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
21 Aug - 22 Aug
Tomorrow
22 Aug - 23 Aug
This weekend
21 Aug - 23 Aug
Next weekend
28 Aug - 30 Aug

Our top choices for Winsted luxury hotels

1. Simsbury 1820 House

Simsbury 1820 House
Simsbury Center
S$269
includes taxes & fees
1 Sept - 2 Sept
Simsbury 1820 House

2. The Litchfield Inn

The Litchfield Inn
Litchfield
  • Upscale Connecticut spa retreat features massages, plush beds, and tranquility near Bantam Lake.
S$399
includes taxes & fees
26 Aug - 27 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.
S$215
includes taxes & fees
30 Aug - 31 Aug
DoubleTree by Hilton Hotel Bristol, Connecticut

4. Delamar West Hartford

Delamar West Hartford
West Hartford
S$512
includes taxes & fees
13 Sept - 14 Sept
Delamar West Hartford

5. The Old Inn On The Green

The Old Inn On The Green
Great Barrington
S$489
includes taxes & fees
1 Sept - 2 Sept
The Old Inn On The Green

6. Belden House & Mews

Belden House & Mews
Litchfield Historic District
S$703
includes taxes & fees
1 Sept - 2 Sept
Belden House & Mews

7. Troutbeck

Troutbeck
Amenia
S$759
includes taxes & fees
30 Aug - 31 Aug
Troutbeck

8. The White Hart

The White Hart
Salisbury
S$502
includes taxes & fees
23 Aug - 24 Aug
The White Hart

9. 9 Academy

9 Academy
Salisbury
S$847
includes taxes & fees
21 Sept - 22 Sept
9 Academy

10. DoubleTree by Hilton Hartford - Bradley Airport

DoubleTree by Hilton Hartford - Bradley Airport
Windsor Locks
S$179
includes taxes & fees
30 Aug - 31 Aug
DoubleTree by Hilton Hartford - Bradley Airport
View all properties

Top Winsted Hotel Reviews

The Litchfield Inn

The Litchfield Inn

10/10 Excellent
"From the first time stepping on the property we felt welcome. The staff was accommodating and invited us to enjoy the amenities while we waited for our room (we were early for check in). We took advantage and walked the property before heading off to explore the area. When we returned, we checked into our dog friendly room (after grabbing a freshly baked chocolate chip cookie). The room was clean and comfortable and our dog enjoyed it as well. The next morning we took advantage of the fitness center and pool and enjoyed a hot breakfast on property (made to order omelets were a hit). Overall I cannot say enough good things about the staff, accommodations and amenities. Highly recommend."
Phillip 1-night trip
Posted 2 hours ago
The Litchfield Inn
Quality Inn Great Barrington

Quality Inn Great Barrington

8/10 Good
"Only real challengeโ€”getting on the hotel wifi was a frustrating challenge! And every time you left your room you had to get on again."
Judith 4-night trip
Posted 4 hours ago
Quality Inn Great Barrington
Sheraton Hartford Hotel at Bradley Airport

Sheraton Hartford Hotel at Bradley Airport

10/10 Excellent
"Everything about this hotel was amazing! The restaurant staff and food was excellent!! Definitely will stay here again. There is no match."
Raymond 1-night trip
Posted 17 hours ago
Sheraton Hartford Hotel at Bradley Airport
The Farmington Inn & Suites

The Farmington Inn & Suites

10/10 Excellent
"Amazing property. If you want a brand new hotel, this isn't it. But if you want an old school New England experience, this is it. Amazing charm. Rooms are c"
Sean 2-night trip
Posted 23 hours ago
The Farmington Inn & Suites
Holiday Inn Express Hotel & Suites Great Barrington by IHG

Holiday Inn Express Hotel & Suites Great Barrington by IHG

8/10 Good
"Excellent staff interaction. Great price and excellent location."
Irene 2-night trip
Posted 23 hours ago
Holiday Inn Express Hotel & Suites Great Barrington by IHG
Simsbury 1820 House

Simsbury 1820 House

10/10 Excellent
"The staff were wonderful. I stayed in room 103 in the main house; it was beautifully decorated with a large canopy bed and very spacious. The bathroom was clean and pretty. Tall ceilings. The continental breakfast was delish. Overall, a great experience and the house had such character. The outside had gorgeous ambiance, I will definitely be returning. I would recommend anybody looking for something that feels homey. I travel a few days a week for work every week and by far this was the best stay I've had."
Jourdan 2-night trip
Posted 2 days ago
Simsbury 1820 House
DoubleTree by Hilton Hotel Bristol, Connecticut

DoubleTree by Hilton Hotel Bristol, Connecticut

8/10 Good
"Great stay overall, but the bathroom door need some attention! The room was clean upon arrival and maintained throughout my stay. Itโ€™s always a relief to walk into a clean room. Staff member I interacted with were welcoming, proactive, and quick to help with any requests. The customer service here is definitely a highlight. The on-site facilities and amenities were exactly as described, which added value and comfort to the stay. The one glaring flaw in an otherwise perfect room was the bathroom door. The hinges were incredibly loud and squeaky, which is highly disruptive, especially when using the restroom in the middle of the night while others were sleeping. Furthermore, the door sticks, making a bit difficult to close. I would gladly stay here again because the hospitality and cleanliness. However, I highly recommend that maintenance takes some WD-40 and a screwdriver to those bathroom door hinges."
Jose 2-night trip
Posted 5 days ago
DoubleTree by Hilton Hotel Bristol, Connecticut
The Little Lion

The Little Lion

10/10 Excellent
"Clean, convenient, remotely operated by the owner, the Red Lion, a short distance away. We could use all the amenities offered by the Red Lion (meals, pool, hot tub) while staying at the much more reasonable Little Lion. A great bargain for Stockbridge!"
Joyce 1-night trip
Posted 5 days ago
The Little Lion

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 20ยฐC, while the coldest months are January and February, with an average of -1ยฐC. 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 Laurel Lanes. If you have some spare time during your trip, you might want to check out The Marina at Highland Lake and Platt Hill State Park.

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