Title: Winsted Vacation Rentals from $275: Search Short-Term Rentals | Expedia.com

[Winsted Travel Guide](https://expedia.com/Winsted.dx3000430645)[Hotels in Winsted](https://expedia.com/Winsted-Hotels.d3000430645.Travel-Guide-Hotels)[Flights to Winsted](https://expedia.com/Cheap-Flights-To-Winsted.d3000430645.Travel-Guide-Flights)[Car Rentals in Winsted](https://expedia.com/Car-Rentals-In-Winsted.d3000430645.Car-Rental-Guide)[Winsted Vacation Packages](https://expedia.com/Winsted.d3000430645.Destination-Travel-Guides)

![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

[Mar 27 - Mar 29](https://www.expedia.com/Hotel-Search?regionId=3000430645&startDate=2026-03-27&endDate=2026-03-29&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two months

[May 8 - May 10](https://www.expedia.com/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 three months

[Jun 5 - Jun 7](https://www.expedia.com/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)

In four months

[Jul 3 - Jul 5](https://www.expedia.com/Hotel-Search?regionId=3000430645&startDate=2026-07-03&endDate=2026-07-05&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

![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)

![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)

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

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

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

Bethlehem

9.8/10

Exceptional

(40 reviews)

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

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

Jennifer Y.

$371 nightly

$421 total

Mar 11 - Mar 12

Total with taxes and fees

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

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

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

![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.com/Granby-Hotels-Peaceful-Meadow-Retreat.h105660083.Hotel-Information)

Granby

10/10

Exceptional

(18 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.

$167 nightly

$189 total

Mar 18 - Mar 19

Total with taxes and fees

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

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

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

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

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

### Litchfield Retreat, Wineries, Foliage & Skiing

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

Torrington

$350 nightly

$397 total

Mar 11 - Mar 12

Total with taxes and fees

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

![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)

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

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

### Guesthouse Cabin vacation rentals in Berkshire County

[](https://www.expedia.com/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.

$609 nightly

$680 total

Mar 12 - Mar 13

Total with taxes and fees

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

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

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

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

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

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

[](https://www.expedia.com/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.

$227 nightly

$258 total

Mar 12 - Mar 13

Total with taxes and fees

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

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

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

![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)

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

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

[](https://www.expedia.com/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.

$236 nightly

$267 total

Mar 11 - Mar 12

Total with taxes and fees

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

![Interior](https://images.trvl-media.com/lodging/107000000/106040000/106031100/106031055/979641d4.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)

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

[](https://www.expedia.com/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.

$627 nightly

$643 total

Mar 11 - Mar 12

Total with taxes and fees

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

![Smart TV, books](https://images.trvl-media.com/lodging/106000000/105240000/105230400/105230373/a2f8cee0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/106000000/105240000/105230400/105230373/8c55822c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor spa tub](https://images.trvl-media.com/lodging/106000000/105240000/105230400/105230373/1c7057e9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Berkshires Cottage! Dog friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing

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

Sherwood Forest

9.8/10

Exceptional

(14 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.

$343 nightly

$383 total

Mar 12 - Mar 13

Total with taxes and fees

[](https://www.expedia.com/Becket-Hotels-Dog-Friendly2B1B-In-The-Berkshires-Private-Lake-Community-Whot-Tub-Canoe.h105230373.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/92000000/91310000/91304700/91304625/970a479f.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)

![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.com/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.

$295 nightly

$339 total

Mar 12 - Mar 13

Total with taxes and fees

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

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

### Big farmhouse in the foothills of the Berkshires

[](https://www.expedia.com/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.

$322 nightly

$340 total

Mar 12 - Mar 13

Total with taxes and fees

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

![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)

![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)

### Home in Great Barrington

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

Great Barrington

9.8/10

Exceptional

(27 reviews)

"The house was pristine, bright, with everything we needed. We hope to come back again to enjoy the area. "

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

maureen k.

$247 nightly

$275 total

Mar 15 - Mar 16

Total with taxes and fees

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

![Property grounds](https://images.trvl-media.com/lodging/94000000/93250000/93241000/93240974/3742bfa1.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)

### Dugway Hideaway Walking Distance to Lime Rock Park

[](https://www.expedia.com/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

$279 nightly

$309 total

Mar 11 - Mar 12

Total with taxes and fees

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

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

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

![Fireplace, books](https://images.trvl-media.com/lodging/121000000/120090000/120084700/120084692/709788c6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

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

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

Torrington

$349 nightly

$403 total

Mar 11 - Mar 12

Total with taxes and fees

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

![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)

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

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

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

[](https://www.expedia.com/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.

$373 nightly

$373 total

Mar 11 - Mar 12

Total with taxes and fees

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

![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)

![Exterior](https://images.trvl-media.com/lodging/116000000/115470000/115470000/115469906/a0f802bf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, DVD player](https://images.trvl-media.com/lodging/116000000/115470000/115470000/115469906/a133e616.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/116000000/115470000/115470000/115469906/0e4076ff.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.com/Becket-Hotels-Dog-Friendly-A-Frame-In-The-Berkshires-Walk-To-Lake-With-Beach-Access.h115469906.Hotel-Information)

Sherwood Forest

10/10

Exceptional

(5 reviews)

"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.

$351 nightly

$392 total

Apr 1 - Apr 2

Total with taxes and fees

[](https://www.expedia.com/Becket-Hotels-Dog-Friendly-A-Frame-In-The-Berkshires-Walk-To-Lake-With-Beach-Access.h115469906.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/acd6c55a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/101000000/100400000/100397900/100397846/4b94d1f9.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.com/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.

$225 nightly

$240 total

Mar 14 - Mar 15

Total with taxes and fees

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

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

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

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

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

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

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

Torrington

10/10

Exceptional

(1 review)

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

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

Jaimie S.

$349 nightly

$403 total

Mar 11 - Mar 12

Total with taxes and fees

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

![Interior](https://images.trvl-media.com/lodging/100000000/99280000/99279300/99279234/dee9e184.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/100000000/99280000/99279300/99279234/9f8d3ced.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![3 bedrooms, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/100000000/99280000/99279300/99279234/f20e9d92.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/100000000/99280000/99279300/99279234/f9e14ab1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### #3 FRESHLY REDONE & NEWLY FURNISHED! A MUST SEE!

[](https://www.expedia.com/Plainville-Hotels-3-FRESHLY-REDONE-NEWLY-FURNISHED-A-MUST-SEE.h99279234.Hotel-Information)

Plainville

8.4/10

Very Good

(12 reviews)

"Great place ! Quiet and safe place! We will be back! "

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

Aubrey C.

$298 nightly

$319 total

Mar 11 - Mar 12

Total with taxes and fees

[](https://www.expedia.com/Plainville-Hotels-3-FRESHLY-REDONE-NEWLY-FURNISHED-A-MUST-SEE.h99279234.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)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/100000000/99280000/99279300/99279229/4ba2a9cd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![4 bedrooms, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/100000000/99280000/99279300/99279229/858394b7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

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

[](https://www.expedia.com/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.

$450 nightly

$480 total

Mar 15 - Mar 16

Total with taxes and fees

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

![TV](https://images.trvl-media.com/lodging/93000000/92900000/92899600/92899508/e3f04cf6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/93000000/92900000/92899600/92899508/dc4b2063.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/93000000/92900000/92899600/92899508/d96d2729.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV](https://images.trvl-media.com/lodging/93000000/92900000/92899600/92899508/c8b2ae4a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Treetop Hideaway in Tyringham

[](https://www.expedia.com/Lee-Hotels-Treetop-Hideaway-In-Tyringham.h92899508.Hotel-Information)

Monterey

9.0/10

Wonderful

(10 reviews)

"This was the perfect location for our mom and daughters weekend! Spacious comfortable. Our only regret was that we didn’t stay longer!"

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

Sarah B.

$526 nightly

$556 total

Mar 11 - Mar 12

Total with taxes and fees

[](https://www.expedia.com/Lee-Hotels-Treetop-Hideaway-In-Tyringham.h92899508.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.com/Hotel-Search?startDate=2026-03-24&endDate=2026-03-25&regionId=3000430645&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true)

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## 

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Members save up to 40% on hotels and homes. Plan this year’s big trip and save.

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## Find vacation rentals that suit your style

Cabins

[](https://www.expedia.com/Hotel-Search?destination=Winsted%2C+Connecticut%2C+United+States+of+America&regionId=3000430645&latLong=41.921207%2C-73.060108&adults=2&startDate=2026-06-08&d1=2026-06-08&endDate=2026-06-11&d2=2026-06-11&lodging=CABIN)

Private vacation homes

[](https://www.expedia.com/Hotel-Search?destination=Winsted%2C+Connecticut%2C+United+States+of+America&regionId=3000430645&latLong=41.921207%2C-73.060108&adults=2&startDate=2026-06-08&d1=2026-06-08&endDate=2026-06-11&d2=2026-06-11&lodging=VACATION_HOME)

Cottages

[](https://www.expedia.com/Hotel-Search?destination=Winsted%2C+Connecticut%2C+United+States+of+America&regionId=3000430645&latLong=41.921207%2C-73.060108&adults=2&startDate=2026-06-08&d1=2026-06-08&endDate=2026-06-11&d2=2026-06-11&lodging=COTTAGE)

Apartments

[](https://www.expedia.com/Hotel-Search?destination=Winsted%2C+Connecticut%2C+United+States+of+America&regionId=3000430645&latLong=41.921207%2C-73.060108&adults=2&startDate=2026-06-08&d1=2026-06-08&endDate=2026-06-11&d2=2026-06-11&lodging=APARTMENT)

Villas

[](https://www.expedia.com/Hotel-Search?destination=Winsted%2C+Connecticut%2C+United+States+of+America&regionId=3000430645&latLong=41.921207%2C-73.060108&adults=2&startDate=2026-06-08&d1=2026-06-08&endDate=2026-06-11&d2=2026-06-11&lodging=VILLA)

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## Top Winsted Hotel Reviews

![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

"100 prevent satisfied "

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

![Springhill Suites Marriott Airport](https://images.trvl-media.com/lodging/3000000/2250000/2242100/2242056/b057ddd2_y.jpg)

### Springhill Suites Marriott Airport

10/10 Excellent

"We all enjoyed the pool. The staff were exceptionally nice and helpful. The rooms were adjoining and quite large."

[](https://expedia.com/Hartford-Hotels-Springhill-Suites-Marriott-Airport.h2242056.Hotel-Information)

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

### Avon Old Farms Hotel

10/10 Excellent

"Beautiful property and complimentary breakfast on the go made our stay memorable, looking to coming back in the future."

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

![Extended Stay America Suites Hartford Farmington](https://images.trvl-media.com/lodging/1000000/160000/151100/151013/df2a9cf4_y.jpg)

### Extended Stay America Suites Hartford Farmington

10/10 Excellent

"Perfect for what we were looking for. We visited family 40 min away and the room was clean and the area was safe. Looking forward to stay here in the future."

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

![Hampton Inn Hartford/Airport](https://images.trvl-media.com/lodging/1000000/900000/892600/892590/396dc82e_y.jpg)

### Hampton Inn Hartford/Airport

10/10 Excellent

"Wonderful hotel! I have stayed at several in this area (visiting family nearby) and this particular Hampton Inn has always been my favorite. The staff is fantastic and always very courteous & helpful. The breakfast and 24/7 coffee/tea/hot chocolate service is wonderful and everything is always kept clean and neat. Great options for breakfast and the rooms are clean and spacious. I will no longer stay anywhere else when I’m in the area. Pool/jacuzzi area is also a huge plus!! "

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

![Homewood Suites by Hilton Hartford-Farmington](https://images.trvl-media.com/lodging/1000000/210000/203500/203496/46de1f34_y.jpg)

### Homewood Suites by Hilton Hartford-Farmington

4/10 Poor

"At check-in the credit card from Hotels.com/Expedia was denied. It was different than the card I had booked the room with, the card in my Hotels.com account. My spouse who was staying at the hotel had to pay for it. Therefore, we were charged twice. I will be calling Chase Bank to dispute the original payment which had already been charged. I will also call Hotels.com regarding this error."

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

![Sheraton Hartford Hotel at Bradley Airport](https://images.trvl-media.com/lodging/1000000/10000/4700/4632/81dcef8a_y.jpg)

### Sheraton Hartford Hotel at Bradley Airport

10/10 Excellent

"Stay was great! "

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

![Hampton Inn & Suites Hartford/Farmington](https://images.trvl-media.com/lodging/3000000/2980000/2970600/2970540/f9413aba_y.jpg)

### Hampton Inn & Suites Hartford/Farmington

10/10 Excellent

"Was perfect for our overnight stay. Breakfast was great with lots of options, desk folks were friendly."

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

![DoubleTree by Hilton Hartford - Bradley Airport](https://images.trvl-media.com/lodging/1000000/20000/14500/14480/b2f4d31b_y.jpg)

### DoubleTree by Hilton Hartford - Bradley Airport

6/10 Okay

"there is an airport shuttle available. hotel is in need of some updating. "

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

## Find out more about Winsted

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

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Winsted vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

**Winsted vacation 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 low season months. For more hustle and bustle, you may prefer to visit Winsted in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $275 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

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

At Expedia, we put the best Winsted vacation 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 vacation.

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.com
- All accommodation types in Winsted

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- [Clearwater Beach Vacation Rentals ](https://www.expedia.com/Clearwater-Beach-Vacation-Rentals.d10759.Travel-Guide-VacationRentals)
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- [Lake of the Ozarks Vacation Rentals ](https://www.expedia.com/Lake-Ozark-Vacation-Rentals.d177772.Travel-Guide-VacationRentals)
- [Florida Vacation Rentals ](https://www.expedia.com/Destinations-In-Florida.d211.Vacation-Rental-Destinations)
- [Hawaii Vacation Rentals ](https://www.expedia.com/Destinations-In-Hawaii.d213.Vacation-Rental-Destinations)
- [Michigan Vacation Rentals ](https://www.expedia.com/Destinations-In-Michigan.d224.Vacation-Rental-Destinations)

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

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Flights

- [Cheap Flights to New Haven](https://expedia.com/Cheap-Flights-To-New-Haven.d180036.Travel-Guide-Flights)
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- [Cheap Flights to Hartford](https://expedia.com/Cheap-Flights-To-Hartford.d180005.Travel-Guide-Flights)

Cars

- [Car rentals in New Haven](https://expedia.com/Car-Rentals-In-New-Haven.d180036.Car-Rental-Guide)
- [Car rentals in Stamford](https://expedia.com/Car-Rentals-In-Stamford.d602523.Car-Rental-Guide)
- [Car rentals in Bridgeport](https://expedia.com/Car-Rentals-In-Bridgeport.d525.Car-Rental-Guide)
- [Car rentals in Hartford](https://expedia.com/Car-Rentals-In-Hartford.d180005.Car-Rental-Guide)
- [Car rentals in Danbury](https://expedia.com/Car-Rentals-In-Danbury.d6046722.Car-Rental-Guide)
- [Car rentals in Waterbury](https://expedia.com/Car-Rentals-In-Waterbury.d10425.Car-Rental-Guide)

Activities

- [Things to do in Hartford](https://expedia.com/Things-To-Do-In-Hartford.d180005.Travel-Guide-Activities)

General

- [Visit Hartford](https://expedia.com/Hartford.dx180005)
- [Visit Stamford](https://expedia.com/Stamford.dx602523)
- [Visit New Haven](https://expedia.com/New-Haven.dx180036)

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