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Check prices for these dates

Tonight
Aug 25 - Aug 26
Tomorrow
Aug 26 - Aug 27
This weekend
Aug 28 - Aug 30
Next weekend
Sep 4 - Sep 6

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Our top choices for Winchester hotels

1. Days Inn by Wyndham Torrington

Days Inn by Wyndham Torrington
Torrington
United States
Juan
₩128,397
₩147,656 total
includes taxes & fees
Aug 27 - Aug 28
Days Inn by Wyndham Torrington

2. Avon Old Farms Hotel

Avon Old Farms Hotel
Avon
United States
Andrew
₩210,904
₩272,731 total
includes taxes & fees
Aug 27 - Aug 28
Avon Old Farms Hotel

3. Americas Best Value Inn Torrington CT

Americas Best Value Inn Torrington CT
Torrington
United States
Carol
₩166,286
₩191,231 total
includes taxes & fees
Aug 26 - Aug 27
Americas Best Value Inn Torrington CT

4. Hampton Inn & Suites Hartford/Farmington

Hampton Inn & Suites Hartford/Farmington
Farmington
United States
Mary Melissa
₩191,465
₩220,185 total
includes taxes & fees
Sep 8 - Sep 9
Hampton Inn & Suites Hartford/Farmington

5. Blackberry River Inn

Blackberry River Inn
Norfolk
United States
Rachel
₩262,508
₩301,884 total
includes taxes & fees
Sep 7 - Sep 8
Blackberry River Inn

6. Extended Stay America Suites Hartford Farmington

Extended Stay America Suites Hartford Farmington
Farmington
United States
Nigel
₩151,964
₩174,758 total
includes taxes & fees
Aug 27 - Aug 28
Extended Stay America Suites Hartford Farmington

7. The Farmington Inn & Suites

The Farmington Inn & Suites
Farmington
United States
Carol
₩205,861
₩260,573 total
includes taxes & fees
Aug 27 - Aug 28
The Farmington Inn & Suites

8. Simsbury 1820 House

Simsbury 1820 House
Simsbury Center
United States
Thomas
₩233,494
₩292,351 total
includes taxes & fees
Aug 27 - Aug 28
Simsbury 1820 House

9. Residence Inn by Marriott Hartford Avon

Residence Inn by Marriott Hartford Avon
Avon
United States
Laura
₩210,144
₩241,665 total
includes taxes & fees
Sep 13 - Sep 14
Residence Inn by Marriott Hartford Avon

10. The Litchfield Inn

The Litchfield Inn
Litchfield
United States
Sandra
₩395,901
₩455,286 total
includes taxes & fees
Aug 26 - Aug 27
The Litchfield Inn

11. Homewood Suites by Hilton Hartford-Farmington

Homewood Suites by Hilton Hartford-Farmington
Farmington
United States
John
₩203,412
₩233,923 total
includes taxes & fees
Sep 7 - Sep 8
Homewood Suites by Hilton Hartford-Farmington

12. Fairfield Inn & Suites by Marriott Plainville

Fairfield Inn & Suites by Marriott Plainville
Plainville
United States
Nicole
₩156,842
₩180,369 total
includes taxes & fees
Sep 6 - Sep 7
Fairfield Inn & Suites by Marriott Plainville

13. Sheraton Hartford Hotel at Bradley Airport

Sheraton Hartford Hotel at Bradley Airport
Windsor Locks
United States
Lisa
₩339,879
₩390,861 total
includes taxes & fees
Aug 31 - Sep 1
Sheraton Hartford Hotel at Bradley Airport

14. Locust Tree Bed and Breakfast LLC

Locust Tree Bed and Breakfast LLC
East Canaan
United States
Regina
₩145,070
₩166,831 total
includes taxes & fees
Sep 7 - Sep 8
Locust Tree Bed and Breakfast LLC

15. Simsbury Inn

Simsbury Inn
Simsbury Center
United States
Rachel
₩330,207
₩409,926 total
includes taxes & fees
Sep 16 - Sep 17
Simsbury Inn

16. DoubleTree by Hilton Hotel Bristol, Connecticut

DoubleTree by Hilton Hotel Bristol, Connecticut
Bristol
United States
DARRON
₩203,412
₩233,924 total
includes taxes & fees
Sep 6 - Sep 7
DoubleTree by Hilton Hotel Bristol, Connecticut

17. Sunny Peace Homestay

Sunny Peace Homestay
Harwinton
United States
Dean
₩180,302
₩286,790 total
includes taxes & fees
Aug 27 - Aug 28
Sunny Peace Homestay

18. Interlaken Inn & Resort

Interlaken Inn & Resort
Lakeville
United States
Stacie
₩297,186
₩341,764 total
includes taxes & fees
Sep 24 - Sep 25
Interlaken Inn & Resort

19. Cornwall Inn and Lodge

Cornwall Inn and Lodge
Cornwall Bridge
United States
Janice
₩292,351
₩336,204 total
includes taxes & fees
Aug 30 - Aug 31
Cornwall Inn and Lodge

20. Truman Gillet House Bed & Breakfast

Truman Gillet House Bed & Breakfast
Granby
United States
Valerie
₩193,427
₩214,704 total
includes taxes & fees
Sep 1 - Sep 2
Truman Gillet House Bed & Breakfast
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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.
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Northwestern Connecticut Community College

Walk around the campus at Northwestern Connecticut Community College as part of your travels around Winchester.
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The Marina at Highland Lake

Explore the waterfront in Winchester with a trip to The Marina at Highland Lake.
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Platt Hill State Park

You can take time to visit Platt Hill State Park during your travels to Winchester.
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Winchester Historical Society

8.0/10 (1 review)
You can spend an afternoon exploring the galleries in Winchester Historical Society during your trip to Winchester. Take in the live music in this relaxing area.
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Walker Field

Explore the great outdoors at Walker Field, a lovely green space in Winchester.
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American Mural Project

You can spend time studying the exhibits at American Mural Project in Winchester.
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Tatro Pond

You can take time to visit Tatro Pond during your travels to Winchester.
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Top Winchester Hotel Reviews

Sheraton Hartford Hotel at Bradley Airport

Sheraton Hartford Hotel at Bradley Airport

8/10 Good
"Perfect hotel for long layover or early departure"
Gerald 1-night trip
Posted 8 hours ago
Sheraton Hartford Hotel at Bradley Airport
Days Inn by Wyndham Torrington

Days Inn by Wyndham Torrington

8/10 Good
"Pretty loud AC"
GARY 2-night trip
Posted 1 day ago
Days Inn by Wyndham Torrington
Avon Old Farms Hotel

Avon Old Farms Hotel

10/10 Excellent
"Good"
Jeremy J 3-night trip
Posted 1 day ago
Avon Old Farms Hotel
Fairfield Inn & Suites by Marriott Plainville

Fairfield Inn & Suites by Marriott Plainville

8/10 Good
"Excellent breakfast"
Maureen O 6-night trip
Posted 2 days ago
Fairfield Inn & Suites by Marriott Plainville
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 2 days ago
Simsbury 1820 House
Mayflower Inn & Spa, Auberge Collection

Mayflower Inn & Spa, Auberge Collection

10/10 Excellent
"Beautiful property with lovely pool and spa area. The rooms are beautifully decorated. The staff are all friendly, welcoming, and very helpful. The grounds and gardens are well maintained. The hiking trail is highly recommended. My room in the main house was a bit noisy; the room above mine appeared to be a utility room that was active early in the morning. I could hear footsteps throughout the day. The dinner was overrated, but the breakfast and lunch were delicious."
Mary 3-night trip
Posted 4 days ago
Mayflower Inn & Spa, Auberge Collection
Extended Stay America Suites Hartford Farmington

Extended Stay America Suites Hartford Farmington

10/10 Excellent
"Dry friendly staff."
Nigel 1-night trip
Posted 8 days ago
Extended Stay America Suites Hartford Farmington
Americas Best Value Inn Torrington CT

Americas Best Value Inn Torrington CT

10/10 Excellent
"All the staff members I met were cheerful & helpful. I asked for a ground floor room, upon arrival, got a very nice one at no extra charge. I was in the area for a music festival, plan on booking a stay again , next year."
Peter 2-night trip
Posted 8 days ago
Americas Best Value Inn Torrington CT

More cheap stays in Winchester

PLYMOUTH MOTOR LODGE

PLYMOUTH MOTOR LODGE

325 Main St Terryville CT
₩122,964
₩141,409 total
Aug 27 - Aug 28
includes taxes & fees
PLYMOUTH MOTOR LODGE
Days Inn by Wyndham Torrington

Days Inn by Wyndham Torrington

492 East Main St Torrington CT
₩128,397
₩147,656 total
Aug 27 - Aug 28
includes taxes & fees
7.4/10 Good! (1,009 reviews)
Days Inn by Wyndham Torrington
Extended Stay America Suites Hartford Farmington

Extended Stay America Suites Hartford Farmington

1 Batterson Park Rd Farmington CT
₩151,964
₩174,758 total
Aug 27 - Aug 28
includes taxes & fees
Extended Stay America Suites Hartford Farmington
Americas Best Value Inn Torrington CT

Americas Best Value Inn Torrington CT

395 Winsted Rd Torrington CT
₩166,286
₩191,231 total
Aug 26 - Aug 27
includes taxes & fees
5.6/10 (813 reviews)
Americas Best Value Inn Torrington CT
Hitching Post Country Motel

Hitching Post Country Motel

45 Kent Rd S Cornwall Bridge CT
₩179,611
₩206,553 total
Aug 27 - Aug 28
includes taxes & fees
6.6/10 (108 reviews)
Hitching Post Country Motel
Hampton Inn & Suites Hartford/Farmington

Hampton Inn & Suites Hartford/Farmington

301 Colt Hwy Farmington CT
₩191,465
₩220,185 total
Sep 8 - Sep 9
includes taxes & fees
Hampton Inn & Suites Hartford/Farmington

Frequently asked questions

What's the best place for a stay in Winchester?
Sheraton Hartford Hotel at Bradley Airport, located 21.9 mi (35.2 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 Homewood Suites by Hilton Hartford-Farmington and The Farmington Inn & Suites. See all available top hotels, or 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: Features a snack bar/deli, an indoor pool, and buffet. Avon Old Farms Hotel and Mayflower Inn & Spa, Auberge Collection 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 19 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, Burr Pond State Park, and The Marina at Highland Lake. A couple of additional sights to add to your agenda are Platt Hill State Park and Laurel Lanes. 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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