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Check prices for these dates

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Sep 17 - Sep 18
Tomorrow
Sep 18 - Sep 19
This weekend
Sep 18 - Sep 20
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Sep 25 - Sep 27

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Our top choices for Winchester hotels

Room
Bathroom
Property amenity
Exterior

1. Days Inn by Wyndham Torrington

Days Inn by Wyndham Torrington
Torrington
United States
Kathleen
￥13,682
￥15,735 total
includes taxes & fees
Oct 18 - Oct 19
Days Inn by Wyndham Torrington
Library
Interior
Living area
Library

2. Blackberry River Inn

Blackberry River Inn
Norfolk
United States
Rachel
￥22,338
￥25,689 total
includes taxes & fees
Sep 21 - Sep 22
Blackberry River Inn
Room
Lobby
Fitness facility
Exterior

3. Americas Best Value Inn Torrington CT

Americas Best Value Inn Torrington CT
Torrington
United States
Carol
￥20,165
￥23,190 total
includes taxes & fees
Sep 21 - Sep 22
Americas Best Value Inn Torrington CT
Exterior
Aerial view
Exterior
Interior

4. Locust Tree Bed and Breakfast LLC

Locust Tree Bed and Breakfast LLC
East Canaan
United States
Nicholas
￥16,289
￥18,732 total
includes taxes & fees
Sep 20 - Sep 21
Locust Tree Bed and Breakfast LLC
Library
King Cabin Room
Lobby sitting area
Lobby sitting area

5. The Litchfield Inn

The Litchfield Inn
Litchfield
Canada
Wei
￥43,567
￥50,103 total
includes taxes & fees
Sep 21 - Sep 22
The Litchfield Inn
Staircase
Lobby lounge
Lobby sitting area
Deluxe Room, 1 King Bed

6. The Farmington Inn & Suites

The Farmington Inn & Suites
Farmington
United States
Rachael Gagner
￥24,034
￥30,335 total
includes taxes & fees
Sep 24 - Sep 25
The Farmington Inn & Suites
BBQ/picnic area
Restaurant
View from property
Exterior

7. Residence Inn by Marriott Hartford Avon

Residence Inn by Marriott Hartford Avon
Avon
United States
Laura
￥22,284
￥25,626 total
includes taxes & fees
Sep 27 - Sep 28
Residence Inn by Marriott Hartford Avon
Exterior
Exterior
Reception
Front of property

8. Simsbury 1820 House

Simsbury 1820 House
Simsbury Center
United States
Brian
￥29,320
￥36,394 total
includes taxes & fees
Sep 21 - Sep 22
Simsbury 1820 House
Exterior
Breakfast area
Pool
Spa

9. Hampton Inn & Suites Hartford/Farmington

Hampton Inn & Suites Hartford/Farmington
Farmington
United States
Nancy
￥24,605
￥28,296 total
includes taxes & fees
Oct 4 - Oct 5
Hampton Inn & Suites Hartford/Farmington
Room
Property amenity
Lobby
Exterior

10. Extended Stay America Suites Hartford Farmington

Extended Stay America Suites Hartford Farmington
Farmington
Canada
MUHAMMAD
￥17,861
￥20,540 total
includes taxes & fees
Sep 20 - Sep 21
Extended Stay America Suites Hartford Farmington
Banquet hall
Meeting facility
Lobby sitting area
Lobby sitting area

11. Avon Old Farms Hotel

Avon Old Farms Hotel
Avon
United States
Andrew
￥29,890
￥37,763 total
includes taxes & fees
Sep 28 - Sep 29
Avon Old Farms Hotel
Property entrance
Interior
Interior
Restaurant

12. Truman Gillet House Bed & Breakfast

Truman Gillet House Bed & Breakfast
Granby
United States
Melanie
￥21,718
￥24,107 total
includes taxes & fees
Sep 28 - Sep 29
Truman Gillet House Bed & Breakfast
Garden
View from property
Indoor pool
Reception hall

13. Simsbury Inn

Simsbury Inn
Simsbury Center
United States
Kristen
￥44,105
￥54,111 total
includes taxes & fees
Sep 29 - Sep 30
Simsbury Inn
Front of property
Luxury Suite, 1 King Bed, Balcony, Garden View | Living area
Front of property
Interior detail

14. Manor House Inn

Manor House Inn
Norfolk
United States
Kevin
￥47,465
￥52,687 total
includes taxes & fees
Sep 23 - Sep 24
Manor House Inn
Double Room, Smoking
Double Room, Smoking
Front of property - evening/night
Bathroom

15. PLYMOUTH MOTOR LODGE

PLYMOUTH MOTOR LODGE
Terryville
United States
SEMORA
￥12,657
￥14,556 total
includes taxes & fees
Oct 4 - Oct 5
PLYMOUTH MOTOR LODGE
Restaurant
Terrace/patio
Rooftop terrace
Suite (Chamber)

16. The Abner Hotel

The Abner Hotel
Litchfield Historic District
United States
Ann S
￥31,414
￥36,127 total
includes taxes & fees
Sep 23 - Sep 24
The Abner Hotel
Exterior
Pool
Lobby
Room

17. Homewood Suites by Hilton Hartford-Farmington

Homewood Suites by Hilton Hartford-Farmington
Farmington
United States
John
￥25,736
￥29,597 total
includes taxes & fees
Oct 4 - Oct 5
Homewood Suites by Hilton Hartford-Farmington
Terrace/patio
Reception
Lobby
Pool

18. DoubleTree by Hilton Hotel Bristol, Connecticut

DoubleTree by Hilton Hotel Bristol, Connecticut
Bristol
United States
DARRON
￥25,314
￥29,111 total
includes taxes & fees
Oct 15 - Oct 16
DoubleTree by Hilton Hotel Bristol, Connecticut
Porch
Bar (on property)
Cottage, Lakeside | Terrace/patio
Penthouse (Penthouse Suite)

19. Interlaken Inn & Resort

Interlaken Inn & Resort
Lakeville
United States
Stacie
￥29,880
￥34,362 total
includes taxes & fees
Oct 18 - Oct 19
Interlaken Inn & Resort
Garden
Standard Double Room, 1 Queen Bed
Living area
Executive House, Multiple Beds | Living area

20. Sunny Peace Homestay

Sunny Peace Homestay
Harwinton
United States
Dean
￥20,245
￥32,202 total
includes taxes & fees
Sep 21 - Sep 22
Sunny Peace Homestay
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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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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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Platt Hill State Park

You can take time to visit Platt Hill State Park during your travels to 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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Northwestern Connecticut Community College Library

After visiting Northwestern Connecticut Community College Library, make a plan to see the other sights and activities in Winchester.
See properties

Top Winchester Hotel Reviews

The Litchfield Inn

The Litchfield Inn

10/10 Excellent
"second time staying here! wonderful place"
Ashley Beth 1-night trip
Posted 20 hours ago
The Litchfield Inn
Home2 Suites by Hilton Bristol

Home2 Suites by Hilton Bristol

10/10 Excellent
"Great stay. We will be back!"
Denise 1-night trip
Posted 2 days ago
Home2 Suites by Hilton Bristol
Sheraton Hartford Hotel at Bradley Airport

Sheraton Hartford Hotel at Bradley Airport

10/10 Excellent
"Amazing new hotel cool airport access great runway views good restaurant access couldn’t be better"
Laura 1-night trip
Posted 3 days ago
Sheraton Hartford Hotel at Bradley Airport
Mayflower Inn & Spa, Auberge Collection

Mayflower Inn & Spa, Auberge Collection

10/10 Excellent
"Everything was perfect—the room, the service, the restaurant, the spa; everything was perfect. An unforgettable experience."
Moshe 2-night trip
Posted 4 days ago
Mayflower Inn & Spa, Auberge Collection
Delamar West Hartford

Delamar West Hartford

10/10 Excellent
"Lovely, comfortable and clean room! Staff upon check-in (8pm) was helpful and friendly."
Aaron 1-night trip
Posted 5 days ago
Delamar West Hartford
DoubleTree by Hilton Hotel Bristol, Connecticut

DoubleTree by Hilton Hotel Bristol, Connecticut

8/10 Good
"It was good."
Ramone 1-night trip
Posted 6 days ago
DoubleTree by Hilton Hotel Bristol, Connecticut
Enjoy a restful stay with fast internet, smart TV and the company of your pet.

Enjoy a restful stay with fast internet, smart TV and the company of your pet.

10/10 Excellent
"Quaint very nice loved the space very cozy the hot tub was a nice touch I did use that a few times helped my sore back LOL everything went as expected I would stay here again"
paul 3-night trip
Posted 10 days ago
Enjoy a restful stay with fast internet, smart TV and the company of your pet.

More cheap stays in Winchester

Days Inn by Wyndham Torrington

Days Inn by Wyndham Torrington

492 East Main St Torrington CT
￥13,682
￥15,735 total
Oct 18 - Oct 19
includes taxes & fees
7.4/10 Good! (1,008 reviews)
Days Inn by Wyndham Torrington
Extended Stay America Suites Hartford Farmington

Extended Stay America Suites Hartford Farmington

1 Batterson Park Rd Farmington CT
￥17,861
￥20,540 total
Sep 20 - Sep 21
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
￥20,165
￥23,190 total
Sep 21 - Sep 22
includes taxes & fees
5.6/10 (821 reviews)
Americas Best Value Inn Torrington CT
Hitching Post Country Motel

Hitching Post Country Motel

45 Kent Rd S Cornwall Bridge CT
￥20,167
￥23,192 total
Sep 20 - Sep 21
includes taxes & fees
6.6/10 (110 reviews)
Hitching Post Country Motel
Hampton Inn & Suites Hartford/Farmington

Hampton Inn & Suites Hartford/Farmington

301 Colt Hwy Farmington CT
￥24,605
￥28,296 total
Oct 4 - Oct 5
includes taxes & fees
9/10 Wonderful! (1,000 reviews)
Hampton Inn & Suites Hartford/Farmington
The Millerton Inn

The Millerton Inn

53 Main St Millerton NY
￥37,672
￥42,618 total
Oct 18 - Oct 19
includes taxes & fees
8.4/10 Very Good! (38 reviews)
The Millerton Inn

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 Extended Stay America Suites Hartford Farmington and Delamar West Hartford. 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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