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Search results; Over 1,000 places in Winchester

Guest favourite
Flat in Woburn
Charming 1 BR private entrance apt commuters dream
1 bed
3–8 Jun
5.0 out of 5 average rating, 96 reviews
Flat in Woburn
New England Farm House
28 Apr – 3 May
4.52 out of 5 average rating, 361 reviews
Superhost
Room in Woburn
Stay with Dzung
Cozy stylish room in newly renovated apt
5–12 May
Guest favourite
Flat in Woburn
Comfy-Spacious-private 1BR conveniently located
2 beds
22–27 Apr
4.96 out of 5 average rating, 105 reviews
Room in Medford
Stay with EduardaHosting for 5 years,
Davis/ Arlington/ Somerville/ Winchester area
26 Apr – 1 May
4.78 out of 5 average rating, 37 reviews
Guest favourite
Flat in Stoneham
Entire guest suite in Stoneham
1 queen bed
14–19 Aug
4.88 out of 5 average rating, 134 reviews
Flat in Woburn
Renovated Enormous 3 Bedroom
3 beds
27 Apr – 2 May
4.65 out of 5 average rating, 26 reviews
Guest favourite
Flat in Medford
Garden Apartment for Vacation & Business Travelers
2 beds
2–7 Jun
4.92 out of 5 average rating, 258 reviews
Guest favourite
Room in Somerville
Stay with Ameziane
Cozy & Clean Private
14–19 Jun
4.96 out of 5 average rating, 26 reviews
Flat in Lexington
Stylish Guest Room King Bed at Aloft Lexington
1 king bed
19–24 Apr
4.6 out of 5 average rating, 116 reviews
Room in Medford
Stay with HaiyanHost,
Private, small bedroom 124/3/A
21–26 Apr
4.77 out of 5 average rating, 71 reviews
Flat in Woburn
NEWLY RENOVATED WITH KING BEDS & PARKING
2 king beds
3–8 May
4.79 out of 5 average rating, 97 reviews
Flat in Reading
Luxury 1BR w/Gym, Steps From Commuter Rail #2013
1 king bed
19–24 Apr
4.8 out of 5 average rating, 55 reviews
Superhost
Flat in Arlington
Spotless and Modern Apt w/2Ba,W/D,King Bed,Parking
20–25 Apr
New place to stay
Guest favourite
Flat in Woburn
Your Cozy 1 BR Apt & Relaxing Retreat
1 queen bed
28 Apr – 3 May
4.94 out of 5 average rating, 66 reviews
Place to stay in Arlington
Cozy private condo near Arlington center
1 double bed
6–11 May
4.81 out of 5 average rating, 21 reviews
Flat in Woburn
WOW! KING BEDS, IN-UNIT LAUNDRY, PARKING & MORE!
4 beds
26 Apr – 1 May
4.72 out of 5 average rating, 47 reviews
Flat in Arlington
Private studio in a quiet and nice area
1 sofa bed
8–13 May
4.83 out of 5 average rating, 60 reviews