Skip to content
We’re sorry, some parts of the Airbnb website don’t work properly without JavaScript enabled.
Homes
Homes
NEW
NEW
Experiences
Experiences, new
NEW
NEW
Services
Services, new
Start your search
Location
Homes in Winchester
Check in / Check out
Any week
Guests
Add guests
Become a host
Help Centre
Become a host
It’s easy to start hosting and earn extra income.
Refer a host
Find a co-host
Log in or sign up
filters
Filters
Price
Type of place
Show map
Search results; Over 1,000 homes in Winchester
Over 1,000 homes in Winchester
Top guest favourite
Guest favourite
Cottage in Winchester
The Little House - a historic New England cottage.
2 bedrooms
,
·
3 beds
,
·
1 private bathroom
7–12 Sept
7–12 Sept
$2,741 SGD
$2,373 SGD
Show price breakdown
for 5 nights
,
·
4.95 out of 5 average rating, 86 reviews
4.95 (86)
Guest favourite
Guest favourite
Flat in Winchester
Winchester Apartment on Greenway
1 bedroom
1 bedroom
,
·
1 bed
1 bed
,
·
1 bathroom
1 bathroom
10–15 Nov
10–15 Nov
$1,041 SGD
Show price breakdown
for 5 nights
$1,041 SGD for 5 nights
4.95 out of 5 average rating, 63 reviews
4.95 (63)
Guest favourite
Guest favourite
Home in Winchester
3 Bedroom Boston-area Gem
3 bedrooms
3 bedrooms
,
·
4 beds
4 beds
,
·
1 bathroom
1 bathroom
14–19 Aug
14–19 Aug
$3,128 SGD
Show price breakdown
for 5 nights
$3,128 SGD for 5 nights
Free cancellation
4.96 out of 5 average rating, 27 reviews
4.96 (27)
Superhost
Superhost
Home in Winchester
Luxury Winchester Villa | 4BR + Loft | Sleeps 10
4 bedrooms
4 bedrooms
,
·
5 beds
5 beds
,
·
4.5 bathrooms
4.5 bathrooms
14–19 Aug
14–19 Aug
$7,473 SGD
Show price breakdown
for 5 nights
$7,473 SGD for 5 nights
Free cancellation
5.0 out of 5 average rating, 3 reviews
5.0 (3)
Top guest favourite
Guest favourite
Flat in Woburn
Comfy-Spacious-private 1BR conveniently located
1 bedroom
1 bedroom
,
·
2 beds
2 beds
,
·
1 bathroom
1 bathroom
10–15 Aug
10–15 Aug
$1,156 SGD
Show price breakdown
for 5 nights
$1,156 SGD for 5 nights
Free cancellation
4.95 out of 5 average rating, 248 reviews
4.95 (248)
Top guest favourite
Guest favourite
Room in Arlington
spacious room by T Tufts Cambridge Davis Sq. 闪家@2
1 double bed
1 double bed
,
·
1 bathroom
1 bathroom
17–22 Aug
17–22 Aug
$649 SGD
$469 SGD
Show price breakdown
for 5 nights
4.96 out of 5 average rating, 169 reviews
4.96 (169)
Top guest favourite
Guest favourite
Flat in Woburn
Sofima-Cozy and Charming 2-bedroom apartment.
2 bedrooms
2 bedrooms
,
·
2 beds
2 beds
,
·
1 bathroom
1 bathroom
26 Sept – 1 Oct
26 Sept – 1 Oct
$1,472 SGD
Show price breakdown
for 5 nights
$1,472 SGD for 5 nights
Free cancellation
4.97 out of 5 average rating, 38 reviews
4.97 (38)
Guest favourite
Guest favourite
Home in Woburn
Quiet 2BD Single-Family, Parking, No Shared Walls!
2 bedrooms
2 bedrooms
,
·
2 queen beds
2 queen beds
,
·
1 bathroom
1 bathroom
9–14 Aug
9–14 Aug
$1,148 SGD
$1,059 SGD
Show price breakdown
for 5 nights
Extended stay discount
4.93 out of 5 average rating, 59 reviews
4.93 (59)
Top guest favourite
Guest favourite
Guest suite in Woburn
Private apartment with driveway parking in Woburn
1 bedroom
1 bedroom
,
·
1 queen bed
1 queen bed
,
·
1 bathroom
1 bathroom
9–14 Aug
9–14 Aug
$1,483 SGD
$1,143 SGD
Show price breakdown
for 5 nights
Free cancellation
4.97 out of 5 average rating, 189 reviews
4.97 (189)
Top guest favourite
Guest favourite
Guest suite in Arlington
Cozy 1 bed apt Cambridge/Somerville/Arlington line
1 bedroom
1 bedroom
,
·
2 beds
2 beds
,
·
1 bathroom
1 bathroom
15–20 Nov
15–20 Nov
$1,005 SGD
Show price breakdown
for 5 nights
$1,005 SGD for 5 nights
Free cancellation
4.93 out of 5 average rating, 227 reviews
4.93 (227)
Guest favourite
Guest favourite
Home in Lexington
Lexington Battle Green
3 bedrooms
3 bedrooms
,
·
3 beds
3 beds
,
·
3 bathrooms
3 bathrooms
7–12 Aug
7–12 Aug
$3,917 SGD
Show price breakdown
for 5 nights
$3,917 SGD for 5 nights
4.95 out of 5 average rating, 22 reviews
4.95 (22)
Top guest favourite
Guest favourite
Home in Stoneham
The Grand Residence
2 bedrooms
2 bedrooms
,
·
2 queen beds
2 queen beds
,
·
1 bathroom
1 bathroom
10–15 Nov
10–15 Nov
$1,052 SGD
Show price breakdown
for 5 nights
$1,052 SGD for 5 nights
4.98 out of 5 average rating, 51 reviews
4.98 (51)
Top guest favourite
Guest favourite
Flat in Woburn
Charming 1 BR private entrance apt commuters dream
1 bedroom
1 bedroom
,
·
1 bathroom
1 bathroom
10–15 Nov
10–15 Nov
$1,084 SGD
Show price breakdown
for 5 nights
$1,084 SGD for 5 nights
4.99 out of 5 average rating, 192 reviews
4.99 (192)
Top guest favourite
Guest favourite
Room in Arlington
Arlington Craftsman Blue Room, Int. Well Restored
1 queen bed
1 queen bed
,
·
1 bathroom
1 bathroom
14–19 Aug
14–19 Aug
$579 SGD
Show price breakdown
for 5 nights
$579 SGD for 5 nights
Free cancellation
4.98 out of 5 average rating, 374 reviews
4.98 (374)
Guest favourite
Guest favourite
Room in Waltham
Nicely Decorated in Boston Suburb- Yellow Room
1 queen bed
1 queen bed
,
·
1 bathroom
1 bathroom
23–28 Aug
23–28 Aug
$571 SGD
Show price breakdown
for 5 nights
$571 SGD for 5 nights
Free cancellation
4.92 out of 5 average rating, 554 reviews
4.92 (554)
Top guest favourite
Guest favourite
Home in Woburn
Large 4Bed 2Bath Clean Alternative to Hotel Living
4 bedrooms
4 bedrooms
,
·
4 queen beds
4 queen beds
,
·
2 bathrooms
2 bathrooms
9–14 Aug
9–14 Aug
$2,982 SGD
$2,569 SGD
Show price breakdown
for 5 nights
4.9 out of 5 average rating, 173 reviews
4.9 (173)
Guest favourite
Guest favourite
Guest suite in Arlington
3 Bedroom 2nd Floor Unit - commute to Boston
3 bedrooms
3 bedrooms
,
·
3 beds
3 beds
,
·
1 bathroom
1 bathroom
6–11 Sept
6–11 Sept
$1,558 SGD
Show price breakdown
for 5 nights
$1,558 SGD for 5 nights
4.89 out of 5 average rating, 54 reviews
4.89 (54)
Guest favourite
Guest favourite
Room in Arlington
Jo's Celtic Queen in shared apt- parking
1 queen bed
1 queen bed
,
·
1 bathroom
1 bathroom
17–22 Aug
17–22 Aug
$514 SGD
Show price breakdown
for 5 nights
$514 SGD for 5 nights
Free cancellation
4.84 out of 5 average rating, 92 reviews
4.84 (92)
Guest favourite
Guest favourite
Room in Belmont
Constellation 4
1 queen bed
1 queen bed
,
·
1.5 bathrooms
1.5 bathrooms
21–26 Sept
21–26 Sept
$408 SGD
$368 SGD
Show price breakdown
for 5 nights
Free cancellation
5.0 out of 5 average rating, 12 reviews
5.0 (12)
1
2
3
4
…
15