Title: Cheshire Vacation Home Rentals from CA $229: Search Top Private Vacation Homes for Rent | Expedia.ca [Hotels in Cheshire](https://expedia.ca/Cheshire-Hotels.d183057.Travel-Guide-Hotels)[Vacation Rentals in Cheshire](https://expedia.ca/Cheshire-Vacation-Rentals.d183057.Travel-Guide-VacationRentals)[Flights to Cheshire](https://expedia.ca/Cheap-Flights-To-Cheshire.d183057.Travel-Guide-Flights)[Cheshire Car Rentals](https://expedia.ca/Car-Rentals-In-Cheshire.d183057.Car-Rental-Guide)[Cheshire Vacation Packages](https://expedia.ca/Cheshire.d183057.Destination-Travel-Guides) ![](https://mediaim.expedia.com/destination/2/ab039a4411a79c16e7c533ffaba43069.jpg?impolicy=fcrop&w=1200&h=500&q=medium) Photo by Tai Bui # Cheshire 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=183057&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=183057&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=183057&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=183057&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 Cheshire Vacation Homes ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/112000000/111110000/111107100/111107034/7f49dba8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/112000000/111110000/111107100/111107034/367417ad.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/112000000/111110000/111107100/111107034/05304b12.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/112000000/111110000/111107100/111107034/42181017.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Family Stays: Middletown, CT Middletown 10/10 Exceptional (16) "The house was great, the welcome snacks and balloons were thoughtful and the kitchen coffee, etc, was much appreciated. This was an excellent stay and I highly recommend it!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Cari M. CA $129 CA $272 total includes taxes & fees Nov 4 - Nov 5 [](https://www.expedia.ca/Middletown-Hotels-Family-Stays-In-Middletown.h111107034.Hotel-Information) ![1 bedroom, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/66000000/65400000/65396400/65396309/bf5d2058.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/66000000/65400000/65396400/65396309/c537ec71.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/66000000/65400000/65396400/65396309/4b37fe37.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV](https://images.trvl-media.com/lodging/66000000/65400000/65396400/65396309/94637ed7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Once the old Schools house now a newly furnished Apartment Wallingford Center 9.0/10 Wonderful (13) "Excellent option for a short stay near the heart of it all in Wallingford." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jeanette W. CA $153 CA $392 total includes taxes & fees Oct 31 - Nov 1 [](https://www.expedia.ca/Wallingford-Hotels-Once-The-Old-Schools-House-Now-A-Newly-Furnished-Apartment.h65396309.Hotel-Information) ![Beach nearby](https://images.trvl-media.com/lodging/106000000/105870000/105862500/105862474/w1440h957x0y3-6274ae75.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/106000000/105870000/105862500/105862474/d3b32f3d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/106000000/105870000/105862500/105862474/af0195f8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/106000000/105870000/105862500/105862474/bbafc8c5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Jewel of The Cove - Historic Coastal Retreat East Shore 10/10 Exceptional (4) "loved it so much, beautiful property 100 % would stay again " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Leilani R. CA $289 CA $726 total includes taxes & fees Nov 16 - Nov 17 [](https://www.expedia.ca/East-Haven-Hotels-The-Jewel-Of-The-Cove-Historic-Coastal-Retreat.h105862474.Hotel-Information) ![Fridge, microwave, oven, coffee/tea maker](https://images.trvl-media.com/lodging/77000000/76970000/76963400/76963336/89c597eb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Flat-screen TV](https://images.trvl-media.com/lodging/77000000/76970000/76963400/76963336/02effb57.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Marina](https://images.trvl-media.com/lodging/77000000/76970000/76963400/76963336/2c0c3b2a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/77000000/76970000/76963400/76963336/2793242f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Gorgeous Waterfront 2 Bedroom 1 Bath Modern Home. Fair Haven 7.6/10 Good (5) "Thanks for hosting us! It was clean and nice. For future guests, a long body mirror might be nice but we had a wonderful time and appreciated you bringing us extra towels quickly!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jamie S. CA $187 CA $350 total includes taxes & fees Oct 30 - Oct 31 [](https://www.expedia.ca/New-Haven-Hotels-Gorgeous-Waterfront-2-Bedroom-1-Bath-Modern-Home.h76963336.Hotel-Information) ![TV](https://images.trvl-media.com/lodging/117000000/116660000/116653300/116653280/4e86762a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Microwave, oven, stovetop, dishwasher](https://images.trvl-media.com/lodging/117000000/116660000/116653300/116653280/03f324a1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/117000000/116660000/116653300/116653280/e5e268a4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Microwave, oven, stovetop, dishwasher](https://images.trvl-media.com/lodging/117000000/116660000/116653300/116653280/519b402d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Clean, Bright & Private WHOLE HOUSE 4 YOU. Safe, Centrally Located, Garage New Britain 10/10 Exceptional (6) "The space was clean and light, great finishes. The home felt comfortable and was easy to find. Thank you for a wonderful weekend. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Lara S. CA $157 CA $347 total includes taxes & fees Nov 6 - Nov 7 [](https://www.expedia.ca/New-Britain-Hotels-Clean.h116653280.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/60000000/59630000/59625600/59625523/41e92d5e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/60000000/59630000/59625600/59625523/58d0e4d3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/60000000/59630000/59625600/59625523/8cacb4e3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/60000000/59630000/59625600/59625523/d1cc68c7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Stocked home close to Yale, in Heart of New Haven Mill River 9.2/10 Wonderful (18) "Great value very close to university. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Lawrence CA $208 CA $353 total includes taxes & fees Oct 30 - Oct 31 [](https://www.expedia.ca/New-Haven-Hotels-Stocked-Home-Close-To-Yale.h59625523.Hotel-Information) ![Outdoor dining](https://images.trvl-media.com/lodging/77000000/76540000/76532900/76532852/w1440h958x0y3-16ec6595.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/77000000/76540000/76532900/76532852/22a7e460.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/77000000/76540000/76532900/76532852/e207012e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/77000000/76540000/76532900/76532852/bf5bce9e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cozy Gem in Heart of East Rock |King Bed| Near DT and Yale | Free Parking East Rock 9.6/10 Exceptional (8) "Property owner takes great care of the place. Instructions were easy to follow and the location was right down the road from the places we were going to. We would rent again if we ever come back to New Haven" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Derek L. CA $186 CA $501 total includes taxes & fees Nov 3 - Nov 4 [](https://www.expedia.ca/New-Haven-Hotels-Cozy-Gem-In-Heart-Of-East-Rock-King-Bed-Near-DT.h76532852.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/108000000/107910000/107908200/107908182/304690d1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/108000000/107910000/107908200/107908182/af74480c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/108000000/107910000/107908200/107908182/3d1b063e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/108000000/107910000/107908200/107908182/65684bb6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Charming 3-Bedroom Home with Modern Comforts in West Hartford West Hartford 9.0/10 Wonderful (8) "Great house in a safe neighborhood with a fenced in yard. Amenities provided. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Ben H. CA $154 CA $380 total includes taxes & fees Oct 29 - Oct 30 [](https://www.expedia.ca/West-Hartford-Hotels-Charming-3-Bedroom-Home-With-Modern-Comforts-In-West-Hartford.h107908182.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/58000000/57700000/57696800/57696731/04508426_edited_1287.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV](https://images.trvl-media.com/lodging/58000000/57700000/57696800/57696731/af23948e.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/58000000/57700000/57696800/57696731/41a9baa9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/58000000/57700000/57696800/57696731/ab91a76d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Newly Remodeled 1-BR Close to Everything yet Very Private Wallingford 10/10 Exceptional (9) "I was very pleased with the accomodations. I had everything I needed and it was comfortable and quiet. I was able to get my research done and enjoyed the peaceful setting, and it was convenient to the friends and family I visited during my stay. I will definitely stay here again. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Paula S. CA $161 CA $403 total includes taxes & fees Oct 30 - Oct 31 [](https://www.expedia.ca/Wallingford-Hotels-Newly-Remodeled-1-BR-Close-To-Everything-Yet-Very-Private.h57696731.Hotel-Information) ![2 bedrooms, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/77000000/76540000/76533100/76533032/w1024h676x0y3-7652554c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/77000000/76540000/76533100/76533032/w1024h676x0y3-f162bd81.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/77000000/76540000/76533100/76533032/092779b5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/77000000/76540000/76533100/76533032/w1440h958x0y3-cc94fd8d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Orange Oasis in East Rock |Free Parking| Near Yale and DT|Large Memory Foam Beds East Rock 9.0/10 Wonderful (8) "the apartment was so beautiful, clean, and spacious! it was a great area to be in! the beds were SUPER comfortable as well, highlight of my trip!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) milly s. CA $195 CA $521 total includes taxes & fees Nov 3 - Nov 4 [](https://www.expedia.ca/New-Haven-Hotels-Orange-Oasis-In-East-Rock-Free-ParkingNear-Yale-DT.h76533032.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/108000000/107980000/107976300/107976290/63307396.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, offices](https://images.trvl-media.com/lodging/108000000/107980000/107976300/107976290/325fc50b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/108000000/107980000/107976300/107976290/62ac79d9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/108000000/107980000/107976300/107976290/00a0d671.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Private Apartment in Berlin Berlin 9.2/10 Wonderful (5) "We visited over a holiday weekend. The house is clean and a good size for the 3 adults in our group and our dog. It is in walking distance to several stores and a park. We would stay again if we were in the area. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Stacy B. CA $165 CA $444 total includes taxes & fees Nov 11 - Nov 12 [](https://www.expedia.ca/Berlin-Hotels-Private-Apartment-In-Berlin.h107976290.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/120000000/119310000/119305500/119305470/1b8a6cf5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/120000000/119310000/119305500/119305470/eb680fc0.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/120000000/119310000/119305500/119305470/b45f0846.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/120000000/119310000/119305500/119305470/faf6d210.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cozy Guest Suite in Historic Home Middletown CA $183 CA $271 total includes taxes & fees Nov 8 - Nov 9 [](https://www.expedia.ca/Middletown-Hotels-Cozy-Guest-Suite-In-Historic-Home.h119305470.Hotel-Information) ![Exterior detail](https://images.trvl-media.com/lodging/94000000/93400000/93397900/93397831/8c48c1bf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, Netflix, Hulu, books](https://images.trvl-media.com/lodging/94000000/93400000/93397900/93397831/498bd184.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/94000000/93400000/93397900/93397831/3625879a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, oven, stovetop, coffee/tea maker](https://images.trvl-media.com/lodging/94000000/93400000/93397900/93397831/38eef8d7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Santiago in Science Park at Yale New Haven Dixwell 8.0/10 Very good (8) "The property was great. Clean and comfortable! Great communication from the owner. Its not the entire house as there was someone staying upstairs. Otherwise the experience was great! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) James D. CA $150 CA $298 total includes taxes & fees Nov 3 - Nov 4 [](https://www.expedia.ca/New-Haven-Hotels-The-Santiago-In-Science-Park-At-Yale-New-Haven.h93397831.Hotel-Information) ![Microwave, oven, stovetop, dishwasher](https://images.trvl-media.com/lodging/119000000/118950000/118949700/118949631/ce1fc249.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/119000000/118950000/118949700/118949631/8e373067.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/119000000/118950000/118949700/118949631/f54053dc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/119000000/118950000/118949700/118949631/57c8df73.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cozy East Haven Home • Near Beach & Yale Momauguin 10/10 Exceptional (4) "Such a cute place, loved all the nautical touches. Great space for a weekend getaway, pretty well-stocked kitchen, clean & cozy. Really appreciated the outdoor space & amenities too! And Michael the host is very responsive & helpful! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Amal A. CA $175 CA $229 total includes taxes & fees Nov 12 - Nov 13 [](https://www.expedia.ca/East-Haven-Hotels-Cozy-Home-Near-New-Haven.h118949631.Hotel-Information) ![Exterior detail](https://images.trvl-media.com/lodging/108000000/107460000/107458300/107458207/650b435b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV](https://images.trvl-media.com/lodging/108000000/107460000/107458300/107458207/fc227418.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/108000000/107460000/107458300/107458207/w1017h1324x0y0-57857bef.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/108000000/107460000/107458300/107458207/w1003h750x5y0-22089762.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 1-bedroom vacation home 22 minutes from Quinnipiac University Wolcott 9.6/10 Exceptional (4) "Very clean and the host was great " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) David G. CA $210 CA $559 total includes taxes & fees Oct 31 - Nov 1 [](https://www.expedia.ca/Waterbury-Hotels-1-Bedroom-Vacation-Home-22-Minutes-From-Quinnipiac-University.h107458207.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/79000000/78180000/78173400/78173305/c1d5dab6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/79000000/78180000/78173400/78173305/6dab1099.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/79000000/78180000/78173400/78173305/f3668968.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Marina](https://images.trvl-media.com/lodging/79000000/78180000/78173400/78173305/8c7a6352.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Gorgeous Waterfront 3 Bedroom, 1.5 Bathroom Unit. Fair Haven 9.6/10 Exceptional (13) "Had a really nice stay, enjoyed this open airy space with comfortable beds and beautiful light with a view of the river. Very nice time, would stay again." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Brian B. CA $259 CA $477 total includes taxes & fees Nov 4 - Nov 5 [](https://www.expedia.ca/New-Haven-Hotels-Gorgeous-Waterfront-3-Bedroom.h78173305.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/112000000/111690000/111683300/111683284/163d5bad.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/112000000/111690000/111683300/111683284/218721ff.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/112000000/111690000/111683300/111683284/6a37565c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/112000000/111690000/111683300/111683284/1366870a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Charming & Private 1-bed & 1 ba ,sleeps 2, on 1st floor of a 5 bed 3ba House, Shelton 9.0/10 Wonderful (2) "The house was very clean. Rudolph and his son were very personable and welcoming. Very much enjoyed our stay." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Alex C. CA $168 CA $275 total includes taxes & fees Oct 29 - Oct 30 [](https://www.expedia.ca/Charming.h111683284.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/19000000/18770000/18760700/18760693/4aaa8de8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/19000000/18770000/18760700/18760693/83198fbf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/19000000/18770000/18760700/18760693/e88adc9d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, DVD player, books](https://images.trvl-media.com/lodging/19000000/18770000/18760700/18760693/20bbb653.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Historic New England home ,Reunions Beach pass Guilford 9.2/10 Wonderful (90) "House was perfect for family get together. Enjoyed walking into town for afternoon shopping and dining." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jennifer D. CA $273 CA $616 total includes taxes & fees Nov 17 - Nov 18 [](https://www.expedia.ca/Guilford-Hotels-Historic-New-England-Home.h18760693.Hotel-Information) ![Smart TV, fireplace](https://images.trvl-media.com/lodging/108000000/107970000/107960200/107960143/7db97143.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/108000000/107970000/107960200/107960143/affcc370.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/108000000/107970000/107960200/107960143/c79da4f1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/108000000/107970000/107960200/107960143/81d94858.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Sun Filled Lake House Living Avon 6.0/10 (3) "Enjoyed my stayConvenient location for restaurants, shopping etcHome was clean and neat and in a nice quiet neighborhood Good value" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Joseph C. CA $119 CA $396 total includes taxes & fees Oct 30 - Oct 31 [](https://www.expedia.ca/Avon-Hotels-Sun-Filled-Lake-House-Living.h107960143.Hotel-Information) ![Smart TV, books](https://images.trvl-media.com/lodging/101000000/100840000/100834300/100834240/w776h683x124y0-ae153ead.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Beach nearby, sun loungers, beach towels](https://images.trvl-media.com/lodging/101000000/100840000/100834300/100834240/93b50094.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/101000000/100840000/100834300/100834240/cd224da3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/101000000/100840000/100834300/100834240/0845eb45.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Clear LI Sound waterview, Wedding pics, Yale&Beach East Shore 10/10 Exceptional (9) "Attended a wedding close by. This house was a comfortable clean place to rest in between events. Lovely water front. Calm and peaceful" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kacy R. CA $409 CA $869 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/East-Haven-Hotels-Clear-LI-Sound-Waterview.h100834240.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=2025-11-11&endDate=2025-11-12®ionId=183057&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%2FCheshire-Private-Vacation-Homes.d183057-aaPrivateVacationHomes.Travel-Guide-Accommodation)[Sign up, it's free](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FCheshire-Private-Vacation-Homes.d183057-aaPrivateVacationHomes.Travel-Guide-Accommodation) ## Top Cheshire Hotel Reviews ![Cambria Hotel New Haven University Area](//images.trvl-media.com/lodging/79000000/78620000/78614500/78614483/a6a28eee_y.jpg) ### Cambria Hotel New Haven University Area 10/10 Excellent "Clean and comfortable. Helpful staff and convenient location to local businesses. " [](https://expedia.ca/New-Haven-Hotels-Cambria-Hotel-New-Haven-University-Area.h78614483.Hotel-Information) ![Hilton Garden Inn Shelton](//images.trvl-media.com/lodging/1000000/290000/287700/287687/18ff21f4_y.jpg) ### Hilton Garden Inn Shelton 10/10 Excellent "the room was very clean and fragrant" [](https://expedia.ca/New-Haven-Hotels-Hilton-Garden-Inn-Shelton.h287687.Hotel-Information) ![Best Western Hartford Hotel & Suites](//images.trvl-media.com/lodging/1000000/20000/12200/12156/cfbe36c4_y.jpg) ### Best Western Hartford Hotel & Suites 10/10 Excellent "Great Place, recommend to others." [](https://expedia.ca/Hartford-Hotels-Best-Western-Hartford-Hotel-Suites.h12156.Hotel-Information) ![New Haven Hotel](//images.trvl-media.com/lodging/1000000/40000/36800/36721/dd69cbb4_y.jpg) ### New Haven Hotel 10/10 Excellent "Great that there was an iron and fridge in the room, as well as bathrobes. Very comfortable mattress. Gold star to front desk staff for being genuinely friendly!" [](https://expedia.ca/New-Haven-Hotels-New-Haven-Hotel.h36721.Hotel-Information) ![Omni New Haven Hotel at Yale](//images.trvl-media.com/lodging/1000000/50000/50000/49957/7466af25_y.jpg) ### Omni New Haven Hotel at Yale 10/10 Excellent "Very nice hotel, clean and add to walk around downtown " [](https://expedia.ca/New-Haven-Hotels-Omni-New-Haven-Hotel-At-Yale.h49957.Hotel-Information) ![Extended Stay America Suites Hartford Farmington](//images.trvl-media.com/lodging/1000000/160000/151100/151013/02939ae3_y.jpg) ### Extended Stay America Suites Hartford Farmington 10/10 Excellent "Thank Staff was Great! Very very nice and attentive. Room very clean, Quiet we rested well! The Great was awesome and exit was wonderful. Parking was smoothe. We’ll return to enjoy another quiet night get away. " [](https://expedia.ca/Hartford-Hotels-Extended-Stay-America-Suites-Hartford-Farmington.h151013.Hotel-Information) ![Hotel Marcel New Haven, Tapestry Collection By Hilton](//images.trvl-media.com/lodging/72000000/71430000/71427300/71427300/1699c03c_y.jpg) ### Hotel Marcel New Haven, Tapestry Collection By Hilton 10/10 Excellent "Helpful staff, clean and spacious rooms. Good location." [](https://expedia.ca/New-Haven-Hotels-Hotel-Marcel-New-Haven.h71427300.Hotel-Information) ![Holiday Inn Express Southington by IHG](//images.trvl-media.com/lodging/1000000/10000/4000/3929/120068a2_y.jpg) ### Holiday Inn Express Southington by IHG 10/10 Excellent "The fan of the HVAC unit in the room was very loud." [](https://expedia.ca/Hartford-Hotels-Holiday-Inn-Express-Southington.h3929.Hotel-Information) ![Clarion Inn](//images.trvl-media.com/lodging/1000000/10000/7600/7519/36377da0_y.jpg) ### Clarion Inn 10/10 Excellent "Very convenient and affordable " [](https://expedia.ca/North-Haven-Hotels-Clarion-Inn.h7519.Hotel-Information) ## Find out more about Cheshire ## Cheshire Vacation Homes information | Number of reviews | 175 | | --- | --- | | Accommodation | 323 Vacation Homes | | Lowest Price | CA $229 | | Highest Price | CA $869 | ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Other - More ways to book - [Hotels near Brookside Park](https://www.expedia.ca/Brookside-Park-Hotels.0-l553248621557919974-0.Travel-Guide-Filter-Hotels) - [B&B in Cheshire Historic District](https://www.expedia.ca/Cheshire-Historic-District-Bed-And-Breakfast.d6346724-aaBedAndBreakfast.Travel-Guide-Accommodation) - [Country Houses in Cheshire Historic District](https://www.expedia.ca/Cheshire-Historic-District-Country-House.d6346724-aaCountryHouse.Travel-Guide-Accommodation) - 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