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Check prices for these dates

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6 Nov - 8 Nov
Next weekend
13 Nov - 15 Nov

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Our top choices for Winchester hotels

A hotel room with a bed, white pillows, a bedside table with a phone, and a wall-mounted TV displaying a scenic sunset.

1. Days Inn by Wyndham Torrington

Days Inn by Wyndham Torrington
2.0 star property
Torrington
7.4 out of 10, Good, (1,006 reviews)
"Rooms were very clean, staff was very nice"
United States
Bethany
The price is 2.562.031 ₫
2.946.336 ₫ total
includes taxes & fees
8 Nov - 9 Nov
Days Inn by Wyndham Torrington
A cozy living room with a fireplace, leather armchairs, a coffee table with fruit, and a bookshelf.

2. Blackberry River Inn

Blackberry River Inn
3.0 star property
Norfolk
9.4 out of 10, Exceptional, (251 reviews)
"Great Breakfast Bed was okay Room very quaint hotel was very nice inside"
United States
Melanie
The price is 4.894.780 ₫
5.628.997 ₫ total
includes taxes & fees
5 Nov - 6 Nov
Blackberry River Inn
A hotel room with a large bed, bedside lamps, a desk with a chair, a mirror, and a coat rack.

3. Americas Best Value Inn Torrington CT

Americas Best Value Inn Torrington CT
2.5 star property
Torrington
5.6 out of 10, (836 reviews)
"Clean and the staffs are friendly"
United States
Tuty
The price is 3.864.042 ₫
4.443.687 ₫ total
includes taxes & fees
11 Nov - 12 Nov
Americas Best Value Inn Torrington CT
A lobby with a chandelier, a reception desk, and a sign indicating an exit.

4. The Litchfield Inn

The Litchfield Inn
4.0 star property
Litchfield
9.2 out of 10, Wonderful, (1,002 reviews)
"Wonderful stay! Beautiful property and pool, breakfast was delicious."
United States
Jacqueline
The price is 7.526.344 ₫
8.655.296 ₫ total
includes taxes & fees
29 Nov - 30 Nov
The Litchfield Inn
A stone fountain with water spouting from the top, surrounded by greenery and a brick building with windows in the background.

5. Simsbury Inn

Simsbury Inn
3.5 star property
Simsbury Center
9.2 out of 10, Wonderful, (321 reviews)
"Loved the 4 post beds and the linens were the nicest I have ever slept in. Lots of free parking on sight with a couple of outdoor fire pits. I would definitely stay there when we are in Simsbury"
Canada
SueEllen and Ian
The price is 7.445.218 ₫
9.124.901 ₫ total
includes taxes & fees
5 Nov - 6 Nov
Simsbury Inn
A restaurant with wooden tables and chairs, a bar area, and hanging spherical light fixtures.

6. The Abner Hotel

The Abner Hotel
3.0 star property
Litchfield Historic District
9.4 out of 10, Exceptional, (123 reviews)
"The Abner Hotel is beautiful, very clean, and has a lovely, welcoming atmosphere. Overall, everything was great, and we had a very pleasant stay."
United States
DIEGO
The price is 6.446.812 ₫
7.413.834 ₫ total
includes taxes & fees
24 Nov - 25 Nov
The Abner Hotel
An outdoor patio with a circular fire pit surrounded by wicker chairs, a grill, and a dining area with tables and chairs.

7. Residence Inn by Marriott Hartford Avon

Residence Inn by Marriott Hartford Avon
3.0 star property
Avon
8.8 out of 10, Excellent, (467 reviews)
"The room was a great size and very clean."
United States
Loren
The price is 3.276.926 ₫
3.768.465 ₫ total
includes taxes & fees
22 Nov - 23 Nov
Residence Inn by Marriott Hartford Avon
A large, historic building with a covered porch and outdoor seating area.

8. Simsbury 1820 House

Simsbury 1820 House
4.0 star property
Simsbury Center
9.4 out of 10, Exceptional, (1,000 reviews)
"Restaurant inside inn was comforting and had a great vibe."
United States
Enrique
The price is 4.611.398 ₫
5.747.503 ₫ total
includes taxes & fees
5 Nov - 6 Nov
Simsbury 1820 House
A sign for 'The Logust Tree Bed & Breakfast' with a contact number.

9. Locust Tree Bed and Breakfast LLC

Locust Tree Bed and Breakfast LLC
3.0 star property
East Canaan
8.8 out of 10, Excellent, (454 reviews)
"Wonderful stay, and wonderful breakfast."
United States
Daniel
The price is 2.705.010 ₫
3.110.762 ₫ total
includes taxes & fees
6 Nov - 7 Nov
Locust Tree Bed and Breakfast LLC
A large, two-story house with a porch and multiple windows, surrounded by a well-maintained lawn.

10. The White Hart

The White Hart
4.0 star property
Salisbury
9.8 out of 10, Exceptional, (156 reviews)
"It’s an exceptional place in every aspect. "
United States
William
The price is 7.682.228 ₫
8.834.562 ₫ total
includes taxes & fees
23 Nov - 24 Nov
The White Hart
A wooden deck with a swing chair and a bench overlooking a lake.

11. Interlaken Inn & Resort

Interlaken Inn & Resort
3.5 star property
Lakeville
8.2 out of 10, Very good, (323 reviews)
"Over eight annual visits to this hotel, it has been a wonderful stay each time."
United States
mary
The price is 6.468.838 ₫
7.439.163 ₫ total
includes taxes & fees
8 Nov - 9 Nov
Interlaken Inn & Resort
A dining area with round tables set for two, a fireplace, and a mural on the wall.

12. The Old Inn On The Green

The Old Inn On The Green
4.0 star property
Great Barrington
9.2 out of 10, Wonderful, (96 reviews)
"Lovely property.unique historic buildings and rooms with updated amenities! Quiet and peaceful beautiful dinner!"
United States
mary ellen
The price is 7.470.980 ₫
9.015.154 ₫ total
includes taxes & fees
6 Nov - 7 Nov
The Old Inn On The Green
A conservatory with a glass ceiling, round tables, and chairs, and a brick wall with an exit sign.

13. Avon Old Farms Hotel

Avon Old Farms Hotel
3.5 star property
Avon
8.4 out of 10, Very good, (1,000 reviews)
"We stay every Fall when visiting family. It never disappoints"
United States
Kristen
The price is 4.382.116 ₫
5.602.462 ₫ total
includes taxes & fees
5 Nov - 6 Nov
Avon Old Farms Hotel
An outdoor dining area with tables and chairs, surrounded by plants and trees.

14. Delamar West Hartford

Delamar West Hartford
4.0 star property
West Hartford
9.8 out of 10, Exceptional, (1,000 reviews)
"We liked that it was right downtown within walking distance to Restaurants and Shopping and Valet Parking was a plus. Breakfast was great! We will stay here again! Thank you!"
United States
Laura
The price is 7.233.767 ₫
8.834.072 ₫ total
includes taxes & fees
15 Nov - 16 Nov
Delamar West Hartford
A large, two-story house with a wrap-around porch, a central entrance, and a flag.

15. Belden House & Mews

Belden House & Mews
5.0 star property
Litchfield Historic District
9.4 out of 10, Exceptional, (14 reviews)
"The staff the rooms the atmosphere location the FOOD. Well deserved best hotel in the state by far."
United States
Anthony
The price is 11.721.710 ₫
14.510.446 ₫ total
includes taxes & fees
1 Dec - 2 Dec
Belden House & Mews
A hotel with a prominent sign, a covered entrance, and a landscaped driveway.

16. Hampton Inn & Suites Hartford/Farmington

Hampton Inn & Suites Hartford/Farmington
2.5 star property
Farmington
9.0 out of 10, Wonderful, (1,000 reviews)
"Very pleased with the hotel & staff. Definitely would stay there again."
United States
Penny
The price is 3.372.246 ₫
3.878.083 ₫ total
includes taxes & fees
3 Dec - 4 Dec
Hampton Inn & Suites Hartford/Farmington
A bar area with a long counter, bar stools, and shelves stocked with bottles.

17. Sheraton Hartford Hotel at Bradley Airport

Sheraton Hartford Hotel at Bradley Airport
3.5 star property
Windsor Locks
9.2 out of 10, Wonderful, (1,004 reviews)
"Location, Location, Location... perfect for departing from BDL. Restaurant was very good and bar area was clean and had a wide open area for seating."
United States
John
The price is 5.890.481 ₫
6.774.053 ₫ total
includes taxes & fees
12 Nov - 13 Nov
Sheraton Hartford Hotel at Bradley Airport
An outdoor seating area with fire pits and umbrellas, surrounded by modern buildings with large windows.

18. DoubleTree by Hilton Hotel Bristol, Connecticut

DoubleTree by Hilton Hotel Bristol, Connecticut
4.0 star property
Bristol
9.0 out of 10, Wonderful, (1,003 reviews)
"Lovely stay, easy check in and kind staff. The room was clean and comfortable"
United States
Julia
The price is 3.781.346 ₫
4.348.548 ₫ total
includes taxes & fees
24 Nov - 25 Nov
DoubleTree by Hilton Hotel Bristol, Connecticut
A spacious foyer with a grand staircase, a chandelier, and a patterned carpet.

19. The Farmington Inn & Suites

The Farmington Inn & Suites
3.0 star property
Farmington
9.0 out of 10, Wonderful, (1,001 reviews)
"A beautiful inn in a beautiful town. Loved our stay and will definitely be back."
United States
Kenneth
The price is 3.222.826 ₫
4.150.774 ₫ total
includes taxes & fees
8 Nov - 9 Nov
The Farmington Inn & Suites
A house with a stone staircase leading to a door, surrounded by lush greenery and a well-maintained garden.

20. Sunny Peace Homestay

Sunny Peace Homestay
3.0 star property
Harwinton
9.0 out of 10, Wonderful, (19 reviews)
"When I arrived after dark, it was hard to tell if I was at the right house. The bedroom was clean and quiet. Appears to be a shared bathroom but lucky one of the two bedrooms were vacant. Good for a quick stay."
United States
Dean
The price is 3.361.941 ₫
5.347.547 ₫ total
includes taxes & fees
11 Nov - 12 Nov
Sunny Peace Homestay
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
View all properties

Compare top hotels in Winchester

A hotel room with a bed, white pillows, a bedside table with a phone, and a wall-mounted TV displaying a scenic sunset.

Days Inn by Wyndham Torrington

2.0 star property
Torrington
View
A cozy living room with a fireplace, leather armchairs, a coffee table with fruit, and a bookshelf.

Blackberry River Inn

3.0 star property
Norfolk
View
A hotel room with a large bed, bedside lamps, a desk with a chair, a mirror, and a coat rack.

Americas Best Value Inn Torrington CT

2.5 star property
Torrington
View
A lobby with a chandelier, a reception desk, and a sign indicating an exit.

The Litchfield Inn

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

Simsbury Inn

3.5 star property
Simsbury Center
View
7.4
Good
1,006 reviews
9.4
Exceptional
251 reviews
5.6
836 reviews
9.2
Wonderful
1,002 reviews
9.2
Wonderful
321 reviews
The price is 2.562.031 ₫
2.946.336 ₫ total
includes taxes & fees
8 Nov - 9 Nov
The price is 4.894.780 ₫
5.628.997 ₫ total
includes taxes & fees
5 Nov - 6 Nov
The price is 3.864.042 ₫
4.443.687 ₫ total
includes taxes & fees
11 Nov - 12 Nov
The price is 7.526.344 ₫
8.655.296 ₫ total
includes taxes & fees
29 Nov - 30 Nov
The price is 7.445.218 ₫
9.124.901 ₫ total
includes taxes & fees
5 Nov - 6 Nov
  • Yes, Breakfast included
  • No Pool
  • No Spa
  • No Pet-friendly
  • Yes, WiFi included
  • Yes, Parking
  • Yes, Breakfast included
  • Yes, Pool
  • No Spa
  • No Pet-friendly
  • Yes, WiFi included
  • Yes, Parking
  • No Breakfast included
  • No Pool
  • No Spa
  • No Pet-friendly
  • Yes, WiFi included
  • Yes, Parking
  • Yes, Breakfast included
  • Yes, Pool
  • Yes, Spa
  • Yes, Pet-friendly
  • Yes, WiFi included
  • Yes, Parking
  • Yes, Breakfast included
  • Yes, Pool
  • No Spa
  • Yes, Pet-friendly
  • Yes, WiFi included
  • Yes, Parking
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Stay near popular Winchester attractions

Highland Lake

Commune with nature and explore the great outdoors at Highland Lake during your travels in Winchester.
See properties

Top Winchester Hotel Reviews

Fairfield Inn & Suites by Marriott Plainville

Fairfield Inn & Suites by Marriott Plainville

8/10 Good
"Staff excellent"
Stephen 2-night trip
Posted 21 hours ago
Fairfield Inn & Suites by Marriott Plainville

More cheap stays in Winchester

PLYMOUTH MOTOR LODGE

PLYMOUTH MOTOR LODGE

325 Main St Terryville CT
The price is 2.292.818 ₫ per night from 12 Nov to 13 Nov
2.292.818 ₫
2.636.741 ₫ total
12 Nov - 13 Nov
includes taxes & fees
7.6/10 Good! (223 reviews)

Frequently asked questions

What's the seasonal weather in Winchester?
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 Winchester are January, February, March and April, with each month seeing an average of 15 cm of snowfall.