Search Guest Houses in Winchester from CA $207

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Browse Select Winchester Guest Houses

A Homey Heaven - Modern, Pet-Friendly, Gaming, Full Kitchen and more.

9.6 out of 10, Exceptional, (10)
"It's a fun, funky little place, that had everything we needed. "
The price is CA $262
CA $544 total
includes taxes & fees
Aug 4 - Aug 5
A Homey Heaven - Modern, Pet-Friendly, Gaming, Full Kitchen and more.

A European Country Getaway ~ 1930s Stone Cottage In Connecticut!

10.0 out of 10, Exceptional, (88)
"Enjoyed staying"
The price is CA $207
CA $365 total
includes taxes & fees
Aug 12 - Aug 13
A European Country Getaway ~ 1930s Stone Cottage In Connecticut!

The Jefferson Guest House, Spacious, Special Views

10.0 out of 10, Exceptional, (6)
"I stayed here for four nights, including one with my son, and it was fantastic.Everything is brand new, clean, and beautifully appointed, with every amenity you could want."
The price is CA $345
CA $456 total
includes taxes & fees
Aug 4 - Aug 5
The Jefferson Guest House, Spacious, Special Views

9 Academy

4.0 star property
9.6 out of 10, Exceptional, (5)
"The Loft was so beautifully decorated and every detail was perfect. "
The price is CA $775
CA $892 total
includes taxes & fees
Aug 11 - Aug 12
9 Academy

53 Geary Ave

2.0 star property
53 Geary Ave

Guest Suite with Scenic View & Private Patio in Central Location

Guest Suite with Scenic View & Private Patio in Central Location
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