Title: Winchester Vacation Rentals from CA $468: Short-Term Rentals for 2026 | Expedia.ca

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## Check prices for these dates

In two weeks

[Mar 6 - Mar 8](https://www.expedia.ca/Hotel-Search?regionId=553248635975869849&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=553248635975869849&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=553248635975869849&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=553248635975869849&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 Winchester vacation rentals

![Interior](https://images.trvl-media.com/lodging/92000000/91500000/91497200/91497114/c99e99e9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/92000000/91500000/91497200/91497114/4bd6d788.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/92000000/91500000/91497200/91497114/c6a9bdfb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace, books](https://images.trvl-media.com/lodging/92000000/91500000/91497200/91497114/b1656412.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cozy & Serene Cabin with Fireplace, Ski Nearby!

[](https://www.expedia.ca/Bethlehem-Hotels-Deer-Ridge-Lake-Cabin.h91497114.Hotel-Information)

Bethlehem

10/10

Exceptional

(39 reviews)

"Very comfortable property. The host had thought of everything!"

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

Jennifer Y.

CA $273

CA $580 total

includes taxes & fees

Feb 22 - Feb 23

[](https://www.expedia.ca/Bethlehem-Hotels-Deer-Ridge-Lake-Cabin.h91497114.Hotel-Information)

![Property grounds](https://images.trvl-media.com/lodging/106000000/105670000/105660100/105660083/df22d08a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, books](https://images.trvl-media.com/lodging/106000000/105670000/105660100/105660083/9f68233b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/106000000/105670000/105660100/105660083/8eda9941.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/106000000/105670000/105660100/105660083/4a573ec1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Peaceful Meadow Retreat

[](https://www.expedia.ca/Granby-Hotels-Peaceful-Meadow-Retreat.h105660083.Hotel-Information)

Granby

10/10

Exceptional

(17 reviews)

"We stayed here as a quick overnight trip for events in the area. We really enjoyed the property, reading through the guestbook, and the local pizza place La Figata. "

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

Kaleigh L.

CA $128

CA $252 total

includes taxes & fees

Feb 23 - Feb 24

[](https://www.expedia.ca/Granby-Hotels-Peaceful-Meadow-Retreat.h105660083.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/114000000/113210000/113200800/113200740/0ed108d0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, books, stereo](https://images.trvl-media.com/lodging/114000000/113210000/113200800/113200740/8a868c6c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/114000000/113210000/113200800/113200740/8c13c550.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/114000000/113210000/113200800/113200740/b853d2e3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Olde Tobacco Barn - East Granby close to airport, restaurants & things to do

[](https://www.expedia.ca/East-Granby-Hotels-The-Olde-Tobacco-Barn-East-Granby-Close-To-Airport.h113200740.Hotel-Information)

East Granby

8.6/10

Excellent

(4 reviews)

"Great Stay at the Olde Tobacco Barn. Was here for a work trip, and the place was perfect for our needs. House is set back really nicely and private. Host was super responsive and easy to deal with. Overall 5/5 stay. Thank you!"

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

Sgt W.

CA $296

CA $733 total

includes taxes & fees

Feb 19 - Feb 20

[](https://www.expedia.ca/East-Granby-Hotels-The-Olde-Tobacco-Barn-East-Granby-Close-To-Airport.h113200740.Hotel-Information)

![Exterior detail](https://images.trvl-media.com/lodging/107000000/106040000/106031100/106031055/3db87cef.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![4 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/107000000/106040000/106031100/106031055/bf37a122.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/107000000/106040000/106031100/106031055/68707c00.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/107000000/106040000/106031100/106031055/979641d4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### CT Gate House Goshen CT, Gate House Goshen CT

[](https://www.expedia.ca/Goshen-Hotels-Gate-House-Goshen-CT.h106031055.Hotel-Information)

Goshen

9.4/10

Exceptional

(9 reviews)

"The property was great and the house was huge even for all 12 of us "

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

Ryan L.

CA $129

CA $868 total

includes taxes & fees

Feb 19 - Feb 20

[](https://www.expedia.ca/Goshen-Hotels-Gate-House-Goshen-CT.h106031055.Hotel-Information)

![Property grounds](https://images.trvl-media.com/lodging/91000000/90830000/90821100/90821015/w905h683x59y0-8f890c79.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/91000000/90830000/90821100/90821015/39eb1814.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/91000000/90830000/90821100/90821015/w904h683x60y0-a0d1107c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, travel crib, WiFi, bed sheets](https://images.trvl-media.com/lodging/91000000/90830000/90821100/90821015/eba05f8b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### River Overlook - Check the view from your deck!

[](https://www.expedia.ca/Canton-Hotels-River-Overlook.h90821015.Hotel-Information)

Collinsville

10/10

Exceptional

(23 reviews)

"The place was perfect for the two of us. It was close to both our kids homes."

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

Tomas M.

CA $183

CA $367 total

includes taxes & fees

Feb 19 - Feb 20

[](https://www.expedia.ca/Canton-Hotels-River-Overlook.h90821015.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/100000000/99970000/99962400/99962392/eca50f2a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/100000000/99970000/99962400/99962392/51b9c734.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/100000000/99970000/99962400/99962392/a764aae5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/100000000/99970000/99962400/99962392/d00ad195.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Guesthouse Cabin vacation rentals in Berkshire County

[](https://www.expedia.ca/Sheffield-Hotels-Guesthouse-Cabin-Vacation-Rentals-In-Berkshire-County.h99962392.Hotel-Information)

Sheffield

10/10

Exceptional

(10 reviews)

"Great place. I highly recommend for a group or family. Amazing views! Beautiful property very private and quiet. Cabin was also very well stocked and had great outdoor space. "

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

deborah d.

CA $545

CA $958 total

includes taxes & fees

Feb 22 - Feb 23

[](https://www.expedia.ca/Sheffield-Hotels-Guesthouse-Cabin-Vacation-Rentals-In-Berkshire-County.h99962392.Hotel-Information)

![Property grounds](https://images.trvl-media.com/lodging/20000000/19110000/19107300/19107245/7377fc19.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/20000000/19110000/19107300/19107245/2350af4a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/20000000/19110000/19107300/19107245/b924c628.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/20000000/19110000/19107300/19107245/f63afa55.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Big farmhouse in the foothills of the Berkshires

[](https://www.expedia.ca/Russell-Hotels-Big-Farmhouse-In-The-Foothills-Of-The-Berkshires.h19107245.Hotel-Information)

Russell

10/10

Exceptional

(143 reviews)

"Perfect spot for a family celebration!"

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

Kerry P.

CA $245

CA $468 total

includes taxes & fees

Mar 15 - Mar 16

[](https://www.expedia.ca/Russell-Hotels-Big-Farmhouse-In-The-Foothills-Of-The-Berkshires.h19107245.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/109000000/108200000/108190300/108190201/ce4ac8e2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/109000000/108200000/108190300/108190201/90ae7f9b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/109000000/108200000/108190300/108190201/8311b1e1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/109000000/108200000/108190300/108190201/ce870576.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Modern Family Retreat | Near Downtown Hartford | Sleeps 10

[](https://www.expedia.ca/Bloomfield-Hotels-Modern-Family-Retreat-Near-Downtown-Hartford-Sleeps-10.h108190201.Hotel-Information)

Bloomfield

7.6/10

Good

(4 reviews)

"There were 7 of us staying for a Wedding near by. The home was bright, clean and very roomy. I would 100% stay here again. Host was on top of everything!! "

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

Joslynn T.

CA $360

CA $906 total

includes taxes & fees

Feb 19 - Feb 20

[](https://www.expedia.ca/Bloomfield-Hotels-Modern-Family-Retreat-Near-Downtown-Hartford-Sleeps-10.h108190201.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/102000000/101460000/101453000/101452935/w1205h697x0y4-3b05e546.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/102000000/101460000/101453000/101452935/7dd95cb5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/102000000/101460000/101453000/101452935/3333094f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/102000000/101460000/101453000/101452935/e30a87e6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Pristine, Walkable downtown, Entire 2 Bedroom apartment

[](https://www.expedia.ca/Torrington-Hotels-Charming-Apartment-Minutes-From-Downtown.h101452935.Hotel-Information)

Torrington

10/10

Exceptional

(16 reviews)

"Everything about our stay was great - Corin and Jen were wonderful hosts. The place is spotless, cozy, comfy. Love that they were right next to the Green Way Trail along the river. Will absolutely stay there again! "

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

Kate B.

CA $230

CA $403 total

includes taxes & fees

Mar 11 - Mar 12

[](https://www.expedia.ca/Torrington-Hotels-Charming-Apartment-Minutes-From-Downtown.h101452935.Hotel-Information)

![Private kitchen](https://images.trvl-media.com/lodging/123000000/122840000/122835900/122835857/f5b911c4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Living area](https://images.trvl-media.com/lodging/123000000/122840000/122835900/122835857/w1504h1042x0y3-2d812057.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/123000000/122840000/122835900/122835857/4ba12a31.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/123000000/122840000/122835900/122835857/6f1f9830.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Litchfield Retreat, Wineries, Foliage & Skiing

[](https://www.expedia.ca/Torrington-Hotels-Litchfield-Retreat.h122835857.Hotel-Information)

Torrington

CA $356

CA $546 total

includes taxes & fees

Feb 28 - Mar 1

[](https://www.expedia.ca/Torrington-Hotels-Litchfield-Retreat.h122835857.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/92000000/91310000/91304700/91304625/eab09613.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Desk, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/92000000/91310000/91304700/91304625/db89ae2d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/92000000/91310000/91304700/91304625/375323f0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/92000000/91310000/91304700/91304625/970a479f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cozy 3 Flr Private 1 Bdrm Apt Tree Line View

[](https://www.expedia.ca/Torrington-Hotels-Cozy-3-Flr-Private-1-Bdrm-Apt-Tree-Line-View.h91304625.Hotel-Information)

Torrington

9.2/10

Wonderful

(5 reviews)

"A couple of the surfaces were not clean but mostly a clean comfy space. The bed was very comfortable and the bathroom was spacious and clean.The stairs are not for the faint of heart. A nice cozy place to stay once the luggage and groceries are up there."

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

Rhonda H.

CA $109

CA $451 total

includes taxes & fees

Feb 19 - Feb 20

[](https://www.expedia.ca/Torrington-Hotels-Cozy-3-Flr-Private-1-Bdrm-Apt-Tree-Line-View.h91304625.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/112000000/111930000/111926200/111926107/e982edfa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, fireplace, stereo](https://images.trvl-media.com/lodging/112000000/111930000/111926200/111926107/30745e0a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/112000000/111930000/111926200/111926107/c726dcdb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, desk, iron/ironing board, WiFi](https://images.trvl-media.com/lodging/112000000/111930000/111926200/111926107/1c343d33.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Jefferson Guest House, Spacious, Special Views

[](https://www.expedia.ca/Litchfield-Hotels-The-Jefferson-House.h111926107.Hotel-Information)

Litchfield

10/10

Exceptional

(8 reviews)

"The place was absolutely spotless and magnificent in every way. Highly recommended."

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

Robert A.

CA $398

CA $515 total

includes taxes & fees

Feb 22 - Feb 23

[](https://www.expedia.ca/Litchfield-Hotels-The-Jefferson-House.h111926107.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/94000000/93250000/93241000/93240974/2df3c8c4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/94000000/93250000/93241000/93240974/0766039e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/94000000/93250000/93241000/93240974/7f9074d6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/94000000/93250000/93241000/93240974/3742bfa1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Dugway Hideaway Walking Distance to Lime Rock Park

[](https://www.expedia.ca/Falls-Village-Hotels-Dugway-Hideaway-Walking-Distance-To-Lime-Rock-Park.h93240974.Hotel-Information)

Salisbury

9.2/10

Wonderful

(15 reviews)

"Super clean, great communication and Super location if you are going to the track. Love my stay there, will definitely do it again and definitely recommend."

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

Brig

CA $273

CA $430 total

includes taxes & fees

Mar 1 - Mar 2

[](https://www.expedia.ca/Falls-Village-Hotels-Dugway-Hideaway-Walking-Distance-To-Lime-Rock-Park.h93240974.Hotel-Information)

![Dining](https://images.trvl-media.com/lodging/126000000/125390000/125380400/125380307/5151bbbf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/126000000/125390000/125380400/125380307/w1124h739x1y0-5bff2f1a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/126000000/125390000/125380400/125380307/08308972.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![WiFi, bed sheets](https://images.trvl-media.com/lodging/126000000/125390000/125380400/125380307/dc7e67a1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Spacious, cozy 3BR Home-Near CCSU, UConn Health

[](https://www.expedia.ca/Spacious.h125380307.Hotel-Information)

New Britain

10/10

Exceptional

(1 review)

"House was perfect for family event. Clean and updated. Communication was very good and quick."

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

Tod B.

CA $259

CA $545 total

includes taxes & fees

Mar 1 - Mar 2

[](https://www.expedia.ca/Spacious.h125380307.Hotel-Information)

![1 bedroom, desk, iron/ironing board, WiFi](https://images.trvl-media.com/lodging/121000000/120090000/120084700/120084692/625a3011.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/121000000/120090000/120084700/120084692/31e98e91.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/121000000/120090000/120084700/120084692/d5c66473.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fireplace, books](https://images.trvl-media.com/lodging/121000000/120090000/120084700/120084692/cc2e7113.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cozy Cabin Style Apt Private 1st Flr 1 Bdrm

[](https://www.expedia.ca/Torrington-Hotels-Cozy-Cabin-Style-Apt-Private-1st-Flr-1-Bdrm.h120084692.Hotel-Information)

Torrington

CA $156

CA $521 total

includes taxes & fees

Feb 19 - Feb 20

[](https://www.expedia.ca/Torrington-Hotels-Cozy-Cabin-Style-Apt-Private-1st-Flr-1-Bdrm.h120084692.Hotel-Information)

![Smart TV](https://images.trvl-media.com/lodging/103000000/102810000/102800600/102800548/6df32599.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/103000000/102810000/102800600/102800548/241d83cf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/103000000/102810000/102800600/102800548/83cbfafe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/103000000/102810000/102800600/102800548/6678550d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Spacious 5-bedroom townhome with WiFi and AC in charming Bloomfield

[](https://www.expedia.ca/Bloomfield-Hotels-Spacious-5-Bedroom-Townhome-With-WiFi-And-AC-In-Charming-Bloomfield.h102800548.Hotel-Information)

Bloomfield

9.0/10

Wonderful

(6 reviews)

"I had a great time and I felt very welcome"

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

Avis b.

CA $420

CA $1,027 total

includes taxes & fees

Feb 19 - Feb 20

[](https://www.expedia.ca/Bloomfield-Hotels-Spacious-5-Bedroom-Townhome-With-WiFi-And-AC-In-Charming-Bloomfield.h102800548.Hotel-Information)

![Property grounds](https://images.trvl-media.com/lodging/115000000/114850000/114848300/114848278/40085f46.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, fireplace](https://images.trvl-media.com/lodging/115000000/114850000/114848300/114848278/98e690c0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/115000000/114850000/114848300/114848278/19a77a44.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Game room](https://images.trvl-media.com/lodging/115000000/114850000/114848300/114848278/27f61679.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Peaceful Cabin with Sauna, Hot Tub & Cold Plunge

[](https://www.expedia.ca/Cornwall-Bridge-Hotels-Cozy-Cabin-On-5-Acres-W-Hot-Tub-Fire-Pit.h114848278.Hotel-Information)

Cornwall

10/10

Exceptional

(5 reviews)

"This cabin is so cute we had a relaxing time , will return"

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

Candice S.

CA $428

CA $771 total

includes taxes & fees

Feb 24 - Feb 25

[](https://www.expedia.ca/Cornwall-Bridge-Hotels-Cozy-Cabin-On-5-Acres-W-Hot-Tub-Fire-Pit.h114848278.Hotel-Information)

![Dining](https://images.trvl-media.com/lodging/121000000/120090000/120084700/120084697/bdda181f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, desk, WiFi, bed sheets](https://images.trvl-media.com/lodging/121000000/120090000/120084700/120084697/4ce1539e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior detail](https://images.trvl-media.com/lodging/121000000/120090000/120084700/120084697/eac31e65.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/121000000/120090000/120084700/120084697/89757bc7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Classy Private Apt - 3 Beds 2nd Flr - Near Downtown

[](https://www.expedia.ca/Torrington-Hotels-Private-Classy-2nd-Flr-3-Bed-Apt-Near-Downtown.h120084697.Hotel-Information)

Torrington

10/10

Exceptional

(1 review)

"Good communication. Clean place in good location. Would stay again. "

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

Jaimie S.

CA $156

CA $524 total

includes taxes & fees

Mar 2 - Mar 3

[](https://www.expedia.ca/Torrington-Hotels-Private-Classy-2nd-Flr-3-Bed-Apt-Near-Downtown.h120084697.Hotel-Information)

![Property grounds](https://images.trvl-media.com/lodging/76000000/75600000/75599900/75599864/665b8282.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/76000000/75600000/75599900/75599864/8f9296e7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/76000000/75600000/75599900/75599864/3e6e58ca.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior detail](https://images.trvl-media.com/lodging/76000000/75600000/75599900/75599864/4ce0af29.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cheerful 3-bedroom cottage with woodstove

[](https://www.expedia.ca/Sheffield-Hotels-Cheerful-3-Bedroom-Cottage-With-Woodstove.h75599864.Hotel-Information)

Sheffield

10/10

Exceptional

(42 reviews)

"The property was centrally located for skiing, and was a comfortable stay."

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

Kelly R.

CA $323

CA $689 total

includes taxes & fees

Mar 8 - Mar 9

[](https://www.expedia.ca/Sheffield-Hotels-Cheerful-3-Bedroom-Cottage-With-Woodstove.h75599864.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/100000000/99280000/99279300/99279229/9aee7816.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/100000000/99280000/99279300/99279229/bd94c256.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/100000000/99280000/99279300/99279229/858394b7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/100000000/99280000/99279300/99279229/7603a317.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### #11 -\* 4 Bedrooms, 3 Baths! Sleeps up to 10

[](https://www.expedia.ca/Plainville-Hotels-11-4-Bedrooms.h99279229.Hotel-Information)

Plainville

10/10

Exceptional

(3 reviews)

"Great weekend with friends!"

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

Neil R.

CA $305

CA $704 total

includes taxes & fees

Mar 11 - Mar 12

[](https://www.expedia.ca/Plainville-Hotels-11-4-Bedrooms.h99279229.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=2026-03-04&endDate=2026-03-05&regionId=553248635975869849&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

Cabins

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Private vacation homes

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Cottages

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Apartments

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Villas

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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=2026-05-19&d1=2026-05-19&endDate=2026-05-22&d2=2026-05-22&lodging=CHALET)

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## Top Winchester Hotel Reviews

![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

"Room clean near and comfortable "

[](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 great, room was cozy. Nice quiet sitting area to relax and have a cup of coffee."

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

"Excellent customer service "

[](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

"Everyone and everything were terrific! This was our first time staying here - meeting up with two other couples over the Super Bowl weekend. Steve was so helpful and happy to adjust our reservation so that we had a very spacious suite where 6 of us could gather to watch the game and to enjoy Frank Pepe pizza on Sunday. With the bitter cold we asked if a microwave might be available and one was waiting for us on the desk when we arrived. We were able to acquire paper plates, utensils, and wine glasses from Kristi and the dining room staff. Proximity to the beautiful Hill-Stead Museum gave us all a pleasant excursion off-site. We also enjoyed the convenience to the lovely restaurant literally next door for two of our dinners. Breakfast in the charmingly appointed "coffee shop" was self-serve but with plenty of options and well laid out. We were more than satisfied. An additional coffee and tea station adjacent to the main lobby was a bonus for anyone looking for a hot beverage any time of day or night! The fitness center was clean and with good equiipment for a cardio workout or time with weights! ALL the staff were lovely and truly wanted to make sure we were happy all weekend. Thank you - you are the perfect example of what the hospitality business should look like!"

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

![Interlaken Inn & Resort](https://images.trvl-media.com/lodging/20000000/19680000/19679700/19679605/dbbfdf3a_y.jpg)

### Interlaken Inn & Resort

10/10 Excellent

"Room was perfect for us. Buffet breakfast was very enjoyable in the morning and staff were all friendly and helpful. Will make this an annual spot to stay when we go to the ski jump competition. "

[](https://expedia.ca/Torrington-Hotels-Interlaken-Inn-Resort.h19679605.Hotel-Information)

![The Litchfield Inn](https://images.trvl-media.com/lodging/5000000/4980000/4978900/4978856/9aa3fa98_y.jpg)

### The Litchfield Inn

10/10 Excellent

"Nice place, great staff, and delicious breakfast! Will be coming back! "

[](https://expedia.ca/Torrington-Hotels-The-Litchfield-Inn.h4978856.Hotel-Information)

![Delamar West Hartford](https://images.trvl-media.com/lodging/19000000/18170000/18166800/18166744/d809cec2_y.jpg)

### Delamar West Hartford

10/10 Excellent

"Room, food, amenities and staff were all excellent!!"

[](https://expedia.ca/Hartford-Hotels-Delamar-West-Hartford.h18166744.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

"Stagg was courteous. Room was very clean. Breakfast was better than most places I stay."

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

![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

"It was perfecr"

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

## Find out more about Winchester

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.  
  
As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Winchester. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.   
  
It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.   

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- [Vacation Homes in Winchester ](https://expedia.ca/Winchester-Private-Vacation-Homes.d553248635975869849-aaPrivateVacationHomes.Travel-Guide-Accommodation)
- [Cottages in Winchester ](https://expedia.ca/Winchester-Cottages.d553248635975869849-aaCottages.Travel-Guide-Accommodation)
- [Apartments in Winchester ](https://expedia.ca/Winchester-Apartments.d553248635975869849-aaApartments.Travel-Guide-Accommodation)
- [Farmstay in Winchester ](https://expedia.ca/Winchester-Agritourism.d553248635975869849-aaAgritourism.Travel-Guide-Accommodation)
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- [B&B in Winchester ](https://expedia.ca/Winchester-Bed-And-Breakfast.d553248635975869849-aaBedAndBreakfast.Travel-Guide-Accommodation)
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- [Motels in Winchester ](https://expedia.ca/Winchester-Motels.d553248635975869849-aaMotels.Travel-Guide-Accommodation)
- [Inns in Winchester ](https://expedia.ca/Winchester-Inns.d553248635975869849-aaInns.Travel-Guide-Accommodation)
- [Condo Rentals in Winchester ](https://expedia.ca/Winchester-Condos.d553248635975869849-aaCondos.Travel-Guide-Accommodation)
- [Chalets in Winchester ](https://expedia.ca/Winchester-Chalets.d553248635975869849-aaChalets.Travel-Guide-Accommodation)
- [Villas in Winchester ](https://expedia.ca/Winchester-Villas.d553248635975869849-aaVillas.Travel-Guide-Accommodation)
- [Lodges in Winchester ](https://expedia.ca/Winchester-Lodges.d553248635975869849-aaLodges.Travel-Guide-Accommodation)
- [Resorts in Winchester ](https://expedia.ca/Winchester-Resort-Hotels.d553248635975869849-aaResortHotels.Travel-Guide-Accommodation)

## Frequently asked questions

### Are there vacation rentals in Winchester?

### What are some of the best vacation rentals that Winchester has to offer?

### How many vacation rentals will I find in Winchester?

### What’s there to see and do in Winchester?

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