deals?rfrr=HTG_SPRING_PROMO_553248635976471516)

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## Learn more about Wainscott Woods

Check out Wolffer Estates Vineyard and Georgica Beach—just a couple of the sights around Wainscott Woods.

[See all hotels in Wainscott Woods](https://www.expedia.ca/Hotel-Search?startDate=2026-03-16&endDate=2026-03-17&adults=2&regionId=553248635976471516)

![If I could only "Trove" a smell.  Delicious  scones and brioches (cinnamon butter and chocolate chip options), etc.](https://images.trvl-media.com/place/6046784/0bf373aa-eedb-4229-8d1d-05cf084d6d0c.jpg?impolicy=fcrop&w=655&h=655&p=1&q=high)

Photo by Miriam Marcus

## Top Wainscott Woods Hotel Reviews

## Recent Reviews in Wainscott Woods

![The Harbor Front Inn](https://images.trvl-media.com/lodging/44000000/43540000/43532300/43532300/46cd22ca_y.jpg)

### The Harbor Front Inn

10/10 Excellent

"Room was beautiful and everyone who worked there was very nice. We’d love to go back! "

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

![Montauk Manor](https://images.trvl-media.com/lodging/13000000/12700000/12694100/12694044/96463a2a_y.jpg)

### Montauk Manor

10/10 Excellent

"Always such a pleasure at the Manor. "

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

![The Sagaponack](https://images.trvl-media.com/lodging/82000000/81150000/81143200/81143153/d64f35e8_y.jpg)

### The Sagaponack

10/10 Excellent

"Enjoyed our stay. Clean room , temperature in room was cozy, bed was comfortable and snack bar in main house was a nice touch."

[](https://expedia.ca/Wainscott-Hotels-The-Wainscott-Inn.h81143153.Hotel-Information)

![The Bentley Hotel Southampton](https://images.trvl-media.com/lodging/54000000/53970000/53963000/53962986/60534d98_y.jpg)

### The Bentley Hotel Southampton

10/10 Excellent

"Nice "

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

![The Maidstone](https://images.trvl-media.com/lodging/10000000/9660000/9652100/9652095/99260f7f_y.jpg)

### The Maidstone

10/10 Excellent

"An absolute gem. Came for a quiet getaway and the perfect storm of calmness. Will is a wonderful host, making sure I was welll taken care of and focusing on every detail. He made sure I was able to check in and reach him during a winter storm and was readily available. The place is wonderful and filled with lots of fireplaces and room amenities that feel spa like and warm. Best night sleep I’ve had in a cloud of pillows and bed, in such a long time. Thank you so much for a wonderful time. "

[](https://expedia.ca/East-Hampton-Hotels-The-Maidstone.h9652095.Hotel-Information)

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

### Sound View Greenport

10/10 Excellent

"The hotel was exceptional! We love staying at soundview during the winter months! "

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

![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

"Greatest "

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

![Offshore Montauk](https://images.trvl-media.com/lodging/114000000/113580000/113578500/113578409/6944012d_y.jpg)

### Offshore Montauk

10/10 Excellent

"The view was beautiful and room was spotless. Robert assisted us to all we needed . Great spot and will definitely book it once again ! "

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

![The Shoals Suites and Slips](https://images.trvl-media.com/lodging/77000000/76720000/76716300/76716269/968755d8_y.jpg)

### The Shoals Suites and Slips

10/10 Excellent

"Clean and spacious room"

[](https://expedia.ca/Southold-Hotels-The-Shoals-Suites-And-Slips.h76716269.Hotel-Information)

## More cheap stays in Wainscott Woods

![The Bentley Hotel Southampton](https://images.trvl-media.com/lodging/54000000/53970000/53963000/53962986/60534d98_y.jpg?impolicy=resizecrop&rw=402&ra=fit)

### The Bentley Hotel Southampton

161 Hills Station Rd Southampton NY

CA $183

CA $210 total

Mar 8 - Mar 9

includes taxes & fees

9.6/10 Exceptional! (441 reviews)

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

![The Atlantic Hotel](https://images.trvl-media.com/lodging/1000000/450000/447900/447803/ad346ab6_y.jpg?impolicy=resizecrop&rw=402&ra=fit)

### The Atlantic Hotel

1655 County Road 39 Southampton NY

CA $171

CA $229 total

Mar 3 - Mar 4

includes taxes & fees

7.2/10 Good! (984 reviews)

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

![Offshore Montauk](https://images.trvl-media.com/lodging/114000000/113580000/113578500/113578409/6944012d_y.jpg?impolicy=resizecrop&rw=402&ra=fit)

### Offshore Montauk

71 S Emerson Ave Montauk NY

CA $150

CA $250 total

Mar 8 - Mar 9

includes taxes & fees

9.4/10 Exceptional! (109 reviews)

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

![Kenny's Tipperary Inn](https://images.trvl-media.com/lodging/9000000/8480000/8475000/8474914/4e86636a_y.jpg?impolicy=resizecrop&rw=402&ra=fit)

### Kenny's Tipperary Inn

432 West Lake Drive Montauk NY

[Get rates](https://expedia.ca/Hotel-Search?startDate=16%2F03%2F2026&endDate=17%2F03%2F2026&selected=8474914&PinnedHotelID=8474914&HadPinnedHotel=true&regionId=553248635976471516)

8.4/10 Very Good! (888 reviews)

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

![Aqua by American Beech - Adults Only](https://images.trvl-media.com/lodging/25000000/24090000/24082000/24081913/deb420de_y.jpg?impolicy=resizecrop&rw=402&ra=fit)

### Aqua by American Beech - Adults Only

15 Bay Ave Riverhead NY

[Get rates](https://expedia.ca/Hotel-Search?startDate=16%2F03%2F2026&endDate=17%2F03%2F2026&selected=24081913&PinnedHotelID=24081913&HadPinnedHotel=true&regionId=553248635976471516)

9.4/10 Exceptional! (316 reviews)

[](https://expedia.ca/Riverhead-Hotels-Aqua-By-American-Beech.h24081913.Hotel-Information)

![Daunt's Albatross Motel](https://images.trvl-media.com/lodging/10000000/9510000/9501200/9501176/a3cd59ff_y.jpg?impolicy=resizecrop&rw=402&ra=fit)

### Daunt's Albatross Motel

44 South Elmwood Ave Montauk NY

[Get rates](https://expedia.ca/Hotel-Search?startDate=16%2F03%2F2026&endDate=17%2F03%2F2026&selected=9501176&PinnedHotelID=9501176&HadPinnedHotel=true&regionId=553248635976471516)

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

## Hotels in Wainscott Woods with star rating

![5 Star Hotels](https://images.trvl-media.com/lodging/1000000/30000/25600/25559/c6e0103a_z.jpg)

5 Star Hotels

2 properties

[](https://expedia.ca/5Star-Wainscott-Woods-Hotels.s50-0-d553248635976471516.Travel-Guide-Filter-Hotels)

![4 Star Hotels](https://images.trvl-media.com/lodging/1000000/30000/23700/23677/6ae928dd_z.jpg)

4 Star Hotels

53 properties

[](https://expedia.ca/4Star-Wainscott-Woods-Hotels.s40-0-d553248635976471516.Travel-Guide-Filter-Hotels)

![3 Star Hotels](https://images.trvl-media.com/lodging/20000000/19690000/19681400/19681371/84fffc75_z.jpg)

3 Star Hotels

231 properties

[](https://expedia.ca/3Star-Wainscott-Woods-Hotels.s30-0-d553248635976471516.Travel-Guide-Filter-Hotels)

![2 Star Hotels](https://images.trvl-media.com/lodging/92000000/91830000/91828000/91827910/6717a2ac_z.jpg)

2 Star Hotels

232 properties

[](https://expedia.ca/2Star-Wainscott-Woods-Hotels.s20-0-d553248635976471516.Travel-Guide-Filter-Hotels)

## Frequently asked questions

### What is the best area to stay in Wainscott Woods?

> This area is the heart of Wainscott Woods, offering a convenient balance of local amenities and access to the region's natural beauty. It's characterised by its charming, well-maintained homes and a few select local businesses, including a renowned bakery and a couple of independent shops. The layout is relatively spread out, with properties often featuring spacious gardens, providing a sense of privacy and tranquility.
> 
>   
> Couples looking for a peaceful escape will find this area particularly appealing. The proximity to Wainscott Pond and the nearby ocean beaches means easy access to scenic walks and quiet moments by the water. There are also high-end dining options within a short drive, superb for an evening out.
> 
>   
> For families, staying near the village centre offers the convenience of being close to essential services while still enjoying a relaxed, residential atmosphere. The open spaces and access to nature provide plenty of opportunities for children to explore.

### When is the best time to go to Wainscott Woods?

> The summer, particularly July and August, is when Wainscott Woods truly comes alive. The weather is consistently warm and sunny, great for enjoying the beaches and outdoor activities. This is peak season, so while it's the busiest, it's also when all facilities and attractions are fully operational, offering the widest range of experiences. Expect lovely warm days and pleasant evenings.
> 
>   
> For those who prefer a slightly quieter experience but still want good weather, June and September are excellent choices. In June, the weather is reliably warm, and the area is less crowded than in the peak summer months. September offers similarly pleasant temperatures, often with the added benefit of slightly cooler evenings and fewer people, making it ideal for relaxing beach days and exploring the local area at a more leisurely pace.
> 
>   
> Late spring (May) and early autumn (October) also offer a pleasant experience. While the weather can be a little cooler and some establishments might have reduced hours, you'll find great value and a very peaceful environment.

### Can I cancel my hotel reservation on Expedia?

### How can I save on a Wainscott Woods hotel booking with Expedia?

### How much is the nightly rate at a Wainscott Woods hotel?

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- [Flights from Bridgehampton ](https://www.expedia.ca/lp/flights/6130684/flights-from-bridgehampton)
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- [Flights from Edmonton (YEA) to East Hampton (HTO) ](https://www.expedia.ca/lp/flights/yea/hto/edmonton-to-east-hampton)
- [Flights from Toronto (YYZ) to New York (NYC) ](https://www.expedia.ca/lp/flights/yyz/nyc/toronto-to-new-york)

- [Visit Bridgehampton ](https://www.expedia.ca/Bridgehampton.dx6130684)
- [East Hampton Main Beach ](https://www.expedia.ca/East-Hampton-Main-Beach-East-Hampton.d6326946.Vacation-Attraction)
- [Georgica Beach ](https://www.expedia.ca/Georgica-Beach-East-Hampton.d553248621554185025.Vacation-Attraction)
- [Longhouse Reserve ](https://www.expedia.ca/LongHouse-Reserve-East-Hampton.d6326942.Vacation-Attraction)
- [Visit Sag Harbor ](https://www.expedia.ca/Sag-Harbor.dx154327)
- [Visit Village of East Hampton ](https://www.expedia.ca/Village-Of-East-Hampton.dx553248634998945224)
- [Wolffer Estates Vineyard ](https://www.expedia.ca/Wolffer-Estates-Vineyard-Sagaponack.d6064497.Vacation-Attraction)

- [Car rental Bridgehampton ](https://www.expedia.ca/Car-Rentals-In-Bridgehampton.d6130684.Car-Rental-Guide)
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- [Enterprise Rental Cars in East Hampton ](https://www.expedia.ca/Enterprise-Car-Rentals-In-East-Hampton.d6069886-c15.Car-Rental-Guide-Suppliers)
- [Hertz Rental Cars in East Hampton ](https://www.expedia.ca/Hertz-Car-Rentals-In-East-Hampton.d6069886-c40.Car-Rental-Guide-Suppliers)

- [Bridgehampton Vacation Rentals ](https://www.expedia.ca/Bridgehampton-Vacation-Rentals.d6130684.Travel-Guide-VacationRentals)
- [Sagaponack Vacation Rentals ](https://www.expedia.ca/Sagaponack-Vacation-Rentals.d3000449529.Travel-Guide-VacationRentals)

- [Things to do in Bridgehampton ](https://www.expedia.ca/Things-To-Do-In-Bridgehampton.d6130684.Travel-Guide-Activities)

- [Book Hotels in Wainscott Woods on Expedia.com ](https://www.expedia.com/Wainscott-Woods-Hotels.d553248635976471516.Travel-Guide-Hotels)

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