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 bathroom with a bathtub, toilet, and granite countertop sink.

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

Alyson

Rp1.506.537

Rp1.732.517 total

includes taxes & fees

25 Oct - 26 Oct

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

2. The Farmington Inn & Suites

Farmington

Brian

Rp3.025.607

Rp3.788.275 total

includes taxes & fees

28 Sept - 29 Sept

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

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

A spacious living area with a brown leather sofa, a glass coffee table, a wooden entertainment unit with a flat-screen TV, and a large window providing a view of the outdoors.

3. Americas Best Value Inn Torrington CT

Torrington

Carol

Rp2.434.629

Rp2.799.850 total

includes taxes & fees

29 Sept - 30 Sept

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

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

A large conference room with multiple round tables, beige chairs, chandeliers, and a wooden floor.

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

4. Avon Old Farms Hotel

Avon

Denise

Rp3.449.371

Rp4.357.948 total

includes taxes & fees

6 Oct - 7 Oct

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

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

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

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

5. Simsbury Inn

Simsbury Center

Kristen

Rp5.173.967

Rp6.341.243 total

includes taxes & fees

28 Sept - 29 Sept

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

A buffet with labeled trays of turkey sausage and cookies.

A coffee station with two espresso machines, a coffee grinder, and various coffee-related items.

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

6. Holiday Inn Express & Suites Bradley Airport by IHG

Windsor Locks

Frank

Rp2.273.681

Rp2.614.733 total

includes taxes & fees

25 Oct - 26 Oct

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.

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

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

7. Hampton Inn & Suites Hartford/Farmington

Farmington

Liam

Rp2.906.731

Rp3.342.741 total

includes taxes & fees

12 Oct - 13 Oct

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

A modern lobby with a reception desk, seating area, and a large wall-mounted screen.

A breakfast buffet with various food items and condiments.

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

8. Springhill Suites Marriott Airport

Windsor Locks

Gary

Rp2.534.170

Rp2.914.296 total

includes taxes & fees

4 Oct - 5 Oct

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

A Marriott hotel with a red roof, a swimming pool, and a well-maintained lawn.

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

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

9. Residence Inn by Marriott Hartford Avon

Avon

Laura

Rp2.571.766

Rp2.957.531 total

includes taxes & fees

4 Oct - 5 Oct

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

A grand foyer with a patterned carpet, a wooden staircase, a chandelier, a mounted deer head, and a large clock.

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

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

10. Simsbury 1820 House

Simsbury Center

Michael

Rp3.383.667

Rp4.200.044 total

includes taxes & fees

28 Sept - 29 Sept

A Stay America hotel with a brick facade, a lobby entrance, and a parking area.

11. Extended Stay America Suites Hartford Farmington

Farmington

Elizabeth

Rp2.193.834

Rp2.522.909 total

includes taxes & fees

5 Oct - 6 Oct

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

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

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

12. The Litchfield Inn

Litchfield

Wei

Rp6.255.273

Rp7.193.564 total

includes taxes & fees

30 Sept - 1 Oct

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

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.

A cozy living room with floral wallpaper, a sofa, a coffee table, and two lamps.

13. Blackberry River Inn

Norfolk

Brian

Rp2.685.450

Rp3.088.267 total

includes taxes & fees

29 Sept - 30 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 bar area with high stools, a counter, and a television mounted on the wall.

14. DoubleTree by Hilton Hartford - Bradley Airport

Windsor Locks

Hayley

Rp2.627.802

Rp3.021.972 total

includes taxes & fees

11 Oct - 12 Oct

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

15. Homewood Suites by Hilton Hartford-Farmington

Farmington

John

Rp2.627.802

Rp3.021.972 total

includes taxes & fees

4 Oct - 5 Oct

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

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

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.

16. Locust Tree Bed and Breakfast LLC

East Canaan

Nicholas

Rp1.879.815

Rp2.161.787 total

includes taxes & fees

28 Sept - 29 Sept

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

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

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

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

17. Hampton Inn Hartford/Airport

Windsor

Angela

Rp2.407.595

Rp2.768.735 total

includes taxes & fees

25 Oct - 26 Oct

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

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.

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

18. Truman Gillet House Bed & Breakfast

Granby

Melanie

Rp2.506.420

Rp2.782.126 total

includes taxes & fees

28 Sept - 29 Sept

A house with a stone staircase leading to a door, surrounded by lush greenery and a well-maintained garden.

A modern living room with a sofa, ottoman, and green armchair, a coffee table with a vase of flowers, and a wooden cabinet with decorative items.

A modern living room with a sofa, ottoman, and green chairs, a coffee table with flowers, and a side table with a lamp and decorative items.

A house with a garden featuring purple flowers and a stone wall.

19. Sunny Peace Homestay

Harwinton

Dean

Rp2.336.341

Rp3.716.214 total

includes taxes & fees

28 Sept - 29 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 hotel room with two beds, a desk, a chair, a lamp, and a window with a view.

A gym with treadmills, an elliptical, a stationary bike, and a bench press.

20. Hampton Inn Westfield

Westfield

Mykola

Rp2.172.708

Rp2.426.915 total

includes taxes & fees

20 Oct - 21 Oct

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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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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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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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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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Northwestern Connecticut Community College Library

This academic sanctuary houses over 40,000 books and extensive research databases for the college community. Enjoy the quiet study atmosphere with comfortable seating and knowledgeable staff assistance.

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Rowley Fields

Rowley Field offers well-maintained sports facilities and green spaces for community gatherings in Winsted, Connecticut. Bring your own equipment and enjoy a picnic in this serene local park perfect for family outings.

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Ledgebrook Plaza

This area shopping centre offers convenient retail options anchored by Stop & Shop supermarket. Visit on weekday mornings for a relaxed experience and look forward to the addition of a Marshalls store in 2025.

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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

The Litchfield Inn

10/10 Excellent

"The personell at the Inn were excellent, couldn't do enough for you. The room was clean and well maintained. The breakfast was great!!"

Quality Inn Great Barrington

10/10 Excellent

"A clean, well maintained, close to everything, motel. Would highly recommend and will stay again next time we are in the area."

DoubleTree by Hilton Hartford - Bradley Airport

10/10 Excellent

"Staff needs to get straight about shuttle availability for local pickups. Only negative after several stays at this great property."

Avon Old Farms Hotel

10/10 Excellent

"We will be returning in May for our Anniversary. Very pleased with everything…"

Extended Stay America Suites Hartford Farmington

8/10 Good

"Walked into room 218 on 22 Sep; the room was absolutely freezing as the AC was set on full blast. Next, the cable didn’t work. Walked to the front desk and Destiny state that they constantly gave to be rebooted. “Unplug the back of the tv, then restart.” Attempt number three finally worked. Not the best, but not the worst…just meh…Destiny was great though. Friendly, inviting, fun and a great attitude. Thanks."

Holiday Inn Express & Suites Bradley Airport by IHG

10/10 Excellent

"Just what was needed for a one night last minute stay due to a Bradley delay. Nice and clean and super convenient shuttle to the airport."

Simsbury 1820 House

8/10 Good

"Excellent stay."

More cheap stays in Winsted

Quality Inn Westfield - Springfield

2 Southampton Rd Westfield MA

Rp1.750.018

Rp1.954.770 total

18 Oct - 19 Oct

includes taxes & fees

Quality Inn Great Barrington

372 Main Street Great Barrington MA

Rp1.810.888

Rp2.022.761 total

18 Oct - 19 Oct

includes taxes & fees

8.6/10 Excellent! (1,002 reviews)

Hampton Inn Westfield

39 Southampton Rd Westfield MA

Rp2.172.708

Rp2.426.915 total

20 Oct - 21 Oct

includes taxes & fees

8.4/10 Very good! (916 reviews)

Extended Stay America Suites Hartford Farmington

1 Batterson Park Rd Farmington CT

Rp2.193.834

Rp2.522.909 total

5 Oct - 6 Oct

includes taxes & fees

Holiday Inn Express & Suites Bradley Airport by IHG

600 Spring St Windsor Locks CT

Rp2.273.681

Rp2.614.733 total

25 Oct - 26 Oct

includes taxes & fees

8.8/10 Excellent! (1,114 reviews)

Americas Best Value Inn Torrington CT

395 Winsted Rd Torrington CT

Rp2.434.629

Rp2.799.850 total

29 Sept - 30 Sept

includes taxes & fees

5.6/10 (821 reviews)

Frequently asked questions

Where is the best place to stay in Winsted?

Quality Inn Great Barrington, located 24.4 mi (39.3 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 The Farmington Inn & Suites 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?

Homewood Suites by Hilton Hartford-Farmington: Offers a snack bar/deli, an indoor pool and buffet. Springhill Suites Marriott Airport and Holiday Inn Express & Suites Bradley Airport by IHG 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 25 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 Northwestern Connecticut Community College Library and American Mural Project. 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 Rp1.732.517

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. The Farmington Inn & Suites

3. Americas Best Value Inn Torrington CT

4. Avon Old Farms Hotel

5. Simsbury Inn

6. Holiday Inn Express & Suites Bradley Airport by IHG

7. Hampton Inn & Suites Hartford/Farmington

8. Springhill Suites Marriott Airport

9. Residence Inn by Marriott Hartford Avon

10. Simsbury 1820 House

11. Extended Stay America Suites Hartford Farmington

12. The Litchfield Inn

13. Blackberry River 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 Hartford/Airport

18. Truman Gillet House Bed & Breakfast

19. Sunny Peace Homestay

20. Hampton Inn Westfield

Stay near popular Winsted attractions

Highland Lake

Northwestern Connecticut Community College

Winchester Historical Society

Platt Hill State Park

American Mural Project

Northwestern Connecticut Community College Library

Rowley Fields

Ledgebrook Plaza

Learn more about Winsted

Top Winsted Hotel Reviews

The Litchfield Inn

Quality Inn Great Barrington

DoubleTree by Hilton Hartford - Bradley Airport

Avon Old Farms Hotel

Extended Stay America Suites Hartford Farmington

Holiday Inn Express & Suites Bradley Airport by IHG

Simsbury 1820 House

More cheap stays in Winsted

Quality Inn Westfield - Springfield

Quality Inn Great Barrington

Hampton Inn Westfield

Extended Stay America Suites Hartford Farmington

Holiday Inn Express & Suites Bradley Airport by IHG

Americas Best Value Inn Torrington CT

Frequently asked questions

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