Title: Winchester Condo Rentals from CA $119 | Expedia.ca

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## Check prices for these dates

In two weeks

[Feb 20 - Feb 22](https://www.expedia.ca/Hotel-Search?regionId=553248635975869849&startDate=2026-02-20&endDate=2026-02-22&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two months

[Apr 3 - Apr 5](https://www.expedia.ca/Hotel-Search?regionId=553248635975869849&startDate=2026-04-03&endDate=2026-04-05&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In three months

[May 1 - May 3](https://www.expedia.ca/Hotel-Search?regionId=553248635975869849&startDate=2026-05-01&endDate=2026-05-03&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In four months

[May 29 - May 31](https://www.expedia.ca/Hotel-Search?regionId=553248635975869849&startDate=2026-05-29&endDate=2026-05-31&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

## Find vacation rentals that suit your style

Cabins

[](https://www.expedia.ca/Hotel-Search?destination=Winchester%2C+Connecticut%2C+United+States+of+America&regionId=553248635975869849&latLong=41.935764%2C-73.111359&adults=2&startDate=2026-05-05&d1=2026-05-05&endDate=2026-05-08&d2=2026-05-08&lodging=CABIN)

Private vacation homes

[](https://www.expedia.ca/Hotel-Search?destination=Winchester%2C+Connecticut%2C+United+States+of+America&regionId=553248635975869849&latLong=41.935764%2C-73.111359&adults=2&startDate=2026-05-05&d1=2026-05-05&endDate=2026-05-08&d2=2026-05-08&lodging=VACATION_HOME)

Cottages

[](https://www.expedia.ca/Hotel-Search?destination=Winchester%2C+Connecticut%2C+United+States+of+America&regionId=553248635975869849&latLong=41.935764%2C-73.111359&adults=2&startDate=2026-05-05&d1=2026-05-05&endDate=2026-05-08&d2=2026-05-08&lodging=COTTAGE)

Apartments

[](https://www.expedia.ca/Hotel-Search?destination=Winchester%2C+Connecticut%2C+United+States+of+America&regionId=553248635975869849&latLong=41.935764%2C-73.111359&adults=2&startDate=2026-05-05&d1=2026-05-05&endDate=2026-05-08&d2=2026-05-08&lodging=APARTMENT)

Villas

[](https://www.expedia.ca/Hotel-Search?destination=Winchester%2C+Connecticut%2C+United+States+of+America&regionId=553248635975869849&latLong=41.935764%2C-73.111359&adults=2&startDate=2026-05-05&d1=2026-05-05&endDate=2026-05-08&d2=2026-05-08&lodging=VILLA)

Chalets

[](https://www.expedia.ca/Hotel-Search?destination=Winchester%2C+Connecticut%2C+United+States+of+America&regionId=553248635975869849&latLong=41.935764%2C-73.111359&adults=2&startDate=2026-05-05&d1=2026-05-05&endDate=2026-05-08&d2=2026-05-08&lodging=CHALET)

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## Top Winchester Hotel Reviews

![Fairfield Inn & Suites by Marriott Plainville](https://images.trvl-media.com/lodging/1000000/10000/10000/9965/01d5897d_y.jpg)

### Fairfield Inn & Suites by Marriott Plainville

10/10 Excellent

"Staff was excellent and room was clean and very warm . Thank you for that."

[](https://expedia.ca/Hartford-Hotels-Fairfield-Inn-Suites-By-Marriott-Plainville.h9965.Hotel-Information)

![Homewood Suites by Hilton Hartford-Farmington](https://images.trvl-media.com/lodging/1000000/210000/203500/203496/4f26a2b3_y.jpg)

### Homewood Suites by Hilton Hartford-Farmington

10/10 Excellent

"Very courteous staff. Room was clean and spotless."

[](https://expedia.ca/Hartford-Hotels-Homewood-Suites-By-Hilton-Hartford-Farmington.h203496.Hotel-Information)

![Sheraton Hartford Hotel at Bradley Airport](https://images.trvl-media.com/lodging/1000000/10000/4700/4632/c8edc11d_y.jpg)

### Sheraton Hartford Hotel at Bradley Airport

10/10 Excellent

"I love this Wonderful Location and the breakfast is astounding!"

[](https://expedia.ca/Hartford-Hotels-Sheraton-Hartford-Hotel-At-Bradley-Airport.h4632.Hotel-Information)

![Simsbury 1820 House](https://images.trvl-media.com/lodging/1000000/50000/42300/42279/6326a611_y.jpg)

### Simsbury 1820 House

10/10 Excellent

"Staff was excellent as was the breakfast selections. The restaurant was a gem. !"

[](https://expedia.ca/Hartford-Hotels-Simsbury-1820-House.h42279.Hotel-Information)

![Avon Old Farms Hotel](https://images.trvl-media.com/lodging/1000000/10000/2700/2635/d997675e_y.jpg)

### Avon Old Farms Hotel

10/10 Excellent

"Room was clean, bed was shockingly comfortable, and it felt very old, but in an endearing way. This will likely be the hotel we have family stay at whenever they visit us."

[](https://expedia.ca/Hartford-Hotels-Avon-Old-Farms-Hotel.h2635.Hotel-Information)

![Home2 Suites by Hilton Bristol](https://images.trvl-media.com/lodging/95000000/94950000/94946700/94946614/74bd7e00_y.jpg)

### Home2 Suites by Hilton Bristol

10/10 Excellent

"One of the Best places I’ve stayed staff is top notch clean breakfast was fresh and delicious room was beautiful "

[](https://expedia.ca/Bristol-Hotels-Home2-Suites-By-Hilton-Bristol.h94946614.Hotel-Information)

![Hampton Inn & Suites Hartford/Farmington](https://images.trvl-media.com/lodging/3000000/2980000/2970600/2970540/393f3b68_y.jpg)

### Hampton Inn & Suites Hartford/Farmington

10/10 Excellent

"The room and common spaces/amenities were clean and modern, and the staff treated us very well!"

[](https://expedia.ca/Hartford-Hotels-Hampton-Inn-And-Suites-HartfordFarmington.h2970540.Hotel-Information)

![The Farmington Inn & Suites](https://images.trvl-media.com/lodging/1000000/20000/10200/10185/1c89931a_y.jpg)

### The Farmington Inn & Suites

10/10 Excellent

"Clean "

[](https://expedia.ca/Hartford-Hotels-The-Farmington-Inn-Suites.h10185.Hotel-Information)

![Extended Stay America Suites Hartford Farmington](https://images.trvl-media.com/lodging/1000000/160000/151100/151013/02939ae3_y.jpg)

### Extended Stay America Suites Hartford Farmington

10/10 Excellent

"Clean although parking lot not cleaned well always enjoy staying at this facility convenient to everything in the area staff is friendly and accommodating "

[](https://expedia.ca/Hartford-Hotels-Extended-Stay-America-Suites-Hartford-Farmington.h151013.Hotel-Information)

## Find out more about Winchester

## Winchester Condo Rentals information

| Number of reviews | 9,804           |
| ----------------- | --------------- |
| Accommodation     | 2 Condo Rentals |
| Lowest Price      | CA $119         |
| Highest Price     | CA $888         |

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