Search Guest Houses in Winchester
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Guest Houses in Winchester
Copley House
Back Bay
9.0 out of 10, Wonderful, (1924)
"Fantastic place to stay and visit Boston."
Poorvajan
Oasis Guest House
Fenway–Kenmore
9.4 out of 10, Exceptional, (1390)
"Lovely stay!
"
Hilary
Clarendon Square
South End
9.2 out of 10, Wonderful, (249)
"In a word: charming"
David
The price is SAR 1,171
SAR 1,414 total
includes taxes & fees
9 Dec - 10 Dec
Beacon Inn 1087
Longwood
8.0 out of 10, Very Good, (779)
"Staff was the best, led me directly to where to park and upgraded me to another room available. The room was extremely spacious with a nice tv and fireplace. The property appears to be a former home divided and has a very homely feel. Stayed one night to attend an event nearby, and was able to leave my car to take public transit to and from the event. "
Kyle
The price is SAR 390
SAR 435 total
includes taxes & fees
17 Dec - 18 Dec
Beacon Inn 1750
Brookline
7.4 out of 10, Good, (758)
"A little older but great location and very nice staff. "
Marc
The price is SAR 390
SAR 435 total
includes taxes & fees
17 Dec - 18 Dec
Coolidge Corner Guest House
Coolidge Corner South Side
8.2 out of 10, Very Good, (625)
"Very pleasant, comfortable stay. "
Valerie
The price is SAR 470
SAR 525 total
includes taxes & fees
1 Jan - 2 January 2026
Tranquil House in Cambridge
Strawberry Hill
8.8 out of 10, Excellent, (159)
"yes, nice and quiet kitchen was nice. "
Sean
The price is SAR 357
SAR 408 total
includes taxes & fees
9 Dec - 10 Dec
The Inn on the Horse Farm
Sudbury
8.0 out of 10, Very Good, (266)
"Great area, historic. Near restaurants. Able to wander the property. Nice to relax before our journey home."
David
The price is SAR 547
SAR 611 total
includes taxes & fees
8 Jan - 9 January 2026
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.
Top Winchester Hotel Reviews
citizenM Boston North Station
10/10 Excellent
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