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
1–6 Sept
1–6 Sept
$2,687 SGD
$2,459 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
$1,042 SGD
Show price breakdown
for 5 nights
$1,042 SGD for 5 nights
Pay $0 today
Free cancellation
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
$3,131 SGD
Show price breakdown
for 5 nights
$3,131 SGD for 5 nights
Pay $0 today
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
$7,478 SGD
Show price breakdown
for 5 nights
$7,478 SGD for 5 nights
Pay $0 today
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
Pay $0 today
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
$671 SGD
$469 SGD
Show price breakdown
for 5 nights
4.96 out of 5 average rating, 169 reviews
4.96 (169)
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
$1,223 SGD
$1,128 SGD
Show price breakdown
for 5 nights
Extended stay discount
4.93 out of 5 average rating, 59 reviews
4.93 (59)
Guest favourite
Guest favourite
Room in Arlington
Jo's Sea Queen shared apt-parking
1 bed
1 bed
,
·
1 bathroom
1 bathroom
19–24 Aug
19–24 Aug
$462 SGD
Show price breakdown
for 5 nights
$462 SGD for 5 nights
Pay $0 today
Free cancellation
4.84 out of 5 average rating, 19 reviews
4.84 (19)
Top guest favourite
Guest favourite
Guest suite in Arlington
2BR Suite - Bright - Modern - Central AC - Parking
2 bedrooms
2 bedrooms
,
·
4 beds
4 beds
,
·
1 bathroom
1 bathroom
7–12 Sept
7–12 Sept
$2,156 SGD
Show price breakdown
for 5 nights
$2,156 SGD for 5 nights
5.0 out of 5 average rating, 168 reviews
5.0 (168)
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
$515 SGD
Show price breakdown
for 5 nights
$515 SGD for 5 nights
Pay $0 today
Free cancellation
4.84 out of 5 average rating, 92 reviews
4.84 (92)
Top guest favourite
Guest favourite
Guest suite in Lexington
Modern Farmhouse Suite in Historic Lexington
2 bedrooms
2 bedrooms
,
·
3 beds
3 beds
,
·
1 bathroom
1 bathroom
11–16 Aug
11–16 Aug
$2,074 SGD
$1,625 SGD
Show price breakdown
for 5 nights
Pay $0 today
Free cancellation
4.97 out of 5 average rating, 181 reviews
4.97 (181)
Top guest favourite
Guest favourite
Flat in Arlington
Sleek & Stylish Condo Retreat, 2BA, W/D
3 bedrooms
3 bedrooms
,
·
5 beds
5 beds
,
·
2 bathrooms
2 bathrooms
30 Aug – 4 Sept
30 Aug – 4 Sept
$2,315 SGD
$1,977 SGD
Show price breakdown
for 5 nights
4.87 out of 5 average rating, 54 reviews
4.87 (54)
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
$1,473 SGD
Show price breakdown
for 5 nights
$1,473 SGD for 5 nights
Pay $0 today
Free cancellation
4.97 out of 5 average rating, 38 reviews
4.97 (38)
Top guest favourite
Guest favourite
Flat in Stoneham
Entire guest suite in Stoneham
1 bedroom
1 bedroom
,
·
1 queen bed
1 queen bed
,
·
1 bathroom
1 bathroom
9–14 Nov
9–14 Nov
$671 SGD
$541 SGD
Show price breakdown
for 5 nights
4.88 out of 5 average rating, 438 reviews
4.88 (438)
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
$1,006 SGD
Show price breakdown
for 5 nights
$1,006 SGD for 5 nights
Pay $0 today
Free cancellation
4.93 out of 5 average rating, 227 reviews
4.93 (227)
Top guest favourite
Guest favourite
Flat in Medford
Garden Apartment for Vacation & Business Travelers
1 bedroom
1 bedroom
,
·
2 beds
2 beds
,
·
1 bathroom
1 bathroom
23–28 Aug
23–28 Aug
$1,373 SGD
Show price breakdown
for 5 nights
$1,373 SGD for 5 nights
4.93 out of 5 average rating, 393 reviews
4.93 (393)
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
$1,487 SGD
$1,170 SGD
Show price breakdown
for 5 nights
Pay $0 today
Free cancellation
4.97 out of 5 average rating, 189 reviews
4.97 (189)
Guest favourite
Guest favourite
Room in Arlington
Comfortable room with private access
1 bed
1 bed
,
·
1.5 bathrooms
1.5 bathrooms
15–20 Sept
15–20 Sept
$696 SGD
Show price breakdown
for 5 nights
$696 SGD for 5 nights
Pay $0 today
Free cancellation
4.94 out of 5 average rating, 18 reviews
4.94 (18)
Guest favourite
Guest favourite
Townhouse in Arlington
Stylish 2BR Near Harvard, MIT & Boston
2 bedrooms
2 bedrooms
,
·
2 beds
2 beds
,
·
1 bathroom
1 bathroom
13–18 Sept
13–18 Sept
$2,040 SGD
$1,623 SGD
Show price breakdown
for 5 nights
Pay $0 today
Free cancellation
4.93 out of 5 average rating, 147 reviews
4.93 (147)
1
2
3
4
…
15