Title: Winsted Vacation Home Rentals from CA $384: Search Top Private Vacation Homes for Rent | Expedia.ca

 

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![A tractor up a tree! And, there's a picnic table underneath.](https://images.trvl-media.com/place/6125522/bf8d15d8-5a06-4bf9-b059-b9dc4d18a280.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

Photo by Kim Knox Beckius

# Winsted Vacation Rentals

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## Check prices for these dates

Next weekend

[Nov 28 - Nov 30](https://www.expedia.ca/Hotel-Search?regionId=3000430645&startDate=2025-11-28&endDate=2025-11-30&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two weeks

[Dec 5 - Dec 7](https://www.expedia.ca/Hotel-Search?regionId=3000430645&startDate=2025-12-05&endDate=2025-12-07&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In one month

[Dec 19 - Dec 21](https://www.expedia.ca/Hotel-Search?regionId=3000430645&startDate=2025-12-19&endDate=2025-12-21&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two months

[Jan 16 - Jan 18](https://www.expedia.ca/Hotel-Search?regionId=3000430645&startDate=2026-01-16&endDate=2026-01-18&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

## Browse Select Winsted Vacation Homes

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

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/107000000/106040000/106031100/106031055/1e32801e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/107000000/106040000/106031100/106031055/e729bc4e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/107000000/106040000/106031100/106031055/31d52781.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Goshen

9.8/10

Exceptional

(7)

"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 $166

CA $929 total

includes taxes & fees

Nov 24 - Nov 25

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

![Private kitchen](https://images.trvl-media.com/lodging/115000000/114880000/114878300/114878238/abcd3f54.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/115000000/114880000/114878300/114878238/5ffcffb1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/115000000/114880000/114878300/114878238/138b1f2d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/115000000/114880000/114878300/114878238/e6df39fa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Russell

10/10

Exceptional

(3)

"We really enjoyed our stay at the Home in the Woods. We stayed for 1 night on the way to Amherst for a graduation. The home is very cozy and clean. Jessica was easy to communicate with and the check-in/check out process was simple. Highly recommend!"

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

Travis H.

CA $238

CA $453 total

includes taxes & fees

Nov 24 - Nov 25

[](https://www.expedia.ca/Westfield-Hotels-Home-In-The-Woods.h114878238.Hotel-Information)

![Outdoor dining](https://images.trvl-media.com/lodging/116000000/115470000/115470000/115469906/ecdea449.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/116000000/115470000/115470000/115469906/51a25809.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, iron/ironing board, travel crib, free WiFi](https://images.trvl-media.com/lodging/116000000/115470000/115470000/115469906/162d61f3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/116000000/115470000/115470000/115469906/83d3f833_edited_d758.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Sherwood Forest

10/10

Exceptional

(4)

"We loved it! Lots of local hiking trails and a wonderful relaxing place."

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

Sharon K.

CA $206

CA $532 total

includes taxes & fees

Nov 24 - Nov 25

[](https://www.expedia.ca/Becket-Hotels-Dog-Friendly-A-Frame-In-The-Berkshires-Walk-To-Lake-With-Beach-Access.h115469906.Hotel-Information)

![Property grounds](https://images.trvl-media.com/lodging/114000000/113210000/113200800/113200740/045435f9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![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)

![Game room](https://images.trvl-media.com/lodging/114000000/113210000/113200800/113200740/be1e6f28.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/114000000/113210000/113200800/113200740/058c7fd2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in East Granby

8.6/10

Excellent

(4)

"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 $195

CA $610 total

includes taxes & fees

Nov 24 - Nov 25

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

![Exterior](https://images.trvl-media.com/lodging/106000000/105240000/105230400/105230373/af01e53f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, books](https://images.trvl-media.com/lodging/106000000/105240000/105230400/105230373/4e64ac0e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/106000000/105240000/105230400/105230373/c04d3199.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, books](https://images.trvl-media.com/lodging/106000000/105240000/105230400/105230373/dba15cbe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Sherwood Forest

9.6/10

Exceptional

(10)

"Very nice location with tons of privacy, yet not too far from things to do. Very easy for our dog to navigate the property as well."

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

James D.

CA $226

CA $553 total

includes taxes & fees

Nov 24 - Nov 25

[](https://www.expedia.ca/Becket-Hotels-Dog-Friendly2B1B-In-The-Berkshires-Private-Lake-Community-Whot-Tub-Canoe.h105230373.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)

![5 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/109000000/108200000/108190300/108190201/104bd215.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)

![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)

### Vacation Home in Bloomfield

9.4/10

Exceptional

(3)

"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 $310

CA $847 total

includes taxes & fees

Nov 25 - Nov 26

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

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/85000000/84680000/84672900/84672833/52bc41a9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/85000000/84680000/84672900/84672833/e0f691bb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/85000000/84680000/84672900/84672833/caf5dd09.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/85000000/84680000/84672900/84672833/c50e9e6c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Great Barrington

9.8/10

Exceptional

(25)

"Enjoyed our stay!!!"

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

Fred W.

CA $230

CA $384 total

includes taxes & fees

Dec 1 - Dec 2

[](https://www.expedia.ca/Great-Barrington-Hotels-Home-In-Great-Barrington.h84672833.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)

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

![Terrace/patio](https://images.trvl-media.com/lodging/20000000/19110000/19107300/19107245/508c5b2a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/20000000/19110000/19107300/19107245/0e82b119.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Russell

10/10

Exceptional

(143)

"Lovely old farmhouse with authentic yet comfortable furnishings. Would recommend!"

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

Jon O.

CA $282

CA $517 total

includes taxes & fees

Nov 24 - Nov 25

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

![Smart TV, fireplace](https://images.trvl-media.com/lodging/108000000/107970000/107960200/107960143/2df5cbed.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/108000000/107970000/107960200/107960143/c79da4f1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Beach](https://images.trvl-media.com/lodging/108000000/107970000/107960200/107960143/6b3e897d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/108000000/107970000/107960200/107960143/affcc370.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Avon

6.0/10

(3)

"Enjoyed my stayConvenient location for restaurants, shopping etcHome was clean and neat and in a nice quiet neighborhood Good value"

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

Joseph C.

CA $121

CA $401 total

includes taxes & fees

Dec 14 - Dec 15

[](https://www.expedia.ca/Avon-Hotels-Sun-Filled-Lake-House-Living.h107960143.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)

![Property grounds](https://images.trvl-media.com/lodging/76000000/75600000/75599900/75599864/f26544ef.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/76000000/75600000/75599900/75599864/99d3f85f.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)

### Vacation Home in Sheffield

10/10

Exceptional

(40)

"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 $334

CA $709 total

includes taxes & fees

Nov 24 - Nov 25

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

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/30000000/29620000/29615600/29615546/505c31c2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/30000000/29620000/29615600/29615546/53261c35.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/30000000/29620000/29615600/29615546/64f95c5c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/30000000/29620000/29615600/29615546/1bcf2f0b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Great Barrington

9.4/10

Exceptional

(25)

"The host was very communicative and responsive during our arrival and check out. The listing and everything was as it said we were very pleased with both the location of the home and the actual home itself and the property walking distance to town truly cannot say enough. Thank you for Your hospitality. Our family is very grateful. "

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

Amy B.

CA $402

CA $731 total

includes taxes & fees

Nov 24 - Nov 25

[](https://www.expedia.ca/Great-Barrington-Hotels-Great-Barrington-Get-Away.h29615546.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/52000000/51690000/51685500/51685419/1bc1a012.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/52000000/51690000/51685500/51685419/w1026h680x0y3-1207c37a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/52000000/51690000/51685500/51685419/4f70f9c0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, books](https://images.trvl-media.com/lodging/52000000/51690000/51685500/51685419/010bda9e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Collinsville

10/10

Exceptional

(61)

"A very nice period home in a beautiful setting. The home is immaculate with all of the necessary essentials for an extended stay. The host is very responsive and keeps in touch to ensure that your stay is as enjoyable and comfortable as possible. "

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

Virginia M.

CA $408

CA $692 total

includes taxes & fees

Nov 30 - Dec 1

[](https://www.expedia.ca/Canton-Hotels-Gorgeous-River-Views-On-Rails-To-Trails-And-Just-Steps-To-Quaint-Collinsville.h51685419.Hotel-Information)

![2 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/123000000/122840000/122835900/122835857/d4ff8995.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)

![Property grounds](https://images.trvl-media.com/lodging/123000000/122840000/122835900/122835857/0ce0753e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/123000000/122840000/122835900/122835857/018830b2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Torrington

CA $327

CA $508 total

includes taxes & fees

Nov 30 - Dec 1

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

![Property grounds](https://images.trvl-media.com/lodging/97000000/96980000/96978000/96977909/07ae7a36.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/97000000/96980000/96978000/96977909/7a49e3f2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace](https://images.trvl-media.com/lodging/97000000/96980000/96978000/96977909/5bf6f7a8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/97000000/96980000/96978000/96977909/2b36fd43.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Hartland

CA $1,269

CA $2,096 total

includes taxes & fees

Nov 26 - Nov 27

[](https://www.expedia.ca/East-Hartland-Hotels-Charming-3-Bedroom-House-In-Pleasant-Hartland.h96977909.Hotel-Information)

![Property grounds](https://images.trvl-media.com/lodging/109000000/108190000/108188500/108188444/f02ef755.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![5 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/109000000/108190000/108188500/108188444/3af0801b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/109000000/108190000/108188500/108188444/7a78b0cd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/109000000/108190000/108188500/108188444/76ed01a5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Bloomfield

10/10

Exceptional

(4)

"The house was newer and the living room and kitchen had open layout that enabled to spend quality time with family."

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

Muhammad G.

CA $310

CA $847 total

includes taxes & fees

Nov 24 - Nov 25

[](https://www.expedia.ca/Bloomfield-Hotels-Stylish-Townhome-Perfect-For-Family-Gatherings-Events.h108188444.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/121000000/120480000/120475300/120475291/a4ce4257.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/121000000/120480000/120475300/120475291/20850d38.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/121000000/120480000/120475300/120475291/81a2cc78.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/121000000/120480000/120475300/120475291/51b25708.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Bloomfield

CA $470

CA $1,501 total

includes taxes & fees

Dec 7 - Dec 8

[](https://www.expedia.ca/Bloomfield-Hotels-Group-Friendly-Townhouse-Stay-Sleeps-Up-To-20.h120475291.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/109000000/108200000/108190400/108190337/57354543.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/109000000/108200000/108190400/108190337/0a476351.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![5 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/109000000/108200000/108190400/108190337/b7b8c9d8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/109000000/108200000/108190400/108190337/54bd1291.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Bloomfield

9.2/10

Wonderful

(5)

"Great stay. "

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

Le Dung H.

CA $406

CA $974 total

includes taxes & fees

Dec 3 - Dec 4

[](https://www.expedia.ca/Bloomfield-Hotels-Premium-3-Story-Townhome-Perfect-For-Large-Groups.h108190337.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/121000000/120480000/120478900/120478833/5e06d78f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/121000000/120480000/120478900/120478833/07a4e6da.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/121000000/120480000/120478900/120478833/52994ebd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/121000000/120480000/120478900/120478833/f3c03178.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Bloomfield

CA $465

CA $1,466 total

includes taxes & fees

Dec 7 - Dec 8

[](https://www.expedia.ca/Bloomfield-Hotels-Family-Friendly-Retreat-Sleeps-20-In-Bloomfield.h120478833.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=2025-12-07&endDate=2025-12-08&regionId=3000430645&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true)

![](https://forever.travel-assets.com/flex/flexmanager/images/2025/11/05/BEX-BF-25_CA_1_Desktop.jpg?impolicy=fcrop&w=1400&h=600&q=mediumHigh)

## 

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[Book now](https://expedia.ca/deals?rfrr=AA_BF_PROMO_3000430645)

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[Sign in](https://expedia.ca/user/signin?ckoflag=0&uurl=e3id%3Dredr%26rurl%3D%2FWinsted-Private-Vacation-Homes.d3000430645-aaPrivateVacationHomes.Travel-Guide-Accommodation)[Sign up, it's free](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FWinsted-Private-Vacation-Homes.d3000430645-aaPrivateVacationHomes.Travel-Guide-Accommodation)

## Top Winsted Hotel Reviews

![Hampton Inn Hartford/Airport](https://images.trvl-media.com/lodging/1000000/900000/892600/892590/4a4de62f_y.jpg)

### Hampton Inn Hartford/Airport

10/10 Excellent

"The airport shuttle for the Hampton Inn was VERY easy. I called and they came in 5 minutes. Dropped us off the next day at the airport at 4am. Super nice. Plus good Coffee in the lobby. Not the yuckky hotel kind."

[](https://expedia.ca/Hartford-Hotels-Hampton-Inn-HartfordAirport.h892590.Hotel-Information)

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

### Simsbury 1820 House

10/10 Excellent

"Amazing staff. Beautiful, clean, large room. Comfortable bed. Great food. Felt like home! Highly recommended"

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

![Hampton Inn Westfield](https://images.trvl-media.com/lodging/3000000/2080000/2076200/2076197/04ad8e9d_y.jpg)

### Hampton Inn Westfield

10/10 Excellent

"All of it. Great place to stay. But there was only one washcloth in the SUITE."

[](https://expedia.ca/Springfield-Hotels-Hampton-Inn-By-Hilton-Westfield.h2076197.Hotel-Information)

![Springhill Suites Marriott Airport](https://images.trvl-media.com/lodging/3000000/2250000/2242100/2242056/7c7d0fd0_y.jpg)

### Springhill Suites Marriott Airport

10/10 Excellent

"great "

[](https://expedia.ca/Hartford-Hotels-Springhill-Suites-Marriott-Airport.h2242056.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

"Ordered room service and it came very quickly. Hotel is under renovation and is very nice. Will say that walls are not well insulated because you can hear a lot of what’s going on in other rooms. "

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

![DoubleTree by Hilton Hotel Bristol, Connecticut](https://images.trvl-media.com/lodging/1000000/10000/5300/5265/7a34507b_y.jpg)

### DoubleTree by Hilton Hotel Bristol, Connecticut

10/10 Excellent

"Room was spotless and spacious "

[](https://expedia.ca/Hartford-Hotels-DoubleTree-By-Hilton-Hotel-Bristol.h5265.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

"I appreciated the fact that they had a laundry room. We were placed right around the corner which was heaven sent. Got quarters from the front desk. Thank you. Kathie was especially helpful with check in but really made went the extra mile when I asked for milk for my toddler who would not go to sleep unless he had a glass of milk. So very thankful. "

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

![Quality Inn Westfield - Springfield](https://images.trvl-media.com/lodging/2000000/1120000/1118900/1118896/532eb0dc_y.jpg)

### Quality Inn Westfield - Springfield

10/10 Excellent

"Yes, everything was to our satisfaction."

[](https://expedia.ca/Springfield-Hotels-Quality-Inn-Westfield-Springfield.h1118896.Hotel-Information)

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

### Delamar West Hartford

10/10 Excellent

"Wonderful as always!"

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

## Find out more about Winsted

## Winsted Vacation Homes information

| Number of reviews | 332 |
| --- | --- |
| Accommodation | 283 Vacation Homes |
| Lowest Price | CA $384 |
| Highest Price | CA $2,096 |

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