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
29 Aug - 30 Aug
Tomorrow
30 Aug - 31 Aug
Next weekend
4 Sep - 6 Sep
In two weeks
11 Sep - 13 Sep

Our top choices for Winsted luxury hotels

1. Simsbury 1820 House

Simsbury 1820 House
Simsbury Center
฿5,556
฿6,956 total
includes taxes & fees
30 Aug - 31 Aug
Simsbury 1820 House

2. The Litchfield Inn

The Litchfield Inn
Litchfield
  • Upscale Connecticut spa retreat features massages, plush beds, and tranquility near Bantam Lake.
฿10,335
฿11,885 total
includes taxes & fees
30 Aug - 31 Aug
The Litchfield Inn

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.
฿4,889
฿5,623 total
includes taxes & fees
6 Sept - 7 Sept
DoubleTree by Hilton Hotel Bristol, Connecticut

4. The Old Inn On The Green

The Old Inn On The Green
Great Barrington
฿10,480
฿12,647 total
includes taxes & fees
1 Sept - 2 Sept
The Old Inn On The Green

5. Belden House & Mews

Belden House & Mews
Litchfield Historic District
฿15,066
฿18,650 total
includes taxes & fees
14 Sept - 15 Sept
Belden House & Mews

6. Delamar West Hartford

Delamar West Hartford
West Hartford
฿11,464
฿13,846 total
includes taxes & fees
13 Sept - 14 Sept
Delamar West Hartford

7. Troutbeck

Troutbeck
Amenia
฿16,169
฿19,606 total
includes taxes & fees
31 Aug - 1 Sept
Troutbeck

8. The White Hart

The White Hart
Salisbury
฿11,287
฿12,980 total
includes taxes & fees
31 Aug - 1 Sept
The White Hart

9. 9 Academy

9 Academy
Salisbury
฿19,660
฿22,609 total
includes taxes & fees
13 Sept - 14 Sept
9 Academy

10. DoubleTree by Hilton Hartford - Bradley Airport

DoubleTree by Hilton Hartford - Bradley Airport
Windsor Locks
฿4,016
฿4,619 total
includes taxes & fees
6 Sept - 7 Sept
DoubleTree by Hilton Hartford - Bradley Airport
View all properties

Top Winsted Hotel Reviews

The Litchfield Inn

The Litchfield Inn

10/10 Excellent
"Charming older hotel. Wish there were more tv options"
Eric 1-night trip
Posted 20 hours ago
The Litchfield Inn
The Little Lion

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."
Bruce 1-night trip
Posted 2 days ago
The Little Lion
Holiday Inn Express Hotel & Suites Great Barrington by IHG

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."
William 1-night trip
Posted 3 days ago
Holiday Inn Express Hotel & Suites Great Barrington by IHG
The Farmington Inn & Suites

The Farmington Inn & Suites

8/10 Good
"The staff were friendly and helpful, but you have to pay 17.25 a day (even the day you check out) for amenities that we never used. The back door we used looks all scratched up and worn metal door on the bottom. Bad 1st impression. Rooms are prettily decorated with wall paper and curtains that match. 4 poster beds looked great and were comfortable. Breakfast was good with enough choices. English tea bags weren't replenished after one day and don't think they have a designated person to handle only the food area. We left early every day and came back late. It was quiet and clean so recommend it, but be aware you pay for amenities whether you use them or not. Staff were helpful and friendly."
Cynthia 3-night trip
Posted 4 days ago
The Farmington Inn & Suites
Avon Old Farms Hotel

Avon Old Farms Hotel

10/10 Excellent
"Good"
Jeremy J 3-night trip
Posted 6 days ago
Avon Old Farms Hotel
Simsbury 1820 House

Simsbury 1820 House

10/10 Excellent
"The staff at Simsbury 1820 were the highlight of the stay. They were expecially friendly and very helpful. They had some suggestions of things to do that were interesting and area specific. Understandably but a bit disappointing was the inadquacy of the plumbing. It's a very old building but toilets could be updated."
Jill 3-night trip
Posted 7 days ago
Simsbury 1820 House

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 Platt Hill State Park and Northwestern Connecticut Community College Library.

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