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Vacation Homes in Winchester

Brackett Cottage
Beach

Brackett Cottage

3.5 star property
Brackett Cottage
Riverview
Exterior

Riverview

3.5 star property
Riverview
Rockmere Inn
House (Rockmere Inn) | Exterior

Rockmere Inn

3.5 star property
Rockmere Inn
Seacity View
House (SeaCity View) | Exterior

Seacity View

2.0 star property
Seacity View
Hollyhock House
House (Hollyhock House) | Exterior

Hollyhock House

3.0 star property
10.0 out of 10, Exceptional, (1)
"Muy cómoda la casita, solamente tiene baño y medio pero el baño completo tiene buen espacio"
Hollyhock House
Sailors Rest
House (Sailors Rest) | Exterior

Sailors Rest

2.0 star property
Sailors Rest
Marblehead Oasis 3 Bedroom Townhouse by RedAwning
Townhome, 3 Bedrooms | Property grounds

Marblehead Oasis 3 Bedroom Townhouse by RedAwning

3.0 star property
10.0 out of 10, Exceptional, (1)
"Nice quiet neighborhood. Seemed newly remodeled. Only negatives are dishwasher is not bolted in and started coming out of its spot when I tried opening it. Also if you struggle with stairs this is not a good place for you. Stairs are very steep. "
Marblehead Oasis 3 Bedroom Townhouse by RedAwning
Broom & Board
Apartment (Broom & Board) | Exterior

Broom & Board

3.5 star property
10.0 out of 10, Exceptional, (1)
"Great stay highly recommended!"
Broom & Board
Riverside Retreat
House (Riverside Retreat) | Beach

Riverside Retreat

3.5 star property
Riverside Retreat
Rockcleft
House (Rockcleft) | Exterior

Rockcleft

2.0 star property
Rockcleft
Kings Rook
Condo | Private kitchen | Fridge, microwave, dishwasher, coffee/tea maker

Kings Rook

3.5 star property
Kings Rook
Blue Hour
House (Blue Hour) | Exterior

Blue Hour

2.0 star property
6.0 out of 10, (1)
"The property itself was beautiful but it was not stocked well. One roll of toilet tissue, One roll of paper towels, not baggies, etc and not a dish cloth in sight to even wipe the counter tops. We had 5 people and I had to call for the extra linens that I paid for and then I trip tried to bill me for more money in an email and also put a charge on my cc after they sent me emails that I paid in full,which they had to refund. It was very disorganized."
Blue Hour
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

Encore Boston Harbor

Encore Boston Harbor

10/10 Excellent
"CLASS is the key word for the hotel. Everything was thought about. From the bathroom’s accessories to the slippers beside the bed, nothing was forgotten. "
Patrick 2-night trip
Posted 9 hours ago
Encore Boston Harbor