Title: Sheffield Island Vacation Home Rentals from CA $196: Search Top Private Vacation Homes for Rent | Expedia.ca [Sheffield Island Travel Guide](https://expedia.ca/Sheffield-Island.dx6353650)[Hotels in Sheffield Island](https://expedia.ca/Sheffield-Island-Hotels.d6353650.Travel-Guide-Hotels)[Vacation Rentals in Sheffield Island](https://expedia.ca/Sheffield-Island-Vacation-Rentals.d6353650.Travel-Guide-VacationRentals)[Sheffield Island Car Rentals](https://expedia.ca/Car-Rentals-In-Sheffield-Island.d6353650.Car-Rental-Guide)[Sheffield Island Vacation Packages](https://expedia.ca/Sheffield-Island.d6353650.Destination-Travel-Guides) ![](https://mediaim.expedia.com/destination/2/0eda6d017413ea4d9213e753ce40e86d.jpg?impolicy=fcrop&w=1200&h=500&q=medium) Photo by Richard Miska # Sheffield Island Vacation Rentals - ![](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=6353650&startDate=2025-11-07&endDate=2025-11-09&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Nov 14 - Nov 16](https://www.expedia.ca/Hotel-Search?regionId=6353650&startDate=2025-11-14&endDate=2025-11-16&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In one month [Nov 28 - Nov 30](https://www.expedia.ca/Hotel-Search?regionId=6353650&startDate=2025-11-28&endDate=2025-11-30&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Dec 26 - Dec 28](https://www.expedia.ca/Hotel-Search?regionId=6353650&startDate=2025-12-26&endDate=2025-12-28&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Browse Select Sheffield Island Vacation Homes ![Pool](https://images.trvl-media.com/lodging/98000000/97480000/97470900/97470860/9f8971d1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/98000000/97480000/97470900/97470860/646e6d85.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/98000000/97480000/97470900/97470860/9ac447c3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor spa tub](https://images.trvl-media.com/lodging/98000000/97480000/97470900/97470860/29e9c151.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Business or Weekend escape Stratford 9.2/10 Wonderful (50) "Great value!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Bruce H. CA $112 CA $196 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Stratford-Hotels-Business-Or-Weekend-Escape.h97470860.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/115000000/114610000/114606200/114606188/7ce63cd7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/115000000/114610000/114606200/114606188/32fb7c3f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/115000000/114610000/114606200/114606188/c1311c5e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, stovetop, coffee/tea maker](https://images.trvl-media.com/lodging/115000000/114610000/114606200/114606188/71684fe5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 2BR, 1 BA, and Kitchenette in Lakeside Home in Greenwich with private dock. Greenwich 9.6/10 Exceptional (19) "Perfect place to rest. Excellent service! " ![Mexico](https://a.travel-assets.com/egds/marks/flags/mx.svg) Lucymar CA $107 CA $280 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Greenwich-Hotels-2-Bedroom-And-1-Full-Bath-In-Lakeside-Home-With-Private-Dock.h114606188.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/96000000/95900000/95891300/95891227/e20a1f50.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/96000000/95900000/95891300/95891227/d50b7da5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/96000000/95900000/95891300/95891227/bcb11e3e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/96000000/95900000/95891300/95891227/7238270e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Marine Theme - 4 BR - Backyard - Fire pit Bridgeport 9.8/10 Exceptional (7) "We were in town for a short stay and everything was very nice" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kevin B. CA $240 CA $606 total includes taxes & fees Nov 4 - Nov 5 [](https://www.expedia.ca/Bridgeport-Hotels-Marine-Theme-4-BR-Backyard-Fire-Pit.h95891227.Hotel-Information) ![Outdoor dining](https://images.trvl-media.com/lodging/120000000/119250000/119248500/119248411/9a855962.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium House, Garden View | Living area](https://images.trvl-media.com/lodging/120000000/119250000/119248500/119248411/7eecbab9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Aerial view](https://images.trvl-media.com/lodging/120000000/119250000/119248500/119248411/e54b764c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium House, Garden View | Living area](https://images.trvl-media.com/lodging/120000000/119250000/119248500/119248411/78c118d1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Beechmont - Perfect for Family Retreat! Bridgeport CA $946 CA $1,577 total includes taxes & fees Nov 4 - Nov 5 [](https://www.expedia.ca/Bridgeport-Hotels-Beechmont.h119248411.Hotel-Information) ![Outdoor dining](https://images.trvl-media.com/lodging/97000000/96140000/96133300/96133224/a07d0d79.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bedrooms, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/97000000/96140000/96133300/96133224/c11fa5dd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Beach](https://images.trvl-media.com/lodging/97000000/96140000/96133300/96133224/4a974bd9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, fireplace, books](https://images.trvl-media.com/lodging/97000000/96140000/96133300/96133224/d0c4b7c2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Top Rated Gem, Fire Pit, Near Beach, Fairfield U, 90 min to NYC Fairfield 10/10 Exceptional (21) "Great family home. Location is perfect, close to everything yet private and quiet. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Margaret W. CA $266 CA $678 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Fairfield-Hotels-Family-Friendly-Renovated.h96133224.Hotel-Information) ![Marina](https://images.trvl-media.com/lodging/82000000/81830000/81827600/81827580/533639ff.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/82000000/81830000/81827600/81827580/9de13056.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/82000000/81830000/81827600/81827580/6c168c11.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bedrooms, desk, travel crib, free WiFi](https://images.trvl-media.com/lodging/82000000/81830000/81827600/81827580/6e8eb9ec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Captain's Cottage - Cold Spring Harbor Water Views Cold Spring Harbor 10/10 Exceptional (70) "Great home to stay. Beautiful area to explore!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Randy W. CA $241 CA $599 total includes taxes & fees Nov 4 - Nov 5 [](https://www.expedia.ca/Cold-Spring-Harbor-Hotels-Captains-Cottage-Cold-Spring-Harbor-Water-Views.h81827580.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/113000000/112370000/112364900/112364813/3138ca99.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Private kitchen](https://images.trvl-media.com/lodging/113000000/112370000/112364900/112364813/2730f6d1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, WiFi, bed sheets](https://images.trvl-media.com/lodging/113000000/112370000/112364900/112364813/880d2845.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Private kitchen](https://images.trvl-media.com/lodging/113000000/112370000/112364900/112364813/bdaff4ee.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Gem by the water - Charming 2-bedroom house in fabulous Stamford with AC, WiFi Waterside 10/10 Exceptional (5) "Exceptional space for our needs. We’d absolutely book again if the opportunity arises. Maritza was communicative and everything was easily accessible" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Joanne CA $220 CA $466 total includes taxes & fees Nov 7 - Nov 8 [](https://www.expedia.ca/Stamford-Hotels-Charming-2-Bedroom-House-In-Fabulous-Stamford-With-AC.h112364813.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/111000000/110280000/110276000/110275967/23bd3ad6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bedrooms, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/111000000/110280000/110276000/110275967/c7b5cd05.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/111000000/110280000/110276000/110275967/0ba0b1bb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, fireplace, books](https://images.trvl-media.com/lodging/111000000/110280000/110276000/110275967/0bc12870.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Bright Escape, Top-Rated Design, Fire pit, Near Beach Fairfield 10/10 Exceptional (10) "This house is adorable! We rented it for our adult children and two grandchildren for our wedding weekend. The owner is excellent at communicating and providing information about things to do in the area. The house is immaculate and the sleeping quarters are perfect! I would definitely recommend this house for a family looking in the area and am keeping their information in my records for future use! Cannot say enough good things about the house and the owner!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Judy F. CA $280 CA $712 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Fairfield-Hotels-Renovated-Retreat-WFire-Pit.h110275967.Hotel-Information) ![WiFi, bed sheets](https://images.trvl-media.com/lodging/121000000/120650000/120646300/120646218/9494f7ec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/121000000/120650000/120646300/120646218/7b6488b3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Hair dryer, towels, soap, toilet paper](https://images.trvl-media.com/lodging/121000000/120650000/120646300/120646218/6991c0ac.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Miscellaneous](https://images.trvl-media.com/lodging/121000000/120650000/120646300/120646218/fef7e7ad.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Newly renovated Private bedroom near Stony Brook University Stony Brook 6.0/10 (1) "A one family home still undergoing renovations to its kitchen, the property was clean and properly appointed for our one-night stay, which only required one bedroom, sheets and towels. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Rudolph CA $144 CA $316 total includes taxes & fees Nov 3 - Nov 4 [](https://www.expedia.ca/Stony-Brook-Hotels-Newly-Renovated-Private-Bedroom-Near-Stony-Brook-University.h120646218.Hotel-Information) ![Coffee/tea maker, spices](https://images.trvl-media.com/lodging/92000000/91310000/91303100/91303070/53120cff.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Coffee/tea maker, spices](https://images.trvl-media.com/lodging/92000000/91310000/91303100/91303070/81bfaea4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/92000000/91310000/91303100/91303070/39f9e627.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Coffee/tea maker, spices](https://images.trvl-media.com/lodging/92000000/91310000/91303100/91303070/2447aae9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Ultra-Modern Studio | Near Hospital & NYCIM | WiFi Huntington 10/10 Exceptional (5) "We stayed here for 2 nights while visiting friends in Syosset. We were blown away by the beauty and high-end features of this place. The place is bright and spacious with all of the amenities we needed and then some. Check in was simple. Communication and instructions were clear and helpful. Highly recommend!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Wendy A. CA $286 CA $554 total includes taxes & fees Nov 11 - Nov 12 [](https://www.expedia.ca/Huntington-Hotels-Ultra-Modern-Studio-Near-Hospital-NYCIM-WiFi.h91303070.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/77000000/76820000/76813800/76813717/46aa940e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/77000000/76820000/76813800/76813717/dbd01f80.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/77000000/76820000/76813800/76813717/976c5077.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/77000000/76820000/76813800/76813717/c1927c5c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Grand Fairfield Getaway- 5BR Fam-Friendly near I95&Shops - Spacious&Gracious Fairfield 9.4/10 Exceptional (20) "My family was thrilled to stay at Andrew's property for a family wedding! The house was beautiful, clean, and spacious.. thanks so much for everything!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Lisa O. CA $452 CA $1,031 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Fairfield-Hotels-Grand-Fairfield-Getaway-5BR-Fam-Friendly-Near-I95Shops-SpaciousGracious.h76813717.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/102000000/101740000/101736200/101736107/0572c584.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/102000000/101740000/101736200/101736107/5959da8d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, stereo, offices](https://images.trvl-media.com/lodging/102000000/101740000/101736200/101736107/3a5591f2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, stereo, offices](https://images.trvl-media.com/lodging/102000000/101740000/101736200/101736107/40fafd0c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The B&W Haven 5BR Home with yard theater + Office Brooklawn - St. Vincent 9.2/10 Wonderful (7) "Host was very polite and communicated well throughout the stay. The property appears well maintained. There are window units but everyone was comfortable for the duration of our stay." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) George M. CA $400 CA $939 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Bridgeport-Hotels-The-BW-Haven-5BR-Home-With-Yard-Theater-Office.h101736107.Hotel-Information) ![Fridge, oven, stovetop, coffee/tea maker](https://images.trvl-media.com/lodging/88000000/87230000/87226100/87226001/33d9009b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/88000000/87230000/87226100/87226001/5886c1c7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, WiFi, bed sheets](https://images.trvl-media.com/lodging/88000000/87230000/87226100/87226001/75f55379.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/88000000/87230000/87226100/87226001/72e8d656.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Centric property close to all the great things in the city Brooklawn - St. Vincent 7.2/10 Good (13) "Parking on the street wasn’t as difficult there was always a good spot it was clean and accommodating" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) juan l. CA $220 CA $415 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Bridgeport-Hotels-Golden-Colonial-Home-Family-Friendly.h87226001.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/100000000/99680000/99676500/99676500/7b207ad2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/100000000/99680000/99676500/99676500/cceb3ce9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/100000000/99680000/99676500/99676500/w1024h680x0y0-c6eed8a3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bedrooms, desk, travel crib, free WiFi](https://images.trvl-media.com/lodging/100000000/99680000/99676500/99676500/w1023h682x1y1-a7d1b30a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Updated, cozy single family in Fairfield County Trumbull 9.4/10 Exceptional (12) "The house was lovely and exactly as pictured. Our family of 5 had plenty of room and enjoyed the games downstairs and the large backyard. The house is very conveniently located to restaurants, shops and the Merritt Parkway. We have family nearby and would live to stay again!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jessica B. CA $322 CA $679 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Trumbull-Hotels-Updated.h99676500.Hotel-Information) ![5 bedrooms, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/92000000/91020000/91013300/91013202/eadcc7a9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/92000000/91020000/91013300/91013202/f7d03663.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/92000000/91020000/91013300/91013202/a3984e5b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, stereo, offices](https://images.trvl-media.com/lodging/92000000/91020000/91013300/91013202/cac274bc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Modern + Spacious 5BR/2BA Home, Renovated Backyard West End - West Side 9.6/10 Exceptional (4) "Used for family weekend at SHU. Convenient location and plenty of space for the whole family! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Laurene S. CA $495 CA $1,074 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Bridgeport-Hotels-Modern-Spacious-5BR2BA-Home.h91013202.Hotel-Information) ![55-inch Smart TV with digital channels, TV, streaming services](https://images.trvl-media.com/lodging/113000000/112050000/112048300/112048293/40355023.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![55-inch Smart TV with digital channels, TV, streaming services](https://images.trvl-media.com/lodging/113000000/112050000/112048300/112048293/7643b925.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/113000000/112050000/112048300/112048293/355638a7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/113000000/112050000/112048300/112048293/b5a9021c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Charming Colonial for Events! – Perfect for Family Reunions and Group Getaways! Bridgeport 9.6/10 Exceptional (4) "Extremely clean and well prepared home stocked with items we may need. Plenty of space for all guests. Comfortable beds. Felt safe with the use of electronic keypad entry and security system. Very well maintained. Historic feel with modern amenities. Great location in regards to where we needed to be. Able to communicate with host who assisted in accommodations. Plenty of parking. Lovely place. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) natalie c. CA $1,004 CA $1,928 total includes taxes & fees Nov 5 - Nov 6 [](https://www.expedia.ca/Bridgeport-Hotels-Charming-Colonial-Retreat-Perfect-For-Family-Getaways.h112048293.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/119000000/118790000/118789100/118789041/10cc8d97.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/119000000/118790000/118789100/118789041/8d7284f0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/119000000/118790000/118789100/118789041/5e748981.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![4 bedrooms, desk, iron/ironing board, WiFi](https://images.trvl-media.com/lodging/119000000/118790000/118789100/118789041/f1633edf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Bella Vista St James! Waterfront house with a beach dock and so much more! Saint James 10/10 Exceptional (1) "This property is beautiful and the host was very responsive. We were in town for a funeral so unfortunately wasnt able to enjoy the house as much as I would have liked to. The view is breathtaking, we saw deer, wild turkeys, swans and more. I would suggest kids 8 would be better suited. I had to chase my little around to ensure they weren't touching or playing with any of the decorations. Plenty of bathrooms and counter space. No cell reception but the Wi-Fi worked throughout the whole home.... ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Devin k. CA $1,908 CA $2,947 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/St-James-Hotels-The-Bella-Vista-St-James-Waterfront-House-With-A-Beach-Dock-And-So-Much-More.h118789041.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/107000000/106570000/106560900/106560827/65239b44.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/107000000/106570000/106560900/106560827/2d5d6a4c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, fireplace, books](https://images.trvl-media.com/lodging/107000000/106570000/106560900/106560827/ec77d4b1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/107000000/106570000/106560900/106560827/690553a1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Norwalk/Westport Border, Near Beach, w/Fire Pit, 60 Min to NYC Norwalk 10/10 Exceptional (7) "We had a very nice family weekend. There was plenty of room, the furniture and beds were comfortable, and the kitchen had everything we needed. Great communication with the owner" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Helen C. CA $365 CA $814 total includes taxes & fees Nov 4 - Nov 5 [](https://www.expedia.ca/Norwalk-Hotels-Family-Friendly.h106560827.Hotel-Information) ![2 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/122000000/121230000/121225400/121225378/26e5405f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, fireplace](https://images.trvl-media.com/lodging/122000000/121230000/121225400/121225378/d92aa957.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/122000000/121230000/121225400/121225378/2285efa9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Shower, hair dryer, towels, soap](https://images.trvl-media.com/lodging/122000000/121230000/121225400/121225378/f566494c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Stylish 2BR House Near Stony Brook University and shopping, fully renovated Stony Brook CA $320 CA $740 total includes taxes & fees Nov 3 - Nov 4 [](https://www.expedia.ca/Stony-Brook-Hotels-Stylish-2BR-House-Near-Stony-Brook-University-And-Shopping.h121225378.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/113000000/112450000/112441800/112441774/176ad9a0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/113000000/112450000/112441800/112441774/60609338.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/113000000/112450000/112441800/112441774/5ea6cd90.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/113000000/112450000/112441800/112441774/d754b963.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Upscale 4BR Retreat at the Reservoir! Bridgeport CA $802 CA $1,296 total includes taxes & fees Nov 4 - Nov 5 [](https://www.expedia.ca/Bridgeport-Hotels-Charming-4-Bedroom-House-In-Wonderful-Bridgeport-With-AC.h112441774.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=2025-11-14&endDate=2025-11-15®ionId=6353650&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&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%2FSheffield-Island-Private-Vacation-Homes.d6353650-aaPrivateVacationHomes.Travel-Guide-Accommodation)[Sign up, it's free](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FSheffield-Island-Private-Vacation-Homes.d6353650-aaPrivateVacationHomes.Travel-Guide-Accommodation) ## Top Sheffield Island Hotel Reviews ![The Circle Hotel Fairfield](//images.trvl-media.com/lodging/10000000/9820000/9816500/9816438/b1e811bb_y.jpg) ### The Circle Hotel Fairfield 10/10 Excellent "Easy check in process " [](https://expedia.ca/New-Haven-Hotels-The-Circle-Hotel-Fairfield.h9816438.Hotel-Information) ![The Armon Stamford Hotel & Conference](//images.trvl-media.com/lodging/90000000/89820000/89818900/89818854/99ae042b_y.jpg) ### The Armon Stamford Hotel & Conference 10/10 Excellent "Excellent! Will be glad to be back for sure!" [](https://expedia.ca/Stamford-Hotels-The-Armon-Hotel-Conference.h89818854.Hotel-Information) ![Amsterdam Hotel](//images.trvl-media.com/lodging/1000000/30000/20800/20793/f5bb9592_y.jpg) ### Amsterdam Hotel 10/10 Excellent "Very nice stay" [](https://expedia.ca/Stamford-Hotels-Amsterdam-Hotel.h20793.Hotel-Information) ![Marriott Melville Long Island](//images.trvl-media.com/lodging/1000000/20000/15800/15742/76d16bae_y.jpg) ### Marriott Melville Long Island 10/10 Excellent "We ordered room service and it was very good. We did not drink at the bar." [](https://expedia.ca/Melville-Hotels-Marriott-Melville-Long-Island.h15742.Hotel-Information) ![Radisson Hotel Hauppauge-Long Island](//images.trvl-media.com/lodging/1000000/20000/10800/10706/db515945_y.jpg) ### Radisson Hotel Hauppauge-Long Island 10/10 Excellent "Yes" [](https://expedia.ca/Hauppauge-Hotels-Radisson-Hotel-Hauppauge-Long-Island.h10706.Hotel-Information) ![Hyatt Regency Greenwich](//images.trvl-media.com/lodging/1000000/20000/18200/18180/19d28016_y.jpg) ### Hyatt Regency Greenwich 10/10 Excellent "Beautiful hotel. Nice stay. Comfortable bed. Will come again. " [](https://expedia.ca/Stamford-Hotels-Hyatt-Regency-Greenwich.h18180.Hotel-Information) ![Sonesta White Plains Downtown](//images.trvl-media.com/lodging/1000000/10000/10000/9979/2c718cc1_y.jpg) ### Sonesta White Plains Downtown 10/10 Excellent "No complaints at all" [](https://expedia.ca/White-Plains-Hotels-Sonesta-White-Plains-Downtown.h9979.Hotel-Information) ![HYATT house White Plains](//images.trvl-media.com/lodging/1000000/430000/427300/427283/458cd7c2_y.jpg) ### HYATT house White Plains 10/10 Excellent "Felt safe " [](https://expedia.ca/White-Plains-Hotels-HYATT-House-White-Plains.h427283.Hotel-Information) ![The Stamford Hotel](//images.trvl-media.com/lodging/1000000/50000/42300/42258/d312d428_y.jpg) ### The Stamford Hotel 10/10 Excellent "Very nice " [](https://expedia.ca/Stamford-Hotels-The-Stamford-Hotel.h42258.Hotel-Information) ## Find out more about Sheffield Island ## Sheffield Island Vacation Homes information | Number of reviews | 252 | | --- | --- | | Accommodation | 310 Vacation Homes | | Lowest Price | CA $196 | | Highest Price | CA $2,947 | ## Explore a world of travel with Expedia - 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[Avis Rental Cars in Norwalk](https://www.expedia.ca/Avis-Car-Rentals-In-Norwalk.d9245-c41.Car-Rental-Guide-Suppliers) - [Car rental Darien](https://www.expedia.ca/Car-Rentals-In-Darien.d7557.Car-Rental-Guide) - [Car rental Norwalk](https://www.expedia.ca/Car-Rentals-In-Norwalk.d9245.Car-Rental-Guide) - [Hertz Rental Cars in Norwalk Islands](https://www.expedia.ca/Hertz-Car-Rentals-In-Norwalk-Islands.d6347888-c40.Car-Rental-Guide-Suppliers) - [Payless Rental Cars in Norwalk Islands](https://www.expedia.ca/Payless-Car-Rentals-In-Norwalk-Islands.d6347888-c38.Car-Rental-Guide-Suppliers) - [Rent A Wreck Rental Cars in Norwalk](https://www.expedia.ca/Rent-A-Wreck-Car-Rentals-In-Norwalk.d9245-c33.Car-Rental-Guide-Suppliers) - [Norwalk Islands Vacation Rentals](https://www.expedia.ca/Norwalk-Islands-Vacation-Rentals.d6347888.Travel-Guide-VacationRentals) - [Norwalk Vacation Rentals](https://www.expedia.ca/Norwalk-Vacation-Rentals.d9245.Travel-Guide-VacationRentals) - [Sherwood Island State Park Vacation Rentals](https://www.expedia.ca/Sherwood-Island-State-Park-Vacation-Rentals.d6248407.Travel-Guide-VacationRentals) - [Things to do in Stamford](https://www.expedia.ca/Things-To-Do-In-Stamford.d602523.Travel-Guide-Activities) - [Book Vacation Homes in Sheffield Island on Expedia.com](https://www.expedia.com/Sheffield-Island-Private-Vacation-Homes.d6353650-aaPrivateVacationHomes.Travel-Guide-Accommodation)