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

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Check availability on Winsted Luxury Hotels

Tonight
5 Oct - 6 Oct
Tomorrow
6 Oct - 7 Oct
This weekend
9 Oct - 11 Oct
Next weekend
16 Oct - 18 Oct

Our top choices for Winsted luxury hotels

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

1. Simsbury 1820 House

Simsbury 1820 House
Simsbury Center
S$280
includes taxes & fees
2 Nov - 3 Nov
Simsbury 1820 House
An outdoor seating area with fire pits and umbrellas, surrounded by modern buildings with large windows.
A modern hotel lobby with a central island, red chairs, a marble countertop, and a large overhead light fixture.
A large indoor swimming pool with clear blue water, surrounded by lounge chairs and a reception area.
A modern lobby with a reception desk, seating area, and a large decorative light fixture.

2. DoubleTree by Hilton Hotel Bristol, Connecticut

DoubleTree by Hilton Hotel Bristol, Connecticut
Bristol
  • Upscale suburban retreat offers saltwater indoor pool, rejuvenating hot tub, and exceptional dining.
S$240
includes taxes & fees
18 Oct - 19 Oct
DoubleTree by Hilton Hotel Bristol, Connecticut
A large, two-story house with a wrap-around porch, a central entrance, and a flag.
A swimming pool with lounge chairs and umbrellas, surrounded by trees.
A modern house with a white exterior, two wooden doors, and a grey awning.
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.

3. Belden House & Mews

Belden House & Mews
Litchfield Historic District
S$693
includes taxes & fees
1 Nov - 2 Nov
Belden House & Mews
An outdoor dining area with tables and chairs, surrounded by plants and trees.
A spacious lobby with a reception desk, seating area, and a large, round, woven coffee table.
A hotel lobby with a fireplace, seating area, and decorative wall sconces.
A multi-level interior with a grand staircase, a chandelier, and a checkered floor.

4. Delamar West Hartford

Delamar West Hartford
West Hartford
S$488
includes taxes & fees
1 Nov - 2 Nov
Delamar West Hartford
A bedroom with a large bed, a chair, and a window with curtains.
A framed painting of a white horse on a wooden dresser, a white fireplace with a black mantle, and two green vases with white flowers on the wall.
A large, two-story house with a porch and multiple windows, surrounded by a well-maintained lawn.
A dining area with yellow chairs and tables, a kitchen in the background, and a clock on the wall.

5. The White Hart

The White Hart
Salisbury
S$662
includes taxes & fees
7 Oct - 8 Oct
The White Hart
A stone building with a wooden staircase and a garden with white flowers.
A garden pathway surrounded by various flowering plants and a wooden structure in the background.
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.

6. Troutbeck

Troutbeck
Amenia
S$795
includes taxes & fees
4 Nov - 5 Nov
Troutbeck
A modern kitchen with a dining area, a large window, and a view of the garden.
A white building with a number '9' sign, a covered entrance, and six planters with shrubs.
A modern kitchen with a wooden dining table, chairs, a pendant light, and a black countertop with a coffee maker and a plant.
A modern outdoor dining area with a round table and white chairs, surrounded by lush greenery and a white railing.

7. 9 Academy

9 Academy
Salisbury
S$873
includes taxes & fees
7 Oct - 8 Oct
9 Academy
View all properties

Top Winsted Hotel Reviews

Quality Inn Great Barrington

Quality Inn Great Barrington

8/10 Good
"The staff was very pleasant and helpful. Breakfast was good. They had delicious and fresh muffins. Parking was right outside our door."
Leslie 2-night trip
Posted 8 hours ago
Quality Inn Great Barrington
Simsbury 1820 House

Simsbury 1820 House

10/10 Excellent
"A charming, quaint and comfortable lodging! Continental breakfast better than most with the homemade breads! Close to good restaurants. Sarah and Glenn were wonderful"
Walter 2-night trip
Posted 1 day ago
Simsbury 1820 House
Quality Inn Westfield - Springfield

Quality Inn Westfield - Springfield

8/10 Good
"Breakfast was decent waffle station eggs sausage and the usual continental fare. Everything was clean the room was a little dark and dismal but everything was new so was fine"
Jennifer 2-night trip
Posted 2 days ago
Quality Inn Westfield - Springfield
The Litchfield Inn

The Litchfield Inn

10/10 Excellent
"The staff was fantastic. Friendly and Informative. Property was very clean. It was nice having the gym and the breakfast"
Marc 2-night trip
Posted 2 days ago
The Litchfield Inn

Frequently asked questions

Are you looking for a luxury hotel for your Winsted holiday?
Winsted has some interesting things to see and do including Highland Lake and Burr Pond State Park, so you might want to take in the local sights during your visit.
What's the best high-end hotel 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.
When can I expect good weather in Winsted?
Planning for the weather is a good way to make your trip to Winsted relaxing and enjoyable, especially when you're splurging. 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.
What's there to see and do in Winsted?
Experience Winsted and visit Highland Lake, Burr Pond State Park and The Marina at Highland Lake. If you have some spare time during your trip, you might want to check out Northwestern Connecticut Community College Library and American Mural Project.

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