Title: Winsted, CT Cottage Rentals from $74 | Expedia.com

[Winsted Travel Guide](https://expedia.com/Winsted.dx3000430645)[Hotels in Winsted](https://expedia.com/Winsted-Hotels.d3000430645.Travel-Guide-Hotels)[Vacation Rentals in Winsted](https://expedia.com/Winsted-Vacation-Rentals.d3000430645.Travel-Guide-VacationRentals)[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 13 - Mar 15](https://www.expedia.com/Hotel-Search?regionId=3000430645&startDate=2026-03-13&endDate=2026-03-15&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two months

[Apr 24 - Apr 26](https://www.expedia.com/Hotel-Search?regionId=3000430645&startDate=2026-04-24&endDate=2026-04-26&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In three months

[May 22 - May 24](https://www.expedia.com/Hotel-Search?regionId=3000430645&startDate=2026-05-22&endDate=2026-05-24&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In four months

[Jun 19 - Jun 21](https://www.expedia.com/Hotel-Search?regionId=3000430645&startDate=2026-06-19&endDate=2026-06-21&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

No exact matches found, but these alternatives could be just right

## Recommended hotels in Winsted

![Terrace/patio](https://images.trvl-media.com/lodging/95000000/94950000/94946700/94946614/a9d938cc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Pool](https://images.trvl-media.com/lodging/95000000/94950000/94946700/94946614/31f305c2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Sports facility](https://images.trvl-media.com/lodging/95000000/94950000/94946700/94946614/d26781d2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/95000000/94950000/94946700/94946614/10e91fff.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Home2 Suites by Hilton Bristol

[](https://www.expedia.com/Bristol-Hotels-Home2-Suites-By-Hilton-Bristol.h94946614.Hotel-Information)

Bristol

9.6/10

Exceptional

(192 reviews)

"Clean room, great staff"

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

Tamiya

$131 nightly

$151 total

Mar 19 - Mar 20

Total with taxes and fees

[](https://www.expedia.com/Bristol-Hotels-Home2-Suites-By-Hilton-Bristol.h94946614.Hotel-Information)

![Property entrance](https://images.trvl-media.com/lodging/13000000/12990000/12986600/12986517/85d74b46.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Restaurant](https://images.trvl-media.com/lodging/13000000/12990000/12986600/12986517/5d161739.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/13000000/12990000/12986600/12986517/5435aab1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Hypo-allergenic bedding, individually decorated, individually furnished](https://images.trvl-media.com/lodging/13000000/12990000/12986600/12986517/c1a6e504.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Truman Gillet House Bed & Breakfast

[](https://www.expedia.com/Hartford-Hotels-Truman-Gillet-House-Bed-Breakfast.h12986517.Hotel-Information)

Granby

9.6/10

Exceptional

(104 reviews)

"Room was spotless and hospitality was outstanding. Had great breakfast and was very welcoming. "

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

Desiree

$140 nightly

$155 total

Feb 24 - Feb 25

Total with taxes and fees

[](https://www.expedia.com/Hartford-Hotels-Truman-Gillet-House-Bed-Breakfast.h12986517.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/8000000/7760000/7754000/7753947/30ceb892.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Aerial view](https://images.trvl-media.com/lodging/8000000/7760000/7754000/7753947/b28516d5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/8000000/7760000/7754000/7753947/9fc87fbd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, bed sheets](https://images.trvl-media.com/lodging/8000000/7760000/7754000/7753947/04ff4b17.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Locust Tree Bed and Breakfast LLC

[](https://www.expedia.com/Torrington-Hotels-Locust-Tree-Bed-And-Breakfast-LLC.h7753947.Hotel-Information)

East Canaan

9.0/10

Wonderful

(415 reviews)

"Great breakfast! Had a wonderful stay!"

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

Michelle

$105 nightly

$121 total

Feb 24 - Feb 25

Total with taxes and fees

[](https://www.expedia.com/Torrington-Hotels-Locust-Tree-Bed-And-Breakfast-LLC.h7753947.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/2000000/1080000/1076200/1076188/a1ad800b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/2000000/1080000/1076200/1076188/748b4faa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/2000000/1080000/1076200/1076188/83dd2b57.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Room, 2 Queen Beds, Non Smoking | Iron/ironing board, free cribs/infant beds, rollaway beds, free WiFi](https://images.trvl-media.com/lodging/2000000/1080000/1076200/1076188/220f6cfe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Monument Mountain Motel

[](https://www.expedia.com/Great-Barrington-Hotels-Monument-Mountain-Motel.h1076188.Hotel-Information)

Great Barrington

9.0/10

Wonderful

(824 reviews)

"The room was clean, and the staff was friendly and helpful. "

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

Damien

$67 nightly

$74 total

Feb 24 - Feb 25

Total with taxes and fees

[](https://www.expedia.com/Great-Barrington-Hotels-Monument-Mountain-Motel.h1076188.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/1000000/130000/128300/128208/1d183ca9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Standard Room, 2 Queen Beds, Non Smoking | Bathroom | Combined shower/tub, deep soaking tub, hydromassage showerhead](https://images.trvl-media.com/lodging/1000000/130000/128300/128208/591bd0b6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Standard Room, 2 Queen Beds, Non Smoking | 1 bedroom, premium bedding, pillowtop beds, desk](https://images.trvl-media.com/lodging/1000000/130000/128300/128208/f25ff27c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Standard Room, 2 Queen Beds, Non Smoking | 1 bedroom, premium bedding, pillowtop beds, desk](https://images.trvl-media.com/lodging/1000000/130000/128300/128208/1650f935.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Quality Inn Great Barrington

[](https://www.expedia.com/Great-Barrington-Hotels-Days-Inn-By-Wyndham-Great-Barrington.h128208.Hotel-Information)

Great Barrington

8.4/10

Very Good

(1,005 reviews)

"Clean room, great location"

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

Andrea

$66 nightly

$74 total

Mar 23 - Mar 24

Total with taxes and fees

[](https://www.expedia.com/Great-Barrington-Hotels-Days-Inn-By-Wyndham-Great-Barrington.h128208.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/2000000/1540000/1536000/1535956/c57c2497.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Free daily continental breakfast](https://images.trvl-media.com/lodging/2000000/1540000/1536000/1535956/0d7cd77e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/2000000/1540000/1536000/1535956/9360dc5d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Standard Room, Multiple Beds | In-room safe, desk, iron/ironing board, free cribs/infant beds](https://images.trvl-media.com/lodging/2000000/1540000/1536000/1535956/5f21961b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

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

Windsor Locks

9.0/10

Wonderful

(1,174 reviews)

"Always my go to hotel when I come home for visits, friendly staff, clean hotel. "

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

Kathleen

$103 nightly

$119 total

Mar 2 - Mar 3

Total with taxes and fees

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

![Lobby](https://images.trvl-media.com/lodging/3000000/2080000/2076200/2076197/34065f96.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Room, 2 Queen Beds, Refrigerator | Premium bedding, desk, laptop workspace, blackout drapes](https://images.trvl-media.com/lodging/3000000/2080000/2076200/2076197/04ad8e9d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fitness facility](https://images.trvl-media.com/lodging/3000000/2080000/2076200/2076197/cd83e31a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/3000000/2080000/2076200/2076197/241daa63.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Hampton Inn Westfield

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

Westfield

8.4/10

Very Good

(828 reviews)

"I will stay again"

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

Jailene

$112 nightly

$125 total

Mar 11 - Mar 12

Total with taxes and fees

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

![Exterior](https://images.trvl-media.com/lodging/2000000/1240000/1239700/1239604/c5a54031.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Suite, 2 Bedrooms, Non Smoking | In-room safe, desk, free cribs/infant beds, free rollaway beds](https://images.trvl-media.com/lodging/2000000/1240000/1239700/1239604/723a5f12.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Pool](https://images.trvl-media.com/lodging/2000000/1240000/1239700/1239604/e351f473.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![In-room safe, desk, free cribs/infant beds, free rollaway beds](https://images.trvl-media.com/lodging/2000000/1240000/1239700/1239604/7c78ca51.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Travelodge by Wyndham Great Barrington Berkshires

[](https://www.expedia.com/Great-Barrington-Hotels-Travelodge-By-Wyndham-Great-Barrington-Berkshires.h1239604.Hotel-Information)

Great Barrington

7.6/10

Good

(572 reviews)

"Excellent location!!"

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

Abdul Samad

$75 nightly

$84 total

Feb 24 - Feb 25

Total with taxes and fees

[](https://www.expedia.com/Great-Barrington-Hotels-Travelodge-By-Wyndham-Great-Barrington-Berkshires.h1239604.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/106000000/105820000/105813900/105813835/c7c6ac1a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior detail](https://images.trvl-media.com/lodging/106000000/105820000/105813900/105813835/7fea6163.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Wilder House Berkshires Room 1 | Premium bedding, individually decorated, individually furnished](https://images.trvl-media.com/lodging/106000000/105820000/105813900/105813835/aa99cb85.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior detail](https://images.trvl-media.com/lodging/106000000/105820000/105813900/105813835/143186d3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Wilder House Berkshires

[](https://www.expedia.com/Sheffield-Hotels-Wilder-House-Berkshires.h105813835.Hotel-Information)

Sheffield

9.8/10

Exceptional

(43 reviews)

"Clean, cute, private, nice location. Breakfast was wonderful. Great value as well. Would definitely go back. "

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

Kristinna

$187 nightly

$209 total

Mar 19 - Mar 20

Total with taxes and fees

[](https://www.expedia.com/Sheffield-Hotels-Wilder-House-Berkshires.h105813835.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/1000000/20000/10200/10185/76286fe1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Staircase](https://images.trvl-media.com/lodging/1000000/20000/10200/10185/1c89931a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/1000000/20000/10200/10185/3d878f20.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby sitting area](https://images.trvl-media.com/lodging/1000000/20000/10200/10185/f73d38df.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Farmington Inn & Suites

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

Farmington

8.8/10

Excellent

(1,004 reviews)

"This place is like a warm hug from your favorite auntie. "

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

kieran

$127 nightly

$146 total

Mar 2 - Mar 3

Total with taxes and fees

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

![Exterior](https://images.trvl-media.com/lodging/126000000/125350000/125340300/125340225/044fa417.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Double Room, Roll-in Shower | Individually decorated, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/126000000/125350000/125340300/125340225/7d38f095.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/126000000/125350000/125340300/125340225/1a233317.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/126000000/125350000/125340300/125340225/9885d0cd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Berkshire Mountain Inn

[](https://www.expedia.com/Great-Barrington-Hotels-The-Berkshire-Mountain-Inn.h125340225.Hotel-Information)

Great Barrington

$200 nightly

$223 total

Feb 24 - Feb 25

Total with taxes and fees

[](https://www.expedia.com/Great-Barrington-Hotels-The-Berkshire-Mountain-Inn.h125340225.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/2000000/1120000/1118900/1118896/d8217024.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Free daily buffet breakfast](https://images.trvl-media.com/lodging/2000000/1120000/1118900/1118896/51285776.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Standard Room, 1 King Bed, Non Smoking | Pillowtop beds, in-room safe, desk, blackout drapes](https://images.trvl-media.com/lodging/2000000/1120000/1118900/1118896/5f79da29.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/2000000/1120000/1118900/1118896/532eb0dc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Quality Inn Westfield - Springfield

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

Westfield

7.2/10

Good

(917 reviews)

"Staff was very friendly. Everything was clean and well kept. Small hotel but very cozy and quiet."

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

Gloria

$88 nightly

$98 total

Mar 22 - Mar 23

Total with taxes and fees

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

![Exterior](https://images.trvl-media.com/lodging/110000000/109830000/109821100/109821051/cefd2663.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Room (5) | Bathroom | Hair dryer, towels, soap, shampoo](https://images.trvl-media.com/lodging/110000000/109830000/109821100/109821051/3ff31723.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Room (5) | Iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/110000000/109830000/109821100/109821051/6375a3f9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/110000000/109830000/109821100/109821051/ecdcd2fa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Millerton Inn

[](https://www.expedia.com/Millerton-Hotels-The-Millerton-Inn.h109821051.Hotel-Information)

Millerton

8.2/10

Very Good

(16 reviews)

"Antonia was wonderful and made our stay special. She was kind and warm and when we were initially unhappy with our room immediately rectified the situation and in the end our stay was perfect! It’s a charming hotel, clean and centrally located, walking distance to all the local shops in town."

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

Jamie

$158 nightly

$179 total

Mar 12 - Mar 13

Total with taxes and fees

[](https://www.expedia.com/Millerton-Hotels-The-Millerton-Inn.h109821051.Hotel-Information)

![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)

![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)

![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 24 - Feb 25

Total with taxes and fees

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

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

![Terrace/patio](https://images.trvl-media.com/lodging/106000000/105240000/105230400/105230373/2281e60c.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)

![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)

### 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

(13 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 24 - Feb 25

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/1000000/900000/892300/892229/eb9d0598.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby lounge](https://images.trvl-media.com/lodging/1000000/900000/892300/892229/e2e7e72f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Premium bedding, pillowtop beds, in-room safe, desk](https://images.trvl-media.com/lodging/1000000/900000/892300/892229/dcdd836c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Indoor pool](https://images.trvl-media.com/lodging/1000000/900000/892300/892229/9ac40a95.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

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

Great Barrington

8.8/10

Excellent

(739 reviews)

"Great property, very accommodating. "

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

Shanice

$103 nightly

$115 total

Mar 1 - Mar 2

Total with taxes and fees

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

![Exterior](https://images.trvl-media.com/lodging/1000000/50000/50000/49932/d4c8ac0c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Desk, free cribs/infant beds, rollaway beds, free WiFi](https://images.trvl-media.com/lodging/1000000/50000/50000/49932/c8b8e6a2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/1000000/50000/50000/49932/3ed0be48.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property amenity](https://images.trvl-media.com/lodging/1000000/50000/50000/49932/bfea9bed.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Days Inn by Wyndham Torrington

[](https://www.expedia.com/Torrington-Hotels-Days-Inn-By-Wyndham-Torrington.h49932.Hotel-Information)

Torrington

7.4/10

Good

(1,001 reviews)

"Very respectable staff and clean environment "

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

Hannah

$90 nightly

$104 total

Mar 1 - Mar 2

Total with taxes and fees

[](https://www.expedia.com/Torrington-Hotels-Days-Inn-By-Wyndham-Torrington.h49932.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/8000000/7670000/7663800/7663779/279dc540.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/8000000/7670000/7663800/7663779/f84b737e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Desk, laptop workspace, iron/ironing board, free cribs/infant beds](https://images.trvl-media.com/lodging/8000000/7670000/7663800/7663779/6fb451ef.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Room, 1 Queen Bed, Mobility Accessible | Desk, laptop workspace, iron/ironing board, free cribs/infant beds](https://images.trvl-media.com/lodging/8000000/7670000/7663800/7663779/9c5d1ec8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Little Lion

[](https://www.expedia.com/Great-Barrington-Hotels-The-Briarcliff-Motel.h7663779.Hotel-Information)

Great Barrington

8.6/10

Excellent

(554 reviews)

"Great friendly staff"

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

Pablo

$110 nightly

$123 total

Feb 24 - Feb 25

Total with taxes and fees

[](https://www.expedia.com/Great-Barrington-Hotels-The-Briarcliff-Motel.h7663779.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)

![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)

### 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 24 - Feb 25

Total with taxes and fees

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

![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/c99e99e9.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)

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

Mar 8 - Mar 9

Total with taxes and fees

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

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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=2026-05-24&d1=2026-05-24&endDate=2026-05-27&d2=2026-05-27&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=2026-05-24&d1=2026-05-24&endDate=2026-05-27&d2=2026-05-27&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=2026-05-24&d1=2026-05-24&endDate=2026-05-27&d2=2026-05-27&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=2026-05-24&d1=2026-05-24&endDate=2026-05-27&d2=2026-05-27&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=2026-05-24&d1=2026-05-24&endDate=2026-05-27&d2=2026-05-27&lodging=CHALET)

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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

"The room was very clean and spacious! The frint staff was very nice and accommodating!"

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

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

### DoubleTree by Hilton Hotel Bristol, Connecticut

10/10 Excellent

"Beautiful!! Spotless and gorgeous "

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

![Quality Inn](https://images.trvl-media.com/lodging/1000000/130000/128300/128208/62e9a326_y.jpg)

### Quality Inn

10/10 Excellent

"Clean, breakfast was a nice option before heading to Butternut mountain nearby "

[](https://expedia.com/Great-Barrington-Hotels-Days-Inn-By-Wyndham-Great-Barrington.h128208.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

"This place is always the best. Staff is incredible and super attentive. "

[](https://expedia.com/Hartford-Hotels-The-Farmington-Inn-Suites.h10185.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

"Great location, amenities, pool and hot tub for the kids, friendly staff, comfortable room."

[](https://expedia.com/Great-Barrington-Hotels-Holiday-Inn-Express-Hotel-Suites-Great-Barrington.h892229.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

"Yes"

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

"Good"

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

![Fairfield Inn & Suites by Marriott Plainville](https://images.trvl-media.com/lodging/1000000/10000/10000/9965/01d5897d_y.jpg)

### Fairfield Inn & Suites by Marriott Plainville

10/10 Excellent

"Really good service and great customer service "

[](https://expedia.com/Hartford-Hotels-Fairfield-Inn-Suites-By-Marriott-Plainville.h9965.Hotel-Information)

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

### Simsbury 1820 House

10/10 Excellent

"Clean room, courteous staff. Very nice place to stay."

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

## Find out more about Winsted

## Winsted Cottages information

| Number of reviews | 9,467       |
| ----------------- | ----------- |
| Accommodation     | 77 Cottages |
| Lowest Price      | $74         |
| Highest Price     | $533        |

## Frequently asked questions

### Why book your cottage in Winsted with Expedia?

### How can I find cheap cottages in Winsted?

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