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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
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
Flat in Woburn
Renovated Clean Quiet 1.5 Bed
2 beds
18–23 Apr
4.74 out of 5 average rating, 23 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
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
Renovated Enormous 3 Bedroom
3 beds
18–23 Apr
4.65 out of 5 average rating, 26 reviews
Flat in Lexington
Stylish Guest Room King Bed at Aloft Lexington
1 king bed
18–23 Apr
4.6 out of 5 average rating, 116 reviews
Flat in Winchester
One BD Apt.for 4 Person, 10 mins to BOS Easy to 93
1 queen bed
22–27 Apr
4.09 out of 5 average rating, 32 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
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
Flat in Reading
Luxury 1BR w/Gym, Steps From Commuter Rail #2013
1 king bed
18–23 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
19–24 Apr
New place to stay
Superhost
Flat in Arlington
#1 Completely Remodeled 3Br Arlington Heights Unit
3 beds
21–26 Apr
4.79 out of 5 average rating, 14 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
Guest favourite
Flat in Woburn
New Construction En Suite
1 bed
21–26 Apr
5.0 out of 5 average rating, 26 reviews
Guest favourite
Flat in Lexington
Warm home in Lexington, walk to town, nature trail
2 beds
12–17 Jun
4.94 out of 5 average rating, 337 reviews
Guest favourite
Flat in Woburn
Apartment in the Heart of Woburn|Pool|Balcony|Gym
2 queen beds
19–24 Apr
5.0 out of 5 average rating, 10 reviews