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Our top choices for Winchester vacation homes
3BR pet-friendly Quincy house w/parking — near Adams Park
3BR pet-friendly Quincy house w/parking — near Adams ParkQuincy
9.8 out of 10, Exceptional, (49 reviews)
"very clean. comfortable beds. Very nice stay."
Stefanie K.
The price is AED 753
AED 1,485 total
includes taxes & fees
5 May - 6 May
2BR Historic Marblehead Home+Minutes to Beach
2BR Historic Marblehead Home+Minutes to BeachMarblehead Historic District
10.0 out of 10, Exceptional, (20 reviews)
"Enjoyed our stay. "
Mary D.
The price is AED 415
AED 1,366 total
includes taxes & fees
13 May - 14 May
Modern Boston Stay, Full-Sized Kitchen, Electric Sauna, Added Driveway Parking
Modern Boston Stay, Full-Sized Kitchen, Electric Sauna, Added Driveway ParkingDorchester
8.8 out of 10, Excellent, (3 reviews)
"Easy check-in, and the host was available to assist with any needs. Space was nice and cozy. Also, the view from the top floor was pretty dope. Will definitely book again."
Breshan B.
The price is AED 465
AED 754 total
includes taxes & fees
14 May - 15 May
3BR3Bth Entire House/Steps to Downtown & TD Garden
3BR3Bth Entire House/Steps to Downtown & TD GardenNorth End
10.0 out of 10, Exceptional, (10 reviews)
"This place is so cool! Was incredibly clean, updated and offered all the amenities you need for a weekend get away. The location is wonderful as well with lots of markets, bakeries and restaurants all within walking distance. This is a must stay! "
mary j.
The price is AED 992
AED 2,267 total
includes taxes & fees
13 May - 14 May
Cozy three-bedroom home close to Boston w/ plenty of parking
Cozy three-bedroom home close to Boston w/ plenty of parkingNorth Braintree
10.0 out of 10, Exceptional, (47 reviews)
"The house was just what we needed and the stay was super simple. "
Chris B.
The price is AED 694
AED 1,600 total
includes taxes & fees
3 May - 4 May
Anchors Away Inn 2 Br Apt 1 min walk to the Beach King & Queen
Anchors Away Inn 2 Br Apt 1 min walk to the Beach King & QueenBayside
9.8 out of 10, Exceptional, (15 reviews)
"Great property, clean, close to a baseball field which we loved. Super close to a beautiful beach that our kids enjoyed skim boarding and swimming in. "
Candice C.
The price is AED 658
AED 1,543 total
includes taxes & fees
12 May - 13 May
Renovated Beach House Close to Everything, Minutes to Boston
Renovated Beach House Close to Everything, Minutes to BostonQuincy
9.4 out of 10, Exceptional, (108 reviews)
"Great location, description was on point, and the communication with the owner was excellent. Would definitely stay here again. "
Don T.
The price is AED 628
AED 1,469 total
includes taxes & fees
3 May - 4 May
PEACEFUL CHARM - Humble Luxury minutes from Boston, Beach & Casino
PEACEFUL CHARM - Humble Luxury minutes from Boston, Beach & CasinoEverett
9.2 out of 10, Wonderful, (5 reviews)
"This is a fantastic home with a lot of amenities. Barry, the host, was awesome to work with and went above and beyond to make our stay perfect. "
Deanna K.
The price is AED 689
AED 1,247 total
includes taxes & fees
4 May - 5 May
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
Club Quarters Hotel Faneuil Hall, Boston
10/10 Excellent
