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Our top choices for Winchester hotels

Locust Tree Bed and Breakfast LLC

Locust Tree Bed and Breakfast LLC
3.0 star property
East Canaan
9.0 out of 10, Wonderful, (416 reviews)
"Clean, good breakfast, friendly staff"
United States
Debra
The price is £90
includes taxes & fees
28 Apr - 29 Apr
Locust Tree Bed and Breakfast LLC

Truman Gillet House Bed & Breakfast

Truman Gillet House Bed & Breakfast
3.0 star property
Granby
9.6 out of 10, Exceptional, (105 reviews)
"Room was spotless and hospitality was outstanding. Had great breakfast and was very welcoming. "
United States
Desiree
The price is £115
includes taxes & fees
27 Apr - 28 Apr
Truman Gillet House Bed & Breakfast

Wilder House Berkshires

Wilder House Berkshires
2.0 star property
Sheffield
9.8 out of 10, Exceptional, (45 reviews)
"Clean, cute, private, nice location. Breakfast was wonderful. Great value as well. Would definitely go back. "
United States
Kristinna
The price is £123
includes taxes & fees
26 Apr - 27 Apr
Wilder House Berkshires

Home2 Suites by Hilton Bristol

Home2 Suites by Hilton Bristol
3.0 star property
Bristol
9.6 out of 10, Exceptional, (214 reviews)
"Great place for a quick family getaway!!"
United States
Rosemary
The price is £119
includes taxes & fees
30 Apr - 1 May
Home2 Suites by Hilton Bristol

Days Inn by Wyndham Torrington

Days Inn by Wyndham Torrington
2.0 star property
Torrington
7.4 out of 10, Good, (1,000 reviews)
"Parking was great, staff very helpful, and the room was really clean. "
United States
Enrisa
The price is £80
includes taxes & fees
25 May - 26 May
Days Inn by Wyndham Torrington

PLYMOUTH MOTOR LODGE

PLYMOUTH MOTOR LODGE
2.5 star property
Terryville
7.6 out of 10, Good, (187 reviews)
"Staff was very rude.The owner was very rude.We'll never stay there again"
United States
Jeff
The price is £66
includes taxes & fees
10 May - 11 May
PLYMOUTH MOTOR LODGE

Blackberry River Inn

Blackberry River Inn
3.0 star property
Norfolk
9.4 out of 10, Exceptional, (173 reviews)
"Charming, quiet, clean very clean with a beautiful dining room for breakfast and very respectful service."
United States
Mara
The price is £122
includes taxes & fees
26 Apr - 27 Apr
Blackberry River Inn

The Millerton Inn

The Millerton Inn
2.0 star property
Millerton
8.4 out of 10, Very good, (18 reviews)
"Nice staff, great restaurant at the inn. Very cute town. "
United States
Valerie
The price is £194
includes taxes & fees
28 Apr - 29 Apr
The Millerton Inn

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 £111
includes taxes & fees
25 Apr - 26 Apr
Hitching Post Country Motel

Gedney Farm

Gedney Farm
3.5 star property
Great Barrington
9.4 out of 10, Exceptional, (136 reviews)
"Beautiful property and rooms."
United States
Kara
The price is £120
includes taxes & fees
17 May - 18 May
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
The price is £542
includes taxes & fees
27 Apr - 28 Apr
Mayflower Inn & Spa, Auberge Collection

The Farmington Inn & Suites

The Farmington Inn & Suites
3.0 star property
Farmington
8.8 out of 10, Excellent, (1,004 reviews)
"Lovely stay!"
United States
Ilana
The price is £128
includes taxes & fees
5 May - 6 May
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)
"Beautiful spot! Very clean ❤️"
Canada
Peggy
The price is £96
includes taxes & fees
26 Apr - 27 Apr
Extended Stay America Suites Hartford Farmington

Cornwall Inn and Lodge

Cornwall Inn and Lodge
3.0 star property
Cornwall Bridge
9.2 out of 10, Wonderful, (158 reviews)
"We stay here frequently…always super clean and the inn keepers are very kind."
United States
Tracy
The price is £180
includes taxes & fees
25 Apr - 26 Apr
Cornwall Inn and Lodge

The Abner Hotel

The Abner Hotel
3.0 star property
Litchfield Historic District
9.4 out of 10, Exceptional, (58 reviews)
"This hotel was absolutely beautiful, the staff was so helpful and attentive. We will definitely be back on our next stay in Litchfield. "
United States
Jessica
The price is £266
includes taxes & fees
30 Apr - 1 May
The Abner Hotel

Hampton Inn & Suites Hartford/Farmington

Hampton Inn & Suites Hartford/Farmington
2.5 star property
Farmington
8.8 out of 10, Excellent, (1,003 reviews)
"Clean room, friendly staff and quiet grounds."
United States
shaneice
The price is £113
includes taxes & fees
25 May - 26 May
Hampton Inn & Suites Hartford/Farmington

9 Academy

9 Academy
4.0 star property
Salisbury
9.2 out of 10, Wonderful, (12 reviews)
"Extremely clean and the rooms are beautifully decorated with warm minimal decor. We will definitely be back!"
United States
Gina
The price is £468
includes taxes & fees
25 Apr - 26 Apr
9 Academy

Dainty New Preston Cottage w/ Dock & Lake Views!

Dainty New Preston Cottage w/ Dock & Lake Views!
3.0 star property
New Preston
The price is £383
includes taxes & fees
27 Apr - 28 Apr
Dainty New Preston Cottage w/ Dock & Lake Views!

Simsbury 1820 House

Simsbury 1820 House
4.0 star property
Simsbury Center
9.2 out of 10, Wonderful, (1,000 reviews)
"The stay was great, very accommodating staff, quaint rooms and lounge area!"
United States
Cathy
The price is £161
includes taxes & fees
30 Apr - 1 May
Simsbury 1820 House

Fairfield Inn & Suites by Marriott Plainville

Fairfield Inn & Suites by Marriott Plainville
3.0 star property
Plainville
8.6 out of 10, Excellent, (963 reviews)
"Average clean rooms, pool small, pizza Resterant good. Staff great at hotel and Resterant. "
United States
Kellie
The price is £93
includes taxes & fees
25 May - 26 May
Fairfield Inn & Suites by Marriott Plainville
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 £66 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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