Title: 4 Stars Hotels in Southold, New York from CA $252 - Find Cheap Southold Hotels With 4 Stars | Expedia.ca

[Southold Travel Guide](https://expedia.ca/Southold.dx183719)[Hotels in Southold](https://expedia.ca/Southold-Hotels.d183719.Travel-Guide-Hotels)[Vacation Rentals in Southold](https://expedia.ca/Southold-Vacation-Rentals.d183719.Travel-Guide-VacationRentals)[Flights to Southold](https://expedia.ca/Cheap-Flights-To-Southold.d183719.Travel-Guide-Flights)[Things to do in Southold](https://expedia.ca/Things-To-Do-In-Southold.d183719.Travel-Guide-Activities)[Southold Car Rentals](https://expedia.ca/Car-Rentals-In-Southold.d183719.Car-Rental-Guide)[Southold Vacation Packages](https://expedia.ca/Southold.d183719.Destination-Travel-Guides)

![Day trip to North Fork wineries. Stopped at this beach for a break before driving back to the city. #sunset #nature #wanderlust #waterlust #beach #colorful #citylife #NikonD7100 #Manfratto tripod. ](https://images.trvl-media.com/place/183719/81468873-e891-4a92-aa0d-1938572ea198.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

Photo by Benny Goh 

![](https://images.trvl-media.com/place/183719/81468873-e891-4a92-aa0d-1938572ea198.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

- ![](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 Southold 4 Star Hotels

Tonight

[Jan 22 - Jan 23](https://www.expedia.ca/Hotel-Search?regionId=183719&startDate=2026-01-22&endDate=2026-01-23&adults=2&star=40&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

Tomorrow

[Jan 23 - Jan 24](https://www.expedia.ca/Hotel-Search?regionId=183719&startDate=2026-01-23&endDate=2026-01-24&adults=2&star=40&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

This weekend

[Jan 23 - Jan 25](https://www.expedia.ca/Hotel-Search?regionId=183719&startDate=2026-01-23&endDate=2026-01-25&adults=2&star=40&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

Next weekend

[Jan 30 - Feb 1](https://www.expedia.ca/Hotel-Search?regionId=183719&startDate=2026-01-30&endDate=2026-02-01&adults=2&star=40&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

## Our top choices for Southold 4-star hotels

![Exterior](https://images.trvl-media.com/lodging/2000000/1210000/1209400/1209378/1ec18076.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/2000000/1210000/1209400/1209378/1ef9d54f.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/2000000/1210000/1209400/1209378/c4093211.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Suite, 2 Bedrooms | View from room](https://images.trvl-media.com/lodging/2000000/1210000/1209400/1209378/79675399.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Madison Beach Hotel

[](https://www.expedia.ca/Madison-Hotels-Madison-Beach-Hotel.h1209378.Hotel-Information)

Madison Center

9.4/10

Exceptional

(344 reviews)

"The Spa was wonderful and the staff was attentive and helpful. "

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

Emma

CA $339

CA $390 total

includes taxes & fees

Feb 19 - Feb 20

[](https://www.expedia.ca/Madison-Hotels-Madison-Beach-Hotel.h1209378.Hotel-Information)

![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)

![Yoga](https://images.trvl-media.com/lodging/16000000/15280000/15273200/15273178/a7c5a78c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Deluxe Room, 1 King Bed](https://images.trvl-media.com/lodging/16000000/15280000/15273200/15273178/ac1b5094.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

8.4/10

Very good

(607 reviews)

"Nice place"

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

Mateusz

CA $186

CA $252 total

includes taxes & fees

Jan 27 - Jan 28

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

![Seasonal outdoor pool, open 8:00 AM to 8:00 PM, pool umbrellas](https://images.trvl-media.com/lodging/84000000/83520000/83519500/83519458/aa9cc8cf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Couples treatment rooms, body treatments, hot stone massages](https://images.trvl-media.com/lodging/84000000/83520000/83519500/83519458/1782c2d9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Daily cooked-to-order breakfast (USD 25 per person)](https://images.trvl-media.com/lodging/84000000/83520000/83519500/83519458/34ace0dc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Bicycling](https://images.trvl-media.com/lodging/84000000/83520000/83519500/83519458/6893dda0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Canoe Place Inn and Cottages

[](https://www.expedia.ca/Hampton-Bays-Hotels-Canoe-Place-Inn-And-Cottages.h83519458.Hotel-Information)

Hampton Bays

9.8/10

Exceptional

(60 reviews)

"Amazing property. Really enjoyed our stay."

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

Dave

[](https://www.expedia.ca/Hampton-Bays-Hotels-Canoe-Place-Inn-And-Cottages.h83519458.Hotel-Information)

![View from property](https://images.trvl-media.com/lodging/24000000/23260000/23252100/23252049/52063f27.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby sitting area](https://images.trvl-media.com/lodging/24000000/23260000/23252100/23252049/338f251a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Suite, 1 King Bed with Sofa bed](https://images.trvl-media.com/lodging/24000000/23260000/23252100/23252049/7418aad9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Free daily on-the-go breakfast](https://images.trvl-media.com/lodging/24000000/23260000/23252100/23252049/ecd1e47d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Journey East Hampton

[](https://www.expedia.ca/East-Hampton-Hotels-Journey-East-Hampton.h23252049.Hotel-Information)

East Hampton North

9.2/10

Wonderful

(162 reviews)

"Amazing stay"

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

Liana

CA $255

CA $321 total

includes taxes & fees

Feb 1 - Feb 2

[](https://www.expedia.ca/East-Hampton-Hotels-Journey-East-Hampton.h23252049.Hotel-Information)

![Beach bar](https://images.trvl-media.com/lodging/92000000/91070000/91069000/91068954/52eefc00.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Waterfront Beach Shack Studio](https://images.trvl-media.com/lodging/92000000/91070000/91069000/91068954/1c4953c1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Waterfront Beach Shack Studio](https://images.trvl-media.com/lodging/92000000/91070000/91069000/91068954/fe6e5945.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![View from room](https://images.trvl-media.com/lodging/92000000/91070000/91069000/91068954/2d824970.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Silver Sands Motel & Beach Bungalows

[](https://www.expedia.ca/Greenport-Hotels-Silver-Sands.h91068954.Hotel-Information)

Greenport

9.8/10

Exceptional

(144 reviews)

"Everything was excellent, best hotel on the north fork. "

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

Dan

[](https://www.expedia.ca/Greenport-Hotels-Silver-Sands.h91068954.Hotel-Information)

![Beach nearby, white sand, sun loungers, beach umbrellas](https://images.trvl-media.com/lodging/11000000/10550000/10547800/10547745/028711b6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Frette Italian sheets, premium bedding, down comforters](https://images.trvl-media.com/lodging/11000000/10550000/10547800/10547745/06408853.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Frette Italian sheets, premium bedding, down comforters](https://images.trvl-media.com/lodging/11000000/10550000/10547800/10547745/a3bdf0f5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Aerial view](https://images.trvl-media.com/lodging/11000000/10550000/10547800/10547745/56f0c16b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Roundtree, Amagansett

[](https://www.expedia.ca/Amagansett-Hotels-The-Roundtree.h10547745.Hotel-Information)

Amagansett North

10/10

Exceptional

(92 reviews)

"Located right in the center of town, the grounds on this property are wonderful with clean and comfortable suites. The staff are engaging and sweet. And the late night cookies are a sweet touch."

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

adam

CA $822

CA $986 total

includes taxes & fees

Feb 22 - Feb 23

[](https://www.expedia.ca/Amagansett-Hotels-The-Roundtree.h10547745.Hotel-Information)

![Breakfast and dinner served](https://images.trvl-media.com/lodging/2000000/1490000/1484300/1484254/fb2335a2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Luxury Room, 1 Bedroom, Non Smoking (Room 322)](https://images.trvl-media.com/lodging/2000000/1490000/1484300/1484254/e11ede87.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior entrance](https://images.trvl-media.com/lodging/2000000/1490000/1484300/1484254/98c270a2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/2000000/1490000/1484300/1484254/a99c206a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Copper Beech Inn

[](https://www.expedia.ca/Old-Saybrook-Hotels-Copper-Beech-Inn.h1484254.Hotel-Information)

Ivoryton

8.6/10

Excellent

(506 reviews)

"Very nice property. Very clean. Staff was very nice - very good breakfast. "

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

Marilyn

CA $386

CA $444 total

includes taxes & fees

Feb 22 - Feb 23

[](https://www.expedia.ca/Old-Saybrook-Hotels-Copper-Beech-Inn.h1484254.Hotel-Information)

![2 restaurants, American cuisine](https://images.trvl-media.com/lodging/2000000/1090000/1085700/1085655/d3bf1318.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Garden](https://images.trvl-media.com/lodging/2000000/1090000/1085700/1085655/67db121e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Reception](https://images.trvl-media.com/lodging/2000000/1090000/1085700/1085655/d269b9f6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Carriage House | Living area](https://images.trvl-media.com/lodging/2000000/1090000/1085700/1085655/6a224301.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The 1770 House Restaurant & Inn

[](https://www.expedia.ca/East-Hampton-Hotels-The-1770-House-Restaurant-Inn.h1085655.Hotel-Information)

East Hampton

9.8/10

Exceptional

(162 reviews)

"The staff was incredibly genuine and the property felt intimate and comfortable."

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

Aniya

CA $408

CA $558 total

includes taxes & fees

Feb 8 - Feb 9

[](https://www.expedia.ca/East-Hampton-Hotels-The-1770-House-Restaurant-Inn.h1085655.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)

![Library](https://images.trvl-media.com/lodging/6000000/5590000/5581400/5581380/88ff99e0.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

(140 reviews)

"Our second home :)"

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

olivia

CA $690

CA $794 total

includes taxes & fees

Jan 29 - Jan 30

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

![Property entrance](https://images.trvl-media.com/lodging/10000000/9660000/9652100/9652095/d7688cb9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior detail](https://images.trvl-media.com/lodging/10000000/9660000/9652100/9652095/32e03a99.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Classic Queen](https://images.trvl-media.com/lodging/10000000/9660000/9652100/9652095/6ddcc118.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Garden](https://images.trvl-media.com/lodging/10000000/9660000/9652100/9652095/3b892c7c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Maidstone

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

East Hampton

8.0/10

Very good

(150 reviews)

"We had a wonderful stay "

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

Sabrina

CA $241

CA $276 total

includes taxes & fees

Feb 5 - Feb 6

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

![Terrace/patio](https://images.trvl-media.com/lodging/7000000/6480000/6473500/6473437/daf99b53.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/7000000/6480000/6473500/6473437/ad990fb5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Breakfast, lunch, dinner served; local cuisine, ocean views ](https://images.trvl-media.com/lodging/7000000/6480000/6473500/6473437/w2880h1617x0y0-215d1f51.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Premium bedding, individually furnished, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/7000000/6480000/6473500/6473437/7a760b80.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Pridwin Hotel

[](https://www.expedia.ca/Shelter-Island-Heights-Hotels-The-Pridwin-Hotel.h6473437.Hotel-Information)

Shelter Island Heights

9.6/10

Exceptional

(84 reviews)

"Overall the places is nice, clean and great views"

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

Dianne

[](https://www.expedia.ca/Shelter-Island-Heights-Hotels-The-Pridwin-Hotel.h6473437.Hotel-Information)

![Aerial view](https://images.trvl-media.com/lodging/32000000/31010000/31007600/31007589/4db6535f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Aerial view](https://images.trvl-media.com/lodging/32000000/31010000/31007600/31007589/d9c11af0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Beach nearby](https://images.trvl-media.com/lodging/32000000/31010000/31007600/31007589/6809b461.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/32000000/31010000/31007600/31007589/bbbb0bf2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### East Hampton Art House Bed & Breakfast

[](https://www.expedia.ca/East-Hampton-Hotels-East-Hampton-Art-House-Bed-Breakfast.h31007589.Hotel-Information)

Clearwater Beach

9.6/10

Exceptional

(65 reviews)

"First class outstanding in every way"

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

Steve

[](https://www.expedia.ca/East-Hampton-Hotels-East-Hampton-Art-House-Bed-Breakfast.h31007589.Hotel-Information)

![Miss Anna James Room](https://images.trvl-media.com/lodging/79000000/78200000/78191100/78191036/w848h631x48y3-ad11e9c5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Katharine Hepburn Room](https://images.trvl-media.com/lodging/79000000/78200000/78191100/78191036/20c673f8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Miss Anna James Room](https://images.trvl-media.com/lodging/79000000/78200000/78191100/78191036/dc6ad011.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Point of interest](https://images.trvl-media.com/lodging/79000000/78200000/78191100/78191036/f09f38b4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### James Pharmacy Bed & Breakfast

[](https://www.expedia.ca/Old-Saybrook-Hotels-James-Pharmacy-Bed-Breakfast.h78191036.Hotel-Information)

Old Saybrook Center

9.0/10

Wonderful

(23 reviews)

"Cute B&B, very nice room, check-in worked well"

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

Isolde

[](https://www.expedia.ca/Old-Saybrook-Hotels-James-Pharmacy-Bed-Breakfast.h78191036.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)

![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)

![Reception](https://images.trvl-media.com/lodging/90000000/89990000/89981800/89981758/w1170h1164x0y1-82df79df.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

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

![Private kitchen](https://images.trvl-media.com/lodging/110000000/109670000/109662700/109662697/1190496c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Front of property](https://images.trvl-media.com/lodging/110000000/109670000/109662700/109662697/5689ac07.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Flat-screen TV](https://images.trvl-media.com/lodging/110000000/109670000/109662700/109662697/ef1a1d3d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Flat-screen TV](https://images.trvl-media.com/lodging/110000000/109670000/109662700/109662697/934c8d81.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Canoe Place Waterfront Residences

[](https://www.expedia.ca/Hampton-Bays-Hotels-Canoe-Place-Waterfront-Residences.h109662697.Hotel-Information)

Hampton Bays

10/10

Exceptional

(1 review)

CA $1,701

CA $2,061 total

includes taxes & fees

Jan 29 - Jan 30

[](https://www.expedia.ca/Hampton-Bays-Hotels-Canoe-Place-Waterfront-Residences.h109662697.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/2000000/1150000/1148900/1148848/b6601c88.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Restaurant](https://images.trvl-media.com/lodging/2000000/1150000/1148900/1148848/94958fa7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Restaurant](https://images.trvl-media.com/lodging/2000000/1150000/1148900/1148848/75ed01fe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/2000000/1150000/1148900/1148848/c880734c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Faraway Sag Harbor

[](https://www.expedia.ca/Sag-Harbor-Hotels-Barons-Cove.h1148848.Hotel-Information)

Sag Harbor

9.0/10

Wonderful

(292 reviews)

"Parking was free and really easy. Great proximity to the main street of town—you can easily walk, but it's not too close where it gets loud at night. The front staff and cleaning team were all lovely and super helpful. We loved the coffee bar in the mornings. "

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

Katherine

[](https://www.expedia.ca/Sag-Harbor-Hotels-Barons-Cove.h1148848.Hotel-Information)

![Reception hall](https://images.trvl-media.com/lodging/13000000/12780000/12779400/12779331/59df497c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Reception](https://images.trvl-media.com/lodging/13000000/12780000/12779400/12779331/7e250b31.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Front of property](https://images.trvl-media.com/lodging/13000000/12780000/12779400/12779331/2c06a5e8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/13000000/12780000/12779400/12779331/3583b9cc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### 434 on Main

[](https://www.expedia.ca/Amagansett-Hotels-434-On-Main.h12779331.Hotel-Information)

Amagansett North

10/10

Exceptional

(36 reviews)

"Great hosts"

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

David

[](https://www.expedia.ca/Amagansett-Hotels-434-On-Main.h12779331.Hotel-Information)

![Smart TV, fireplace, table tennis, stereo](https://images.trvl-media.com/lodging/54000000/53900000/53890800/53890717/w3455h2297x0y1-853cf7f5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/54000000/53900000/53890800/53890717/367ac402_edited_0ea9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/54000000/53900000/53890800/53890717/754e4cf1_edited_1afd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/54000000/53900000/53890800/53890717/5ff0ea97.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Pool/5 min walk to Beach/Restaurants/Museums- Village House w/backyard

[](https://www.expedia.ca/Sag-Harbor-Hotels-5-Min-Walk-To-Beach-Restaurants-Museums-Village-House-With-Large-Backyard.h53890717.Hotel-Information)

Sag Harbor

10/10

Exceptional

(11 reviews)

"Great house, close to the town, would definitely rent again "

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

Jared W.

[](https://www.expedia.ca/Sag-Harbor-Hotels-5-Min-Walk-To-Beach-Restaurants-Museums-Village-House-With-Large-Backyard.h53890717.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/36000000/35040000/35037700/35037604/3c3104d4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/36000000/35040000/35037700/35037604/7dfc3af5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor spa tub](https://images.trvl-media.com/lodging/36000000/35040000/35037700/35037604/a812151b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/36000000/35040000/35037700/35037604/094d4d1c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Historic House Getaway

[](https://www.expedia.ca/Peconic-Hotels-NORTHFORK-COTTAGE-With-POOL-HOTTUB.h35037604.Hotel-Information)

Peconic

9.6/10

Exceptional

(139 reviews)

"Friends enjoyed the pool and jacuzzi and liked the house"

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

Fionan M.

[](https://www.expedia.ca/Peconic-Hotels-NORTHFORK-COTTAGE-With-POOL-HOTTUB.h35037604.Hotel-Information)

![Front of property](https://images.trvl-media.com/lodging/91000000/90790000/90786400/90786314/07d5462f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Romantic Room](https://images.trvl-media.com/lodging/91000000/90790000/90786400/90786314/06263549.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/91000000/90790000/90786400/90786314/7187781f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/91000000/90790000/90786400/90786314/6bd86bf4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Farmhouse Bed and Breakfast

[](https://www.expedia.ca/Cutchogue-Hotels-The-Farmhouse-Bed-And-Breakfast.h90786314.Hotel-Information)

Cutchogue

10/10

Exceptional

(13 reviews)

"very comfortable stay. "

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

Valentine

[](https://www.expedia.ca/Cutchogue-Hotels-The-Farmhouse-Bed-And-Breakfast.h90786314.Hotel-Information)

![](https://a.travel-assets.com/pricing-claim/sparkle_dark.svg)

Save an average of 15% on thousands of hotels when you're signed in

[Sign in

](https://expedia.ca/user/signin?ckoflag=0&uurl=e3id%3Dredr%26rurl%3D%2F4Star-Southold-Hotels.s40-0-d183719.Travel-Guide-Filter-Hotels)[

Sign up, it's free

](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2F4Star-Southold-Hotels.s40-0-d183719.Travel-Guide-Filter-Hotels)

## Explore similar 5-star hotels

Many 5-star hotels have the same amenities as 4-star hotels. See all 5-star hotels in Southold.

![Mill House Inn](https://images.trvl-media.com/lodging/3000000/2870000/2861900/2861838/e0e0def6_y.jpg?impolicy=resizecrop&rw=402&ra=fit)

### Mill House Inn

31 North Main Street East Hampton NY

CA $346

CA $435 total

Jan 29 - Jan 30

includes taxes & fees

8.8/10 Excellent! (77 reviews)

[](https://expedia.ca/East-Hampton-Hotels-Mill-House-Inn.h2861838.Hotel-Information)

![Casa Newmark Holiday home 7 BestStayz.1](https://images.trvl-media.com/lodging/33000000/32420000/32411100/32411044/23f4590c_y.jpg?impolicy=resizecrop&rw=402&ra=fit)

### Casa Newmark Holiday home 7 BestStayz.1

112 Northwest Path Sagaponack NY

[Get rates](https://expedia.ca/Hotel-Search?startDate=06%2F02%2F2026&endDate=07%2F02%2F2026&selected=32411044&PinnedHotelID=32411044&HadPinnedHotel=true&regionId=183719)

[](https://expedia.ca/Sagaponack-Hotels-Casa-Newmark-Holiday-Home-7-BestStayz1.h32411044.Hotel-Information)

Still don't see what you're looking for?

[See all properties in Southold.](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=24%2F01%2F2026&endDate=25%2F01%2F2026&regionId=183719&star=40)

You can also use these popular filters to refine your search.

[Pool](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=24%2F01%2F2026&endDate=25%2F01%2F2026&regionId=183719&star=40&star=40&amenities=POOL)[Spa](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=24%2F01%2F2026&endDate=25%2F01%2F2026&regionId=183719&star=40&star=40&amenities=SPA_ON_SITE)[Hot tub](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=24%2F01%2F2026&endDate=25%2F01%2F2026&regionId=183719&star=40&star=40&amenities=HOT_TUB)[Breakfast included](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=24%2F01%2F2026&endDate=25%2F01%2F2026&regionId=183719&star=40&star=40&amenities=FREE_BREAKFAST)[Waterpark](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=24%2F01%2F2026&endDate=25%2F01%2F2026&regionId=183719&star=40&star=40&amenities=WATER_PARK)

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.

## Learn more about Southold

Vineyards and farm stands dot the landscape of this North Fork gem, inviting visitors to sample local wines and fresh produce. Stroll along the pebble beaches, explore historic lighthouses, or take a ferry to nearby Shelter Island for a day trip.

[See all hotels in Southold](https://www.expedia.ca/Hotel-Search?startDate=2026-02-06&endDate=2026-02-07&adults=2&regionId=183719)

![Day trip to North Fork wineries. Stopped at this beach for a break before driving back to the city. #sunset #nature #wanderlust #waterlust #beach #colorful #citylife #NikonD7100 #Manfratto tripod. ](https://images.trvl-media.com/place/183719/81468873-e891-4a92-aa0d-1938572ea198.jpg?impolicy=fcrop&w=899&h=600&p=1&q=high)

Photo by Benny Goh 

## Top Southold Hotel Reviews

![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)

## Find out more about Southold

If you’re looking for a spot with great rates, just-for-you amenities, and a world of luxurious little perks, the best 4 Stars hotels in Southold are calling your name. Known for providing first-rate service in amazing locations, each of the Southold 4 Stars hotels lets discerning travelers bask in an unforgettable experience.

Kick back in your spacious room. Relax in the lobby’s sumptuous surroundings. Start the day with delicious room service, and then use the complimentary body care items to freshen up before you head out for the day.

It’s all waiting for you at the top four star hotels in Southold. Plus, when you book with Expedia.ca, you might find a cheap deal on a 4 Stars hotel in Southold, New York, neighbourhoods near the most popular attractions, so you can see the sights and bask in the discounts all in one trip. Whether you’re planning a romantic retreat or simply want to experience everything the area has to offer, the top Southold hotels with 4 Stars provide everything you need to unwind in style.

## Frequently asked questions

### What are the best 4-star hotels in Southold?

### How much does it cost to stay in a 4-star hotel in Southold?

> - Search for the lowest price from CA $435

### What's the difference between 5-star and 4-star hotels in Southold?

## Explore a world of travel with Expedia

- Lodging
- Flights
- Packages
- Cars
- Vacation Rental
- Other
- More ways to book

- [1 Star Hotels in Hamptons ](https://www.expedia.ca/1Star-Hamptons-Hotels.s10-0-d6056452.Travel-Guide-Filter-Hotels)
- [1 Star Hotels in Plandome Heights ](https://www.expedia.ca/1Star-Plandome-Heights-Hotels.s10-0-d553248634998735582.Travel-Guide-Filter-Hotels)
- [2 Star Hotels in Lindenhurst ](https://www.expedia.ca/2Star-Lindenhurst-Hotels.s20-0-d183693.Travel-Guide-Filter-Hotels)
- [2 Star Hotels in Manorhaven ](https://www.expedia.ca/2Star-Manorhaven-Hotels.s20-0-d553248634998695724.Travel-Guide-Filter-Hotels)
- [2 Star Hotels in Wheatley Heights ](https://www.expedia.ca/2Star-Wheatley-Heights-Hotels.s20-0-d3000450118.Travel-Guide-Filter-Hotels)
- [3 Star Hotels in Flanders ](https://www.expedia.ca/3Star-Flanders-Hotels.s30-0-d3000475689.Travel-Guide-Filter-Hotels)
- [3 Star Hotels in Greenport ](https://www.expedia.ca/3Star-Greenport-Hotels.s30-0-d110728.Travel-Guide-Filter-Hotels)
- [3 Star Hotels in Jones Beach Island ](https://www.expedia.ca/3Star-Jones-Beach-Island-Hotels.s30-0-d553248635083904017.Travel-Guide-Filter-Hotels)
- [3 Star Hotels in Sag Harbor ](https://www.expedia.ca/3Star-Sag-Harbor-Hotels.s30-0-d154327.Travel-Guide-Filter-Hotels)
- [3 Star Hotels in Speonk ](https://www.expedia.ca/3Star-Speonk-Hotels.s30-0-d553248635942949979.Travel-Guide-Filter-Hotels)
- [4 Star Hotels in Armonk ](https://www.expedia.ca/4Star-Armonk-Hotels.s40-0-d9324.Travel-Guide-Filter-Hotels)
- [4 Star Hotels in Huntington Bay ](https://www.expedia.ca/4Star-Huntington-Bay-Hotels.s40-0-d553248635975876613.Travel-Guide-Filter-Hotels)
- [4 Star Hotels in Long Island ](https://www.expedia.ca/4Star-Long-Island-Hotels.s40-0-d602887.Travel-Guide-Filter-Hotels)
- [4 Star Hotels in Montauk ](https://www.expedia.ca/4Star-Montauk-Hotels.s40-0-d10637.Travel-Guide-Filter-Hotels)
- [4 Star Hotels in Rye Brook ](https://www.expedia.ca/4Star-Rye-Brook-Hotels.s40-0-d10820.Travel-Guide-Filter-Hotels)
- [4 Star Hotels in Sag Harbor ](https://www.expedia.ca/4Star-Sag-Harbor-Hotels.s40-0-d154327.Travel-Guide-Filter-Hotels)
- [5 Star Hotels in Amagansett Lanes ](https://www.expedia.ca/5Star-Amagansett-Lanes-Amagansett-Hotels.s50-n553248635976471387-0.Travel-Guide-Filter-Hotels)
- [5 Star Hotels in Beach Hampton ](https://www.expedia.ca/5Star-Beach-Hampton-Amagansett-Hotels.s50-n553248635976481908-0.Travel-Guide-Filter-Hotels)
- [5 Star Hotels in Dix Hills ](https://www.expedia.ca/5Star-Dix-Hills-Hotels.s50-0-d3000448347.Travel-Guide-Filter-Hotels)
- [5 Star Hotels in Fire Island ](https://www.expedia.ca/5Star-Fire-Island-Hotels.s50-0-d183671.Travel-Guide-Filter-Hotels)
- [5 Star Hotels in Greenport ](https://www.expedia.ca/5Star-Greenport-Hotels.s50-0-d110728.Travel-Guide-Filter-Hotels)
- [5 Star Hotels in Hamptons ](https://www.expedia.ca/5Star-Hamptons-Hotels.s50-0-d6056452.Travel-Guide-Filter-Hotels)
- [5 Star Hotels in Indian Island County Park ](https://www.expedia.ca/5Star-Indian-Island-County-Park-Hotels.s50-0-d6224460.Travel-Guide-Filter-Hotels)
- [5 Star Hotels in Jones Beach Island ](https://www.expedia.ca/5Star-Jones-Beach-Island-Hotels.s50-0-d553248635083904017.Travel-Guide-Filter-Hotels)
- [5 Star Hotels in Long Island ](https://www.expedia.ca/5Star-Long-Island-Hotels.s50-0-d602887.Travel-Guide-Filter-Hotels)
- [5 Star Hotels in Montauk ](https://www.expedia.ca/5Star-Montauk-Hotels.s50-0-d10637.Travel-Guide-Filter-Hotels)
- [5 Star Hotels in North Fork ](https://www.expedia.ca/5Star-North-Fork-Hotels.s50-0-d553248635074841663.Travel-Guide-Filter-Hotels)
- [5 Star Hotels in Oakdale ](https://www.expedia.ca/5Star-Oakdale-Hotels.s50-0-d9561.Travel-Guide-Filter-Hotels)
- [5 Star Hotels in Sag Harbor ](https://www.expedia.ca/5Star-Sag-Harbor-Hotels.s50-0-d154327.Travel-Guide-Filter-Hotels)
- [5 Star Hotels in West Islip ](https://www.expedia.ca/5Star-West-Islip-Hotels.s50-0-d553248634999217120.Travel-Guide-Filter-Hotels)
- [Hotels near Crescent Beach ](https://www.expedia.ca/Crescent-Beach-Hotels.0-l553248621554204758-0.Travel-Guide-Filter-Hotels)
- [Town of Southold Town Hotels ](https://www.expedia.ca/Destinations-In-Town-Of-Southold-Town.d553248635976002319.Hotel-Destinations)
- [B&B in Greenport ](https://www.expedia.ca/Greenport-Bed-And-Breakfast.d110728-aaBedAndBreakfast.Travel-Guide-Accommodation)
- [Cabin Rentals in Greenport ](https://www.expedia.ca/Greenport-Cabins.d110728-aaCabins.Travel-Guide-Accommodation)
- [Adults Only Resorts & in Greenport ](https://www.expedia.ca/Greenport-Hotels-Adults-Only-Resorts.0-0-d110728-tAdultsOnlyResorts.Travel-Guide-Filter-Hotels)
- [Beach Hotel Hotels in Greenport ](https://www.expedia.ca/Greenport-Hotels-Beach-Hotel.0-0-d110728-tBeachHotel.Travel-Guide-Filter-Hotels)
- [Boutique Hotels in Greenport ](https://www.expedia.ca/Greenport-Hotels-Boutique-Hotel.0-0-d110728-tBoutiqueHotel.Travel-Guide-Filter-Hotels)
- [Cheap Hotels in Greenport ](https://www.expedia.ca/Greenport-Hotels-Cheap-Hotels.0-0-d110728-tCheapHotels.Travel-Guide-Filter-Hotels)
- [Hotels & Resorts for Couples in Greenport ](https://www.expedia.ca/Greenport-Hotels-Couples-Resorts-Hotels.0-0-d110728-tCouplesResortsHotels.Travel-Guide-Filter-Hotels)
- [Lake Hotels in Greenport ](https://www.expedia.ca/Greenport-Hotels-Lake-Hotels.0-0-d110728-tLakeHotels.Travel-Guide-Filter-Hotels)
- [Luxury Hotels in Greenport ](https://www.expedia.ca/Greenport-Hotels-Luxury-Hotel.0-0-d110728-tLuxuryHotel.Travel-Guide-Filter-Hotels)
- [Oceanfront Hotels in Greenport ](https://www.expedia.ca/Greenport-Hotels-Oceanfront-Hotels.0-0-d110728-tOceanfrontHotels.Travel-Guide-Filter-Hotels)
- [Shopping Hotels in Greenport ](https://www.expedia.ca/Greenport-Hotels-Shopping-Hotel.0-0-d110728-tShoppingHotel.Travel-Guide-Filter-Hotels)
- [Spa Hotels in Greenport ](https://www.expedia.ca/Greenport-Hotels-Spa-Hotel.0-0-d110728-tSpaHotel.Travel-Guide-Filter-Hotels)
- [Waterpark Hotels in Greenport ](https://www.expedia.ca/Greenport-Hotels-Waterpark-Hotels.0-0-d110728-tWaterparkHotels.Travel-Guide-Filter-Hotels)
- [Greenport Hotels ](https://www.expedia.ca/Greenport-Hotels.d110728.Travel-Guide-Hotels)
- [Motels in Greenport ](https://www.expedia.ca/Greenport-Motels.d110728-aaMotels.Travel-Guide-Accommodation)
- [Hotels near Greenport Station ](https://www.expedia.ca/Greenport-Station-Hotels.d6186190.Travel-Guide-Hotels)
- [Beach Hotel Hotels in Greenport West ](https://www.expedia.ca/Greenport-West-Hotels-Beach-Hotel.0-0-d553248635975876381-tBeachHotel.Travel-Guide-Filter-Hotels)
- [Cheap Hotels in Greenport West ](https://www.expedia.ca/Greenport-West-Hotels-Cheap-Hotels.0-0-d553248635975876381-tCheapHotels.Travel-Guide-Filter-Hotels)
- [Greenport West Hotels ](https://www.expedia.ca/Greenport-West-Hotels.d553248635975876381.Travel-Guide-Hotels)
- [New York Hotels ](https://www.expedia.ca/New-York-Hotels.d178293.Travel-Guide-Hotels)
- [Beach Hotel Hotels in Peconic ](https://www.expedia.ca/Peconic-Hotels-Beach-Hotel.0-0-d144477-tBeachHotel.Travel-Guide-Filter-Hotels)
- [Ski Hotels in Peconic ](https://www.expedia.ca/Peconic-Hotels-Ski-Hotel.0-0-d144477-tSkiHotel.Travel-Guide-Filter-Hotels)
- [Peconic Hotels ](https://www.expedia.ca/Peconic-Hotels.d144477.Travel-Guide-Hotels)
- [Motels in Peconic ](https://www.expedia.ca/Peconic-Motels.d144477-aaMotels.Travel-Guide-Accommodation)
- [Vacation Homes in Peconic ](https://www.expedia.ca/Peconic-Private-Vacation-Homes.d144477-aaPrivateVacationHomes.Travel-Guide-Accommodation)
- [Villas in Peconic ](https://www.expedia.ca/Peconic-Villas.d144477-aaVillas.Travel-Guide-Accommodation)
- [Hotels near Pindar Vineyards ](https://www.expedia.ca/Pindar-Vineyards-Hotels.0-l6326965-0.Travel-Guide-Filter-Hotels)
- [B&B in Shelter Island ](https://www.expedia.ca/Shelter-Island-Bed-And-Breakfast.d157359-aaBedAndBreakfast.Travel-Guide-Accommodation)
- [B&B in Shelter Island Heights ](https://www.expedia.ca/Shelter-Island-Heights-Bed-And-Breakfast.d183716-aaBedAndBreakfast.Travel-Guide-Accommodation)
- [Beach Hotel Hotels in Shelter Island Heights ](https://www.expedia.ca/Shelter-Island-Heights-Hotels-Beach-Hotel.0-0-d183716-tBeachHotel.Travel-Guide-Filter-Hotels)
- [Boutique Hotels in Shelter Island Heights ](https://www.expedia.ca/Shelter-Island-Heights-Hotels-Boutique-Hotel.0-0-d183716-tBoutiqueHotel.Travel-Guide-Filter-Hotels)
- [Hotels & Resorts for Couples in Shelter Island Heights ](https://www.expedia.ca/Shelter-Island-Heights-Hotels-Couples-Resorts-Hotels.0-0-d183716-tCouplesResortsHotels.Travel-Guide-Filter-Hotels)
- [Pet-Friendly Hotels in Shelter Island Heights ](https://www.expedia.ca/Shelter-Island-Heights-Hotels-Pet-Friendly-Hotel.0-0-d183716-tPetfriendlyHotel.Travel-Guide-Filter-Hotels)
- [Spa Hotels in Shelter Island Heights ](https://www.expedia.ca/Shelter-Island-Heights-Hotels-Spa-Hotel.0-0-d183716-tSpaHotel.Travel-Guide-Filter-Hotels)
- [Shelter Island Heights Hotels ](https://www.expedia.ca/Shelter-Island-Heights-Hotels.d183716.Travel-Guide-Hotels)
- [Resorts in Shelter Island Heights ](https://www.expedia.ca/Shelter-Island-Heights-Resort-Hotels.d183716-aaResortHotels.Travel-Guide-Accommodation)
- [Adults Only Resorts & in Shelter Island ](https://www.expedia.ca/Shelter-Island-Hotels-Adults-Only-Resorts.0-0-d157359-tAdultsOnlyResorts.Travel-Guide-Filter-Hotels)
- [Beach Hotel Hotels in Shelter Island ](https://www.expedia.ca/Shelter-Island-Hotels-Beach-Hotel.0-0-d157359-tBeachHotel.Travel-Guide-Filter-Hotels)
- [Boutique Hotels in Shelter Island ](https://www.expedia.ca/Shelter-Island-Hotels-Boutique-Hotel.0-0-d157359-tBoutiqueHotel.Travel-Guide-Filter-Hotels)
- [Cheap Hotels in Shelter Island ](https://www.expedia.ca/Shelter-Island-Hotels-Cheap-Hotels.0-0-d157359-tCheapHotels.Travel-Guide-Filter-Hotels)
- [Hotels & Resorts for Couples in Shelter Island ](https://www.expedia.ca/Shelter-Island-Hotels-Couples-Resorts-Hotels.0-0-d157359-tCouplesResortsHotels.Travel-Guide-Filter-Hotels)
- [Family Hotels in Shelter Island ](https://www.expedia.ca/Shelter-Island-Hotels-Family-Hotel.0-0-d157359-tFamilyHotel.Travel-Guide-Filter-Hotels)
- [Hotels with Free Breakfast in Shelter Island ](https://www.expedia.ca/Shelter-Island-Hotels-Hotels-With-Free-Breakfast.0-0-d157359-tHotelswithFreeBreakfast.Travel-Guide-Filter-Hotels)
- [Luxury Hotels in Shelter Island ](https://www.expedia.ca/Shelter-Island-Hotels-Luxury-Hotel.0-0-d157359-tLuxuryHotel.Travel-Guide-Filter-Hotels)
- [Oceanfront Hotels in Shelter Island ](https://www.expedia.ca/Shelter-Island-Hotels-Oceanfront-Hotels.0-0-d157359-tOceanfrontHotels.Travel-Guide-Filter-Hotels)
- [Shopping Hotels in Shelter Island ](https://www.expedia.ca/Shelter-Island-Hotels-Shopping-Hotel.0-0-d157359-tShoppingHotel.Travel-Guide-Filter-Hotels)
- [Shelter Island Hotels ](https://www.expedia.ca/Shelter-Island-Hotels.d157359.Travel-Guide-Hotels)
- [Houseboats in Shelter Island ](https://www.expedia.ca/Shelter-Island-Houseboats.d157359-aaHouseboats.Travel-Guide-Accommodation)
- [Resorts in Shelter Island ](https://www.expedia.ca/Shelter-Island-Resort-Hotels.d157359-aaResortHotels.Travel-Guide-Accommodation)
- [Adults Only Resorts & in Silver Beach ](https://www.expedia.ca/Silver-Beach-Shelter-Island-Hotels-Adults-Only-Resorts.0-n553248635976481903-0-tAdultsOnlyResorts.Travel-Guide-Filter-Hotels)
- [Silver Beach Hotels ](https://www.expedia.ca/Silver-Beach-Shelter-Island-Hotels.0-n553248635976481903-0.Travel-Guide-Filter-Hotels)
- [Hotels near Sunset Beach ](https://www.expedia.ca/Sunset-Beach-Hotels.0-l553248626388141313-0.Travel-Guide-Filter-Hotels)
- [The Heights Hotels ](https://www.expedia.ca/The-Heights-Shelter-Island-Heights-Hotels.0-n553248635976473534-0.Travel-Guide-Filter-Hotels)

- [Flights to Greenport ](https://www.expedia.ca/Cheap-Flights-To-Greenport.d110728.Travel-Guide-Flights)
- [Flights to Shelter Island ](https://www.expedia.ca/Cheap-Flights-To-Shelter-Island.d157359.Travel-Guide-Flights)
- [Flights from Shelter Island ](https://www.expedia.ca/lp/flights/157359/flights-from-shelter-island)
- [Flights from Toronto (YYZ) to New York (NYC) ](https://www.expedia.ca/lp/flights/yyz/nyc/toronto-to-new-york)

- [Bedell Cellars ](https://www.expedia.ca/Bedell-Cellars-Cutchogue.d553248621532665643.Vacation-Attraction)
- [Visit Pipes Cove ](https://www.expedia.ca/Greenport-Pipes-Cove.dx553248635976473295)
- [Pindar Vineyards ](https://www.expedia.ca/Pindar-Vineyards-Peconic.d6326965.Vacation-Attraction)
- [Shelter Island Heights Vacations ](https://www.expedia.ca/Shelter-Island-Heights.d183716.Destination-Travel-Guides)
- [Visit Shelter Island ](https://www.expedia.ca/Shelter-Island.dx157359)

- [Car rental Greenport ](https://www.expedia.ca/Car-Rentals-In-Greenport.d110728.Car-Rental-Guide)
- [Car rental Shelter Island ](https://www.expedia.ca/Car-Rentals-In-Shelter-Island.d157359.Car-Rental-Guide)

- [Shelter Island Vacation Rentals ](https://www.expedia.ca/Shelter-Island-Vacation-Rentals.d157359.Travel-Guide-VacationRentals)

- [Things to do in Greenport ](https://www.expedia.ca/Things-To-Do-In-Greenport.d110728.Travel-Guide-Activities)
- [Things to do in Shelter Island Heights ](https://www.expedia.ca/Things-To-Do-In-Shelter-Island-Heights.d183716.Travel-Guide-Activities)
- [Things to do in Shelter Island ](https://www.expedia.ca/Things-To-Do-In-Shelter-Island.d157359.Travel-Guide-Activities)

- [Book 4 Star Hotels in Southold on Expedia.com ](https://www.expedia.com/4Star-Southold-Hotels.s40-0-d183719.Travel-Guide-Filter-Hotels)