Search Guest Houses in Winchester from CA $207

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Check prices for these dates

Next weekend
Aug 22 - Aug 24
In two weeks
Aug 29 - Aug 31
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Sep 12 - Sep 14
In two months
Oct 10 - Oct 12

Browse Select Winchester Guest Houses

The Jefferson Guest House, Spacious, Special Views
1 bedroom, desk, iron/ironing board, WiFi

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 $457 total
includes taxes & fees
Aug 19 - Aug 20
The Jefferson Guest House, Spacious, Special Views
A European Country Getaway ~ 1930s Stone Cottage In Connecticut!
Exterior detail

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

10.0 out of 10, Exceptional, (88)
"Enjoyed staying"
The price is CA $207
CA $371 total
includes taxes & fees
Aug 24 - Aug 25
A European Country Getaway ~ 1930s Stone Cottage In Connecticut!
A Homey Heaven - Modern, Pet-Friendly, Gaming, Full Kitchen and more.
Interior

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 $516 total
includes taxes & fees
Sep 8 - Sep 9
A Homey Heaven - Modern, Pet-Friendly, Gaming, Full Kitchen and more.
9 Academy
The Parlor Suite

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 $760
CA $874 total
includes taxes & fees
Sep 7 - Sep 8
9 Academy
The Farmington Guest House
Fridge, microwave, oven, stovetop

The Farmington Guest House

9.4 out of 10, Exceptional, (10)
"Clean, easy process, quiet, great central location. Right on the river so my pup and I frequented the trails down to the river for a number of beautiful walks. Off street parking is always a great amenity as well."
The Farmington Guest House
53 Geary Ave
Private kitchen

53 Geary Ave

2.0 star property
53 Geary Ave
Guest Suite with Scenic View & Private Patio in Central Location
1 bedroom, desk, iron/ironing board, free WiFi

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

Avon Old Farms Hotel

Avon Old Farms Hotel

10/10 Excellent
"very nice property. friendly and helpful staff."
james 1-night trip
Posted 3 days ago
Avon Old Farms Hotel