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Check prices for these dates

Next weekend
Aug 7 - Aug 9
In two weeks
Aug 14 - Aug 16

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Our top choices for Winchester hotels

Desk, cribs (free), rollaway beds (surcharge), WiFi (free)

1. Days Inn by Wyndham Torrington

Days Inn by Wyndham Torrington
2.0 star property
Torrington
7.4 out of 10, Good, (1,002 reviews)
"Was clean, didn't smell weird and was exactly what we were looking for, just a place to sleep while our home was being repaired, no complaints at all."
United States
Graeme
The price is ļæ„16,291
ļæ„18,735 total
includes taxes & fees
Sep 2 - Sep 3
Days Inn by Wyndham Torrington
Library

2. Blackberry River Inn

Blackberry River Inn
3.0 star property
Norfolk
9.4 out of 10, Exceptional, (200 reviews)
"Excellent breakfast, very nice staff."
United States
Leslie
The price is ļæ„29,308
ļæ„33,704 total
includes taxes & fees
Aug 4 - Aug 5
Blackberry River Inn
Premium bedding, down comforters, Select Comfort beds, in-room safe

3. Americas Best Value Inn Torrington CT

Americas Best Value Inn Torrington CT
2.5 star property
Torrington
5.6 out of 10, (808 reviews)
"Location for the event I attended was very good. Has possibilities of being a very good place to stay."
United States
Carol
The price is ļæ„23,608
ļæ„27,150 total
includes taxes & fees
Sep 1 - Sep 2
Americas Best Value Inn Torrington CT
Library

4. The Litchfield Inn

The Litchfield Inn
4.0 star property
Litchfield
9.2 out of 10, Wonderful, (1,002 reviews)
"Beautiful place 5 stars"
United States
Sandra
The price is ļæ„47,779
ļæ„54,946 total
includes taxes & fees
Aug 9 - Aug 10
The Litchfield Inn
BBQ/picnic area

5. Residence Inn by Marriott Hartford Avon

Residence Inn by Marriott Hartford Avon
3.0 star property
Avon
8.8 out of 10, Excellent, (453 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 ļæ„22,524
ļæ„25,902 total
includes taxes & fees
Aug 16 - Aug 17
Residence Inn by Marriott Hartford Avon
Exterior

6. Locust Tree Bed and Breakfast LLC

Locust Tree Bed and Breakfast LLC
3.0 star property
East Canaan
8.8 out of 10, Excellent, (437 reviews)
"This is a quiet location and easy to find. It has a working-farm vibe rather than a luxury-vacation vibe. French toast was delicious. Guest meals are prepared in a home kitchen without a dishwasher or secondary sink."
United States
Kay
The price is ļæ„16,527
ļæ„19,006 total
includes taxes & fees
Aug 3 - Aug 4
Locust Tree Bed and Breakfast LLC
Staircase

7. The Farmington Inn & Suites

The Farmington Inn & Suites
3.0 star property
Farmington
8.8 out of 10, Excellent, (1,005 reviews)
"Wonderful breakfast and great staff."
United States
Carol
The price is ļæ„26,601
ļæ„33,306 total
includes taxes & fees
Aug 3 - Aug 4
The Farmington Inn & Suites
Exterior

8. Hampton Inn & Suites Hartford/Farmington

Hampton Inn & Suites Hartford/Farmington
2.5 star property
Farmington
9.0 out of 10, Wonderful, (1,001 reviews)
"Great stay and would definitely be back to stay again"
United States
Mary Melissa
The price is ļæ„21,812
ļæ„25,084 total
includes taxes & fees
Aug 31 - Sep 1
Hampton Inn & Suites Hartford/Farmington
Lobby

9. Fairfield Inn & Suites by Marriott Plainville

Fairfield Inn & Suites by Marriott Plainville
3.0 star property
Plainville
8.6 out of 10, Excellent, (1,000 reviews)
"Great Service and food was decent."
United States
Sy A
The price is ļæ„17,944
ļæ„20,636 total
includes taxes & fees
Aug 9 - Aug 10
Fairfield Inn & Suites by Marriott Plainville
Front of property

10. Manor House Inn

Manor House Inn
3.0 star property
Norfolk
9.4 out of 10, Exceptional, (139 reviews)
"Excellent bed and breakfast, room was clean and comfortable."
United States
Kevin
The price is ļæ„47,642
ļæ„52,883 total
includes taxes & fees
Aug 31 - Sep 1
Manor House Inn
Banquet hall

11. Avon Old Farms Hotel

Avon Old Farms Hotel
3.5 star property
Avon
8.4 out of 10, Very Good, (1,003 reviews)
"Great stay"
United States
Andrew
The price is ļæ„30,328
ļæ„38,316 total
includes taxes & fees
Aug 5 - Aug 6
Avon Old Farms Hotel
Reception hall

12. Simsbury Inn

Simsbury Inn
3.5 star property
Simsbury Center
9.2 out of 10, Wonderful, (305 reviews)
"Great little historical hotel with nice amenities, such as sports courts and a breakfast buffet. The room was large and comfortable!"
United States
Rachel
The price is ļæ„45,489
ļæ„55,752 total
includes taxes & fees
Aug 3 - Aug 4
Simsbury Inn
Desk, iron/ironing board, WiFi (free), bed sheets

13. Extended Stay America Suites Hartford Farmington

Extended Stay America Suites Hartford Farmington
2.5 star property
Farmington
8.0 out of 10, Very Good, (1,002 reviews)
"Great value!"
United States
Katelyn
The price is ļæ„15,581
ļæ„17,918 total
includes taxes & fees
Aug 3 - Aug 4
Extended Stay America Suites Hartford Farmington
Exterior

14. Simsbury 1820 House

Simsbury 1820 House
4.0 star property
Simsbury Center
9.4 out of 10, Exceptional, (1,000 reviews)
"I loved the staff! So friendly and helpful! The coffee was great, the location was perfect!"
United States
Nazli
The price is ļæ„29,749
ļæ„36,926 total
includes taxes & fees
Aug 3 - Aug 4
Simsbury 1820 House
Property entrance

15. Truman Gillet House Bed & Breakfast

Truman Gillet House Bed & Breakfast
3.0 star property
Granby
9.6 out of 10, Exceptional, (116 reviews)
"Cute place. Antiquey Excellent breakfast!"
United States
Valerie
The price is ļæ„22,036
ļæ„24,460 total
includes taxes & fees
Aug 3 - Aug 4
Truman Gillet House Bed & Breakfast
Double Room, Smoking | Iron/ironing board (on request), WiFi (free), bed sheets

16. PLYMOUTH MOTOR LODGE

PLYMOUTH MOTOR LODGE
2.5 star property
Terryville
7.8 out of 10, Good, (203 reviews)
"Everything was nice! I'd stay here again!"
United States
SEMORA
The price is ļæ„12,888
ļæ„14,821 total
includes taxes & fees
Aug 3 - Aug 4
PLYMOUTH MOTOR LODGE
Exterior

17. Homewood Suites by Hilton Hartford-Farmington

Homewood Suites by Hilton Hartford-Farmington
3.0 star property
Farmington
8.4 out of 10, Very Good, (1,003 reviews)
"the staff was helpful and very friendly and the property and the breakfast were great! we enjoyed our stay and will be back."
United States
Kelly
The price is ļæ„23,361
ļæ„26,865 total
includes taxes & fees
Aug 30 - Aug 31
Homewood Suites by Hilton Hartford-Farmington
Front of property

18. Gedney Farm

Gedney Farm
3.5 star property
Great Barrington
9.2 out of 10, Wonderful, (140 reviews)
"Beautiful property, relaxing landscape."
United States
Jane
The price is ļæ„35,942
ļæ„39,428 total
includes taxes & fees
Aug 3 - Aug 4
Gedney Farm
WiFi (free), bed sheets

19. Hitching Post Country Motel

Hitching Post Country Motel
2.5 star property
Cornwall Bridge
6.8 out of 10, (101 reviews)
"Clean...cheap and comfortable bed"
United States
leo
The price is ļæ„20,462
ļæ„23,531 total
includes taxes & fees
Aug 4 - Aug 5
Hitching Post Country Motel
Interior detail

20. Wilder House Berkshires

Wilder House Berkshires
2.0 star property
Sheffield
9.8 out of 10, Exceptional, (59 reviews)
"Great stay and the breakfast was fantastic"
United States
Jennifer
The price is ļæ„27,915
ļæ„31,180 total
includes taxes & fees
Aug 9 - Aug 10
Wilder House Berkshires
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

Avon Old Farms Hotel

Avon Old Farms Hotel

10/10 Excellent
"Everything was great! Staff was helpful."
frankie 3-night trip
Posted 2 hours ago
Avon Old Farms Hotel

More cheap stays in Winchester

PLYMOUTH MOTOR LODGE

PLYMOUTH MOTOR LODGE

325 Main St Terryville CT
The price is ļæ„12,888 per night from Aug 3 to Aug 4
ļæ„12,888
ļæ„14,821 total
Aug 3 - Aug 4
includes taxes & fees

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 Sheraton Hartford Hotel at Bradley Airport and Avon Old Farms Hotel. See all available top hotels, or vacation rentals in Winchester.
What's the top vacation rental in Winchester?
Family-Friendly Highland Lake Waterfront w/ Private Dock & Shallow Walk-In ā€” 5BR: This Winchester vacation home rental is located on a lake and has a balcony, a garden, and air-conditioning to put you at ease 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?
Avon Old Farms Hotel: Offers a sauna, a seasonal outdoor pool, and buffet. Homewood Suites by Hilton Hartford-Farmington and Hampton Inn & Suites Hartford/Farmington 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 Platt Hill State Park, Highland Lake, and Burr Pond State Park. A couple of additional sights to add to your agenda are The Marina at Highland Lake and Winchester Historical Society. 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 67Ā°F, while the coldest months are January and February with an average of 30Ā°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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