Title: Cheshire Vacation Home Rentals from CA $228: 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 ![calendar shield illustration](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.svg) ### Change your mind Book hotels with free cancellation ![deals illustration](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) ![bed illustration](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 In two weeks [Oct 17 - Oct 19](https://www.expedia.ca/Hotel-Search?regionId=183057&startDate=2025-10-17&endDate=2025-10-19&adults=2&lodging=VACATION_HOME&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In one month [Oct 31 - Nov 2](https://www.expedia.ca/Hotel-Search?regionId=183057&startDate=2025-10-31&endDate=2025-11-02&adults=2&lodging=VACATION_HOME&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Nov 28 - Nov 30](https://www.expedia.ca/Hotel-Search?regionId=183057&startDate=2025-11-28&endDate=2025-11-30&adults=2&lodging=VACATION_HOME&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In three months [Dec 26 - Dec 28](https://www.expedia.ca/Hotel-Search?regionId=183057&startDate=2025-12-26&endDate=2025-12-28&adults=2&lodging=VACATION_HOME&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Browse Select Cheshire Vacation Homes ![Interior](https://images.trvl-media.com/lodging/84000000/83230000/83221200/83221101/b3c56889.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/84000000/83230000/83221200/83221101/153626bd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/84000000/83230000/83221200/83221101/3ef07775.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/84000000/83230000/83221200/83221101/w381h683x321y0-2a42c217.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cozy 2 bedroom home located minutes from downtown West New Haven 9.6/10 Exceptional (30) "A very comfortable short stay in a convenient location" [](https://www.expedia.ca/New-Haven-Hotels-Cozy-2-Bedroom-Home-Located-Minutes-From-Downtown.h83221101.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/102000000/101950000/101940900/101940832/ac2eb1be.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/102000000/101950000/101940900/101940832/95857e89.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/102000000/101950000/101940900/101940832/59afcbd6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace](https://images.trvl-media.com/lodging/102000000/101950000/101940900/101940832/056a1402.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### McAngel Haven: 5 mins from Yale West Haven 9.6/10 Exceptional (14) "My family and I stayed at the property for a wedding in Milford. The house had plenty of space for our group to say, and the bedrooms were comfortable. The three bathrooms were helpful for our group to efficiently get ready for the wedding, and the kitchen was adequately appointed for us to have meals." CA $319 CA $718 total includes taxes & fees Oct 6 - Oct 7 [](https://www.expedia.ca/West-Haven-Hotels-McAngel-Haven-5-Mins-From-Yale.h101940832.Hotel-Information) ![Beach nearby](https://images.trvl-media.com/lodging/100000000/99630000/99620900/99620843/83071483.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/100000000/99630000/99620900/99620843/w505h683x260y0-dff3cc35.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/100000000/99630000/99620900/99620843/w932h683x46y0-282f628e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/100000000/99630000/99620900/99620843/w848h683x88y0-c6c8bfc0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### BEACH BUM CARRIAGE HOUSE with kayaks - steps to beach, park, marinas & brewery! Branford Center 9.4/10 Exceptional (14) "This Carriage House is exactly as described. Wonderful location and setting, just steps away from Branford Point. Hope to visit again soon! " [](https://www.expedia.ca/Branford-Hotels-BEACH-BUM-CARRIAGE-HOUSE-With-Kayaks-Steps-To-Beach.h99620843.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/63000000/62990000/62980600/62980514/e04d2628.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![4 bedrooms, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/63000000/62990000/62980600/62980514/69c5b430.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/63000000/62990000/62980600/62980514/fe8d70c6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/63000000/62990000/62980600/62980514/3a878ff2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### New Madison beach house - Ocean front- Great views- booking Summer 2025 Madison 10/10 Exceptional (67) "The house is perfectly located. Quiet area but close to downtown Madison and Guilford and so much the CT shoreline has to offer. " [](https://www.expedia.ca/Madison-Hotels-New-Madison-Beach-House-Ocean-Front-Great-Views-Booking-Summer-2025.h62980514.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/93000000/92150000/92144500/92144443/40ad266c.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/93000000/92150000/92144500/92144443/5172d08d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/93000000/92150000/92144500/92144443/65309dba.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/93000000/92150000/92144500/92144443/983a4146.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Ranch style living at its best with country garden & patio! North Haven 9.6/10 Exceptional (14) "the host was really great about getting back to us when we had a question or problem . his home was comfortable and artistic. the location was also easy to get to and the neighborhood was quiet and comvenient to all your needs." [](https://www.expedia.ca/Ranch-Style-Living-At-Its-Best-Wsaltwater-Pool.h92144443.Hotel-Information) ![Dining](https://images.trvl-media.com/lodging/20000000/19180000/19176900/19176844/73c68d22.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![On the beach, sun loungers, beach towels](https://images.trvl-media.com/lodging/20000000/19180000/19176900/19176844/4653b8e5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/20000000/19180000/19176900/19176844/w1198h799x1y1-8c5b60c9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, books, stereo](https://images.trvl-media.com/lodging/20000000/19180000/19176900/19176844/w1199h799x1y1-28353281.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Exclusive Weekend Summer Sale here Waterfront Beach Home🏖️Hot Tub+Stunning Views Branford 9.8/10 Exceptional (68) "Great family get together where we all were very comfortable. " [](https://www.expedia.ca/Branford-Hotels-Private-Sandy-Beach-Hot-Tub.h19176844.Hotel-Information) ![On the beach, sun loungers, beach towels](https://images.trvl-media.com/lodging/34000000/33700000/33694400/33694344/182d5c2f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/34000000/33700000/33694400/33694344/aee04e62.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/34000000/33700000/33694400/33694344/484d2f10.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/34000000/33700000/33694400/33694344/6766f487.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Beach Front Arts & Crafts House With Gorgeous Views Of The Sound Milford 10/10 Exceptional (127) "Fantastic all around!" [](https://www.expedia.ca/Milford-Hotels-Beach-Front-Arts-Crafts-House-With-Gorgeous-Views-Of-The-Sound.h33694344.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/100000000/99400000/99393000/99392995/9b1b575b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/100000000/99400000/99393000/99392995/28398309.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/100000000/99400000/99393000/99392995/459b15b8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/100000000/99400000/99393000/99392995/7a882891.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### New!Quaint & Convenient Hideaway: Great Location East Hartford 9.6/10 Exceptional (14) "Our family of 4 stayed there while visiting Hartford for our daughter’s college graduation. Great location great property and responsive host. Would def stay again!" [](https://www.expedia.ca/East-Hartford-Hotels-NewQuaint-Convenient-Hideaway-Great-Location.h99392995.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/98000000/97110000/97100900/97100855/ba76d023.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/98000000/97110000/97100900/97100855/aca62d31.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/98000000/97110000/97100900/97100855/43064cc8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/98000000/97110000/97100900/97100855/33b638af.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Prime West Hartford Center Location: Historic Gem West Hartford 10/10 Exceptional (28) "The house is very spacious, clean and comfortable. Will definitely book again!" [](https://www.expedia.ca/West-Hartford-Hotels-Prime-West-Hartford-Center-Location-Historic-Gem.h97100855.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) ![Exterior detail](https://images.trvl-media.com/lodging/117000000/116660000/116653300/116653280/c63f512b.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) ![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) ### Clean, Bright & Private WHOLE HOUSE 4 YOU. 7 Beds New Britain 10/10 Exceptional (5) CA $198 CA $396 total includes taxes & fees Oct 1 - Oct 2 [](https://www.expedia.ca/New-Britain-Hotels-Clean.h116653280.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/70000000/69940000/69931800/69931787/d325241e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/70000000/69940000/69931800/69931787/397b71c5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, offices](https://images.trvl-media.com/lodging/70000000/69940000/69931800/69931787/968a43db.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/70000000/69940000/69931800/69931787/2d0eef68.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Amazing Lakefront Property Middlefield 9.8/10 Exceptional (26) "Great views and a good central location for day trips 👌. " [](https://www.expedia.ca/Hartford-Hotels-Amazing-Lakefront-Property.h69931787.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) ![Interior](https://images.trvl-media.com/lodging/101000000/100840000/100834300/100834240/5a216515.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) ![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 (7) "Attended a wedding close by. This house was a comfortable clean place to rest in between events. Lovely water front. Calm and peaceful" CA $407 CA $852 total includes taxes & fees Oct 6 - Oct 7 [](https://www.expedia.ca/East-Haven-Hotels-Clear-LI-Sound-Waterview.h100834240.Hotel-Information) ![Beach nearby, sun loungers, beach towels](https://images.trvl-media.com/lodging/28000000/27130000/27128600/27128565/864cae7c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/28000000/27130000/27128600/27128565/124d7de1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/28000000/27130000/27128600/27128565/01935b15.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/28000000/27130000/27128600/27128565/58477b10.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Steps to beach! Custom-built house with panoramic ocean views, wrap-around deck. Guilford Center 10/10 Exceptional (48) "Absolutely, beautiful and great hostess" [](https://www.expedia.ca/Guilford-Hotels-Spacious-Water-View-House-Nxt-To-Sandy-Beach.h27128565.Hotel-Information) ![Outdoor dining](https://images.trvl-media.com/lodging/113000000/112180000/112176300/112176226/99f4bea7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/113000000/112180000/112176300/112176226/24e82e23.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/113000000/112180000/112176300/112176226/8438de2e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/113000000/112180000/112176300/112176226/511bc03d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Charming 2-bedroom Lake Front Cottage with WiFi, AC in welcoming Harwinton Northwest Harwinton 10/10 Exceptional (11) "I stayed with my mom and the 2 bedroom 1 bath was perfect for our stay. The house way cozy and in a quiet area. Would absolutely stay again; my mom is already talking about coming back to explore more of the surrounding areas!" [](https://www.expedia.ca/Harwinton-Hotels-Charming-2-Bedroom-Lake-Front-Cottage-With-WiFi.h112176226.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/96000000/95700000/95697000/95696989/w510h683x257y0-8b88c76f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/96000000/95700000/95697000/95696989/w507h683x259y0-21a83672.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/96000000/95700000/95697000/95696989/w433h683x296y0-7c0b99a7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/96000000/95700000/95697000/95696989/w742h683x141y0-b0142700.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 🌾Welcoming Tiny Home! Downtown & Beachy☀️ Guilford 9.8/10 Exceptional (15) "The owner knows how to create a welcoming feel and comfortable vibe! This listing is excellent - thank you Stacey! " [](https://www.expedia.ca/Guilford-Hotels-Brand-New-Tiny-Home-Downtown-Beachy.h95696989.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/109000000/108480000/108472400/108472348/5fe6aa61.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/109000000/108480000/108472400/108472348/w1233h900x1y0-9d2661f4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/109000000/108480000/108472400/108472348/96bf62b6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/109000000/108480000/108472400/108472348/0f09d09f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### #37 - Luxury Collection Stratford 8.8/10 Excellent (3) "We enjoyed the coziest getaway at this property. Newly renovated, clean and tucked away without being accessible to local attractions. " [](https://www.expedia.ca/Shelton-Hotels-37-Luxury-Collection.h108472348.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/117000000/116680000/116671100/116671011/4f95070c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/117000000/116680000/116671100/116671011/9d3fd888.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/117000000/116680000/116671100/116671011/83631fba.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Microwave, oven, stovetop, dishwasher](https://images.trvl-media.com/lodging/117000000/116680000/116671100/116671011/553fabbf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 3-bedroom house just walking distance from Yale and Downtown Dixwell CA $313 CA $570 total includes taxes & fees Oct 1 - Oct 2 [](https://www.expedia.ca/New-Haven-Hotels-3-Bedroom-House-Just-Walking-Distance-From-Yale-And-Downtown.h116671011.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) ![Smart TV](https://images.trvl-media.com/lodging/119000000/118950000/118949700/118949631/7f5d3999.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) ### Cozy East Haven Home • Near Beach & Yale Momauguin 10/10 Exceptional (3) "Beautiful seaside cottage. Updated and well appointed, bidet, fire pit and more. Very close to several beaches. Driving distance to many attractions, statue of liberty, and more. I would stay again. " CA $174 CA $228 total includes taxes & fees Oct 29 - Oct 30 [](https://www.expedia.ca/East-Haven-Hotels-Cozy-Home-Near-New-Haven.h118949631.Hotel-Information) ![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/112000000/111110000/111107100/111107034/42181017.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/112000000/111110000/111107100/111107034/e34d6d04.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Family Stays: Middletown, CT Middletown 10/10 Exceptional (13) "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!" CA $160 CA $293 total includes taxes & fees Oct 14 - Oct 15 [](https://www.expedia.ca/Middletown-Hotels-Family-Stays-In-Middletown.h111107034.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/92000000/91310000/91304300/91304295/d79d48ba.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/92000000/91310000/91304300/91304295/74c48534.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/92000000/91310000/91304300/91304295/dd85d551.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/92000000/91310000/91304300/91304295/5e075c23.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Connecticut Chalet - On 5 Acres! Southington 9.8/10 Exceptional (7) "Highly recommend this property if you're heading to the area!" [](https://www.expedia.ca/Plantsville-Hotels-The-Connecticut-Chalet-On-5-Acres.h91304295.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=2025-10-14&endDate=2025-10-15®ionId=183057&adults=2&lodging=VACATION_HOME&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%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 ![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 "good" [](https://expedia.ca/Hartford-Hotels-Best-Western-Hartford-Hotel-Suites.h12156.Hotel-Information) ![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 "It is very close to the medical school. The front desk is very friendly and helpful. " [](https://expedia.ca/New-Haven-Hotels-Cambria-Hotel-New-Haven-University-Area.h78614483.Hotel-Information) ![Hyatt Place Milford / New Haven](//images.trvl-media.com/lodging/2000000/1570000/1562800/1562702/0336d577_y.jpg) ### Hyatt Place Milford / New Haven 10/10 Excellent "Na" [](https://expedia.ca/New-Haven-Hotels-Hyatt-Place-Milford-New-Haven.h1562702.Hotel-Information) ![New Haven Hotel](//images.trvl-media.com/lodging/1000000/40000/36800/36721/dd69cbb4_y.jpg) ### New Haven Hotel 10/10 Excellent "Very friendly staff at the desk! " [](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 "Great location good view" [](https://expedia.ca/New-Haven-Hotels-Omni-New-Haven-Hotel-At-Yale.h49957.Hotel-Information) ![The Capitol Hotel](//images.trvl-media.com/lodging/1000000/10000/6800/6777/2c26b973_y.jpg) ### The Capitol Hotel 10/10 Excellent "Very nice and spacious room, clean and well maintained" [](https://expedia.ca/Hartford-Hotels-The-Capitol-Hotel.h6777.Hotel-Information) ![Wyndham Southbury](//images.trvl-media.com/lodging/16000000/15660000/15651900/15651820/412fe155_y.jpg) ### Wyndham Southbury 10/10 Excellent "Front desk staff were incredible !!! Five stars!!! " [](https://expedia.ca/Danbury-Hotels-Wyndham-Southbury.h15651820.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 "Comfortable and quiet " [](https://expedia.ca/Hartford-Hotels-Holiday-Inn-Express-Southington.h3929.Hotel-Information) ![Hampton Inn & Suites Hartford/East Hartford](//images.trvl-media.com/lodging/3000000/2950000/2943100/2943093/5cf369a5_y.jpg) ### Hampton Inn & Suites Hartford/East Hartford 10/10 Excellent "Very clean, quiet and comfortable with free parking and breakfast. Good value." [](https://expedia.ca/Hartford-Hotels-Hampton-Inn-Suites-HartfordEast-Hartford.h2943093.Hotel-Information) ## Find out more about Cheshire ## Cheshire Vacation Homes information | Number of reviews | 472 | | --- | --- | | Accommodation | 323 Vacation Homes | | Lowest Price | CA $228 | | Highest Price | CA $852 | ## 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) - [Guest Houses in Cheshire Historic District](https://www.expedia.ca/Cheshire-Historic-District-Guest-Houses.d6346724-aaGuestHouses.Travel-Guide-Accommodation) - 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