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
Sep 10 - Sep 11
Tomorrow
Sep 11 - Sep 12
This weekend
Sep 11 - Sep 13
Next weekend
Sep 18 - Sep 20

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 large, historic house with multiple chimneys, a covered porch, and lush greenery.
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
₩253,260
₩314,364 total
includes taxes & fees
Sep 13 - Sep 14
Simsbury 1820 House
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.

2. The Litchfield Inn

The Litchfield Inn
Litchfield
  • Upscale Connecticut spa retreat features massages, plush beds, and tranquility near Bantam Lake.
₩330,886
₩380,520 total
includes taxes & fees
Sep 14 - Sep 15
The Litchfield Inn
An outdoor seating area with fire pits and umbrellas, surrounded by modern buildings with large windows.
A modern lobby with a reception desk, seating area, and a large decorative light fixture.
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.

3. 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.
₩204,832
₩235,557 total
includes taxes & fees
Sep 20 - Sep 21
DoubleTree by Hilton Hotel Bristol, Connecticut
A dining area with round tables set for two, a fireplace, and a mural on the wall.
A cozy room with a fireplace, wooden walls, a bed with a patterned bedspread, and two wall-mounted lamps.
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.
A room with a leather armchair, a table with a potted plant, a lamp, and a fireplace with decorative elements.

4. The Old Inn On The Green

The Old Inn On The Green
Great Barrington
₩442,200
₩533,601 total
includes taxes & fees
Sep 13 - Sep 14
The Old Inn On The Green
A bedroom with a large bed, a chair, and a window with curtains.
A covered porch with a dining area, a sofa, and decorative wall art.
A dining area with yellow chairs and tables, a kitchen in the background, and a clock on the wall.
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.

5. The White Hart

The White Hart
Salisbury
₩461,496
₩530,720 total
includes taxes & fees
Sep 15 - Sep 16
The White Hart
An outdoor dining area with tables and chairs, surrounded by plants and trees.
A restaurant with a brick floor, wooden chairs, and tables. There is a bar area with bottles and glasses.
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.

6. Delamar West Hartford

Delamar West Hartford
West Hartford
₩473,808
₩571,679 total
includes taxes & fees
Sep 27 - Sep 28
Delamar West Hartford
A stone building with a wooden staircase and a garden with white flowers.
A wooden deck with a railing, a cushioned chair, and a small table with a bottle and glass.
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 room with a hanging rattan chair, a wooden sofa, a small round table, and a ceiling fan. Large windows provide views of greenery outside.

7. Troutbeck

Troutbeck
Amenia
₩689,095
₩833,138 total
includes taxes & fees
Sep 27 - Sep 28
Troutbeck
A large, two-story house with a wrap-around porch, a central entrance, and a flag.
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 dining area with a round table, chairs, a fireplace, and a variety of plants.
A modern house with a white exterior, two wooden doors, and a grey awning.

8. Belden House & Mews

Belden House & Mews
Litchfield Historic District
₩676,700
₩831,805 total
includes taxes & fees
Oct 4 - Oct 5
Belden House & Mews
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 outdoor dining area with a round table and white chairs, surrounded by lush greenery and a white railing.
A modern kitchen with a dining area, a sofa, and a TV mounted on the wall.

9. 9 Academy

9 Academy
Salisbury
₩795,625
₩914,969 total
includes taxes & fees
Sep 13 - Sep 14
9 Academy
A hot tub in a backyard with a house, trees, and a clear sky.
A living room with a sofa, ottoman, glass coffee table, and a patterned rug. There are two lamps, a decorative statue, and a framed artwork on the wall.
A hot tub with a wicker basket, lounge chairs, and a barbecue grill in a backyard.
A spacious living room with a dining area, large windows, and a chandelier.

10. Las Flores Villa

Las Flores Villa
New Preston
₩3,618,000
₩4,696,700 total
includes taxes & fees
Oct 1 - Oct 2
Las Flores Villa
View all properties

Top Winsted Hotel Reviews

The Farmington Inn & Suites

The Farmington Inn & Suites

10/10 Excellent
"Amazing in every way! I will stay again when I come from Chicago to Avon to visit my son at school..no detail was overlooked! Beautiful, quant and quiet hotel and wonderful staff"
Andrea 2-night trip
Posted 5 hours ago
The Farmington Inn & Suites
Sheraton Hartford Hotel at Bradley Airport

Sheraton Hartford Hotel at Bradley Airport

10/10 Excellent
"It’s handy to the air port and when ever we fly we stay at the hotel"
Sandy 1-night trip
Posted 8 hours ago
Sheraton Hartford Hotel at Bradley Airport
Quality Inn Westfield - Springfield

Quality Inn Westfield - Springfield

10/10 Excellent
"This is definitely an a-ok place to stay. We loved that the front door could be opened and we were able to sit outside. The bed was comfortable. The cleaning staff arrived daily. The refrigerator worked. The included breakfast provides something to eat. My preference is a local restaurant for breakfast with healthier choices. We would stay here again. It was convenient to my son's house and to I-90. We were traveling for a family event."
Patricia 5-night trip
Posted 3 days ago
Quality Inn Westfield - Springfield
Avon Old Farms Hotel

Avon Old Farms Hotel

10/10 Excellent
"Clean, quiet, great restaurant and pub. Food was over the top delicious!"
Kathryn 1-night trip
Posted 7 days ago
Avon Old Farms Hotel
The Little Lion

The Little Lion

10/10 Excellent
"Easy check in. The rooms were clean. Beds comfy."
Jackie 1-night trip
Posted 8 days ago
The Little Lion
Simsbury 1820 House

Simsbury 1820 House

10/10 Excellent
"Quaint Inn in a scienic location."
Brian 1-night trip
Posted 10 days ago
Simsbury 1820 House

Frequently asked questions

Are you looking for a luxury hotel for your Winsted vacation?
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 travelers 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 temp of 67°F, while the coldest months are January and February with an average of 30°F. The snowiest months in Winsted are January, February, March, and April, with each month seeing an average of 6 inches 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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