Title: Holiday Rentals Winsted from £189: Find Short-Term Rentals & Holiday Accommodations | Expedia.co.uk

[Hotels in Winsted](https://expedia.co.uk/Winsted-Hotels.d3000430645.Travel-Guide-Hotels)[Winsted Car Hire](https://expedia.co.uk/Compare-Cheap-Car-Hire-In-Winsted.d3000430645.Car-Hire-Guide)[Winsted Holidays](https://expedia.co.uk/Winsted.d3000430645.Holidays-City-Breaks)

![Old houses in the Old Salem Historic District, in downtown Winst](https://images.trvl-media.com/place/3000430645/bb9cdd61-3489-4aed-b910-e06295b1d904.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

![](https://images.trvl-media.com/place/3000430645/bb9cdd61-3489-4aed-b910-e06295b1d904.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

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## Check prices for these dates

In two weeks

[27 Feb - 1 Mar](https://www.expedia.co.uk/Hotel-Search?regionId=3000430645&startDate=2026-02-27&endDate=2026-03-01&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two months

[10 Apr - 12 Apr](https://www.expedia.co.uk/Hotel-Search?regionId=3000430645&startDate=2026-04-10&endDate=2026-04-12&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In three months

[8 May - 10 May](https://www.expedia.co.uk/Hotel-Search?regionId=3000430645&startDate=2026-05-08&endDate=2026-05-10&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In four months

[5 Jun - 7 Jun](https://www.expedia.co.uk/Hotel-Search?regionId=3000430645&startDate=2026-06-05&endDate=2026-06-07&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

## Our top choices for Winsted holiday rentals

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

![TV](https://images.trvl-media.com/lodging/107000000/106040000/106031100/106031055/38f44943.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)

![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.co.uk/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.

£458

includes taxes & fees

11 Feb - 12 Feb

[](https://www.expedia.co.uk/Goshen-Hotels-Gate-House-Goshen-CT.h106031055.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)

![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)

![Smart TV, books](https://images.trvl-media.com/lodging/106000000/105670000/105660100/105660083/5bf6da4a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Peaceful Meadow Retreat

[](https://www.expedia.co.uk/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.

£138

includes taxes & fees

15 Feb - 16 Feb

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

![Interior](https://images.trvl-media.com/lodging/101000000/100400000/100397900/100397846/453bb440.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/101000000/100400000/100397900/100397846/86a2247f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/101000000/100400000/100397900/100397846/acd6c55a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/101000000/100400000/100397900/100397846/b44a1a8b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### #31 - Downtown Terryville- 1 Br

[](https://www.expedia.co.uk/Terryville-Hotels-31-Downtown-Terryville-1-Br.h100397846.Hotel-Information)

Plymouth

10/10

Exceptional

(1 review)

"In convenient safe area. Os is easy to contact"

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

Gina P.

£188

includes taxes & fees

14 Feb - 15 Feb

[](https://www.expedia.co.uk/Terryville-Hotels-31-Downtown-Terryville-1-Br.h100397846.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/111000000/110380000/110372000/110371901/996b1a71.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior detail](https://images.trvl-media.com/lodging/111000000/110380000/110372000/110371901/5f2a3ee6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/111000000/110380000/110372000/110371901/c14b3372.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV](https://images.trvl-media.com/lodging/111000000/110380000/110372000/110371901/0612bb56.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Sun Filled Cozy Creamery

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

Plainville

8.8/10

Excellent

(25 reviews)

"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.

£186

includes taxes & fees

11 Feb - 12 Feb

[](https://www.expedia.co.uk/Plainville-Hotels-The-Sun-Filled-Cozy-Creamery.h110371901.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)

![Interior](https://images.trvl-media.com/lodging/92000000/91310000/91304700/91304625/ba8d6f83.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)

![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)

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

[](https://www.expedia.co.uk/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.

£240

includes taxes & fees

3 Mar - 4 Mar

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

![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)

![Interior](https://images.trvl-media.com/lodging/92000000/91500000/91497200/91497114/633e19d7.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.co.uk/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.

£312

includes taxes & fees

16 Feb - 17 Feb

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

![Exterior](https://images.trvl-media.com/lodging/92000000/91310000/91304800/91304720/89d11901.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/92000000/91310000/91304800/91304720/9b25a8e7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/92000000/91310000/91304800/91304720/547f43df.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, books](https://images.trvl-media.com/lodging/92000000/91310000/91304800/91304720/89b8eb54.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cozy Modern Farmhouse Private Apt - 3 Beds

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

Torrington

10/10

Exceptional

(4 reviews)

"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.

£286

includes taxes & fees

11 Feb - 12 Feb

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

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

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/91000000/90830000/90821100/90821015/w904h683x60y0-ee72444b.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)

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

[](https://www.expedia.co.uk/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.

£199

includes taxes & fees

11 Feb - 12 Feb

[](https://www.expedia.co.uk/Canton-Hotels-River-Overlook.h90821015.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)

![Outdoor dining](https://images.trvl-media.com/lodging/114000000/113210000/113200800/113200740/b853d2e3.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)

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

[](https://www.expedia.co.uk/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.

£393

includes taxes & fees

11 Feb - 12 Feb

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

![2 bedrooms, desk, free WiFi, bed sheets](https://images.trvl-media.com/lodging/102000000/101460000/101453000/101452935/dc8af495.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)

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

![Smart TV](https://images.trvl-media.com/lodging/102000000/101460000/101453000/101452935/757359f2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Charming apartment 7 minute walk to downtown

[](https://www.expedia.co.uk/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.

£182

includes taxes & fees

1 Mar - 2 Mar

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

![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/106000000/105240000/105230400/105230373/2281e60c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

![2 bedrooms, desk, iron/ironing board, travel cot](https://images.trvl-media.com/lodging/106000000/105240000/105230400/105230373/8c55822c.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.co.uk/Becket-Hotels-Dog-Friendly2B1B-In-The-Berkshires-Private-Lake-Community-Whot-Tub-Canoe.h105230373.Hotel-Information)

Sherwood Forest

9.8/10

Exceptional

(11 reviews)

"Nicole was very attentive and very quick to respond to any question we had. Her cottage was perfect for a quiet getaway, just what everybody needs!"

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

Matthew F.

£289

includes taxes & fees

11 Feb - 12 Feb

[](https://www.expedia.co.uk/Becket-Hotels-Dog-Friendly2B1B-In-The-Berkshires-Private-Lake-Community-Whot-Tub-Canoe.h105230373.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/20000000/19110000/19107300/19107245/0f27818f.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.co.uk/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.

£234

includes taxes & fees

11 Feb - 12 Feb

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

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/103000000/102810000/102800600/102800548/c9e93f59.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.co.uk/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.

£553

includes taxes & fees

11 Feb - 12 Feb

[](https://www.expedia.co.uk/Bloomfield-Hotels-Spacious-5-Bedroom-Townhome-With-WiFi-And-AC-In-Charming-Bloomfield.h102800548.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/100000000/99280000/99279300/99279229/7603a317.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/bd94c256.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

[](https://www.expedia.co.uk/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.

£377

includes taxes & fees

11 Mar - 12 Mar

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

![Interior](https://images.trvl-media.com/lodging/109000000/108190000/108188500/108188444/76ed01a5.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)

![Smart TV](https://images.trvl-media.com/lodging/109000000/108190000/108188500/108188444/a8bdd677.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

### Stylish Townhome | Perfect for Family Gatherings & Events

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

Bloomfield

10/10

Exceptional

(4 reviews)

"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.

£522

includes taxes & fees

11 Feb - 12 Feb

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

![Property grounds](https://images.trvl-media.com/lodging/85000000/84680000/84672900/84672833/caf5dd09.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)

### Home in Great Barrington

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

Great Barrington

9.8/10

Exceptional

(27 reviews)

"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.

£189

includes taxes & fees

23 Feb - 24 Feb

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

![Property grounds](https://images.trvl-media.com/lodging/100000000/99970000/99962400/99962392/d00ad195.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)

![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.co.uk/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.

£494

includes taxes & fees

12 Feb - 13 Feb

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

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

![Outdoor dining](https://images.trvl-media.com/lodging/94000000/93250000/93241000/93240974/446492ff.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.co.uk/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

£228

includes taxes & fees

1 Mar - 2 Mar

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

![Exterior](https://images.trvl-media.com/lodging/124000000/123030000/123028900/123028859/e6a8de71.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/124000000/123030000/123028900/123028859/07647859.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/124000000/123030000/123028900/123028859/9f6d0429.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/124000000/123030000/123028900/123028859/4ac89d04.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Sequoia House Charming Goshen Getaway – Quiet Retreat in Litchfield Hills

[](https://www.expedia.co.uk/Goshen-Hotels-Sequoia-House-Charming-Goshen-Getaway-Quiet-Retreat-In-Litchfield-Hills.h123028859.Hotel-Information)

Goshen

10/10

Exceptional

(1 review)

"Without a doubt, we will be back! Your home was so beautiful, warm and comfortable. Our host was so helpful and friendly. We can't thank you enough for providing such a wonderful experience to our trip. "

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

Linda D.

£395

includes taxes & fees

23 Feb - 24 Feb

[](https://www.expedia.co.uk/Goshen-Hotels-Sequoia-House-Charming-Goshen-Getaway-Quiet-Retreat-In-Litchfield-Hills.h123028859.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)

![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)

![Interior](https://images.trvl-media.com/lodging/112000000/111930000/111926200/111926107/368587af.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

[](https://www.expedia.co.uk/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.

£272

includes taxes & fees

11 Feb - 12 Feb

[](https://www.expedia.co.uk/Litchfield-Hotels-The-Jefferson-House.h111926107.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.co.uk/Hotel-Search?startDate=2026-02-24&endDate=2026-02-25&regionId=3000430645&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true)

## Find holiday rentals that suit your style

Cottages

[](https://www.expedia.co.uk/Hotel-Search?destination=Winsted%2C+Connecticut%2C+United+States+of+America&regionId=3000430645&latLong=41.921207%2C-73.060108&adults=2&startDate=2026-05-11&d1=2026-05-11&endDate=2026-05-14&d2=2026-05-14&lodging=COTTAGE)

Cabins

[](https://www.expedia.co.uk/Hotel-Search?destination=Winsted%2C+Connecticut%2C+United+States+of+America&regionId=3000430645&latLong=41.921207%2C-73.060108&adults=2&startDate=2026-05-11&d1=2026-05-11&endDate=2026-05-14&d2=2026-05-14&lodging=CABIN)

Apartments

[](https://www.expedia.co.uk/Hotel-Search?destination=Winsted%2C+Connecticut%2C+United+States+of+America&regionId=3000430645&latLong=41.921207%2C-73.060108&adults=2&startDate=2026-05-11&d1=2026-05-11&endDate=2026-05-14&d2=2026-05-14&lodging=APARTMENT)

Private holiday homes

[](https://www.expedia.co.uk/Hotel-Search?destination=Winsted%2C+Connecticut%2C+United+States+of+America&regionId=3000430645&latLong=41.921207%2C-73.060108&adults=2&startDate=2026-05-11&d1=2026-05-11&endDate=2026-05-14&d2=2026-05-14&lodging=VACATION_HOME)

Chalets

[](https://www.expedia.co.uk/Hotel-Search?destination=Winsted%2C+Connecticut%2C+United+States+of+America&regionId=3000430645&latLong=41.921207%2C-73.060108&adults=2&startDate=2026-05-11&d1=2026-05-11&endDate=2026-05-14&d2=2026-05-14&lodging=CHALET)

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## 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

"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.co.uk/Hartford-Hotels-The-Farmington-Inn-Suites.h10185.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.co.uk/Hartford-Hotels-Homewood-Suites-By-Hilton-Hartford-Farmington.h203496.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

"Very satisfied "

[](https://expedia.co.uk/Hartford-Hotels-Holiday-Inn-Express-Suites-Bradley-Airport.h1535956.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

"Very comfortable room, very nice staff. Breakfast was great. "

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

"It is very rare , the floors were vinyl flooring instead of dirty carpets. Lots of parking spots, very quiete and good working ac system. I strongly recommend this hotel to everyone and I-84 connection is 20 seconds "

[](https://expedia.co.uk/Hartford-Hotels-Extended-Stay-America-Suites-Hartford-Farmington.h151013.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

"Friendly casual staff. Plenty good room."

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

"the front desk was excellent . the shuttle driver was very gracious my husband arrived 1:30 in the morning after a ski trip drove him to the car so he could put his skis in the car, waited for him and drove him to the front door again Just the extra little service! "

[](https://expedia.co.uk/Hartford-Hotels-DoubleTree-By-Hilton-Hartford-Bradley-Airport.h14480.Hotel-Information)

![Holiday Inn Express Hotel & Suites Great Barrington by IHG](https://images.trvl-media.com/lodging/1000000/900000/892300/892229/eb9d0598_y.jpg)

### Holiday Inn Express Hotel & Suites Great Barrington by IHG

10/10 Excellent

"The staff was very nice. The breakfast very good. Comfortable bed. Adjustable temperature."

[](https://expedia.co.uk/Great-Barrington-Hotels-Holiday-Inn-Express-Hotel-Suites-Great-Barrington.h892229.Hotel-Information)

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

### Hampton Inn Hartford/Airport

10/10 Excellent

"Clean. Friendly. Convenient to highway. "

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

## Find out more about Winsted

**Everything you need to know about** **Winsted** **holiday rentals**

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Winsted holiday rental for you. At Expedia, you can take your pick from private holiday homes, [apartments](https://www.expedia.co.uk/aa/Apartments), cottages, [apart-hotels](https://www.expedia.co.uk/aa/ApartHotels), cabins, [villas](https://www.expedia.co.uk/aa/Villas)... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Winsted holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

**Winsted holiday rentals: An excellent choice for every season**

Whenever you want to travel, a warm welcome awaits you in Winsted. If you’re looking for a little peace, consider booking during the quieter months, such as . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Winsted holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in. The selection of Winsted holiday rentals we have selected for you start as low as £189 per night. Entering your travel dates in the search wizard you might find even better deals!

**How to find incredible deals on Winsted rentals**

At Expedia, we put the best Winsted holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Winsted rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Winsted holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Winsted. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

## Explore a world of travel with Expedia

- Trending destinations on Expedia.co.uk
- All accommodation types in Winsted

### Trending destinations on Expedia.co.uk

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- [Northumberland Holiday Rentals ](https://www.expedia.com/Destinations-In-Northumberland.d6046225.Vacation-Rental-Destinations)
- [Herefordshire Holiday Rentals ](https://www.expedia.co.uk/Destinations-In-Herefordshire.d6046203.Holiday-Rental-Destinations)
- [Essex Holiday Rentals ](https://www.expedia.co.uk/Destinations-In-Essex.d6046201.Holiday-Rental-Destinations)
- [Cumbria Holiday Rentals ](https://www.expedia.co.uk/Destinations-In-Cumbria.d6046194.Holiday-Rental-Destinations)
- [Yorkshire Holiday Rentals ](https://www.expedia.co.uk/Yorkshire-Holiday-Rentals.d6342462.Travel-Guide-HolidayRentals)
- [South Wales Holiday Rentals ](https://www.expedia.co.uk/South-Wales-Holiday-Rentals.d6054274.Travel-Guide-HolidayRentals)
- [North Wales Holiday Rentals ](https://www.expedia.co.uk/North-Wales-Holiday-Rentals.d6054276.Travel-Guide-HolidayRentals)
- [London Holiday Rentals ](https://www.expedia.co.uk/London-Holiday-Rentals.d178279.Travel-Guide-HolidayRentals)
- [York Holiday Rentals ](https://www.expedia.co.uk/York-Holiday-Rentals.d5489.Travel-Guide-HolidayRentals)
- [Blackpool Holiday Rentals ](https://www.expedia.co.uk/Blackpool-Holiday-Rentals.d619.Travel-Guide-HolidayRentals)
- [Isle of Wight Holiday Rentals ](https://www.expedia.com/Destinations-In-Isle-Of-Wight.d6046218.Vacation-Rental-Destinations)
- [Scarborough Holiday Rentals ](https://www.expedia.co.uk/Scarborough-Holiday-Rentals.d5680.Travel-Guide-HolidayRentals)
- [Edinburgh Holiday Rentals ](https://www.expedia.co.uk/Edinburgh-Holiday-Rentals.d6069845.Travel-Guide-HolidayRentals)
- [Bath Holiday Rentals ](https://www.expedia.co.uk/Bath-Holiday-Rentals.d6084496.Travel-Guide-HolidayRentals)
- [Bournemouth Holiday Rentals ](https://www.expedia.co.uk/Bournemouth-Holiday-Rentals.d654.Travel-Guide-HolidayRentals)
- [England Holiday Rentals ](https://www.expedia.co.uk/Destinations-In-England.d11218.Holiday-Rental-Destinations)
- [Scotland Holiday Rentals ](https://www.expedia.co.uk/Destinations-In-Scotland.d11219.Holiday-Rental-Destinations)
- [Cornwall Holiday Rentals ](https://www.expedia.co.uk/Destinations-In-Cornwall.d6046193.Holiday-Rental-Destinations)
- [Wales Holiday Rentals ](https://www.expedia.co.uk/Destinations-In-Wales.d11220.Holiday-Rental-Destinations)
- [Northern Ireland Holiday Rentals ](https://www.expedia.co.uk/Destinations-In-Northern-Ireland.d11221.Holiday-Rental-Destinations)

- [Cottages in Winsted ](https://expedia.co.uk/Winsted-Cottages.d3000430645-aaCottages.Travel-Guide-Accommodation)

## Frequently asked questions

### Can I find holiday rentals in Winsted?

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

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

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

### What are holiday rentals like in Winsted?

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