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Compare 16 Guest Houses in Winchester with updated reviews, rates, and availability.

Copley House
Property entrance

Copley House

3.0 star property
8.8 out of 10, Excellent, (1506)
"Great stay! Great location! Great atmosphere!"
The price is SAR 695
SAR 799 total
includes taxes & fees
23 Dec - 24 Dec
Copley House
Oasis Guest House
Room

Oasis Guest House

2.5 star property
9.4 out of 10, Exceptional, (1129)
"The room was spacious. The staff was friendly & helpful"
The price is SAR 390
SAR 449 total
includes taxes & fees
25 Dec - 26 Dec
Oasis Guest House
Beacon Inn 1087
Exterior

Beacon Inn 1087

2.5 star property
7.8 out of 10, Good, (674)
"Thanks for another great stay"
The price is SAR 410
SAR 458 total
includes taxes & fees
23 Dec - 24 Dec
Beacon Inn 1087
The Inn on the Horse Farm
Property grounds

The Inn on the Horse Farm

3.0 star property
8.0 out of 10, Very Good, (242)
"This is our second Thanksgiving staying here. We love the homey decor, comfortable rooms and quiet of the inn. Thank you!"
The price is SAR 595
SAR 665 total
includes taxes & fees
12 Jan - 13 January 2025
The Inn on the Horse Farm
A Tranquil House In Cambridge
Front of property

A Tranquil House In Cambridge

3.0 star property
8.8 out of 10, Excellent, (136)
"The house was indeed tranquil and very clean. It included parking and was relatively convenient for our planned outing in Cambridge and our trip to the airport the next morning. The room was quite small, but the shared bathroom was convenient and clean. Before arriving, we received an email from the property informing us that check-in time would be 2 pm, but when we arrived a few minutes before 4 pm, we were informed that we could not enter until 4 (ultimately we got in a few minutes after 4)."
The price is SAR 334
SAR 383 total
includes taxes & fees
23 Dec - 24 Dec
A Tranquil House In Cambridge
Coolidge Corner Guest House
Lobby sitting area

Coolidge Corner Guest House

3.5 star property
8.2 out of 10, Very Good, (599)
"Lovely room, great location."
The price is SAR 447
SAR 499 total
includes taxes & fees
23 Dec - 24 Dec
Coolidge Corner Guest House
Davis Square Inn
Exterior

Davis Square Inn

3.0 star property
9.6 out of 10, Exceptional, (55)
"Great location and fantastic home with great amenities."
Davis Square Inn
Beacon Inn 1750
Exterior

Beacon Inn 1750

3.0 star property
7.4 out of 10, Good, (682)
"Great place to stay but they need to let you know that there is no elevator. I'm to old to climb 3 floors every time I come and go."
The price is SAR 410
SAR 458 total
includes taxes & fees
23 Dec - 24 Dec
Beacon Inn 1750
Your Perfect Getaway Awaits: 15 mins to Boston!
Room

Your Perfect Getaway Awaits: 15 mins to Boston!

9.4 out of 10, Exceptional, (13)
"Staying at The Adelaide Guest house was very cozy and a quiet neighborhood. Host was very friendly and accommodating. We would definitely come back again!"
Your Perfect Getaway Awaits: 15 mins to Boston!
Copley House - 1 Bedroom Suite
Living area

Copley House - 1 Bedroom Suite

9.2 out of 10, Wonderful, (5)
"Great location! Really nice space. The only negative is it can get a little noisy late at night. Not too bad though. We’d definitely stay there again. "
Copley House - 1 Bedroom Suite
Clarendon Square
Property amenity

Clarendon Square

4.0 star property
9.2 out of 10, Wonderful, (238)
"We enjoyed a beautiful time in Boston with our home base being Clarendon square. Thank you Stephen for your family’s hospitality in a tremendously cozy home. We are already looking forward to next time 🙏"
Clarendon Square
Moroccan Boutique Guest House
Room

Moroccan Boutique Guest House

3.5 star property
9.2 out of 10, Wonderful, (121)
"This was one of the best Inn’s we’ve stayed in. Elizabeth was so pleasant and warm and the room was perfect. I couldn’t find a single thing that I would have changed or I was not happy with. She has everything you need and it was so comfortable. The area is safe and close to everything. "
Moroccan Boutique Guest House
ESJACPE GUEST HOUSE
Exterior

ESJACPE GUEST HOUSE

2.0 star property
3.2 out of 10, (15)
"Well, I didn't have big things to complaint about, other than the bathroom zinc, the cold and the hot water cannot mix together. In the zinc, each one located separately. I understand that's an old building, but they still can change certain things. "
The price is SAR 263
SAR 682 total
includes taxes & fees
23 Dec - 24 Dec
ESJACPE GUEST HOUSE
Private Furnished Rooms near Longwood Medical and Coolidge Corner
Rm 11: Private with queen bed, private bath, dresser, and work space:

Private Furnished Rooms near Longwood Medical and Coolidge Corner

Private Furnished Rooms near Longwood Medical and Coolidge Corner
Oakwood at 234 Newbury
Exterior

Oakwood at 234 Newbury

2.0 star property
Oakwood at 234 Newbury
Rooms in Family House in Salem Boston
Front of property

Rooms in Family House in Salem Boston

3.0 star property
8.0 out of 10, Very Good, (21)
"Very nice home, owners were very friendly. Wish we had known it was a home not a hotel prior to arriving. We were uncomfortable with the traditions of the house, not really sure what was acceptable or not."
Rooms in Family House in Salem Boston
Bedroom office free parking laundry wifi
Room

Bedroom office free parking laundry wifi

3.0 star property
Bedroom office free parking laundry wifi
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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Other property types in Winchester

Sleep up to 4 Guest New Apt. 10 mins to Boston Easy to I-93
Private kitchen

Sleep up to 4 Guest New Apt. 10 mins to Boston Easy to I-93

7.4 out of 10, Good, (30)
"I give this place 3 stars, its a nice place with a good amount of room but there are a few issues. Our stay was Monday - Friday, just 2 adults. Pros - lots of room. Cons - no ac. There is a portable ac unit on wheels in the bedroom however, the exhaust vent goes behind a curtain to the window but not outside. There is no way to open the window for the exhaust vent to take the hot air outside so it just pumps all the hot air back into the room. Be prepared to wake up at 7:30am every morning...
Sleep up to 4 Guest New Apt. 10 mins to Boston Easy to I-93
Sonder 907 Main
Room

Sonder 907 Main

4.0 star property
8.2 out of 10, Very Good, (405)
"Perfect location!"
The price is SAR 483
SAR 560 total
includes taxes & fees
23 Dec - 24 Dec
Sonder 907 Main
Maverick Suites at 28 Fenway
Lobby sitting area

Maverick Suites at 28 Fenway

3.0 star property
9.0 out of 10, Wonderful, (156)
"Great stay. "
The price is SAR 372
SAR 795 total
includes taxes & fees
24 Dec - 25 Dec
Maverick Suites at 28 Fenway
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.