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Nov 6 - Nov 8
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Nov 13 - Nov 15

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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, (1,004 reviews)
"Rooms were very clean, staff was very nice"
United States
Bethany
The price is ￥15,134
￥17,404 total
includes taxes & fees
Nov 12 - Nov 13
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 ￥27,840
￥32,016 total
includes taxes & fees
Nov 8 - Nov 9
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, (833 reviews)
"Clean and the staffs are friendly"
United States
Tuty
The price is ￥24,471
￥28,143 total
includes taxes & fees
Nov 8 - Nov 9
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, (1,001 reviews)
"Wonderful stay! Beautiful property and pool, breakfast was delicious."
United States
Jacqueline
The price is ￥45,736
￥52,597 total
includes taxes & fees
Dec 2 - Dec 3
The Litchfield Inn
A bedroom with a large bed, a chair, and a window with curtains.

5. 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 ￥46,984
￥54,032 total
includes taxes & fees
Nov 23 - Nov 24
The White Hart
An outdoor patio with a circular fire pit surrounded by wicker chairs, a grill, and a dining area with tables and chairs.

6. Residence Inn by Marriott Hartford Avon

Residence Inn by Marriott Hartford Avon
3.0 star property
Avon
8.8 out of 10, Excellent, (466 reviews)
"It was such a great experience, the hotel was so nice and clean. Plenty of things for the kids to do. And we were able to walk to get ice cream after dinner."
United States
Laura
The price is ￥20,042
￥23,049 total
includes taxes & fees
Nov 19 - Nov 20
Residence Inn by Marriott Hartford Avon
A sign for 'The Logust Tree Bed & Breakfast' with a contact number.

7. Locust Tree Bed and Breakfast LLC

Locust Tree Bed and Breakfast LLC
3.0 star property
East Canaan
8.8 out of 10, Excellent, (453 reviews)
"Wonderful stay, and wonderful breakfast."
United States
Daniel
The price is ￥16,544
￥19,026 total
includes taxes & fees
Nov 2 - Nov 3
Locust Tree Bed and Breakfast LLC
A stone fountain with water spouting from the top, surrounded by greenery and a brick building with windows in the background.

8. 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 ￥45,535
￥55,808 total
includes taxes & fees
Nov 2 - Nov 3
Simsbury Inn
A large, historic building with a covered porch and outdoor seating area.

9. 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 ￥26,490
￥33,182 total
includes taxes & fees
Nov 10 - Nov 11
Simsbury 1820 House
A restaurant with wooden tables and chairs, a bar area, and hanging spherical light fixtures.

10. The Abner Hotel

The Abner Hotel
3.0 star property
Litchfield Historic District
9.4 out of 10, Exceptional, (122 reviews)
"Friendly staff, good location, clean and cute room and thoughtful design. Good breakfast"
United States
Lanny
The price is ￥38,252
￥43,990 total
includes taxes & fees
Nov 22 - Nov 23
The Abner Hotel
A dining area with round tables set for two, a fireplace, and a mural on the wall.

11. 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 ￥45,692
￥55,136 total
includes taxes & fees
Nov 2 - Nov 3
The Old Inn On The Green
A hotel with a prominent sign, a covered entrance, and a landscaped driveway.

12. Hampton Inn & Suites Hartford/Farmington

Hampton Inn & Suites Hartford/Farmington
2.5 star property
Farmington
9.0 out of 10, Wonderful, (1,003 reviews)
"Clean and nice property Helpful staff"
United States
Raed
The price is ￥21,160
￥24,334 total
includes taxes & fees
Nov 19 - Nov 20
Hampton Inn & Suites Hartford/Farmington
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, (1,001 reviews)
"We stay every Fall when visiting family. It never disappoints"
United States
Kristen
The price is ￥26,191
￥33,562 total
includes taxes & fees
Nov 5 - Nov 6
Avon Old Farms Hotel
An outdoor seating area with sofas and chairs, a glass-top table with a fire feature, and yellow chairs in the background.

14. Home2 Suites by Hilton Bristol

Home2 Suites by Hilton Bristol
3.0 star property
Bristol
9.6 out of 10, Exceptional, (284 reviews)
"Everything was wonderful , we enjoy a lot the hot tub and the go to pool that feels amazing"
United States
Gabriela
The price is ￥20,543
￥23,624 total
includes taxes & fees
Nov 8 - Nov 9
Home2 Suites by Hilton Bristol
A bar area with a long counter, bar stools, and shelves stocked with bottles.

15. Sheraton Hartford Hotel at Bradley Airport

Sheraton Hartford Hotel at Bradley Airport
3.5 star property
Windsor Locks
9.2 out of 10, Wonderful, (1,002 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 ￥33,348
￥38,350 total
includes taxes & fees
Nov 8 - Nov 9
Sheraton Hartford Hotel at Bradley Airport
A hotel with multiple buildings, a parking lot, and a well-maintained lawn.

16. Homewood Suites by Hilton Hartford-Farmington

Homewood Suites by Hilton Hartford-Farmington
3.0 star property
Farmington
8.4 out of 10, Very good, (1,000 reviews)
"Breakfast was great and the rooms were very clean and comfortable. Staff was also very friendly and courteous."
United States
EDWARD
The price is ￥23,973
￥27,569 total
includes taxes & fees
Nov 29 - Nov 30
Homewood Suites by Hilton Hartford-Farmington
A spacious foyer with a grand staircase, a chandelier, and a patterned carpet.

17. The Farmington Inn & Suites

The Farmington Inn & Suites
3.0 star property
Farmington
8.8 out of 10, Excellent, (1,006 reviews)
"A beautiful inn in a beautiful town. Loved our stay and will definitely be back."
United States
Kenneth
The price is ￥19,711
￥25,386 total
includes taxes & fees
Nov 8 - Nov 9
The Farmington Inn & Suites
A wooden deck with a swing chair and a bench overlooking a lake.

18. 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 ￥40,572
￥46,657 total
includes taxes & fees
Dec 2 - Dec 3
Interlaken Inn & Resort
An outdoor seating area with fire pits and umbrellas, surrounded by modern buildings with large windows.

19. 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 ￥22,868
￥26,298 total
includes taxes & fees
Nov 8 - Nov 9
DoubleTree by Hilton Hotel Bristol, Connecticut
A large, two-story house with a wrap-around porch, a central entrance, and a flag.

20. Belden House & Mews

Belden House & Mews
5.0 star property
Litchfield Historic District
9.4 out of 10, Exceptional, (13 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 ￥71,690
￥88,746 total
includes taxes & fees
Dec 1 - Dec 2
Belden House & Mews
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.
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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

Interlaken Inn & Resort

Interlaken Inn & Resort

8/10 Good
"Sunnyside area could use some updating.The carpet seemed to be worn and drapes looked old."
Claudia 2-night trip
Posted 1 hour ago
Interlaken Inn & Resort

More cheap stays in Winchester

PLYMOUTH MOTOR LODGE

PLYMOUTH MOTOR LODGE

325 Main St Terryville CT
The price is ￥13,322 per night from Dec 2 to Dec 3
￥13,322
￥15,320 total
Dec 2 - Dec 3
includes taxes & fees
7.6/10 Good! (223 reviews)

Frequently asked questions

What's the best place for a stay in Winchester?
The Farmington Inn & Suites, located 20.6 mi (33.1 km) from the heart of Winchester, is a top choice for your stay based on our traveler data. Other good choices for your visit to the area are Delamar West Hartford and Extended Stay America Suites Hartford Farmington. See all available top hotels, or vacation rentals in Winchester.
What's the top vacation rental in Winchester?
Waterfront House & Guest House Available in Winchester, CT!: This Winchester vacation home rental is located on a lake and offers a patio, air-conditioning, and laundry facilities to help you feel perfectly comfortable in your new surroundings. See all vacation rentals in Winchester.
If I need to cancel my hotel reservation in Winchester, will I receive a refund?
Yes! You'll find that most hotel reservations are refundable provided that you cancel prior to the hotel's cancellation deadline, which is often 24 or 48 hours before check in. If you booked a non-refundable reservation, it might still be possible to cancel it and be given a refund within a 24-hour period of your booking. Filter your search by fully refundable to find flexible hotel deals in Winchester.
Where can I learn more about changing or cancelling my trip to Winchester?
To access more information about picking new dates or cancelling your trip to Winchester, head over to our customer service page.
What are some hotels with pools in Winchester?
Homewood Suites by Hilton Hartford-Farmington: Offers a snack bar/deli, an indoor pool, and buffet. Mayflower Inn & Spa, Auberge Collection and Avon Old Farms Hotel are two additional hotels with an onsite pool. View all hotels with pools in Winchester.
What is staying in Winchester like?
Visitors to Winchester are sure to find plenty to explore and enjoy. In Winchester, there are 21 hotels and other accommodations to choose from. Find out more about Winchester.
What should I do while I'm visiting Winchester?
Favorite places to visit include Highland Lake, The Marina at Highland Lake, and Burr Pond State Park. A couple of additional sights to add to your agenda are Winchester Historical Society and American Museum of Tort Law. Check out what more to see and do in Expedia's Winchester guide.
What's the seasonal weather like in Winchester?
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 Winchester are January, February, March, and April, with each month seeing an average of 6 inches of snowfall.

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