Title: Cheshire Vacation Home Rentals from CA $204: 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)

![Castle Craig at Hubbard Park, Meriden, CT. easily replaceable sky. with a clean, classic view of the tower. Very recognizable image of this historic structure.](https://images.trvl-media.com/place/183057/92c74fd9-1a45-4931-a43e-251e181e803f.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

![](https://images.trvl-media.com/place/183057/92c74fd9-1a45-4931-a43e-251e181e803f.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

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## Check prices for these dates

In two weeks

[Mar 6 - Mar 8](https://www.expedia.ca/Hotel-Search?regionId=183057&startDate=2026-03-06&endDate=2026-03-08&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two months

[Apr 17 - Apr 19](https://www.expedia.ca/Hotel-Search?regionId=183057&startDate=2026-04-17&endDate=2026-04-19&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In three months

[May 15 - May 17](https://www.expedia.ca/Hotel-Search?regionId=183057&startDate=2026-05-15&endDate=2026-05-17&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In four months

[Jun 12 - Jun 14](https://www.expedia.ca/Hotel-Search?regionId=183057&startDate=2026-06-12&endDate=2026-06-14&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

## Our top choices for Cheshire vacation homes

![Property grounds](https://images.trvl-media.com/lodging/91000000/90710000/90707200/90707157/f4556137.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/91000000/90710000/90707200/90707157/772b2c5d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/91000000/90710000/90707200/90707157/28ce53e8.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/91000000/90710000/90707200/90707157/d2e5a74a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### #24 \*Serenity\* A Lakefront Cottage Retreat

[](https://www.expedia.ca/Middletown-Hotels-24-Serenity-A-Lakefront-Cottage-Retreat.h90707157.Hotel-Information)

Middletown

9.8/10

Exceptional

(21 reviews)

"It was our 3rd time staying and everything was as expected. New updates to the bathroom were nice surprise. Thanks again for a lovely stay while we visited our daughter at Wesleyan. "

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

Robb F.

CA $183

CA $431 total

includes taxes & fees

Feb 22 - Feb 23

[](https://www.expedia.ca/Middletown-Hotels-24-Serenity-A-Lakefront-Cottage-Retreat.h90707157.Hotel-Information)

![2 bedrooms, WiFi, bed sheets](https://images.trvl-media.com/lodging/108000000/107980000/107976300/107976290/da7468b6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, offices](https://images.trvl-media.com/lodging/108000000/107980000/107976300/107976290/f293483a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/108000000/107980000/107976300/107976290/433534ed.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/108000000/107980000/107976300/107976290/1bf4de91.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Private Apartment in Berlin

[](https://www.expedia.ca/Berlin-Hotels-Private-Apartment-In-Berlin.h107976290.Hotel-Information)

Berlin

9.2/10

Wonderful

(5 reviews)

"Place was great, not to small and not to big. Beds were extremely comfortable. Berlin is a busy town but the house in tucked far enough away from it all. Great place and would gladly stay again! "

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

Daniel L.

CA $125

CA $372 total

includes taxes & fees

Feb 25 - Feb 26

[](https://www.expedia.ca/Berlin-Hotels-Private-Apartment-In-Berlin.h107976290.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/112000000/111110000/111107100/111107034/42181017.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/112000000/111110000/111107100/111107034/7e65e0ed.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/112000000/111110000/111107100/111107034/ffcbfb18.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/112000000/111110000/111107100/111107034/6924fd2f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Family Stays: Middletown, CT

[](https://www.expedia.ca/Middletown-Hotels-Family-Stays-In-Middletown.h111107034.Hotel-Information)

Middletown

10/10

Exceptional

(21 reviews)

"A truly wonderful experience! The host and home were amazing and we’ll definitely be staying here again!"

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

Harmony R.

CA $171

CA $325 total

includes taxes & fees

Mar 2 - Mar 3

[](https://www.expedia.ca/Middletown-Hotels-Family-Stays-In-Middletown.h111107034.Hotel-Information)

![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)

![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)

![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)

### Charming & Private 1-bed & 1 ba ,sleeps 2, on 1st floor of a 5 bed 3ba House,

[](https://www.expedia.ca/Charming.h111683284.Hotel-Information)

Shelton

9.0/10

Wonderful

(2 reviews)

"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 $164

CA $267 total

includes taxes & fees

Feb 22 - Feb 23

[](https://www.expedia.ca/Charming.h111683284.Hotel-Information)

![Private kitchen](https://images.trvl-media.com/lodging/125000000/124360000/124360000/124359908/e5b7b978.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Hair dryer, towels, soap, toilet paper](https://images.trvl-media.com/lodging/125000000/124360000/124360000/124359908/c78a3042.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/125000000/124360000/124360000/124359908/89f59934.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/125000000/124360000/124360000/124359908/66ba29c2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Welcoming 4-bedroom house in charming Hamden

[](https://www.expedia.ca/Hamden-Hotels-Welcoming-4-Bedroom-House-In-Charming-Hamden.h124359908.Hotel-Information)

Hamden

10/10

Exceptional

(1 review)

"Host was kind and attentive. Location was convenient and the home was clean and spacious. "

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

Renee H.

CA $313

CA $579 total

includes taxes & fees

Feb 22 - Feb 23

[](https://www.expedia.ca/Hamden-Hotels-Welcoming-4-Bedroom-House-In-Charming-Hamden.h124359908.Hotel-Information)

![Marina](https://images.trvl-media.com/lodging/79000000/78180000/78173400/78173305/8c7a6352.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)

![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/w719h480x1y0-c345a495.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Gorgeous Waterfront 3 Bedroom, 1.5 Bathroom Unit.

[](https://www.expedia.ca/New-Haven-Hotels-Gorgeous-Waterfront-3-Bedroom.h78173305.Hotel-Information)

Fair Haven

9.6/10

Exceptional

(15 reviews)

"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 $231

CA $440 total

includes taxes & fees

Feb 25 - Feb 26

[](https://www.expedia.ca/New-Haven-Hotels-Gorgeous-Waterfront-3-Bedroom.h78173305.Hotel-Information)

![Terrace/patio](https://images.trvl-media.com/lodging/106000000/105870000/105862500/105862474/w1280h845x0y4-a67617b9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace, DVD player, books](https://images.trvl-media.com/lodging/106000000/105870000/105862500/105862474/w1280h851x0y2-33646ec7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/106000000/105870000/105862500/105862474/w1280h851x0y2-c348eea3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Beach nearby](https://images.trvl-media.com/lodging/106000000/105870000/105862500/105862474/w1280h851x0y2-772c3b64.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Jewel of The Cove - Historic Coastal Retreat

[](https://www.expedia.ca/East-Haven-Hotels-The-Jewel-Of-The-Cove-Historic-Coastal-Retreat.h105862474.Hotel-Information)

East Shore

9.8/10

Exceptional

(7 reviews)

"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 $283

CA $703 total

includes taxes & fees

Mar 1 - Mar 2

[](https://www.expedia.ca/East-Haven-Hotels-The-Jewel-Of-The-Cove-Historic-Coastal-Retreat.h105862474.Hotel-Information)

![Dining](https://images.trvl-media.com/lodging/102000000/101950000/101940900/101940832/8cb41f39.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Game room](https://images.trvl-media.com/lodging/102000000/101950000/101940900/101940832/f199c771.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/102000000/101950000/101940900/101940832/82269a82.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/102000000/101950000/101940900/101940832/059a32ee.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### McAngel Haven: 5 mins from Yale

[](https://www.expedia.ca/West-Haven-Hotels-McAngel-Haven-5-Mins-From-Yale.h101940832.Hotel-Information)

West Haven

9.6/10

Exceptional

(20 reviews)

"Excellent location Clean and spacious Comfortable beds "

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

Joseph T.

CA $314

CA $722 total

includes taxes & fees

Feb 22 - Feb 23

[](https://www.expedia.ca/West-Haven-Hotels-McAngel-Haven-5-Mins-From-Yale.h101940832.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/120000000/119310000/119305500/119305470/faf6d210.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/120000000/119310000/119305500/119305470/96041570.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)

![Interior](https://images.trvl-media.com/lodging/120000000/119310000/119305500/119305470/1b8a6cf5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cozy Guest Suite in Historic Home

[](https://www.expedia.ca/Middletown-Hotels-Cozy-Guest-Suite-In-Historic-Home.h119305470.Hotel-Information)

Middletown

10/10

Exceptional

(1 review)

"Perfect for a single traveler. Clean, roomy, quaint room. "

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

Brooke

CA $224

CA $322 total

includes taxes & fees

Mar 8 - Mar 9

[](https://www.expedia.ca/Middletown-Hotels-Cozy-Guest-Suite-In-Historic-Home.h119305470.Hotel-Information)

![Smart TV](https://images.trvl-media.com/lodging/119000000/118950000/118949700/118949631/7f5d3999.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![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)

### Cozy East Haven Home • Near Beach & Yale

[](https://www.expedia.ca/East-Haven-Hotels-Cozy-Home-Near-New-Haven.h118949631.Hotel-Information)

Momauguin

10/10

Exceptional

(5 reviews)

"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 $154

CA $204 total

includes taxes & fees

Mar 1 - Mar 2

[](https://www.expedia.ca/East-Haven-Hotels-Cozy-Home-Near-New-Haven.h118949631.Hotel-Information)

![Smart TV, books](https://images.trvl-media.com/lodging/101000000/100840000/100834300/100834240/w901h683x62y0-7195bf6a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/101000000/100840000/100834300/100834240/w467h683x278y0-44c63d7a.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/101000000/100840000/100834300/100834240/3c48bfc1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Clear LI Sound waterview, Wedding pics, Yale&Beach

[](https://www.expedia.ca/East-Haven-Hotels-Clear-LI-Sound-Waterview.h100834240.Hotel-Information)

East Shore

10/10

Exceptional

(10 reviews)

"Great stay! Would definitely stay again! "

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

Frankie O.

CA $787

CA $1,340 total

includes taxes & fees

Feb 23 - Feb 24

[](https://www.expedia.ca/East-Haven-Hotels-Clear-LI-Sound-Waterview.h100834240.Hotel-Information)

![Outdoor pool](https://images.trvl-media.com/lodging/125000000/124670000/124662800/124662794/ece7430b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/125000000/124670000/124662800/124662794/a495f57a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace, DVD player, books](https://images.trvl-media.com/lodging/125000000/124670000/124662800/124662794/d7613f87.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/125000000/124670000/124662800/124662794/49a44f58.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cozy 1-bedroom apartment in lovely Oxford

[](https://www.expedia.ca/Oxford-Hotels-Cozy-1-Bedroom-Apartment-In-Lovely-Oxford.h124662794.Hotel-Information)

Oxford

10/10

Exceptional

(1 review)

"I made a late reservation, and my host, Jackie, was always accommodating, welcoming, and in regular communication with me. The amenities were just what I needed, right down to the coffee pod and snack selection! The apartment is well laid out, as if I were walking into my own home, convenient to shopping and friends.Thank you, Jackie!"

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

LIsa G.

CA $153

CA $219 total

includes taxes & fees

Feb 22 - Feb 23

[](https://www.expedia.ca/Oxford-Hotels-Cozy-1-Bedroom-Apartment-In-Lovely-Oxford.h124662794.Hotel-Information)

![TV, Netflix, Hulu, books](https://images.trvl-media.com/lodging/94000000/93400000/93397900/93397831/b1bea7a7.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/94000000/93400000/93397900/93397831/4d7eefe7.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)

![Interior](https://images.trvl-media.com/lodging/94000000/93400000/93397900/93397831/6c2acb13.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Santiago in Science Park at Yale New Haven

[](https://www.expedia.ca/New-Haven-Hotels-The-Santiago-In-Science-Park-At-Yale-New-Haven.h93397831.Hotel-Information)

Dixwell

8.0/10

Very good

(8 reviews)

"The property had everything needed and was a short distance to so many campus sites. Would definitely stay again."

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

Natalie B.

CA $343

CA $580 total

includes taxes & fees

Mar 7 - Mar 8

[](https://www.expedia.ca/New-Haven-Hotels-The-Santiago-In-Science-Park-At-Yale-New-Haven.h93397831.Hotel-Information)

![Marina](https://images.trvl-media.com/lodging/77000000/76970000/76963400/76963336/2c0c3b2a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![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)

![Interior](https://images.trvl-media.com/lodging/77000000/76970000/76963400/76963336/c08fe3a2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/77000000/76970000/76963400/76963336/3be531e8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Gorgeous Waterfront 2 Bedroom 1 Bath Modern Home.

[](https://www.expedia.ca/New-Haven-Hotels-Gorgeous-Waterfront-2-Bedroom-1-Bath-Modern-Home.h76963336.Hotel-Information)

Fair Haven

7.6/10

Good

(5 reviews)

"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 $175

CA $335 total

includes taxes & fees

Feb 24 - Feb 25

[](https://www.expedia.ca/New-Haven-Hotels-Gorgeous-Waterfront-2-Bedroom-1-Bath-Modern-Home.h76963336.Hotel-Information)

![Dining](https://images.trvl-media.com/lodging/60000000/59630000/59625600/59625523/d1cc68c7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![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)

### Stocked home close to Yale, in Heart of New Haven

[](https://www.expedia.ca/New-Haven-Hotels-Stocked-Home-Close-To-Yale.h59625523.Hotel-Information)

Mill River

9.2/10

Wonderful

(19 reviews)

"Great value very close to university. "

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

Lawrence

CA $172

CA $310 total

includes taxes & fees

Feb 25 - Feb 26

[](https://www.expedia.ca/New-Haven-Hotels-Stocked-Home-Close-To-Yale.h59625523.Hotel-Information)

![Microwave, oven, stovetop, dishwasher](https://images.trvl-media.com/lodging/123000000/122500000/122493300/122493219/a0ee27b3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/123000000/122500000/122493300/122493219/de0359b8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Pool](https://images.trvl-media.com/lodging/123000000/122500000/122493300/122493219/454eaea7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV](https://images.trvl-media.com/lodging/123000000/122500000/122493300/122493219/5cbf3c9c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### One private bedroom with work space and shared home with spa.

[](https://www.expedia.ca/Rocky-Hill-Hotels-One-Private-Bedroom-With-Work-Space-And-Shared-Home-With-Spa.h122493219.Hotel-Information)

Rocky Hill

CA $142

CA $206 total

includes taxes & fees

Feb 22 - Feb 23

[](https://www.expedia.ca/Rocky-Hill-Hotels-One-Private-Bedroom-With-Work-Space-And-Shared-Home-With-Spa.h122493219.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/100000000/99480000/99476700/99476616/7ce55fe4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/100000000/99480000/99476700/99476616/b3af2d99.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/100000000/99480000/99476700/99476616/897c3b48.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/100000000/99480000/99476700/99476616/519bb10d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### #26 Beautifully Renovated 2 BR Home

[](https://www.expedia.ca/Plainville-Hotels-26-Beautifully-Renovated-2-BR-Home.h99476616.Hotel-Information)

Plainville

10/10

Exceptional

(4 reviews)

"We thoroughly enjoyed our stay! The space was great for our family of 4\. Would recommend!"

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

LaTanya W.

CA $204

CA $388 total

includes taxes & fees

Feb 27 - Feb 28

[](https://www.expedia.ca/Plainville-Hotels-26-Beautifully-Renovated-2-BR-Home.h99476616.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/92000000/91570000/91561700/91561648/e0d341a0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/92000000/91570000/91561700/91561648/83d8c959.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, foosball, table tennis, books](https://images.trvl-media.com/lodging/92000000/91570000/91561700/91561648/cb920c33.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/92000000/91570000/91561700/91561648/6d6be001.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Luxury New Haven Retreat • Private Pool, Gym, Cinema • Near Yale & Beaches

[](https://www.expedia.ca/East-Haven-Hotels-RARE-New-Haven-GetawayPRIVATE-POOLWalk-To-BEACH.h91561648.Hotel-Information)

East Shore

8.8/10

Excellent

(3 reviews)

"Fantastic place, amazing hosts, 100% recommend! "

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

Zach P.

CA $303

CA $633 total

includes taxes & fees

Mar 1 - Mar 2

[](https://www.expedia.ca/East-Haven-Hotels-RARE-New-Haven-GetawayPRIVATE-POOLWalk-To-BEACH.h91561648.Hotel-Information)

![Smart TV](https://images.trvl-media.com/lodging/102000000/101280000/101274700/101274646/2a0dbd64.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/102000000/101280000/101274700/101274646/0452fb41.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Hair dryer, towels](https://images.trvl-media.com/lodging/102000000/101280000/101274700/101274646/719863dc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/102000000/101280000/101274700/101274646/e1135337.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### #29 - Modern 5 Bedroom/2 Bath

[](https://www.expedia.ca/Middletown-Hotels-29-Modern-5-Bedroom2-Bath.h101274646.Hotel-Information)

Middletown

9.4/10

Exceptional

(6 reviews)

"Great place! "

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

Gail R.

[](https://www.expedia.ca/Middletown-Hotels-29-Modern-5-Bedroom2-Bath.h101274646.Hotel-Information)

![Desk, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/125000000/124240000/124230500/124230498/20c6428a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/125000000/124240000/124230500/124230498/9cca1b11.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/125000000/124240000/124230500/124230498/e6267bd5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV](https://images.trvl-media.com/lodging/125000000/124240000/124230500/124230498/w1349h900x0y0-4a802386.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### 1 Min to I-91 - Newly Renovated Modern 2 BR Home

[](https://www.expedia.ca/Berlin-Hotels-1-Min-To-I-91-Newly-Renovated-Modern-2-BR-Home.h124230498.Hotel-Information)

Berlin

CA $228

CA $450 total

includes taxes & fees

Mar 14 - Mar 15

[](https://www.expedia.ca/Berlin-Hotels-1-Min-To-I-91-Newly-Renovated-Modern-2-BR-Home.h124230498.Hotel-Information)

Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

[View all properties](https://expedia.ca/Hotel-Search?startDate=2026-03-07&endDate=2026-03-08&regionId=183057&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true)

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## Find vacation rentals that suit your style

Cottages

[](https://www.expedia.ca/Hotel-Search?destination=Cheshire%2C+Connecticut%2C+United+States+of+America&regionId=183057&latLong=41.508366%2C-72.910622&adults=2&startDate=2026-05-22&d1=2026-05-22&endDate=2026-05-25&d2=2026-05-25&lodging=COTTAGE)

Apartments

[](https://www.expedia.ca/Hotel-Search?destination=Cheshire%2C+Connecticut%2C+United+States+of+America&regionId=183057&latLong=41.508366%2C-72.910622&adults=2&startDate=2026-05-22&d1=2026-05-22&endDate=2026-05-25&d2=2026-05-25&lodging=APARTMENT)

Private vacation homes

[](https://www.expedia.ca/Hotel-Search?destination=Cheshire%2C+Connecticut%2C+United+States+of+America&regionId=183057&latLong=41.508366%2C-72.910622&adults=2&startDate=2026-05-22&d1=2026-05-22&endDate=2026-05-25&d2=2026-05-25&lodging=VACATION_HOME)

Aparthotels

[](https://www.expedia.ca/Hotel-Search?destination=Cheshire%2C+Connecticut%2C+United+States+of+America&regionId=183057&latLong=41.508366%2C-72.910622&adults=2&startDate=2026-05-22&d1=2026-05-22&endDate=2026-05-25&d2=2026-05-25&lodging=APART_HOTEL)

Cabins

[](https://www.expedia.ca/Hotel-Search?destination=Cheshire%2C+Connecticut%2C+United+States+of+America&regionId=183057&latLong=41.508366%2C-72.910622&adults=2&startDate=2026-05-22&d1=2026-05-22&endDate=2026-05-25&d2=2026-05-25&lodging=CABIN)

Condos

[](https://www.expedia.ca/Hotel-Search?destination=Cheshire%2C+Connecticut%2C+United+States+of+America&regionId=183057&latLong=41.508366%2C-72.910622&adults=2&startDate=2026-05-22&d1=2026-05-22&endDate=2026-05-25&d2=2026-05-25&lodging=CONDO)

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## Top Cheshire Hotel Reviews

![Homewood Suites by Hilton Orange New Haven](https://images.trvl-media.com/lodging/39000000/38980000/38980000/38979983/cf46bed4_y.jpg)

### Homewood Suites by Hilton Orange New Haven

10/10 Excellent

"Excellent "

[](https://expedia.ca/New-Haven-Hotels-Homewood-Suites-By-Hilton-Orange-New-Haven.h38979983.Hotel-Information)

![New Haven Hotel](https://images.trvl-media.com/lodging/1000000/40000/36800/36721/d665dc9c_y.jpg)

### New Haven Hotel

10/10 Excellent

"Great stay"

[](https://expedia.ca/New-Haven-Hotels-New-Haven-Hotel.h36721.Hotel-Information)

![Motel 6 New Haven - Branford, CT](https://images.trvl-media.com/lodging/1000000/60000/50400/50320/c15293e5_y.jpg)

### Motel 6 New Haven - Branford, CT

10/10 Excellent

"Good service"

[](https://expedia.ca/New-Haven-Hotels-Motel-6-New-Haven-Branford.h50320.Hotel-Information)

![Hyatt House Shelton](https://images.trvl-media.com/lodging/4000000/3490000/3482200/3482162/0d731ede_y.jpg)

### Hyatt House Shelton

10/10 Excellent

"Everything was great"

[](https://expedia.ca/New-Haven-Hotels-HYATT-House-Shelton.h3482162.Hotel-Information)

![Omni New Haven Hotel at Yale](https://images.trvl-media.com/lodging/1000000/50000/50000/49957/7466af25_y.jpg)

### Omni New Haven Hotel at Yale

10/10 Excellent

"Great "

[](https://expedia.ca/New-Haven-Hotels-Omni-New-Haven-Hotel-At-Yale.h49957.Hotel-Information)

![Cambria Hotel New Haven University Area](https://images.trvl-media.com/lodging/79000000/78620000/78614500/78614483/a6a28eee_y.jpg)

### Cambria Hotel New Haven University Area

10/10 Excellent

"Very modern new clean facilities"

[](https://expedia.ca/New-Haven-Hotels-Cambria-Hotel-New-Haven-University-Area.h78614483.Hotel-Information)

![The Capitol Hotel](https://images.trvl-media.com/lodging/1000000/10000/6800/6777/2c26b973_y.jpg)

### The Capitol Hotel

10/10 Excellent

"Yes"

[](https://expedia.ca/Hartford-Hotels-The-Capitol-Hotel.h6777.Hotel-Information)

![Home2 Suites by Hilton East Haven New Haven](https://images.trvl-media.com/lodging/1000000/10000/1500/1461/b5c018f9_y.jpg)

### Home2 Suites by Hilton East Haven New Haven

10/10 Excellent

"I had never stayed in a Home2 Suites location, so I had no idea what to expect. The room was spacious and clean. They had a great breakfast buffet area with tasty food options. The beds were super comfortable! I will definitely stay at a Home2 Suites again!"

[](https://expedia.ca/East-Haven-Hotels-Home2-Suites-By-Hilton-East-Haven-New-Haven.h1461.Hotel-Information)

![Courtyard by Marriott Waterbury Downtown](https://images.trvl-media.com/lodging/1000000/40000/34300/34227/c0e669e8_y.jpg)

### Courtyard by Marriott Waterbury Downtown

10/10 Excellent

"Clean and comfortable. Great stay. "

[](https://expedia.ca/New-Haven-Hotels-Courtyard-By-Marriott-Waterbury-Downtown.h34227.Hotel-Information)

## Find out more about Cheshire

## Cheshire Vacation Homes information

| Number of reviews | 145                |
| ----------------- | ------------------ |
| Accommodation     | 305 Vacation Homes |
| Lowest Price      | CA $204            |
| Highest Price     | CA $1,340          |

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