Find hotels in Winchester, CT from CA $119

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Our top choices for Winchester hotels

Truman Gillet House Bed & Breakfast

Truman Gillet House Bed & Breakfast
3.0 star property
Granby
9.6 out of 10, Exceptional, (104 reviews)
"Room was spotless and hospitality was outstanding. Had great breakfast and was very welcoming. "
United States
Desiree
The price is CA $192
CA $213 total
includes taxes & fees
Mar 24 - Mar 25
Truman Gillet House Bed & Breakfast

Locust Tree Bed and Breakfast LLC

Locust Tree Bed and Breakfast LLC
3.0 star property
East Canaan
9.0 out of 10, Wonderful, (415 reviews)
"Great breakfast! Had a wonderful stay!"
United States
Michelle
The price is CA $144
CA $166 total
includes taxes & fees
Mar 24 - Mar 25
Locust Tree Bed and Breakfast LLC

Home2 Suites by Hilton Bristol

Home2 Suites by Hilton Bristol
3.0 star property
Bristol
9.6 out of 10, Exceptional, (202 reviews)
"Great place good people decent breakfast great room service "
United States
JULES
The price is CA $178
CA $205 total
includes taxes & fees
Apr 2 - Apr 3
Home2 Suites by Hilton Bristol

Wilder House Berkshires

Wilder House Berkshires
2.0 star property
Sheffield
9.8 out of 10, Exceptional, (43 reviews)
"Clean, cute, private, nice location. Breakfast was wonderful. Great value as well. Would definitely go back. "
United States
Kristinna
The price is CA $205
CA $230 total
includes taxes & fees
Mar 29 - Mar 30
Wilder House Berkshires

Days Inn by Wyndham Torrington

Days Inn by Wyndham Torrington
2.0 star property
Torrington
7.4 out of 10, Good, (1,001 reviews)
"Staff was very attentive to my needs. I required support on two occasions during the length of my stay and they took care of the problem immediately. "
United States
Michele
The price is CA $115
CA $133 total
includes taxes & fees
Mar 29 - Mar 30
Days Inn by Wyndham Torrington

Blackberry River Inn

Blackberry River Inn
3.0 star property
Norfolk
9.4 out of 10, Exceptional, (171 reviews)
"Courteous welcoming staff, amazing breakfast, and restful stay, highly recommend."
United States
Paulina
The price is CA $197
CA $227 total
includes taxes & fees
Mar 25 - Mar 26
Blackberry River Inn

The Millerton Inn

The Millerton Inn
2.0 star property
Millerton
8.4 out of 10, Very good, (18 reviews)
"Perfect "
United States
Zhigang
The price is CA $212
CA $240 total
includes taxes & fees
Mar 29 - Mar 30
The Millerton Inn

PLYMOUTH MOTOR LODGE

PLYMOUTH MOTOR LODGE
2.5 star property
Terryville
7.8 out of 10, Good, (183 reviews)
"Nice amount of space"
United States
Amanda
The price is CA $103
CA $119 total
includes taxes & fees
Mar 30 - Mar 31
PLYMOUTH MOTOR LODGE

The Abner Hotel

The Abner Hotel
3.0 star property
Litchfield Historic District
9.4 out of 10, Exceptional, (55 reviews)
"My stay was flawless. From staff to the clean room and comfortable bedding all made for an amazing experience."
United States
Francis
The price is CA $364
CA $418 total
includes taxes & fees
Mar 24 - Mar 25
The Abner Hotel

The Farmington Inn & Suites

The Farmington Inn & Suites
3.0 star property
Farmington
8.8 out of 10, Excellent, (1,005 reviews)
"Lovely stay!"
United States
Ilana
The price is CA $169
CA $218 total
includes taxes & fees
Apr 1 - Apr 2
The Farmington Inn & Suites

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)
"Feels like home ! Great experience! "
United States
Yong
The price is CA $141
CA $162 total
includes taxes & fees
Mar 31 - Apr 1
Extended Stay America Suites Hartford Farmington

Fairfield Inn & Suites by Marriott Plainville

Fairfield Inn & Suites by Marriott Plainville
3.0 star property
Plainville
8.6 out of 10, Excellent, (950 reviews)
"Average clean rooms, pool small, pizza Resterant good. Staff great at hotel and Resterant. "
United States
Kellie
The price is CA $134
CA $155 total
includes taxes & fees
Mar 29 - Mar 30
Fairfield Inn & Suites by Marriott Plainville

Simsbury 1820 House

Simsbury 1820 House
4.0 star property
Simsbury Center
9.2 out of 10, Wonderful, (1,001 reviews)
"The stay was great, very accommodating staff, quaint rooms and lounge area!"
United States
Cathy
The price is CA $218
CA $275 total
includes taxes & fees
Mar 24 - Mar 25
Simsbury 1820 House

Cornwall Inn and Lodge

Cornwall Inn and Lodge
3.0 star property
Cornwall Bridge
9.2 out of 10, Wonderful, (157 reviews)
"We stay here frequently…always super clean and the inn keepers are very kind."
United States
Tracy
The price is CA $290
CA $334 total
includes taxes & fees
Mar 24 - Mar 25
Cornwall Inn and Lodge

Hitching Post Country Motel

Hitching Post Country Motel
2.5 star property
Cornwall Bridge
6.6 out of 10, (83 reviews)
"Checkin was easy, room was clean and comfortable "
United States
Greg
The price is CA $178
CA $205 total
includes taxes & fees
Mar 24 - Mar 25
Hitching Post Country Motel

Hampton Inn & Suites Hartford/Farmington

Hampton Inn & Suites Hartford/Farmington
2.5 star property
Farmington
8.8 out of 10, Excellent, (1,005 reviews)
"Clean , quiet and friendly staff !! Excellent stay "
United States
Theresa
The price is CA $168
CA $193 total
includes taxes & fees
Apr 11 - Apr 12
Hampton Inn & Suites Hartford/Farmington

Interlaken Inn & Resort

Interlaken Inn & Resort
3.5 star property
Lakeville
8.2 out of 10, Very good, (289 reviews)
"The restaurant, food and wait staff were fab!!! "
United States
Jacqueline
The price is CA $246
CA $283 total
includes taxes & fees
Mar 24 - Mar 25
Interlaken Inn & Resort

Gedney Farm

Gedney Farm
3.5 star property
Great Barrington
9.4 out of 10, Exceptional, (136 reviews)
"We loved our stay at Gedney. Michael was a sweetheart, and the grounds are GORGEOUS. We loved our room with fireplace - the whole setting is just country and updated/old. For anyone who loves farms and barns and rustic, this is for you. Can't wait to return."
United States
Lynda
The price is CA $255
CA $279 total
includes taxes & fees
Mar 24 - Mar 25
Gedney Farm

Mayflower Inn & Spa, Auberge Collection

Mayflower Inn & Spa, Auberge Collection
5.0 star property
Washington
9.4 out of 10, Exceptional, (59 reviews)
"Clean room "
United States
Casey
Mayflower Inn & Spa, Auberge Collection

The White Hart

The White Hart
4.0 star property
Salisbury
9.8 out of 10, Exceptional, (147 reviews)
"Such a cozy, authentic New England hotel, with all its charm. "
United States
Maulik
The price is CA $343
CA $394 total
includes taxes & fees
Mar 24 - Mar 25
The White Hart
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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Frequently asked questions

What is the best area to stay in Winchester?
The best area to stay in Winchester, Connecticut, is the town centre, particularly around Main Street and the historic district.

This area offers a blend of convenience and local character. Main Street is where you'll find most of the town's shops, local eateries, and services. The historic district, just a short walk from Main Street, features well-preserved architecture and a quieter, more residential feel.

Couples often enjoy the town centre for its relaxed pace and access to local dining. You can easily stroll to a nice restaurant for an evening meal or explore the small independent shops during the day. The proximity to scenic drives around the Litchfield Hills also makes it a good base for day trips.

For those looking for a peaceful retreat, the areas slightly outside the immediate town centre, but still within Winchester, offer a tranquil experience.
When is the best time to go to Winchester?
The best time to visit Winchester, Connecticut, is during the autumn months, particularly from late September to late October.

This period offers pleasant weather with cooler temperatures and significantly less humidity, making it ideal for outdoor activities and exploring the natural beauty of the Litchfield Hills. The main draw during these months is the spectacular fall foliage, where the trees transform into a vibrant display of reds, oranges, and yellows. It's a truly picturesque time to be in New England.

Couples looking for a romantic getaway will find the autumn particularly appealing. You can enjoy scenic drives along winding country roads, visit local farms for apple picking, or explore the many hiking trails in the surrounding state parks, such as Burr Pond State Park, which is just a short drive away. The crisp air and stunning scenery create a memorable backdrop for a relaxing break.

Solo travellers who appreciate nature and a quieter pace will also find autumn to be an excellent choice. The cooler weather is great for long walks or cycling excursions without the summer crowds.
Can I cancel my hotel reservation on Expedia?
You can cancel your hotel reservation on Expedia, though it depends on the cancellation policy of your booking. Most bookings are refundable if canceled within 24-48 hours of the scheduled arrival. Be sure to check your booking confirmation for the exact cancellation policy. If free cancellation is available, you can cancel directly through your Expedia account by logging in, going to "My Trips", and selecting your reservation. To find flexible deals, filter your search by "Fully refundable property" for hotels in Winchester.
How can I save on a Winchester hotel booking with Expedia?
Members always get our best prices. Find our best Winchester hotel deals by joining Expedia's free travel rewards program today. As a member, you can unlock instant savings and member perks when you're logged in to your account. Another tip is to book your hotel and flights together on Expedia, where bundling can result in significant savings.
How much is the nightly rate at a Winchester hotel?
Prices for hotels in Winchester often vary, but you can find a great deal from CA $119 on Expedia. All sorts of factors affect price, such as the time of year or the days of the week you choose for your stay. Find the best deals by being flexible with your dates, and sort search results by "Price: low to high" for the cheapest rate.

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