Title: Southold Guest Houses from CA $216 | 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) ![](https://mediaim.expedia.com/destination/1/2af9844708ff5148df98a90729e7edaf.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Search Guest Houses in Southold from CA $216 ![](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 prices for these dates Next weekend [Nov 7 - Nov 9](https://www.expedia.ca/Hotel-Search?regionId=183719&startDate=2025-11-07&endDate=2025-11-09&adults=2&lodging=GUEST_HOUSE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Nov 14 - Nov 16](https://www.expedia.ca/Hotel-Search?regionId=183719&startDate=2025-11-14&endDate=2025-11-16&adults=2&lodging=GUEST_HOUSE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In one month [Nov 28 - Nov 30](https://www.expedia.ca/Hotel-Search?regionId=183719&startDate=2025-11-28&endDate=2025-11-30&adults=2&lodging=GUEST_HOUSE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Dec 26 - Dec 28](https://www.expedia.ca/Hotel-Search?regionId=183719&startDate=2025-12-26&endDate=2025-12-28&adults=2&lodging=GUEST_HOUSE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Browse Select Southold Guest Houses ![Outdoor pool, a heated pool](https://images.trvl-media.com/lodging/106000000/105960000/105953400/105953388/5a24caee.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Beach nearby, sun loungers, beach towels](https://images.trvl-media.com/lodging/106000000/105960000/105953400/105953388/7abafcfb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/106000000/105960000/105953400/105953388/f1ad96fa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/106000000/105960000/105953400/105953388/a79f88d6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### New and Modern Bridgehampton Accommodations Bridgehampton 9.6/10 Exceptional (15) "Great home, as pictured, perfect place to stay!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Peter R. CA $246 CA $604 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Bridgehampton-Hotels-New-And-Modern-Bridgehampton-Accommodations.h105953388.Hotel-Information) ![View from property](https://images.trvl-media.com/lodging/13000000/12620000/12611000/12610909/51be5ca3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Restaurant](https://images.trvl-media.com/lodging/13000000/12620000/12611000/12610909/ae8f0ca6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/13000000/12620000/12611000/12610909/fdb9f048.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/13000000/12620000/12611000/12610909/d7311f73.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### House on Chase Creek The Heights 9.4/10 Exceptional (77) " This was my husband and my first time visiting Shelter Island and I feel lucky that my stay was at the House of ChaseCreek. Bill was excellent in helping us navigate our stay on the Island which made for an enjoyable experience. The house was charming , very clean , and had easy access to the town restaurant s, and Ferry. Highly recommend ! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Maureen CA $259 CA $296 total includes taxes & fees Nov 3 - Nov 4 [](https://www.expedia.ca/Shelter-Island-Heights-Hotels-House-On-Chase-Creek.h12610909.Hotel-Information) ![Apartment, 2 Bedrooms | Private kitchen](https://images.trvl-media.com/lodging/11000000/10220000/10211600/10211593/4e100a77.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/11000000/10220000/10211600/10211593/a37c2d73.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/11000000/10220000/10211600/10211593/6142ad8a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/11000000/10220000/10211600/10211593/ae2cccbf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hampton's Vacation Inn Hampton Bays 9.0/10 Wonderful (322) "A great Hampton location that's less than a thirty minutes drive from Coopers Beach and South Hampton main street." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Maggie CA $189 CA $216 total includes taxes & fees Oct 28 - Oct 29 [](https://www.expedia.ca/Hampton-Bays-Hotels-Bowens-By-The-Bays.h10211593.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=2025-11-10&endDate=2025-11-11®ionId=183719&adults=2&lodging=GUEST_HOUSE&sort=RECOMMENDED&openPlayBack=true) ![](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%2FSouthold-Guest-Houses.d183719-aaGuestHouses.Travel-Guide-Accommodation)[Sign up, it's free](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FSouthold-Guest-Houses.d183719-aaGuestHouses.Travel-Guide-Accommodation) ## Top Southold Hotel Reviews ![The Bentley Hotel Southampton](//images.trvl-media.com/lodging/54000000/53970000/53963000/53962986/60534d98_y.jpg) ### The Bentley Hotel Southampton 10/10 Excellent "Beautiful room w large living room and bedroom very nice bathroom touches and comfort level Fantastic finishes and decor" [](https://expedia.ca/Southampton-Hotels-Bentley-Southampton.h53962986.Hotel-Information) ![Sound View Greenport](//images.trvl-media.com/lodging/16000000/15280000/15273200/15273178/b52e0fa4_y.jpg) ### Sound View Greenport 10/10 Excellent "Breakfast and the Halyard restaurant are top shelf. A few quirks with our room(s) - no cable service, a locked bathroom door that couldn’t be opened, and a dead bolt that didn’t work- but the staff were helpful and accommodating and did everything they could to make things right." [](https://expedia.ca/Greenport-Hotels-Sound-View-Greenport.h15273178.Hotel-Information) ![Quality Inn Old Saybrook - Westbrook](//images.trvl-media.com/lodging/1000000/10000/4000/3988/228c4607_y.jpg) ### Quality Inn Old Saybrook - Westbrook 10/10 Excellent "Breakfast had a nice variety from Waffles that came out perfect to pantries fresh fruit and the place was clean! And fresh smelling." [](https://expedia.ca/Old-Saybrook-Hotels-Quality-Inn-Old-Saybrook-Westbrook.h3988.Hotel-Information) ![Saybrook Point Resort & Marina](//images.trvl-media.com/lodging/1000000/40000/38800/38715/5e605108_y.jpg) ### Saybrook Point Resort & Marina 10/10 Excellent "Beautiful hotel in the marine. CT summer playground. " [](https://expedia.ca/Old-Saybrook-Hotels-Saybrook-Point-Resort-Marina.h38715.Hotel-Information) ![Spark by Hilton Guilford](//images.trvl-media.com/lodging/1000000/990000/983200/983128/08241fb2_y.jpg) ### Spark by Hilton Guilford 10/10 Excellent "One night. Friendly staff. All good." [](https://expedia.ca/Guilford-Hotels-Spark-By-Hilton-Guilford.h983128.Hotel-Information) ![The Atlantic Hotel](//images.trvl-media.com/lodging/1000000/450000/447900/447803/0c137ed2_y.jpg) ### The Atlantic Hotel 10/10 Excellent "Easy parking " [](https://expedia.ca/Southampton-Hotels-The-Atlantic-Hotel.h447803.Hotel-Information) ![Pier Blue Inn Old Saybrook - Essex](//images.trvl-media.com/lodging/1000000/20000/12200/12143/a912ee6f_y.jpg) ### Pier Blue Inn Old Saybrook - Essex 10/10 Excellent "Very nice staff, amenities great, an older place, but well kept. Wish there was more than 1 window, a bit stuffy. Felt safe in parking lot and in my room." [](https://expedia.ca/Old-Saybrook-Hotels-Pier-Blue-Inn-Old-Saybrook-Essex.h12143.Hotel-Information) ![Greenview Inn Riverhead](//images.trvl-media.com/lodging/2000000/1380000/1374000/1373980/d1b868c8_y.jpg) ### Greenview Inn Riverhead 10/10 Excellent "Area was kinda dark but overall brand new hotel. " [](https://expedia.ca/Riverhead-Hotels-Greenview-Inn-Riverhead.h1373980.Hotel-Information) ![Hotel Indigo East End by IHG](//images.trvl-media.com/lodging/4000000/3480000/3475700/3475618/75016698_y.jpg) ### Hotel Indigo East End by IHG 10/10 Excellent "100% recommended " [](https://expedia.ca/Riverhead-Hotels-Hotel-Indigo-East-End.h3475618.Hotel-Information) ## Find out more about Southold ## Southold Guest Houses information | Number of reviews | 413 | | --- | --- | | Accommodation | 5 Guest Houses | | Lowest Price | CA $216 | | Highest Price | CA $604 | ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rental - Other - More ways to book - [3 Star Hotels in Greenport](https://www.expedia.ca/3Star-Greenport-Hotels.s30-0-d110728.Travel-Guide-Filter-Hotels) - [5 Star Hotels in Greenport](https://www.expedia.ca/5Star-Greenport-Hotels.s50-0-d110728.Travel-Guide-Filter-Hotels) - [Hotels near Crescent Beach](https://www.expedia.ca/Crescent-Beach-Hotels.0-l553248621554204758-0.Travel-Guide-Filter-Hotels) - [Chalets in Cutchogue](https://www.expedia.ca/Cutchogue-Chalets.d183659-aaChalets.Travel-Guide-Accommodation) - [Hotels with Bar in Cutchogue](https://www.expedia.ca/Cutchogue-Hotels-Hotels-With-Bar.0-0-d183659-tHotelswithBar.Travel-Guide-Filter-Hotels) - [Hotel Wedding Venues Hotels in Cutchogue](https://www.expedia.ca/Cutchogue-Hotels-Wedding-Hotels.0-0-d183659-tWeddingHotels.Travel-Guide-Filter-Hotels) - [Cutchogue Hotels](https://www.expedia.ca/Cutchogue-Hotels.d183659.Travel-Guide-Hotels) - [Cottages in Dering Harbor](https://www.expedia.ca/Dering-Harbor-Cottages.d553248634998885605-aaCottages.Travel-Guide-Accommodation) - [Dering Harbor Hotels](https://www.expedia.ca/Dering-Harbor-Hotels.d553248634998885605.Travel-Guide-Hotels) - [Residences in Dering Harbor](https://www.expedia.ca/Dering-Harbor-Residences.d553248634998885605-aaResidences.Travel-Guide-Accommodation) - [Town of Southold Town Hotels](https://www.expedia.ca/Destinations-In-Town-Of-Southold-Town.d553248635976002319.Hotel-Destinations) - [Farmstay in East Marion](https://www.expedia.ca/East-Marion-Agritourism.d6069914-aaAgritourism.Travel-Guide-Accommodation) - [Cabin Rentals in East Marion](https://www.expedia.ca/East-Marion-Cabins.d6069914-aaCabins.Travel-Guide-Accommodation) - [B&B in Fishers Island](https://www.expedia.ca/Fishers-Island-Bed-And-Breakfast.d1208-aaBedAndBreakfast.Travel-Guide-Accommodation) - [Guest Houses in Fishers Island](https://www.expedia.ca/Fishers-Island-Guest-Houses.d1208-aaGuestHouses.Travel-Guide-Accommodation) - [Inns in Fishers Island](https://www.expedia.ca/Fishers-Island-Inns.d1208-aaInns.Travel-Guide-Accommodation) - [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) - [Apartments in Mattituck](https://www.expedia.ca/Mattituck-Apartments.d6223780-aaApartments.Travel-Guide-Accommodation) - [B&B in Mattituck](https://www.expedia.ca/Mattituck-Bed-And-Breakfast.d6223780-aaBedAndBreakfast.Travel-Guide-Accommodation) - [Motels in Mattituck](https://www.expedia.ca/Mattituck-Motels.d6223780-aaMotels.Travel-Guide-Accommodation) - [Guest Houses in New Suffolk](https://www.expedia.ca/New-Suffolk-Guest-Houses.d3000449151-aaGuestHouses.Travel-Guide-Accommodation) - [Motels in New Suffolk](https://www.expedia.ca/New-Suffolk-Motels.d3000449151-aaMotels.Travel-Guide-Accommodation) - [Vacation Homes in New Suffolk](https://www.expedia.ca/New-Suffolk-Private-Vacation-Homes.d3000449151-aaPrivateVacationHomes.Travel-Guide-Accommodation) - [New York Hotels](https://www.expedia.ca/New-York-Hotels.d178293.Travel-Guide-Hotels) - [Chalets in North Haven](https://www.expedia.ca/North-Haven-Chalets.d553248634998589872-aaChalets.Travel-Guide-Accommodation) - [Residences in North Haven](https://www.expedia.ca/North-Haven-Residences.d553248634998589872-aaResidences.Travel-Guide-Accommodation) - [B&B in Noyack](https://www.expedia.ca/Noyack-Bed-And-Breakfast.d6217344-aaBedAndBreakfast.Travel-Guide-Accommodation) - [Guest Houses in Noyack](https://www.expedia.ca/Noyack-Guest-Houses.d6217344-aaGuestHouses.Travel-Guide-Accommodation) - [Aparthotels in Orient](https://www.expedia.ca/Orient-Apart-Hotels.d6326191-aaApartHotels.Travel-Guide-Accommodation) - [B&B in Orient](https://www.expedia.ca/Orient-Bed-And-Breakfast.d6326191-aaBedAndBreakfast.Travel-Guide-Accommodation) - [Inns in Orient](https://www.expedia.ca/Orient-Inns.d6326191-aaInns.Travel-Guide-Accommodation) - [Resorts in Orient](https://www.expedia.ca/Orient-Resort-Hotels.d6326191-aaResortHotels.Travel-Guide-Accommodation) - [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 a Pool in Shelter Island](https://www.expedia.ca/Shelter-Island-Hotels-Hotel-With-Pool.0-0-d157359-tHotelwithPool.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) - [Kontokosta Winery](https://www.expedia.ca/Kontokosta-Winery-Greenport.d6326928.Vacation-Attraction) - [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 Guest Houses in Southold on Expedia.com](https://www.expedia.com/Southold-Guest-Houses.d183719-aaGuestHouses.Travel-Guide-Accommodation)