Title: Book the Best ADVENTURE Hotels in Southold in 2026 | Expedia.ca

[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)[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 

# Find Hotels & Resorts for Couples in Southold, NY 

- ![](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 Hotels & Resorts for Couples

Tonight

[Dec 19 - Dec 20](https://www.expedia.ca/Hotel-Search?regionId=183719&startDate=2025-12-19&endDate=2025-12-20&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

Tomorrow

[Dec 20 - Dec 21](https://www.expedia.ca/Hotel-Search?regionId=183719&startDate=2025-12-20&endDate=2025-12-21&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

This weekend

[Dec 19 - Dec 21](https://www.expedia.ca/Hotel-Search?regionId=183719&startDate=2025-12-19&endDate=2025-12-21&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

Next weekend

[Dec 26 - Dec 28](https://www.expedia.ca/Hotel-Search?regionId=183719&startDate=2025-12-26&endDate=2025-12-28&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

## Our top choices for Southold adventure hotels

![Front of property - evening/night](https://images.trvl-media.com/lodging/3000000/2870000/2861900/2861838/e0e0def6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Graybarn Cottage](https://images.trvl-media.com/lodging/3000000/2870000/2861900/2861838/d1fe07eb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Graybarn Cottage | Room amenity](https://images.trvl-media.com/lodging/3000000/2870000/2861900/2861838/1d639007.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Meeting facility](https://images.trvl-media.com/lodging/3000000/2870000/2861900/2861838/8e47f99f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Mill House Inn

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

Pantigo Road Historic District

9.0/10

Wonderful

(75)

"the rooms are outdated and the front desk staff was overbearing the location is great but it’s noisy the breakfast was awesome as was the chef "

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

Sharon

CA $413

CA $519 total

includes taxes & fees

Dec 21 - Dec 22

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

![Property amenity](https://images.trvl-media.com/lodging/11000000/10550000/10547800/10547745/fa70e85b.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)

![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)

### The Roundtree, Amagansett

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

Amagansett North

10/10

Exceptional

(91)

"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 $819

CA $982 total

includes taxes & fees

Jan 1 - Jan 2, 2026

[](https://www.expedia.ca/Amagansett-Hotels-The-Roundtree.h10547745.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=2026-01-02&endDate=2026-01-03&regionId=183719&adults=2&nearby_group=recreation&sort=RECOMMENDED&openPlayBack=true)

## Top Southold Hotel Reviews

## Frequently asked questions

### Why book your hotel for couples in Southold with Expedia?

### How can I find cheap hotels for couples in Southold?

## Explore a world of travel with Expedia

- Lodging
- Flights
- More ways to book

- [Beach Hotel Hotels in Brooklyn ](https://www.expedia.ca/Brooklyn-Hotels-Beach-Hotel.0-0-d177851-tBeachHotel.Travel-Guide-Filter-Hotels)
- [Business Hotels in Brooklyn ](https://www.expedia.ca/Brooklyn-Hotels-Business-Hotel.0-0-d177851-tBusinessHotel.Travel-Guide-Filter-Hotels)
- [Honeymoon Resorts and in Brooklyn ](https://www.expedia.ca/Brooklyn-Hotels-Honeymoon-Hotels.0-0-d177851-tHoneymoonHotels.Travel-Guide-Filter-Hotels)
- [Hotels with Waterslides in Brooklyn ](https://www.expedia.ca/Brooklyn-Hotels-Hotels-With-Waterslides.0-0-d177851-tHotelswithWaterslides.Travel-Guide-Filter-Hotels)
- [Ski Hotels in Brooklyn ](https://www.expedia.ca/Brooklyn-Hotels-Ski-Hotel.0-0-d177851-tSkiHotel.Travel-Guide-Filter-Hotels)
- [Waterpark Hotels in Brooklyn ](https://www.expedia.ca/Brooklyn-Hotels-Waterpark-Hotels.0-0-d177851-tWaterparkHotels.Travel-Guide-Filter-Hotels)
- [Winery Hotels in Brooklyn ](https://www.expedia.ca/Brooklyn-Hotels-Winery-Hotel.0-0-d177851-tWineryHotel.Travel-Guide-Filter-Hotels)
- [Adults Only Resorts & in Central New York City ](https://www.expedia.ca/Central-New-York-City-New-York-Hotels-Adults-Only-Resorts.0-n553248633938969338-0-tAdultsOnlyResorts.Travel-Guide-Filter-Hotels)
- [Beach Hotel Hotels in Central New York City ](https://www.expedia.ca/Central-New-York-City-New-York-Hotels-Beach-Hotel.0-n553248633938969338-0-tBeachHotel.Travel-Guide-Filter-Hotels)
- [Business Hotels in Central New York City ](https://www.expedia.ca/Central-New-York-City-New-York-Hotels-Business-Hotel.0-n553248633938969338-0-tBusinessHotel.Travel-Guide-Filter-Hotels)
- [Hotels & Resorts for Couples in Central New York City ](https://www.expedia.ca/Central-New-York-City-New-York-Hotels-Couples-Resorts-Hotels.0-n553248633938969338-0-tCouplesResortsHotels.Travel-Guide-Filter-Hotels)
- [Golf Hotels in Central New York City ](https://www.expedia.ca/Central-New-York-City-New-York-Hotels-Golf-Hotel.0-n553248633938969338-0-tGolfHotel.Travel-Guide-Filter-Hotels)
- [Green Hotels in Central New York City ](https://www.expedia.ca/Central-New-York-City-New-York-Hotels-Green-Sustainable.0-n553248633938969338-0-tGreenSustainable.Travel-Guide-Filter-Hotels)
- [Historic Hotels in Central New York City ](https://www.expedia.ca/Central-New-York-City-New-York-Hotels-Historic-Hotel.0-n553248633938969338-0-tHistoricHotel.Travel-Guide-Filter-Hotels)
- [Honeymoon Resorts and in Central New York City ](https://www.expedia.ca/Central-New-York-City-New-York-Hotels-Honeymoon-Hotels.0-n553248633938969338-0-tHoneymoonHotels.Travel-Guide-Filter-Hotels)
- [Hotels with Balconies in Central New York City ](https://www.expedia.ca/Central-New-York-City-New-York-Hotels-Hotels-With-Balconies.0-n553248633938969338-0-tHotelswithBalconies.Travel-Guide-Filter-Hotels)
- [Hotels with Childcare in Central New York City ](https://www.expedia.ca/Central-New-York-City-New-York-Hotels-Hotels-With-Childcare.0-n553248633938969338-0-tHotelswithChildcare.Travel-Guide-Filter-Hotels)
- [Hotels with Free Airport Shuttle in Central New York City ](https://www.expedia.ca/Central-New-York-City-New-York-Hotels-Hotels-With-Free-Airport-Shuttle.0-n553248633938969338-0-tHotelswithFreeAirportShuttle.Travel-Guide-Filter-Hotels)
- [Hotels with Free Breakfast in Central New York City ](https://www.expedia.ca/Central-New-York-City-New-York-Hotels-Hotels-With-Free-Breakfast.0-n553248633938969338-0-tHotelswithFreeBreakfast.Travel-Guide-Filter-Hotels)
- [Hotels with Hot Tubs in Central New York City ](https://www.expedia.ca/Central-New-York-City-New-York-Hotels-Hotels-With-Hot-Tubs.0-n553248633938969338-0-tHotelsWithHotTubs.Travel-Guide-Filter-Hotels)
- [Hotels with Tennis Courts in Central New York City ](https://www.expedia.ca/Central-New-York-City-New-York-Hotels-Hotels-With-Tennis-Courts.0-n553248633938969338-0-tHotelswithTennisCourts.Travel-Guide-Filter-Hotels)
- [Hotels with Waterslides in Central New York City ](https://www.expedia.ca/Central-New-York-City-New-York-Hotels-Hotels-With-Waterslides.0-n553248633938969338-0-tHotelswithWaterslides.Travel-Guide-Filter-Hotels)
- [Lgbt Friendly Hotels in Central New York City ](https://www.expedia.ca/Central-New-York-City-New-York-Hotels-LGBT-Friendly-Hotel.0-n553248633938969338-0-tLGBTFriendlyHotel.Travel-Guide-Filter-Hotels)
- [Lake Hotels in Central New York City ](https://www.expedia.ca/Central-New-York-City-New-York-Hotels-Lake-Hotels.0-n553248633938969338-0-tLakeHotels.Travel-Guide-Filter-Hotels)
- [Mountain Hotels in Central New York City ](https://www.expedia.ca/Central-New-York-City-New-York-Hotels-Mountain-Hotels.0-n553248633938969338-0-tMountainHotels.Travel-Guide-Filter-Hotels)
- [Oceanfront Hotels in Central New York City ](https://www.expedia.ca/Central-New-York-City-New-York-Hotels-Oceanfront-Hotels.0-n553248633938969338-0-tOceanfrontHotels.Travel-Guide-Filter-Hotels)
- [Pet-Friendly Hotels in Central New York City ](https://www.expedia.ca/Central-New-York-City-New-York-Hotels-Pet-Friendly-Hotel.0-n553248633938969338-0-tPetfriendlyHotel.Travel-Guide-Filter-Hotels)
- [Romantic Hotels in Central New York City ](https://www.expedia.ca/Central-New-York-City-New-York-Hotels-Romantic-Hotel.0-n553248633938969338-0-tRomanticHotel.Travel-Guide-Filter-Hotels)
- [Ski Hotels in Central New York City ](https://www.expedia.ca/Central-New-York-City-New-York-Hotels-Ski-Hotel.0-n553248633938969338-0-tSkiHotel.Travel-Guide-Filter-Hotels)
- [Spa Hotels in Central New York City ](https://www.expedia.ca/Central-New-York-City-New-York-Hotels-Spa-Hotel.0-n553248633938969338-0-tSpaHotel.Travel-Guide-Filter-Hotels)
- [Waterpark Hotels in Central New York City ](https://www.expedia.ca/Central-New-York-City-New-York-Hotels-Waterpark-Hotels.0-n553248633938969338-0-tWaterparkHotels.Travel-Guide-Filter-Hotels)
- [Hotel Wedding Venues Hotels in Central New York City ](https://www.expedia.ca/Central-New-York-City-New-York-Hotels-Wedding-Hotels.0-n553248633938969338-0-tWeddingHotels.Travel-Guide-Filter-Hotels)
- [Winery Hotels in Central New York City ](https://www.expedia.ca/Central-New-York-City-New-York-Hotels-Winery-Hotel.0-n553248633938969338-0-tWineryHotel.Travel-Guide-Filter-Hotels)
- [Beach Hotel Hotels in Fishers Island ](https://www.expedia.ca/Fishers-Island-Hotels-Beach-Hotel.0-0-d1208-tBeachHotel.Travel-Guide-Filter-Hotels)
- [Boutique Hotels in Fishers Island ](https://www.expedia.ca/Fishers-Island-Hotels-Boutique-Hotel.0-0-d1208-tBoutiqueHotel.Travel-Guide-Filter-Hotels)
- [Cheap Hotels in Fishers Island ](https://www.expedia.ca/Fishers-Island-Hotels-Cheap-Hotels.0-0-d1208-tCheapHotels.Travel-Guide-Filter-Hotels)
- [Golf Hotels in Fishers Island ](https://www.expedia.ca/Fishers-Island-Hotels-Golf-Hotel.0-0-d1208-tGolfHotel.Travel-Guide-Filter-Hotels)
- [Luxury Hotels in Fishers Island ](https://www.expedia.ca/Fishers-Island-Hotels-Luxury-Hotel.0-0-d1208-tLuxuryHotel.Travel-Guide-Filter-Hotels)
- [Spa Hotels in Fishers Island ](https://www.expedia.ca/Fishers-Island-Hotels-Spa-Hotel.0-0-d1208-tSpaHotel.Travel-Guide-Filter-Hotels)
- [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)
- [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)
- [All Inclusive Resorts and in Long Island ](https://www.expedia.ca/Long-Island-Hotels-All-Inclusive-Hotel.0-0-d602887-tAllInclusiveHotel.Travel-Guide-Filter-Hotels)
- [Green Hotels in Long Island ](https://www.expedia.ca/Long-Island-Hotels-Green-Sustainable.0-0-d602887-tGreenSustainable.Travel-Guide-Filter-Hotels)
- [Hotels with Balconies in Long Island ](https://www.expedia.ca/Long-Island-Hotels-Hotels-With-Balconies.0-0-d602887-tHotelswithBalconies.Travel-Guide-Filter-Hotels)
- [Hotels with Free Breakfast in Long Island ](https://www.expedia.ca/Long-Island-Hotels-Hotels-With-Free-Breakfast.0-0-d602887-tHotelswithFreeBreakfast.Travel-Guide-Filter-Hotels)
- [Lgbt Friendly Hotels in Long Island ](https://www.expedia.ca/Long-Island-Hotels-LGBT-Friendly-Hotel.0-0-d602887-tLGBTFriendlyHotel.Travel-Guide-Filter-Hotels)
- [Beach Hotel Hotels in Manhattan ](https://www.expedia.ca/Manhattan-New-York-Hotels-Beach-Hotel.0-n129440-0-tBeachHotel.Travel-Guide-Filter-Hotels)
- [Hotels & Resorts for Couples in Manhattan ](https://www.expedia.ca/Manhattan-New-York-Hotels-Couples-Resorts-Hotels.0-n129440-0-tCouplesResortsHotels.Travel-Guide-Filter-Hotels)
- [Golf Hotels in Manhattan ](https://www.expedia.ca/Manhattan-New-York-Hotels-Golf-Hotel.0-n129440-0-tGolfHotel.Travel-Guide-Filter-Hotels)
- [Green Hotels in Manhattan ](https://www.expedia.ca/Manhattan-New-York-Hotels-Green-Sustainable.0-n129440-0-tGreenSustainable.Travel-Guide-Filter-Hotels)
- [Honeymoon Resorts and in Manhattan ](https://www.expedia.ca/Manhattan-New-York-Hotels-Honeymoon-Hotels.0-n129440-0-tHoneymoonHotels.Travel-Guide-Filter-Hotels)
- [Hotels with Wifi in Manhattan ](https://www.expedia.ca/Manhattan-New-York-Hotels-Hotel-With-Wifi.0-n129440-0-tHotelwithwifi.Travel-Guide-Filter-Hotels)
- [Hotels with a Lazy River in Manhattan ](https://www.expedia.ca/Manhattan-New-York-Hotels-Hotels-With-A-Lazy-River.0-n129440-0-tHotelswithaLazyRiver.Travel-Guide-Filter-Hotels)
- [Hotels with Childcare in Manhattan ](https://www.expedia.ca/Manhattan-New-York-Hotels-Hotels-With-Childcare.0-n129440-0-tHotelswithChildcare.Travel-Guide-Filter-Hotels)
- [Lgbt Friendly Hotels in Manhattan ](https://www.expedia.ca/Manhattan-New-York-Hotels-LGBT-Friendly-Hotel.0-n129440-0-tLGBTFriendlyHotel.Travel-Guide-Filter-Hotels)
- [Mountain Hotels in Manhattan ](https://www.expedia.ca/Manhattan-New-York-Hotels-Mountain-Hotels.0-n129440-0-tMountainHotels.Travel-Guide-Filter-Hotels)
- [Oceanfront Hotels in Manhattan ](https://www.expedia.ca/Manhattan-New-York-Hotels-Oceanfront-Hotels.0-n129440-0-tOceanfrontHotels.Travel-Guide-Filter-Hotels)
- [Winery Hotels in Manhattan ](https://www.expedia.ca/Manhattan-New-York-Hotels-Winery-Hotel.0-n129440-0-tWineryHotel.Travel-Guide-Filter-Hotels)
- [Adults Only Resorts & in Midtown East ](https://www.expedia.ca/Midtown-East-New-York-Hotels-Adults-Only-Resorts.0-n6141525-0-tAdultsOnlyResorts.Travel-Guide-Filter-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)
- [Casino Hotels in Purchase ](https://www.expedia.ca/Purchase-Hotels-Casino-Hotel.0-0-d6172129-tCasinoHotel.Travel-Guide-Filter-Hotels)
- [Hotels with Free Airport Shuttle in Purchase ](https://www.expedia.ca/Purchase-Hotels-Hotels-With-Free-Airport-Shuttle.0-0-d6172129-tHotelswithFreeAirportShuttle.Travel-Guide-Filter-Hotels)
- [Spa Hotels in Purchase ](https://www.expedia.ca/Purchase-Hotels-Spa-Hotel.0-0-d6172129-tSpaHotel.Travel-Guide-Filter-Hotels)
- [Adults Only Resorts & in Queens ](https://www.expedia.ca/Queens-New-York-Hotels-Adults-Only-Resorts.0-n149004-0-tAdultsOnlyResorts.Travel-Guide-Filter-Hotels)
- [Shopping Hotels in Queens ](https://www.expedia.ca/Queens-New-York-Hotels-Shopping-Hotel.0-n149004-0-tShoppingHotel.Travel-Guide-Filter-Hotels)
- [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)
- [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)
- [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)
- [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)
- [Boutique Hotels in West Side ](https://www.expedia.ca/West-Side-Hotels-Boutique-Hotel.0-0-d6203488-tBoutiqueHotel.Travel-Guide-Filter-Hotels)
- [Cheap Hotels in West Side ](https://www.expedia.ca/West-Side-Hotels-Cheap-Hotels.0-0-d6203488-tCheapHotels.Travel-Guide-Filter-Hotels)
- [Family Hotels in West Side ](https://www.expedia.ca/West-Side-Hotels-Family-Hotel.0-0-d6203488-tFamilyHotel.Travel-Guide-Filter-Hotels)
- [Hotels with Free Breakfast in West Side ](https://www.expedia.ca/West-Side-Hotels-Hotels-With-Free-Breakfast.0-0-d6203488-tHotelswithFreeBreakfast.Travel-Guide-Filter-Hotels)
- [Luxury Hotels in West Side ](https://www.expedia.ca/West-Side-Hotels-Luxury-Hotel.0-0-d6203488-tLuxuryHotel.Travel-Guide-Filter-Hotels)
- [Winery Hotels in West Side ](https://www.expedia.ca/West-Side-Hotels-Winery-Hotel.0-0-d6203488-tWineryHotel.Travel-Guide-Filter-Hotels)

- [Flights from Toronto (YYZ) to New York (NYC) ](https://www.expedia.ca/lp/flights/yyz/nyc/toronto-to-new-york)

- [Book Hotels & Resorts for Couples in Southold on Expedia.com ](https://www.expedia.com/Southold-Hotels-Couples-Resorts-Hotels.0-0-d183719-tCouplesResortsHotels.Travel-Guide-Filter-Hotels)