Title: Winsted Vacation Rentals from $263: 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

[Feb 27 - Mar 1](https://www.expedia.com/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

[Apr 10 - Apr 12](https://www.expedia.com/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

[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 four 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)

## Our top choices for Winsted vacation 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)

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

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

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

$614 nightly

$629 total

Feb 10 - Feb 11

Total with taxes and fees

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

![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)

![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)

### Peaceful Meadow Retreat

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

$164 nightly

$185 total

Feb 15 - Feb 16

Total with taxes and fees

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

![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)

![Interior](https://images.trvl-media.com/lodging/101000000/100400000/100397900/100397846/86a2247f.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.

$238 nightly

$254 total

Feb 14 - Feb 15

Total with taxes and fees

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

![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)

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

### The Sun Filled Cozy Creamery

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

$236 nightly

$251 total

Feb 10 - Feb 11

Total with taxes and fees

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

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

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

### 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.

$288 nightly

$329 total

Mar 3 - Mar 4

Total with taxes and fees

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

$372 nightly

$422 total

Feb 10 - Feb 11

Total with taxes and fees

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

![Property grounds](https://images.trvl-media.com/lodging/92000000/91310000/91304800/91304720/abd1a92f.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)

### Cozy Modern Farmhouse Private Apt - 3 Beds

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

$339 nightly

$390 total

Feb 10 - Feb 11

Total with taxes and fees

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

![Smart TV](https://images.trvl-media.com/lodging/91000000/90830000/90821100/90821015/39eb1814.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)

![Interior](https://images.trvl-media.com/lodging/91000000/90830000/90821100/90821015/w904h683x60y0-a0d1107c.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

Feb 10 - Feb 11

Total with taxes and fees

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

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

![2 bedrooms, desk, free WiFi, bed sheets](https://images.trvl-media.com/lodging/114000000/113210000/113200800/113200740/35b02266.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.com/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.

$470 nightly

$533 total

Feb 10 - Feb 11

Total with taxes and fees

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

![Smart TV](https://images.trvl-media.com/lodging/102000000/101460000/101453000/101452935/757359f2.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/102000000/101460000/101453000/101452935/6fe17c14.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Charming apartment 7 minute walk to downtown

[](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.

$219 nightly

$248 total

Mar 1 - Mar 2

Total with taxes and fees

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

![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)

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

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

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

[](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

(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.

$353 nightly

$395 total

Feb 11 - Feb 12

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)

![Property grounds](https://images.trvl-media.com/lodging/20000000/19110000/19107300/19107245/7377fc19.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)

![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.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.

$303 nightly

$320 total

Feb 10 - Feb 11

Total with taxes and fees

[](https://www.expedia.com/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/103000000/102810000/102800600/102800548/83cbfafe.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)

![Smart TV](https://images.trvl-media.com/lodging/103000000/102810000/102800600/102800548/241d83cf.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.com/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.

$661 nightly

$748 total

Feb 10 - Feb 11

Total with taxes and fees

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

![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)

![Smart TV](https://images.trvl-media.com/lodging/100000000/99280000/99279300/99279229/bd94c256.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.

$473 nightly

$507 total

Mar 11 - Mar 12

Total with taxes and fees

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

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

![Interior](https://images.trvl-media.com/lodging/109000000/108190000/108188500/108188444/349b6d9c.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)

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

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

$633 nightly

$717 total

Feb 10 - Feb 11

Total with taxes and fees

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

![Exterior](https://images.trvl-media.com/lodging/85000000/84680000/84672900/84672833/6137aab0.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.com/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.

$236 nightly

$263 total

Feb 23 - Feb 24

Total with taxes and fees

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

![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)

![Interior](https://images.trvl-media.com/lodging/100000000/99970000/99962400/99962392/51b9c734.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.

$621 nightly

$694 total

Feb 11 - Feb 12

Total with taxes and fees

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

![Outdoor dining](https://images.trvl-media.com/lodging/94000000/93250000/93241000/93240974/446492ff.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

![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.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

$282 nightly

$312 total

Mar 1 - Mar 2

Total with taxes and fees

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

$485 nightly

$550 total

Feb 10 - Feb 11

Total with taxes and fees

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

![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)

![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.

$375 nightly

$375 total

Feb 10 - Feb 11

Total with taxes and fees

[](https://www.expedia.com/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.com/Hotel-Search?startDate=2026-02-23&endDate=2026-02-24&regionId=3000430645&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true)

## 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=2026-05-10&d1=2026-05-10&endDate=2026-05-13&d2=2026-05-13&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=2026-05-10&d1=2026-05-10&endDate=2026-05-13&d2=2026-05-13&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=2026-05-10&d1=2026-05-10&endDate=2026-05-13&d2=2026-05-13&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=2026-05-10&d1=2026-05-10&endDate=2026-05-13&d2=2026-05-13&lodging=APARTMENT)

Chalets

[](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=2026-05-10&d1=2026-05-10&endDate=2026-05-13&d2=2026-05-13&lodging=CHALET)

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## Top Winsted Hotel Reviews

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

### Simsbury 1820 House

10/10 Excellent

"Gorgeous."

[](https://expedia.com/Hartford-Hotels-Simsbury-1820-House.h42279.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.com/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.com/Hartford-Hotels-Sheraton-Hartford-Hotel-At-Bradley-Airport.h4632.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

"Was really nice "

[](https://expedia.com/Hartford-Hotels-Holiday-Inn-Express-Suites-Bradley-Airport.h1535956.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.com/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.com/Great-Barrington-Hotels-Holiday-Inn-Express-Hotel-Suites-Great-Barrington.h892229.Hotel-Information)

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

### The Farmington Inn & Suites

10/10 Excellent

"From desk staff "

[](https://expedia.com/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

"Very courteous staff. Room was clean and spotless."

[](https://expedia.com/Hartford-Hotels-Homewood-Suites-By-Hilton-Hartford-Farmington.h203496.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.com/Hartford-Hotels-Hampton-Inn-HartfordAirport.h892590.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 $263 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

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- [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?

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

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Flights

- [Cheap Flights to New Haven](https://expedia.com/Cheap-Flights-To-New-Haven.d180036.Travel-Guide-Flights)
- [Hartford Flights](https://expedia.com/lp/flights/180005/flights-from-hartford)
- [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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