Hotels in Winsted

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Where to stay in Winsted?

An outdoor dining area with tables and chairs, surrounded by plants and trees.

A hotel lobby with a fireplace, seating area, and decorative wall sconces.

A spacious lobby with a reception desk, seating area, and a large, round, woven coffee table.

A multi-level interior with a grand staircase, a chandelier, and a checkered floor.

1. Delamar West Hartford

West Hartford

$337

$408 total

includes taxes & fees

Nov 1 - Nov 2

An outdoor seating area with sofas and chairs, a glass-top table with a fire feature, and yellow chairs in the background.

A modern breakfast area with a counter, seating, and a refrigerator.

A modern hotel building with multiple floors and a prominent "HOME 2 SUITES BY HILTON" sign.

A large indoor swimming pool with multiple seating areas and large windows.

2. Home2 Suites by Hilton Bristol

Bristol

$130

$150 total

includes taxes & fees

Nov 1 - Nov 2

A house with a porch, American flags, and a pathway leading to a bench.

A wooden desk with a notebook, two mugs, a framed sign, a telephone, and a decorative bowl.

A four-poster bed with floral bedding, two bedside lamps, and a wooden floor.

A dining room with a table set for four, surrounded by wooden chairs. A chandelier hangs above the table, and a vase with flowers is on the table.

3. Truman Gillet House Bed & Breakfast

Granby

$140

$155 total

includes taxes & fees

Oct 18 - Oct 19

A modern living room with grey sofas, a wooden coffee table, a stone fireplace, and a kitchen in the background.

A grassy outdoor area with four blue Adirondack chairs arranged in a circle.

A modern living room with a grey sofa, a wooden coffee table, and a dining area with a round table and chairs.

A hotel room with two beds, a desk, a TV, and a window with curtains.

4. East Rock Inn

Great Barrington

$132

$147 total

includes taxes & fees

Nov 11 - Nov 12

A stone building with a wooden staircase and a garden with white flowers.

A spacious hotel room with a large bed, a sitting area with a sofa and chairs, a dining table, and a kitchen area with cabinets and a coffee machine.

A wooden deck with a railing, a cushioned chair, and a small table with a bottle and glass.

A room with a hanging rattan chair, a wooden sofa, a small round table, and a ceiling fan. Large windows provide views of greenery outside.

5. Troutbeck

Amenia

$542

$653 total

includes taxes & fees

Nov 9 - Nov 10

A Fairfield by Marriott hotel with a covered entrance, multiple stories, and a well-maintained lawn.

A modern hotel lobby with a seating area, a sofa, and a large window with curtains.

A corner market with a sign reading "the Corner Market" and shelves stocked with various snacks and groceries.

An indoor swimming pool with a diving board, lounge chairs, and a 'No Diving' sign.

6. Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

Great Barrington

$144

$160 total

includes taxes & fees

Nov 2 - Nov 3

A restaurant with wooden tables and chairs, a bar area, and hanging spherical light fixtures.

A spacious foyer with a wooden staircase, a reception desk, and a seating area.

An outdoor patio area with wooden flooring, green metal chairs, and tables under umbrellas.

A hotel room with a bed, a sofa, a small table, a floor lamp, and two windows with curtains.

7. The Abner Hotel

Litchfield Historic District

$228

$262 total

includes taxes & fees

Nov 8 - Nov 9

A large, historic building with a covered porch and outdoor seating area.

A grand staircase with patterned carpet, a wooden table with a vase of flowers, a chandelier, and a clock.

A sign for the Simsbury House, indicating it is a historic building from 1820.

A large, historic house with multiple chimneys, a covered porch, and lush greenery.

8. Simsbury 1820 House

Simsbury Center

$175

$219 total

includes taxes & fees

Nov 4 - Nov 5

A cozy living room with a fireplace, leather armchairs, a coffee table with fruit, and a bookshelf.

A grand hallway with a chandelier, a staircase, and a table with flowers.

A dining area with multiple tables set for service, wooden floors, and large windows offering a view of the outdoors.

A room with a fireplace, two striped armchairs, and a floral drape.

9. Blackberry River Inn

Norfolk

$190

$219 total

includes taxes & fees

Oct 14 - Oct 15

A patio with a round metal table, a glass of white wine, and a red umbrella.

A dining table with a plate of food and two wine glasses, set in a room with leather furniture and a fireplace in the background.

A cozy room with a fireplace, comfortable seating, and large windows offering a view of the outdoors.

A grand staircase with a wooden railing, leading to a room with large windows and a patterned ceiling.

10. Manor House Inn

Norfolk

$349

$387 total

includes taxes & fees

Oct 19 - Oct 20

A modern kitchen with a dining area, a large window, and a view of the garden.

A modern kitchen with a wooden dining table, chairs, a pendant light, and a black countertop with a coffee maker and a plant.

A white building with a number '9' sign, a covered entrance, and six planters with shrubs.

A modern outdoor dining area with a round table and white chairs, surrounded by lush greenery and a white railing.

11. 9 Academy

Salisbury

$594

$683 total

includes taxes & fees

Oct 14 - Oct 15

A lobby with a chandelier, a reception desk, and a sign indicating an exit.

A rustic bedroom with a large bed, wooden headboard, and a wooden floor. There is a chair and a small table with a lamp.

A spacious living room with a fireplace, a dining area, and a sofa.

A white building with a covered patio area, a brick chimney, and a garden with various plants and flowers.

12. The Litchfield Inn

Litchfield

$319

$367 total

includes taxes & fees

Nov 2 - Nov 3

A stone fountain with water spouting from the top, surrounded by greenery and a brick building with windows in the background.

A brick building with a covered patio, a fountain, and a staircase leading to a second floor.

A large, multi-story building surrounded by dense forest, with a parking lot and a small green structure nearby.

A person in a blue swimsuit relaxing in a hot tub with a pool in the background.

13. Simsbury Inn

Simsbury Center

$289

$354 total

includes taxes & fees

Oct 14 - Oct 15

A modern hotel lobby with seating arrangements, a central dining table, and a kitchenette area.

A hotel kitchenette with a microwave, coffee maker, and a sink.

A hotel room with a large window, a sofa, a chair, a small table, a TV, and a chessboard.

A reception desk with a wooden backdrop and a large, detailed drawing of a ship.

14. Sheraton Hartford Hotel at Bradley Airport

Windsor Locks

$254

$292 total

includes taxes & fees

Nov 1 - Nov 2

A dining area with wooden tables and chairs, large windows with white frames, and wall-mounted light fixtures.

A two-story building with a sign for Cornwall Inn, featuring a front porch and a mailbox.

A covered patio with a wooden table and chairs, a sofa, and a ceiling fan.

A wooden counter with a wine bottle, glasses, and a sign.

15. Cornwall Inn and Lodge

Cornwall Bridge

$212

$243 total

includes taxes & fees

Nov 1 - Nov 2

A dining area with round tables set for two, a fireplace, and a mural on the wall.

A white two-story house with a front door, windows, and a chimney.

A room with a leather armchair, a table with a potted plant, a lamp, and a fireplace with decorative elements.

A room with two brown leather armchairs, a wooden side table with a lamp, a potted plant, and a window with a view of a snowy landscape.

16. The Old Inn On The Green

Great Barrington

$290

$350 total

includes taxes & fees

Nov 1 - Nov 2

A hotel with a prominent sign, a covered entrance, and a landscaped driveway.

An indoor swimming pool with clear blue water, surrounded by lounge chairs and large windows offering a view of greenery outside.

A spacious lobby with high ceilings, a fireplace, comfortable seating, and a dining area with tables and chairs.

An outdoor patio with tables, chairs, and umbrellas, adjacent to a brick building.

17. Hampton Inn & Suites Hartford/Farmington

Farmington

$148

$170 total

includes taxes & fees

Oct 30 - Oct 31

An outdoor seating area with fire pits and umbrellas, surrounded by modern buildings with large windows.

A large indoor swimming pool with clear blue water, surrounded by lounge chairs and a reception area.

A spacious lobby with large windows, a central plant, and multiple hanging lights.

A modern lobby with a reception desk, seating area, and a large decorative light fixture.

18. DoubleTree by Hilton Hotel Bristol, Connecticut

Bristol

$163

$187 total

includes taxes & fees

Nov 8 - Nov 9

A large, two-story house with a wrap-around porch, a central entrance, and a flag.

A dining area with a round table, chairs, a fireplace, and a variety of plants.

A spacious living room with a large sectional sofa, a round coffee table, and a chandelier. There are large windows with curtains, a fireplace, and a view of greenery outside.

A swimming pool with lounge chairs and umbrellas, surrounded by trees.

19. Belden House & Mews

Litchfield Historic District

$455

$563 total

includes taxes & fees

Nov 1 - Nov 2

A spacious foyer with a grand staircase, a chandelier, and a patterned carpet.

A four-poster bed in a hotel room with a blue carpet, a desk with a lamp, a chair, and a bedside table with a lamp.

A well-lit room with a fireplace, two armchairs, a sofa, and a coffee table.

A well-lit living room with a patterned sofa, armchairs, a television, and a patterned carpet.

20. The Farmington Inn & Suites

Farmington

$139

$177 total

includes taxes & fees

Nov 8 - Nov 9

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Go beyond your typical stay in Winsted

Pet friendly

Pool

Family friendly

Cottage

Top landmarks in Winsted

Highland Lake

Highland Lake is 2.6 mi (4.3 km) from central Winchester, why not stop by during your stay.

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The Marina at Highland Lake

Imagine strolling along The Marina at Highland Lake for some great waterfront pics. It's located 1.8 mi (2.9 km) from central Winchester.

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Northwestern Connecticut Community College

If you'd like to get a taste of Winchester student life, check out Northwestern Connecticut Community College, in the heart of the town.

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Northwestern Connecticut Community College Library

Northwestern Connecticut Community College Library is worth a visit when in central Winchester.

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Winchester Historical Society

8.0/10 (1 review)

You might want to get your camera out and head to Winchester Historical Society— just one of the landmarks located 1.9 mi (3.1 km) from central Winchester.

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American Mural Project

The center of Winchester is home to cultural attractions like American Mural Project, so you might want to stop by during your stay. If you want to experience more of the culture Winchester has to offer, head to Highland Lake, The Village, and Northwestern Connecticut Community College.

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Rowley Fields

If you like quiet time surrounded by flowers and greenery, then make a stop at Rowley Fields in the heart of Winchester. Want to stretch your legs some more? Head to Walker Field, just a short walk away.

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Ledgebrook Plaza

If you like shopping, take time out to go to Ledgebrook Plaza when in Winchester. Splash some more cash at Ames Plaza Shopping Center.

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Learn more about Winsted

Winsted is well-known for its attractions such as Highland Lake and Burr Pond State Park.

See all hotels in Winsted

A tranquil lake with a stone tower, surrounded by autumn-colored trees and a clear sky.

Check out reviews of Winsted hotels guests love

Sheraton Hartford Hotel at Bradley Airport

10/10 Excellent

"Super convenient location; a very short walk to the terminal and security checkpoint. Room was nice and the bed was comfy. Check-in was easy and the bar/restaurant staff were friendly. The only negative is the cost, but you pay for the convenience. We’d stay again."

DoubleTree by Hilton Hotel Bristol, Connecticut

10/10 Excellent

"The front desk staff was so amazing. They helped us from the moment of our arrival. Will definitely stay there again !!!"

The Farmington Inn & Suites

8/10 Good

"The room was nice though a few stains on the bathroom ceiling and the floor creaked a lot when the people above walked around but overall it was very nice. I was looking forward to waffles for breakfast but they were out of batter and I didn’t have a lot of time to wait and find someone to refill it. I enjoyed my stay and would stay again though I thought it was a bit pricey."

Quality Inn Great Barrington

10/10 Excellent

"Beds were comfortable, room was clean, train was not often"

The Litchfield Inn

10/10 Excellent

"Quite simply excellent. This was an overnight stop on our Fall Foliage tour of New England this year. It is not often that I can't think of something that could be improved but nothing comes to mind about this place."

Delamar West Hartford

10/10 Excellent

"Best value in Greater Hartford - 1st class accomodations - fair price"

Simsbury 1820 House

10/10 Excellent

"Lovely comfortable place!!"

Interlaken Inn & Resort

10/10 Excellent

"The Interlaken is a lovely property "between the lakes" in Lakeville. We stayed in the main building, which I recommend (there is also another building on the property with a view of the lake). We had a nice screened-in balcony porch attached to our room which we enjoyed each evening. The lobby is cozy with a fireplace. The staff were friendly and helpful."

Frequently asked questions

What accommodations do travelers like in Winsted?

Guests like Days Inn by Wyndham Torrington.

Can I book a refundable hotel in Winsted?

If you're looking for the flexibility to change your travel plans to Winsted, most properties offer refundable* bookable rates. You can find these accommodations by searching our site and using the "fully refundable" filter to narrow the results down.

Where can I stay in Winsted if I want a vacation home instead of a traditional hotel?

You'll find 12 vacation homes on our site. In addition, you can choose from 5 apartments.

What will the weather in Winsted be like during my vacation?

The warmest months in Winsted are usually July and August with an average temp of 67°F. January and February are the chilliest months when the average temp is 30°F. The rainiest months are July and October.

Why should I book my Winsted hotel with Hotels.com?

There are plenty of reasons to book your Winsted travel with us: our free cancellations on selected hotels gives you the flexibility you're looking for, and with One Key™, our rewards program, you will be able to earn and use OneKeyCash™* on all eligible bookings such as hotels, car rentals, flights, vacation rentals and more on Hotels.com, Expedia and Vrbo.

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