Winsted Holiday Rentals, Connecticut: Private House Rentals

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

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Our top choices for Winsted hotels

A hotel room with a bed, white pillows, a bedside table with a phone, and a wall-mounted TV displaying a scenic sunset.

A Days Inn sign with a sunburst design, surrounded by trees.

A kitchen area with a counter, a microwave, a coffee machine, and a display case with pastries.

A Days Inn building with a blue awning, a lobby entrance, and a well-maintained lawn with various plants.

1. Days Inn by Wyndham Torrington

Torrington

Juan

฿3,186

฿3,664 total

includes taxes & fees

31 Aug - 1 Sept

A Holiday Inn Express hotel with a covered entrance, multiple floors, and a landscaped driveway.

A hotel room with a bed, a sofa, a desk with a chair, a TV, and a lamp.

A Holiday Inn Express hotel with a modern design, multiple floors, and a well-lit entrance.

An indoor swimming pool with clear water, a lifeguard chair, and a changing room with a shower.

2. Holiday Inn Express & Suites Bradley Airport by IHG

Windsor Locks

Enrique

฿4,338

฿4,988 total

includes taxes & fees

6 Sept - 7 Sept

A hotel room with two beds, a desk, a chair, a small table, and a view of an airport.

A modern hotel room with a large dining table, multiple chairs, a sofa, a TV, and a view through large windows.

3. Sheraton Hartford Hotel at Bradley Airport

Windsor Locks

Lisa

฿7,852

฿9,030 total

includes taxes & fees

13 Sept - 14 Sept

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

A long wooden table with potted plants and candle holders in a modern interior setting.

4. The Litchfield Inn

Litchfield

Sandra

฿10,514

฿12,091 total

includes taxes & fees

31 Aug - 1 Sept

An outdoor patio with a circular fire pit surrounded by wicker chairs, a grill, and a dining area with tables and chairs.

A swimming pool with lounge chairs and a covered seating area, surrounded by multi-story buildings with visible windows and a brick facade.

A hotel lobby with a long reception desk, multiple seating areas, and a large screen TV.

A stone fireplace with a flat-screen TV above it, surrounded by two chairs and a small table.

5. Residence Inn by Marriott Hartford Avon

Avon

Laura

฿5,036

฿5,792 total

includes taxes & fees

13 Sept - 14 Sept

A modern hotel with a flat roof, large windows, and a covered entrance.

An indoor swimming pool with a tiled floor, a pool ladder, and a few lounge chairs.

A hotel room with a bed, a desk, a chair, a sofa, a microwave, and a coffee machine.

A breakfast buffet with various food items and condiments.

6. Springhill Suites Marriott Airport

Windsor Locks

Harinda

฿4,112

฿4,729 total

includes taxes & fees

7 Sept - 8 Sept

A hotel room with a large bed, bedside lamps, a desk with a chair, a mirror, and a coat rack.

A gym with various exercise equipment, a mirror, and a blue wall.

A motel with a covered entrance, a parking lot, and a building with a sign that reads "LARRY'S".

7. Americas Best Value Inn Torrington CT

Torrington

Carol

฿4,273

฿4,914 total

includes taxes & fees

30 Aug - 31 Aug

A modern hotel room with a dining area, seating arrangements, and a large TV screen.

A modern hotel room with a seating area, a flat-screen TV, and a dining table.

A modern living room with a grey sofa, a black exercise bike, and a large mirror reflecting the room.

An indoor swimming pool area with tiled flooring, lounge chairs, and tables with umbrellas.

8. Hampton Inn Hartford/Airport

Windsor

Cesar Wander

฿4,286

฿4,929 total

includes taxes & fees

7 Sept - 8 Sept

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

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

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

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

9. Simsbury 1820 House

Simsbury Center

Thomas

฿5,556

฿6,956 total

includes taxes & fees

30 Aug - 31 Aug

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

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

A spacious lobby with a patterned rug, a potted plant, and a television.

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

10. The Farmington Inn & Suites

Farmington

Carol

฿4,898

฿6,200 total

includes taxes & fees

30 Aug - 31 Aug

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.

11. Blackberry River Inn

Norfolk

Rachel

฿6,246

฿7,183 total

includes taxes & fees

2 Sept - 3 Sept

A conservatory with a glass ceiling, round tables, and chairs, and a brick wall with an exit sign.

A spacious lobby with a grand staircase, multiple seating areas, and a reception desk.

A spacious indoor dining area with high ceilings, large windows, and a brick wall.

A spacious lobby with a grand staircase, multiple seating areas, and a central decorative table.

12. Avon Old Farms Hotel

Avon

฿5,054

฿6,536 total

includes taxes & fees

3 Sept - 4 Sept

A spacious, well-lit event space with a glass ceiling, white tables, and a chandelier.

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

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

A sign for The Simsbury Inn, featuring a swan on water.

13. Simsbury Inn

Simsbury Center

Rachel

฿7,857

฿9,753 total

includes taxes & fees

16 Sept - 17 Sept

An indoor swimming pool with clear glass walls, a blue pool area, and sunlit seating areas.

A modern reception area with a digital display, a reception desk, and a seating area with patterned ottomans.

A DoubleTree by Hilton hotel with a 'Shade Grill' sign, a well-maintained lawn, and a clear sky at dusk.

A modern hotel lobby with a fireplace, comfortable seating, and artwork on the walls.

14. DoubleTree by Hilton Hartford - Bradley Airport

Windsor Locks

Hayley

฿4,016

฿4,619 total

includes taxes & fees

6 Sept - 7 Sept

A hotel with multiple buildings, a parking lot, and a well-maintained lawn.

A modern kitchen with a central island, built-in cabinets, and a coffee station.

A swimming pool with lounge chairs and a red door.

A modern lobby with a yellow sofa, marble table, and two armchairs.

15. Homewood Suites by Hilton Hartford-Farmington

Farmington

John

฿4,448

฿5,115 total

includes taxes & fees

7 Sept - 8 Sept

A sign for 'The Logust Tree Bed & Breakfast' with a contact number.

A two-story building with a flat roof, solar panels, and a small patio area.

A dining room with a wooden table, chairs, a vase with flowers, and red curtains.

A bedroom with a wooden bed, two bedside tables, a window with curtains, and a radiator.

16. Locust Tree Bed and Breakfast LLC

East Canaan

Regina

฿3,452

฿3,969 total

includes taxes & fees

31 Aug - 1 Sept

A hotel lobby with a reception desk, seating area, and a dining section.

A snack and beverage display area with shelves stocked with chips and a refrigerated section with bottled water and soda.

A modern dining area with tables and chairs, a patterned carpet, and a wall-mounted TV.

A hotel room with two beds, a desk, a chair, a lamp, and a window with a view.

17. Hampton Inn Westfield

Westfield

Mykola

฿4,107

฿4,588 total

includes taxes & fees

8 Sept - 9 Sept

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

A hot tub with a metal ladder, surrounded by tiled walls, with a view of trees through a window.

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

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

18. Hampton Inn & Suites Hartford/Farmington

Farmington

Lauren

฿4,556

฿5,239 total

includes taxes & fees

7 Sept - 8 Sept

A modern dining area with a high ceiling, large windows, and a mix of wooden and upholstered furniture.

A modern office space with a large window overlooking a parking lot and trees.

A hotel room with a large bed, a chair, a nightstand with a phone, a wall-mounted light, and a window with curtains.

A modern hotel lobby with a reception desk, a coffee machine, a plant, a leather sofa, and a dining area.

19. Quality Inn Westfield - Springfield

Westfield

Thomas

฿3,518

฿3,930 total

includes taxes & fees

29 Sept - 30 Sept

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

A living room with a fireplace, a wooden cabinet, a plaid sofa, and a patterned rug.

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.

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

20. Truman Gillet House Bed & Breakfast

Granby

Valerie

฿4,602

฿5,108 total

includes taxes & fees

7 Sept - 8 Sept

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Stay near popular Winsted attractions

Highland Lake

Highland Lake's crystal-clear waters span 445 acres across three bays, perfect for boating and fishing enthusiasts. Enjoy smallmouth bass fishing or kayak along Connecticut's scenic shoreline.

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Northwestern Connecticut Community College

NCCC houses Connecticut's only Veterinary Technology Programme on its historic campus dating to 1895. Explore the Learning Resource Centre or attend one of the college's cultural events showcasing local talent.

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The Marina at Highland Lake

Explore the waterfront in Winchester with a trip to The Marina at Highland Lake.

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Platt Hill State Park

Platt Hill State Park offers 159 acres of serene forest trails and scenic overlooks in Winchester, Connecticut. Hikers can enjoy peaceful solitude while exploring unmarked paths and seasonal wild blueberry picking.

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Winchester Historical Society

8.0/10 (1 review)

Step inside the 1813 Solomon Rockwell House to discover Winchester's rich history through Victorian fashions and military artefacts. This Classical Revival mansion offers a glimpse into 19th-century Connecticut life.

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Walker Field

Walker Field serves as Winsted's community sports hub with recently upgraded LED lighting for evening games. Catch a local baseball match or football tournament to experience authentic small-town Connecticut spirit.

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American Mural Project

The world's largest indoor collaborative mural towers five stories high, celebrating American workers across generations. Stand beneath this vibrant 120-foot masterpiece to appreciate its intricate details.

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Tatro Pond

Tatro Pond offers a serene escape with peaceful waters perfect for fishing and bird watching. Enjoy a family picnic by the shoreline or participate in the annual Elks Kids' Fishing Derby held each May.

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Learn more about Winsted

Highland Lake offers refreshing swimming and boating during summer months, with a small beach perfect for families. Explore the American Museum of Tort Law founded by Ralph Nader, then grab coffee at one of Main Street's welcoming cafes.

See all hotels in Winsted

Top Winsted Hotel Reviews

Holiday Inn Express & Suites Bradley Airport by IHG

10/10 Excellent

"I especially like that the hallway and room were not carpeted. No icky carpets. The room has lots of charging stations which is great. They provide easy to carry breakfast items like banana, yogurt and muffins for those leaving on super early flights."

Homewood Suites by Hilton Hartford-Farmington

10/10 Excellent

"nons"

DoubleTree by Hilton Hartford - Bradley Airport

8/10 Good

"The staff was very polite and helpful"

Fairfield Inn & Suites by Marriott Plainville

10/10 Excellent

"The staff was very accommodating and the breakfast was delicious. Lots of choices and always enough available."

Hampton Inn & Suites Hartford/Farmington

10/10 Excellent

"The staff was super helpful and the facilities were c clean and modern. Breakfast was fresh and had good choices."

The Litchfield Inn

10/10 Excellent

"Charming older hotel. Wish there were more tv options"

Springhill Suites Marriott Airport

10/10 Excellent

"Clean and staff was friendly"

The Little Lion

8/10 Good

"Clean and comfortable room for reasonable price. Central area/lobby is nice place to sit and read, relax, and/or eat breakfast (coffee provided). Also red Adirondack chairs up on hill behind rooms and small tables/chairs in front of some rooms. Can use the outdoor pool and whirl pool a few miles away at the Red Lion Inn, which is desirable feature on summer days. A few negatives. While the building and rooms are set back from the road, it’s located off a busy road that goes between Stockbridge and Great Barrington. You will hear the cars during the day. It’s also not what I would consider an “Inn” as it’s really a motel. It used to be the Briarcliff Motel before the Red Lion Inn purchased it. Any questions, requests, or comments need to contact them as the Little Lion didn’t have any full time staff and no one at front desk in the lobby when we stayed. We received text with code for room door."

Holiday Inn Express Hotel & Suites Great Barrington by IHG

10/10 Excellent

"It was much better than expected. Subtle lighting in the room was a nice touch. Clean and very comfortable bedding and bathroom. Everything in the fitness room was was clean and operational. The breakfast was superb. A very enjoyable stay."

More cheap stays in Winsted

Quality Inn Great Barrington

372 Main Street Great Barrington MA

฿3,046

฿3,402 total

22 Sept - 23 Sept

includes taxes & fees

Days Inn by Wyndham Torrington

492 East Main St Torrington CT

฿3,186

฿3,664 total

31 Aug - 1 Sept

includes taxes & fees

Hampton Inn Westfield

39 Southampton Rd Westfield MA

฿4,107

฿4,588 total

8 Sept - 9 Sept

includes taxes & fees

Americas Best Value Inn Torrington CT

395 Winsted Rd Torrington CT

฿4,273

฿4,914 total

30 Aug - 31 Aug

includes taxes & fees

5.6/10 (813 reviews)

Holiday Inn Express & Suites Bradley Airport by IHG

600 Spring St Windsor Locks CT

฿4,338

฿4,988 total

6 Sept - 7 Sept

includes taxes & fees

9/10 Wonderful! (1,121 reviews)

Hampton Inn & Suites Hartford/Farmington

301 Colt Hwy Farmington CT

฿4,556

฿5,239 total

7 Sept - 8 Sept

includes taxes & fees

9/10 Wonderful! (1,002 reviews)

Frequently asked questions

Where is the best place to stay in Winsted?

Sheraton Hartford Hotel at Bradley Airport, located 19.3 mi (31 km) from the heart of Winsted, is a top choice for your stay, based on our traveller data. Two other options for your visit to the area are Holiday Inn Express & Suites Bradley Airport by IHG and Homewood Suites by Hilton Hartford-Farmington. See all available top hotels, or vacation rentals in Winsted.

If I need to cancel my hotel reservation in Winsted, will I receive a refund?

Yes, you'll find most room reservations are fully refundable as long as you cancel prior to the accommodation's cancellation deadline, which often is within 24-48 hours of the scheduled arrival. If you have a reservation that's non-refundable, you might still have the option to cancel and get a refund within a 24-hour period of your booking. Filter your search by fully refundable to find flexible hotel deals in Winsted.

What's the best luxury place to stay in Winsted?

Rock Hall Luxe Lodging is a luxury B&B with spa services and in-room fireplaces, and it's a popular choice for Expedia travellers looking for an elegant place to stay. Find more luxury hotels in Winsted.

What are some accommodation options with pools in Winsted?

Holiday Inn Express & Suites Bradley Airport by IHG: Offers daily, an indoor pool and complimentary high-speed (wired) Internet access. Homewood Suites by Hilton Hartford-Farmington and Springhill Suites Marriott Airport are two additional hotels with an on-site pool. View all hotels with pools in Winsted.

What's it like staying in Winsted?

Travellers to Winsted will find plenty to explore and enjoy. In Winsted, there are 24 hotels and other accommodation options to choose from. Find out more about Winsted.

What should I see while I'm in Winsted?

Favourite places to visit include Highland Lake, Burr Pond State Park and The Marina at Highland Lake. A couple of additional sights to add to your itinerary are Platt Hill State Park and Northwestern Connecticut Community College Library. Take a look at what more there is to see and do in Expedia's Winsted guide.

What's the seasonal weather like in Winsted?

The hottest months are usually July and August, with an average temperature of 20°C, while the coldest months are January and February, with an average of -1°C. The snowiest months in Winsted are January, February, March and April, with each month seeing an average of 15 cm of snowfall.

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Book Hotels in Winsted on Expedia.com

Find hotels in Winsted, CT from ฿3,365

Change your mind

Treat yourself

Be picky

Go beyond your typical stay in Winsted

Check prices for these dates

Filter by

Star rating

Guest rating

Our top choices for Winsted hotels

1. Days Inn by Wyndham Torrington

2. Holiday Inn Express & Suites Bradley Airport by IHG

3. Sheraton Hartford Hotel at Bradley Airport

4. The Litchfield Inn

5. Residence Inn by Marriott Hartford Avon

6. Springhill Suites Marriott Airport

7. Americas Best Value Inn Torrington CT

8. Hampton Inn Hartford/Airport

9. Simsbury 1820 House

10. The Farmington Inn & Suites

11. Blackberry River Inn

12. Avon Old Farms Hotel

13. Simsbury Inn

14. DoubleTree by Hilton Hartford - Bradley Airport

15. Homewood Suites by Hilton Hartford-Farmington

16. Locust Tree Bed and Breakfast LLC

17. Hampton Inn Westfield

18. Hampton Inn & Suites Hartford/Farmington

19. Quality Inn Westfield - Springfield

20. Truman Gillet House Bed & Breakfast

Stay near popular Winsted attractions

Highland Lake

Northwestern Connecticut Community College

The Marina at Highland Lake

Platt Hill State Park

Winchester Historical Society

Walker Field

American Mural Project

Tatro Pond

Learn more about Winsted

Top Winsted Hotel Reviews

Holiday Inn Express & Suites Bradley Airport by IHG

Homewood Suites by Hilton Hartford-Farmington

DoubleTree by Hilton Hartford - Bradley Airport

Fairfield Inn & Suites by Marriott Plainville

Hampton Inn & Suites Hartford/Farmington

The Litchfield Inn

Springhill Suites Marriott Airport

The Little Lion

Holiday Inn Express Hotel & Suites Great Barrington by IHG

More cheap stays in Winsted

Quality Inn Great Barrington

Days Inn by Wyndham Torrington

Hampton Inn Westfield

Americas Best Value Inn Torrington CT

Holiday Inn Express & Suites Bradley Airport by IHG

Hampton Inn & Suites Hartford/Farmington

Frequently asked questions

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