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Next weekend
Oct 10 - Oct 12
In two weeks
Oct 17 - Oct 19
In one month
Oct 31 - Nov 2
In two months
Nov 28 - Nov 30

B&B in Winchester

Simsbury 1820 House
Front of property

Simsbury 1820 House

4.0 star property
9.2 out of 10, Wonderful, (994)
"Staff are super friendly and kind, the room is clean "
$178 nightly
The price is $205
Nov 2 - Nov 3
Total with taxes and fees
Simsbury 1820 House
Blackberry River Inn
Library

Blackberry River Inn

3.0 star property
9.4 out of 10, Exceptional, (136)
"Loved everything especially Lucas and Joe💟☮️"
$164 nightly
The price is $189
Oct 6 - Oct 7
Total with taxes and fees
Blackberry River Inn
Locust Tree Bed and Breakfast LLC
Terrace/patio

Locust Tree Bed and Breakfast LLC

3.0 star property
9.0 out of 10, Wonderful, (404)
"Peaceful area and great staff; Thank you for the service and experience "
$105 nightly
The price is $121
Oct 5 - Oct 6
Total with taxes and fees
Locust Tree Bed and Breakfast LLC
Wilder House Berkshires
Wilder House Berkshires Room 3 | 1 bedroom, premium bedding, individually decorated

Wilder House Berkshires

2.0 star property
9.8 out of 10, Exceptional, (35)
"Highly recommend this beautiful bed & breakfast! The room was wonderful and overlooked the property, the breakfast was delicious, and the hospitality was amazing. I had a fantastic stay, and will definitely stay at The Wilder House again when I'm in the area."
$165 nightly
The price is $185
Nov 2 - Nov 3
Total with taxes and fees
Wilder House Berkshires
Truman Gillet House Bed & Breakfast
Property grounds

Truman Gillet House Bed & Breakfast

3.0 star property
9.6 out of 10, Exceptional, (94)
"It was a lovely stay overnight with a delicious homemade breakfast. Very clean and hosts were so nice."
$140 nightly
The price is $155
Oct 6 - Oct 7
Total with taxes and fees
Truman Gillet House Bed & Breakfast
Sunny Peace Homestay
Exterior

Sunny Peace Homestay

2.0 star property
9.4 out of 10, Exceptional, (8)
"Angela is very respectful and generous to her guests."
Sunny Peace Homestay
Manor House Inn
Interior detail

Manor House Inn

3.0 star property
9.4 out of 10, Exceptional, (138)
"Excellent bed and breakfast, room was clean and comfortable."
$310 nightly
The price is $345
Oct 13 - Oct 14
Total with taxes and fees
Manor House Inn
Green Acres B&B
Seasonal outdoor pool

Green Acres B&B

3.0 star property
9.8 out of 10, Exceptional, (150)
"Gracious hosts, many amenities and the best breakfast!"
Green Acres B&B
Rock Hall Luxe Lodging
Outdoor pool

Rock Hall Luxe Lodging

4.5 star property
10.0 out of 10, Exceptional, (4)
Rock Hall Luxe Lodging
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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Top Winchester Hotel Reviews

Extended Stay America Suites Hartford Farmington

Extended Stay America Suites Hartford Farmington

10/10 Excellent
"The staff was welcoming and friendly. The clerk noticed that I had booked a handicap room, which I was unaware of, and upgraded me to a regular room without a problem. This location is excellent as it is right off the interstate, and easy access to shops nearby."
Stephen 4-night trip
Posted 20 hours ago
Extended Stay America Suites Hartford Farmington

Find out more about Winchester

Find out more about Winchester

Winchester B&B information

Number of reviews
1,776
Accommodation
9 B&B
Lowest Price
$121
Highest Price
$345

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