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

In two months

[May 1 - May 3](https://www.expedia.com/Hotel-Search?regionId=3000430645&startDate=2026-05-01&endDate=2026-05-03&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In three months

[May 29 - May 31](https://www.expedia.com/Hotel-Search?regionId=3000430645&startDate=2026-05-29&endDate=2026-05-31&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In four months

[Jun 26 - Jun 28](https://www.expedia.com/Hotel-Search?regionId=3000430645&startDate=2026-06-26&endDate=2026-06-28&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

![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/2000000/1080000/1076200/1076188/83dd2b57.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)

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

### Motel in Great Barrington

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

9.0/10

Wonderful

(826 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

Mar 5 - Mar 6

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/8000000/7760000/7754000/7753947/30ceb892.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)

![Exterior](https://images.trvl-media.com/lodging/8000000/7760000/7754000/7753947/9c157bdc.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)

### Bed & Breakfast in East Canaan

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

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

Mar 5 - Mar 6

Total with taxes and fees

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

![Interior](https://images.trvl-media.com/lodging/13000000/12990000/12986600/12986517/2f45bdb0.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)

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

### Bed & Breakfast in Granby

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

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

Mar 6 - Mar 7

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/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)

![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)

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

### Motel in Great Barrington

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

7.6/10

Good

(573 reviews)

"Excellent location!!"

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

Abdul Samad

$74 nightly

$82 total

Mar 5 - Mar 6

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/1000000/130000/128300/128208/1d183ca9.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)

![Lobby](https://images.trvl-media.com/lodging/1000000/130000/128300/128208/ed6ed4e8.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)

### Hotel in Great Barrington

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

8.4/10

Very Good

(1,002 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/126000000/125350000/125340300/125340225/63dfffc9.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)

![50-inch flat-screen TV with digital channels, Netflix, toys](https://images.trvl-media.com/lodging/126000000/125350000/125340300/125340225/17c4dc13.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/126000000/125350000/125340300/125340225/1c579ba7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Bed & Breakfast in Great Barrington

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

$146 nightly

$163 total

Mar 5 - Mar 6

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/2000000/1540000/1536000/1535956/c57c2497.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)

![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)

### Hotel in Windsor Locks

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

9.0/10

Wonderful

(1,160 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

$105 nightly

$121 total

Mar 23 - Mar 24

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)

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

![Lobby](https://images.trvl-media.com/lodging/3000000/2080000/2076200/2076197/cde7c3e2.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)

### Hotel in Westfield

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

8.4/10

Very Good

(830 reviews)

"I will stay again"

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

Jailene

$116 nightly

$129 total

Apr 2 - Apr 3

Total with taxes and fees

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

![Terrace/patio](https://images.trvl-media.com/lodging/95000000/94950000/94946700/94946614/a9d938cc.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)

![Exterior](https://images.trvl-media.com/lodging/95000000/94950000/94946700/94946614/7588ab8c.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)

### Hotel in Bristol

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

9.6/10

Exceptional

(197 reviews)

"Clean room, great staff"

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

Tamiya

$126 nightly

$145 total

Mar 29 - Mar 30

Total with taxes and fees

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

![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)

![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)

### Motel in Torrington

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

7.4/10

Good

(1,002 reviews)

"Staff was very friendly, room was clean. Overall great stay, thanks!"

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

Nathaniel

$98 nightly

$112 total

Mar 10 - Mar 11

Total with taxes and fees

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

![Terrace/patio](https://images.trvl-media.com/lodging/105000000/104370000/104369400/104369320/f403f26b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Reception](https://images.trvl-media.com/lodging/105000000/104370000/104369400/104369320/5288546f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Restaurant](https://images.trvl-media.com/lodging/105000000/104370000/104369400/104369320/efe74a4f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Suite (Chamber) | In-room safe, free WiFi](https://images.trvl-media.com/lodging/105000000/104370000/104369400/104369320/786946b2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Hotel in Litchfield Historic District

[](https://www.expedia.com/Litchfield-Hotels-Hotel-Abner.h104369320.Hotel-Information)

9.4/10

Exceptional

(52 reviews)

"My stay was flawless. From staff to the clean room and comfortable bedding all made for an amazing experience."

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

Francis

$201 nightly

$231 total

Mar 25 - Mar 26

Total with taxes and fees

[](https://www.expedia.com/Litchfield-Hotels-Hotel-Abner.h104369320.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/106000000/105820000/105813900/105813835/0603c149.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)

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

### Bed & Breakfast in Sheffield

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

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

$186 nightly

$208 total

Mar 11 - Mar 12

Total with taxes and fees

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

![Outdoor dining](https://images.trvl-media.com/lodging/92000000/91500000/91497200/91497114/c6a9bdfb.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/c99e99e9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cabin in Bethlehem

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

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.

$375 nightly

$425 total

Mar 8 - Mar 9

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/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)

![Lunch, dinner, brunch served; Mediterranean cuisine ](https://images.trvl-media.com/lodging/110000000/109830000/109821100/109821051/5fe2b5b2.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)

### Hotel in Millerton

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

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

$161 nightly

$182 total

Mar 11 - Mar 12

Total with taxes and fees

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

### Hotel in Farmington

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

8.8/10

Excellent

(1,001 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

$122 nightly

$141 total

Mar 11 - Mar 12

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/8000000/7670000/7663800/7663779/279dc540.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)

![Exterior](https://images.trvl-media.com/lodging/8000000/7670000/7663800/7663779/ef9bad04.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)

### Motel in Great Barrington

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

8.6/10

Excellent

(554 reviews)

"Great friendly staff"

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

Pablo

$107 nightly

$120 total

Mar 5 - Mar 6

Total with taxes and fees

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

### Hotel in Great Barrington

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

8.8/10

Excellent

(742 reviews)

"Great property, very accommodating. "

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

Shanice

$107 nightly

$120 total

Mar 9 - Mar 10

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/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)

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

![Business center](https://images.trvl-media.com/lodging/2000000/1120000/1118900/1118896/afa8b6b0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Hotel in Westfield

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

7.2/10

Good

(917 reviews)

"Pleasantly surprised by this hotel. For a budget-friendly option, it was clean, comfortable, and far better than I expected. Great value for the price"

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

Amanda

$97 nightly

$108 total

Mar 29 - Mar 30

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/103000000/102810000/102807000/102806911/fbd2cba0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Premium Apartment, 2 Bedrooms, Fireplace, Mountain View | Living area | 55-inch Smart TV with digital channels, Netflix, Hulu](https://images.trvl-media.com/lodging/103000000/102810000/102807000/102806911/75dbf9d4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Classic Double Room, 2 Queen Beds, Courtyard View | Premium bedding, pillowtop beds, in-room safe, blackout drapes](https://images.trvl-media.com/lodging/103000000/102810000/102807000/102806911/3d6dcf9e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/103000000/102810000/102807000/102806911/22135a72.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Motel in Great Barrington

[](https://www.expedia.com/Great-Barrington-Hotels-East-Rock-Inn.h102806911.Hotel-Information)

9.6/10

Exceptional

(38 reviews)

"The room was clean and comfortable wi will back next year:) "

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

Nadya

$127 nightly

$142 total

Mar 18 - Mar 19

Total with taxes and fees

[](https://www.expedia.com/Great-Barrington-Hotels-East-Rock-Inn.h102806911.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/1000000/20000/14500/14480/4eecd098.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Bar (on property)](https://images.trvl-media.com/lodging/1000000/20000/14500/14480/a43bdbab.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/1000000/20000/14500/14480/59cef280.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Reception](https://images.trvl-media.com/lodging/1000000/20000/14500/14480/89115d93.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Hotel in Windsor Locks

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

8.2/10

Very Good

(1,003 reviews)

"The room was nice and the heat was amazing during the coldest time of the year. Front desk was accommodating and friendly."

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

NiKole

$120 nightly

$138 total

Apr 4 - Apr 5

Total with taxes and fees

[](https://www.expedia.com/Hartford-Hotels-DoubleTree-By-Hilton-Hartford-Bradley-Airport.h14480.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=2026-06-02&d1=2026-06-02&endDate=2026-06-05&d2=2026-06-05&lodging=CABIN)

Private vacation homes

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Cottages

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Apartments

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Villas

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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=2026-06-02&d1=2026-06-02&endDate=2026-06-05&d2=2026-06-05&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

8/10 Good

"Breakfast was great, staff was friendly and room was clean. "

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

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

### Hampton Inn & Suites Hartford/Farmington

10/10 Excellent

"Clean , quiet and friendly staff !! Excellent stay "

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

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

### Extended Stay America Suites Hartford Farmington

4/10 Poor

"Breakfast is only instant oatmeal, nutri grain bar and coffee."

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

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

### The Farmington Inn & Suites

8/10 Good

"Yes"

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

![Quality Inn Great Barrington](https://images.trvl-media.com/lodging/1000000/130000/128300/128208/ed6ed4e8_y.jpg)

### Quality Inn Great Barrington

8/10 Good

"The rooms were nice. Thick mattresses. Refrigerator and microwave in rooms. Staff was very friendly. Breakfast offered waffles, eggs and sausage. More than enough parking. If you are visiting the Mahaiwe Theater, it's a five minute walk. I recommend NO.10 for a meal before the show. "

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

"The staff here is both friendly and efficient. We had some questions about transportation, and the Front Desk people were eager to help us. Although our stay was brief, we enjoyed it and plan to return."

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

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

### Avon Old Farms Hotel

8/10 Good

"Large room, comfy bed, great breakfast. There’s an odor that’s either from smoking or an air freshener trying to cover up the odor that is a bit strong. Our room was non smoking and it was fine but the hallways smell a bit. "

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

![Simsbury 1820 House](https://images.trvl-media.com/lodging/1000000/50000/42300/42279/7e4b3c86_y.jpg)

### Simsbury 1820 House

10/10 Excellent

"Always gracious and helpful - a great small town inn "

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

![Home2 Suites by Hilton Bristol](https://images.trvl-media.com/lodging/95000000/94950000/94946700/94946614/ebe022ed_y.jpg)

### Home2 Suites by Hilton Bristol

10/10 Excellent

"Clean room and bathroom "

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

## Find out more about Winsted

## Winsted Cottages information

| Number of reviews | 9,274       |
| ----------------- | ----------- |
| Accommodation     | 77 Cottages |
| Lowest Price      | $74         |
| Highest Price     | $425        |

## Frequently asked questions

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

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