Title: Winsted Vacation Rentals from CA $511: Short-Term Rentals for 2026 | Expedia.ca

[Hotels in Winsted](https://expedia.ca/Winsted-Hotels.d3000430645.Travel-Guide-Hotels)[Winsted Car Rentals](https://expedia.ca/Car-Rentals-In-Winsted.d3000430645.Car-Rental-Guide)[Winsted Vacation Packages](https://expedia.ca/Winsted.d3000430645.Destination-Travel-Guides)

![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

- ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.svg)  
###  
Change your mind  
Book hotels with free cancellation
- ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__deals.svg)  
###  
Treat yourself  
Sign in to save 10% or more on thousands of hotels  
[Sign in](https://www.expedia.ca/login)
- ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__bed.svg)  
###  
Be picky  
Search almost a million properties worldwide

## Check prices for these dates

In two weeks

[Jan 9 - Jan 11](https://www.expedia.ca/Hotel-Search?regionId=3000430645&startDate=2026-01-09&endDate=2026-01-11&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two months

[Feb 20 - Feb 22](https://www.expedia.ca/Hotel-Search?regionId=3000430645&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 three months

[Mar 20 - Mar 22](https://www.expedia.ca/Hotel-Search?regionId=3000430645&startDate=2026-03-20&endDate=2026-03-22&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In four months

[Apr 17 - Apr 19](https://www.expedia.ca/Hotel-Search?regionId=3000430645&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)

## Our top choices for Winsted vacation rentals

![Property grounds](https://images.trvl-media.com/lodging/73000000/72400000/72396900/72396823/cba1dcde.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/73000000/72400000/72396900/72396823/1691fc0d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/73000000/72400000/72396900/72396823/50478178.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace](https://images.trvl-media.com/lodging/73000000/72400000/72396900/72396823/6b861862.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Enjoy a restful stay with fast internet, smart TV and the company of your pet.

[](https://www.expedia.ca/Winsted-Hotels-Enjoy-A-Restful-Stay-With-Fast-Internet.h72396823.Hotel-Information)

winsted

9.2/10

Wonderful

(46)

"Fantastic hosts and great facilities would highly recommend"

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

Steve

CA $122

CA $230 total

includes taxes & fees

Dec 28 - Dec 29

[](https://www.expedia.ca/Winsted-Hotels-Enjoy-A-Restful-Stay-With-Fast-Internet.h72396823.Hotel-Information)

![Outdoor dining](https://images.trvl-media.com/lodging/108000000/107910000/107901600/107901536/0abb9e84.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/108000000/107910000/107901600/107901536/4b7e6ce7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/108000000/107910000/107901600/107901536/4d11d50d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, desk, WiFi, bed sheets](https://images.trvl-media.com/lodging/108000000/107910000/107901600/107901536/6c3350df.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Historic Hideaway

[](https://www.expedia.ca/Avon-Hotels-The-Historic-Hideaway.h107901536.Hotel-Information)

Avon

7.0/10

Good

(2)

"House exactly as listed. We had a question and the property owner replied instantly - great communication. Close to Talcott Mountain which was an amazing hike with beautiful views. "

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

Nicole M.

CA $75

CA $333 total

includes taxes & fees

Jan 9 - Jan 10, 2026

[](https://www.expedia.ca/Avon-Hotels-The-Historic-Hideaway.h107901536.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)

![TV](https://images.trvl-media.com/lodging/92000000/91310000/91304700/91304625/9905df8f.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)

![Interior](https://images.trvl-media.com/lodging/92000000/91310000/91304700/91304625/375323f0.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

9.6/10

Exceptional

(4)

"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 $122

CA $467 total

includes taxes & fees

Dec 30 - Dec 31

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

![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)

![Interior](https://images.trvl-media.com/lodging/107000000/106040000/106031100/106031055/1c3ab355.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

9.8/10

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 $121

CA $849 total

includes taxes & fees

Jan 4 - Jan 5, 2026

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

![Terrace/patio](https://images.trvl-media.com/lodging/106000000/105670000/105660100/105660083/90132e1c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/106000000/105670000/105660100/105660083/3272ac43.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)

![Interior](https://images.trvl-media.com/lodging/106000000/105670000/105660100/105660083/04dbb84f.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

(16)

"Beautiful property comfy, cozy and clean little cottage."

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

Denise T.

CA $128

CA $253 total

includes taxes & fees

Jan 6 - Jan 7, 2026

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

![Terrace/patio](https://images.trvl-media.com/lodging/110000000/109820000/109819700/109819681/15822565.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/110000000/109820000/109819700/109819681/2ff9979a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/110000000/109820000/109819700/109819681/c063db04.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, desk, WiFi, bed sheets](https://images.trvl-media.com/lodging/110000000/109820000/109819700/109819681/0bd64cc7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Charming 1-bedroom in welcoming West Hartford with WiFi, AC

[](https://www.expedia.ca/West-Hartford-Hotels-Charming-1-Bedroom-In-Welcoming-West-Hartford-With-WiFi.h109819681.Hotel-Information)

West Hartford

CA $98

CA $172 total

includes taxes & fees

Dec 31 - Jan 1, 2026

[](https://www.expedia.ca/West-Hartford-Hotels-Charming-1-Bedroom-In-Welcoming-West-Hartford-With-WiFi.h109819681.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)

![Interior](https://images.trvl-media.com/lodging/108000000/107970000/107960200/107960143/affcc370.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)

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

### Sun Filled Lake House Living

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

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 $83

CA $343 total

includes taxes & fees

Jan 6 - Jan 7, 2026

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

![Exterior](https://images.trvl-media.com/lodging/92000000/91310000/91304800/91304720/56277967.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/92000000/91310000/91304800/91304720/683fbe15.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/92000000/91310000/91304800/91304720/c89ff53f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/92000000/91310000/91304800/91304720/ef6535b3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cozy Modern Farmhouse Private Apt - 3 Beds

[](https://www.expedia.ca/Torrington-Hotels-Cozy-Modern-Farmhouse-Private-2-Bdrm-Apartment.h91304720.Hotel-Information)

Torrington

10/10

Exceptional

(4)

"My husband and I came down from Boston for Christmas to see family and couldn’t find one decent hotel in the area. We were relieved to find this place. Cute, comfortable, clean environment and just what we needed. "

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

Louisa A.

CA $156

CA $521 total

includes taxes & fees

Dec 28 - Dec 29

[](https://www.expedia.ca/Torrington-Hotels-Cozy-Modern-Farmhouse-Private-2-Bdrm-Apartment.h91304720.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)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/85000000/84680000/84672900/84672833/dcb799f2.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)

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

### Home in Great Barrington

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

Great Barrington

9.8/10

Exceptional

(26)

"Great stay in a cool, new space, totally walkable to Railroad St. I would definitely go back to GB and would try to stay here again. "

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

Cameron M.

CA $207

CA $352 total

includes taxes & fees

Jan 5 - Jan 6, 2026

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

![Interior](https://images.trvl-media.com/lodging/111000000/110380000/110372000/110371901/f21d6204.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/111000000/110380000/110372000/110371901/8c27e57e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/111000000/110380000/110372000/110371901/0f29f441.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/111000000/110380000/110372000/110371901/35dab9cd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Sun Filled Cozy Creamery

[](https://www.expedia.ca/Plainville-Hotels-The-Sun-Filled-Cozy-Creamery.h110371901.Hotel-Information)

Plainville

8.8/10

Excellent

(25)

"Very cozy and comfortable.The location was perfect for our stay in the area."

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

Heather T.

CA $235

CA $532 total

includes taxes & fees

Dec 30 - Dec 31

[](https://www.expedia.ca/Plainville-Hotels-The-Sun-Filled-Cozy-Creamery.h110371901.Hotel-Information)

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

![Interior](https://images.trvl-media.com/lodging/121000000/120090000/120084700/120084697/f6cc328d.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)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/121000000/120090000/120084700/120084697/f8de9a55.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)

"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 $167

CA $535 total

includes taxes & fees

Dec 30 - Dec 31

[](https://www.expedia.ca/Torrington-Hotels-Private-Classy-2nd-Flr-3-Bed-Apt-Near-Downtown.h120084697.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/116000000/115470000/115470000/115469906/4bbc4f9b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Wintery Cabin-Berkshires! Dog-friendly. Hike/Ski Appalachian Tr. Walk to lake!

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

Sherwood Forest

10/10

Exceptional

(5)

"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 $199

CA $511 total

includes taxes & fees

Jan 4 - Jan 5, 2026

[](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)

![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)

![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)

### 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)

"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 $274

CA $699 total

includes taxes & fees

Jan 2 - Jan 3, 2026

[](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)

![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)

![Terrace/patio](https://images.trvl-media.com/lodging/106000000/105240000/105230400/105230373/347359ba.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Wintery Cottage in the Berkshires! Dog friendly, Hot Tub, Hiking, Shopping, Dine

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

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 $219

CA $536 total

includes taxes & fees

Jan 4 - Jan 5, 2026

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

![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)

![Interior](https://images.trvl-media.com/lodging/102000000/101460000/101453000/101452935/30f9da27.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/102000000/101460000/101453000/101452935/b9dd43b7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, desk, free WiFi, bed sheets](https://images.trvl-media.com/lodging/102000000/101460000/101453000/101452935/4ae56ab0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Charming apartment 7 minute walk to downtown

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

Torrington

10/10

Exceptional

(16)

"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 $196

CA $354 total

includes taxes & fees

Jan 1 - Jan 2, 2026

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

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/100000000/99280000/99279300/99279231/c3f9be09.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/100000000/99280000/99279300/99279231/fd21d433.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/100000000/99280000/99279300/99279231/0ebd3fae.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/100000000/99280000/99279300/99279231/44c5681d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### #2 \*Beautiful 1 BR Apartment - Central CT\*

[](https://www.expedia.ca/Plainville-Hotels-2-Beautiful-1-BR-Apartment-Central-CT.h99279231.Hotel-Information)

Plainville

9.0/10

Wonderful

(2)

"I try to come up to Connecticut at least once a year if possible and this really worked out perfect for me first floor no steps easy to bring luggage in very comfortable. Would definitely come back and stay there again."

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

Rodney L.

CA $176

CA $341 total

includes taxes & fees

Dec 28 - Dec 29

[](https://www.expedia.ca/Plainville-Hotels-2-Beautiful-1-BR-Apartment-Central-CT.h99279231.Hotel-Information)

![Dining](https://images.trvl-media.com/lodging/100000000/99970000/99962400/99962392/9fa6f837.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/100000000/99970000/99962400/99962392/13f82703.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/100000000/99970000/99962400/99962392/edf60411.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace, books](https://images.trvl-media.com/lodging/100000000/99970000/99962400/99962392/565807cf.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

(9)

"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 $537

CA $923 total

includes taxes & fees

Jan 4 - Jan 5, 2026

[](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/20000000/19110000/19107300/19107245/508c5b2a.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)

![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)

"Perfect spot for a family celebration!"

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

Kerry P.

CA $274

CA $496 total

includes taxes & fees

Dec 29 - Dec 30

[](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)

![Smart TV](https://images.trvl-media.com/lodging/109000000/108200000/108190300/108190201/ce870576.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)

### 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

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 $421

CA $975 total

includes taxes & fees

Jan 18 - Jan 19, 2026

[](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/91000000/90830000/90821100/90821015/w905h683x60y0-7e221032.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)

![Exterior](https://images.trvl-media.com/lodging/91000000/90830000/90821100/90821015/2faa1b74.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)

"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 $243

CA $438 total

includes taxes & fees

Jan 19 - Jan 20, 2026

[](https://www.expedia.ca/Canton-Hotels-River-Overlook.h90821015.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=2026-01-09&endDate=2026-01-10&regionId=3000430645&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true)

![](https://a.travel-assets.com/pricing-claim/sparkle_dark.svg)

Save an average of 15% on thousands of hotels when you're signed in

[Sign in

](https://expedia.ca/user/signin?ckoflag=0&uurl=e3id%3Dredr%26rurl%3D%2FWinsted-Vacation-Rentals.d3000430645.Travel-Guide-VacationRentals)[

Sign up, it's free

](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FWinsted-Vacation-Rentals.d3000430645.Travel-Guide-VacationRentals)

## Top Winsted Hotel Reviews

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

### The Farmington Inn & Suites

10/10 Excellent

"Love the inn"

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

![DoubleTree by Hilton Hartford - Bradley Airport](https://images.trvl-media.com/lodging/1000000/20000/14500/14480/775bdf7d_y.jpg)

### DoubleTree by Hilton Hartford - Bradley Airport

10/10 Excellent

"Room was clean. Staff was wonderful."

[](https://expedia.ca/Hartford-Hotels-DoubleTree-By-Hilton-Hartford-Bradley-Airport.h14480.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

"Clean spacious room."

[](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

"Front desk staff was very courteous and helpful. Room was very clean. There was something different each morning for breakfast. Will definitely stay here again. "

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

"This was a great facility. The hotel was clean and the staff was extremely friendly. Michael S. at the reception desk was exceptional. He was very helpful, professional and went above and beyond in ensuring our comfort. "

[](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

"So convenient for early departures, great rooms and friendly staff."

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

"Shuttle to airport on time and helpful. "

[](https://expedia.ca/Hartford-Hotels-Springhill-Suites-Marriott-Airport.h2242056.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 room, friendly check in."

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

![Holiday Inn Express & Suites Bradley Airport by IHG](https://images.trvl-media.com/lodging/2000000/1540000/1536000/1535956/c57c2497_y.jpg)

### Holiday Inn Express & Suites Bradley Airport by IHG

10/10 Excellent

" Clean room."

[](https://expedia.ca/Hartford-Hotels-Holiday-Inn-Express-Suites-Bradley-Airport.h1535956.Hotel-Information)

## Find out more about Winsted

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 Winsted. 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.   

## Explore a world of travel with Expedia

- Trending destinations on Expedia.ca
- All accommodation types in Winsted

### Trending destinations on Expedia.ca

- [Canmore Vacation Rentals ](https://www.expedia.ca/Canmore-Vacation-Rentals.d10131.Travel-Guide-VacationRentals)
- [Maui Vacation Rentals ](https://www.expedia.ca/Maui-Vacation-Rentals.d180073.Travel-Guide-VacationRentals)
- [Kelowna Vacation Rentals ](https://www.expedia.ca/Kelowna-Vacation-Rentals.d3997.Travel-Guide-VacationRentals)
- [Whistler Vacation Rentals ](https://www.expedia.ca/Whistler-Vacation-Rentals.d4115.Travel-Guide-VacationRentals)
- [Florida Vacation Rentals ](https://www.expedia.ca/Destinations-In-Florida.d211.Vacation-Rental-Destinations)
- [Victoria Vacation Rentals ](https://www.expedia.ca/Victoria-Vacation-Rentals.d4138.Travel-Guide-VacationRentals)
- [Vancouver Vacation Rentals ](https://www.expedia.ca/Vancouver-Vacation-Rentals.d178315.Travel-Guide-VacationRentals)
- [Palm Springs Vacation Rentals ](https://www.expedia.ca/Palm-Springs-Vacation-Rentals.d180676.Travel-Guide-VacationRentals)
- [Tofino Vacation Rentals ](https://www.expedia.ca/Tofino-Vacation-Rentals.d6094955.Travel-Guide-VacationRentals)
- [Calgary Vacation Rentals ](https://www.expedia.ca/Calgary-Vacation-Rentals.d178245.Travel-Guide-VacationRentals)
- [Costa Rica Vacation Rentals ](https://www.expedia.ca/Destinations-In-Costa-Rica.d42.Vacation-Rental-Destinations)
- [Vancouver Island Vacation Rentals ](https://www.expedia.ca/Vancouver-Island-Vacation-Rentals.d6058387.Travel-Guide-VacationRentals)
- [Puerto Vallarta Vacation Rentals ](https://www.expedia.ca/Puerto-Vallarta-Vacation-Rentals.d180016.Travel-Guide-VacationRentals)
- [Hawaii Vacation Rentals ](https://www.expedia.ca/Destinations-In-Hawaii.d213.Vacation-Rental-Destinations)
- [Toronto Vacation Rentals ](https://www.expedia.ca/Toronto-Vacation-Rentals.d178314.Travel-Guide-VacationRentals)
- [Banff Vacation Rentals ](https://www.expedia.ca/Banff-Vacation-Rentals.d10550.Travel-Guide-VacationRentals)
- [Penticton Vacation Rentals ](https://www.expedia.ca/Penticton-Vacation-Rentals.d4135.Travel-Guide-VacationRentals)
- [Osoyoos Vacation Rentals ](https://www.expedia.ca/Osoyoos-Vacation-Rentals.d181782.Travel-Guide-VacationRentals)
- [Mont Tremblant Vacation Rentals ](https://www.expedia.ca/Mont-Tremblant-Vacation-Rentals.d55374.Travel-Guide-VacationRentals)
- [Big White Ski Resort Vacation Rentals ](https://www.expedia.ca/Big-White-Ski-Resort-Vacation-Rentals.d6058319.Travel-Guide-VacationRentals)
- [Ontario Vacation Rentals ](https://www.expedia.ca/Destinations-In-Ontario.d11178.Vacation-Rental-Destinations)
- [British Columbia Vacation Rentals ](https://www.expedia.ca/Destinations-In-British-Columbia.d11117.Vacation-Rental-Destinations)
- [Prince Edward Island Vacation Rentals ](https://www.expedia.ca/Destinations-In-Prince-Edward-Island.d6058122.Vacation-Rental-Destinations)
- [Québec Vacation Rentals ](https://www.expedia.ca/Quebec-Vacation-Rentals.d180017.Travel-Guide-VacationRentals)

- [Vacation Homes in Winsted ](https://expedia.ca/Winsted-Private-Vacation-Homes.d3000430645-aaPrivateVacationHomes.Travel-Guide-Accommodation)
- [Cottages in Winsted ](https://expedia.ca/Winsted-Cottages.d3000430645-aaCottages.Travel-Guide-Accommodation)
- [Apartments in Winsted ](https://expedia.ca/Winsted-Apartments.d3000430645-aaApartments.Travel-Guide-Accommodation)
- [Cabin Rentals in Winsted ](https://expedia.ca/Winsted-Cabins.d3000430645-aaCabins.Travel-Guide-Accommodation)
- [Farmstay in Winsted ](https://expedia.ca/Winsted-Agritourism.d3000430645-aaAgritourism.Travel-Guide-Accommodation)
- [Motels in Winsted ](https://expedia.ca/Winsted-Motels.d3000430645-aaMotels.Travel-Guide-Accommodation)
- [B&B in Winsted ](https://expedia.ca/Winsted-Bed-And-Breakfast.d3000430645-aaBedAndBreakfast.Travel-Guide-Accommodation)
- [Guest Houses in Winsted ](https://expedia.ca/Winsted-Guest-Houses.d3000430645-aaGuestHouses.Travel-Guide-Accommodation)
- [Inns in Winsted ](https://expedia.ca/Winsted-Inns.d3000430645-aaInns.Travel-Guide-Accommodation)
- [Condo Rentals in Winsted ](https://expedia.ca/Winsted-Condos.d3000430645-aaCondos.Travel-Guide-Accommodation)
- [Chalets in Winsted ](https://expedia.ca/Winsted-Chalets.d3000430645-aaChalets.Travel-Guide-Accommodation)
- [Villas in Winsted ](https://expedia.ca/Winsted-Villas.d3000430645-aaVillas.Travel-Guide-Accommodation)
- [Lodges in Winsted ](https://expedia.ca/Winsted-Lodges.d3000430645-aaLodges.Travel-Guide-Accommodation)
- [Resorts in Winsted ](https://expedia.ca/Winsted-Resort-Hotels.d3000430645-aaResortHotels.Travel-Guide-Accommodation)

## Frequently asked questions

### Can I find vacation rentals in Winsted?

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

### How many vacation rentals are there in Winsted?

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

### What are vacation rentals like in Winsted?

### Expedia's Latest Trends

Hotels

- [Best Hotels in Honolulu](https://expedia.ca/Honolulu-Hotels.d1488.Travel-Guide-Hotels)
- [Best Hotels in Bangor](https://expedia.ca/Bangor-Hotels.d6050918.Travel-Guide-Hotels)
- [Best Hotels in Mystic](https://expedia.ca/Mystic-Hotels.d9007.Travel-Guide-Hotels)
- [Best Hotels in Grand Forks](https://expedia.ca/Grand-Forks-Hotels.d1312.Travel-Guide-Hotels)
- [Best Hotels in Kalispell](https://expedia.ca/Kalispell-Hotels.d6056415.Travel-Guide-Hotels)
- [Best Hotels in Fargo](https://expedia.ca/Fargo-Hotels.d6059376.Travel-Guide-Hotels)
- [Best Hotels in New Haven](https://expedia.ca/New-Haven-Hotels.d180036.Travel-Guide-Hotels)
- [Best Hotels in Hartford](https://expedia.ca/Hartford-Hotels.d180005.Travel-Guide-Hotels)
- [Best Hotels in Norwalk](https://expedia.ca/Norwalk-Hotels.d9245.Travel-Guide-Hotels)
- [Best Hotels in Palm Springs](https://expedia.ca/Palm-Springs-Hotels.d180676.Travel-Guide-Hotels)
- [Best Hotels in Stamford](https://expedia.ca/Stamford-Hotels.d602523.Travel-Guide-Hotels)
- [Best Hotels in Danbury](https://expedia.ca/Danbury-Hotels.d6046722.Travel-Guide-Hotels)
- [Best Hotels in Bridgeport](https://expedia.ca/Bridgeport-Hotels.d525.Travel-Guide-Hotels)
- [Best Hotels in Stratford](https://expedia.ca/Stratford-Hotels.d8127.Travel-Guide-Hotels)

Flights

- [Flights to HVN](https://expedia.ca/Cheap-Flights-To-New-Haven.d180036.Travel-Guide-Flights)
- [Flights to LGA](https://expedia.ca/Cheap-Flights-To-Stamford.d602523.Travel-Guide-Flights)
- [Flights to PSP](https://expedia.ca/Cheap-Flights-To-Palm-Springs.d180676.Travel-Guide-Flights)

Cars

- [Car rentals in Palm Springs](https://expedia.ca/Car-Rentals-In-Palm-Springs.d180676.Car-Rental-Guide)

Activities

- [Things to do in New Haven](https://expedia.ca/Things-To-Do-In-New-Haven.d180036.Travel-Guide-Activities)
- [Things to do in Hartford](https://expedia.ca/Things-To-Do-In-Hartford.d180005.Travel-Guide-Activities)
- [Things to do in Stamford](https://expedia.ca/Things-To-Do-In-Stamford.d602523.Travel-Guide-Activities)

Packages

- [Disney Holidays](https://expedia.ca/Disney.d3000453867.Destination-Travel-Guides)
- [Honolulu Holidays](https://expedia.ca/Honolulu.d1488.Destination-Travel-Guides)
- [Central Holidays](https://expedia.ca/Central.d10503.Destination-Travel-Guides)
- [Canadian Holidays](https://expedia.ca/Canadian.d6127256.Destination-Travel-Guides)

General

- [Visit Danbury](https://expedia.ca/Danbury.dx6046722)
- [Visit Bridgeport](https://expedia.ca/Bridgeport.dx525)
- [Visit New Haven](https://expedia.ca/New-Haven.dx180036)
- [Visit Hartford](https://expedia.ca/Hartford.dx180005)
- [Visit Branford](https://expedia.ca/Branford.dx6243)

![](https://a.travel-assets.com/mad-service/footer/bnaBanners/BEX_Footer.jpg)

## Go further with the Expedia app

Save on select hotels and earn double points when you book on the app. Our app deals help you to save on trips so you can travel more and manage it all on the go.

Scan the QR code with your device camera and download our app