Skip to content
We’re sorry, some parts of the Airbnb website don’t work properly without JavaScript enabled.
Start your search
Location
Winchester
Check-in / Checkout
Any week
Guests
Add guests
Stays
Experiences
Online Experiences
Where
Search by region
I’m flexible
I’m flexible
Europe
Europe
Italy
Italy
Caribbean
Caribbean
Mexico
Mexico
South America
South America
Check in
Add dates
Check out
Add dates
Who
Add guests
Search
Airbnb your home
Sign up
Log in
Gift cards
Airbnb your home
Help Centre
%{visible} of %{smart_count_str} Airbnb Category showing||||%{visible} of %{smart_count_str} Airbnb Categories showing
Your search
Rooms
Amazing views
Amazing pools
Skiing
Trending
Beachfront
Lake
Chef's kitchens
Countryside
Bed & breakfasts
Play
Vineyards
Cabins
New
Farms
Lakefront
Design
Tiny homes
Grand pianos
Barns
Golfing
Surfing
Camping
Ski-in/out
Beach
Filters
0
Show map
Search results; Over 1,000 places in Winchester
Over 1,000 places in Winchester
Guest favourite
Guest favourite
Guest suite in Winchester
Warm and cozy 1st flr sweet guest suite w parking
1 queen bed
1 queen bed
Aug. 14 – 19
Aug. 14 – 19
$207 CAD
night
$207 CAD per night
·
$1,035 CAD total
$1,035 CAD total
Show price breakdown
5.0 out of 5 average rating, 95 reviews
5.0 (95)
Home in Winchester
Spacious New Construction Home With Stunning Views
Mar. 19 – 24
Mar. 19 – 24
$1,176 CAD
night
$1,176 CAD per night
·
$5,879 CAD total
$5,879 CAD total
Show price breakdown
New place to stay
New
Home in Winchester
House on A+ school area w/AC & W/D
3 beds
3 beds
Apr. 17 – 22
Apr. 17 – 22
$296 CAD
night
$296 CAD per night
·
$1,480 CAD total
$1,480 CAD total
Show price breakdown
4.7 out of 5 average rating, 20 reviews
4.7 (20)
Guest favourite
Guest favourite
Home in Woburn
Stone Cottage with meadow view
3 beds
3 beds
May 8 – 13
May 8 – 13
$560 CAD
night
$560 CAD per night
·
$2,801 CAD total
$2,801 CAD total
Show price breakdown
4.96 out of 5 average rating, 28 reviews
4.96 (28)
Guest favourite
Guest favourite
Apartment in Woburn
Charming 1 BR private entrance apt commuters dream
1 bed
1 bed
Mar. 24 – 29
Mar. 24 – 29
$207 CAD
night
$207 CAD per night
·
$1,035 CAD total
$1,035 CAD total
Show price breakdown
5.0 out of 5 average rating, 91 reviews
5.0 (91)
Guest favourite
Guest favourite
Home in Woburn
Spotless/Spacious home, 20 min to Boston
2 beds
2 beds
Mar. 19 – 24
Mar. 19 – 24
$492 CAD
$356 CAD
night
$356 CAD per night, originally $492 CAD
·
$1,778 CAD total
$1,778 CAD total
Show price breakdown
4.92 out of 5 average rating, 37 reviews
4.92 (37)
Guest favourite
Guest favourite
Cottage in Winchester
The Little House - A Historic New England cottage
3 beds
3 beds
May 20 – 25
May 20 – 25
$634 CAD
night
$634 CAD per night
·
$3,168 CAD total
$3,168 CAD total
Show price breakdown
4.96 out of 5 average rating, 47 reviews
4.96 (47)
Guest favourite
Guest favourite
Home in Winchester
3 Bedroom Boston-area Gem
4 beds
4 beds
May 25 – 30
May 25 – 30
$580 CAD
night
$580 CAD per night
·
$2,898 CAD total
$2,898 CAD total
Show price breakdown
5.0 out of 5 average rating, 5 reviews
5.0 (5)
Superhost
Superhost
Guest suite in Winchester
Traveler's home
3 beds
3 beds
Apr. 6 – 11
Apr. 6 – 11
$276 CAD
night
$276 CAD per night
·
$1,380 CAD total
$1,380 CAD total
Show price breakdown
4.33 out of 5 average rating, 3 reviews
4.33 (3)
Guest favourite
Guest favourite
Guest suite in Medford
Beautiful 1 Bedroom, 1 Bathroom in Medford
1 queen bed
1 queen bed
Mar. 31 – Apr. 5
Mar. 31 – Apr. 5
$207 CAD
night
$207 CAD per night
·
$1,035 CAD total
$1,035 CAD total
Show price breakdown
4.92 out of 5 average rating, 120 reviews
4.92 (120)
Apartment in Winchester
One BD Apt.for 4 Person, 10 mins to BOS Easy to 93
1 queen bed
1 queen bed
Mar. 19 – 24
Mar. 19 – 24
$178 CAD
night
$178 CAD per night
·
$889 CAD total
$889 CAD total
Show price breakdown
4.09 out of 5 average rating, 32 reviews
4.09 (32)
Guest favourite
Guest favourite
Apartment in Woburn
Comfy-Spacious-private 1BR conveniently located
2 beds
2 beds
Mar. 23 – 28
Mar. 23 – 28
$236 CAD
night
$236 CAD per night
·
$1,182 CAD total
$1,182 CAD total
Show price breakdown
4.98 out of 5 average rating, 99 reviews
4.98 (99)
Guest favourite
Guest favourite
Home in Woburn
Large 4Bed 2Bath Clean Alternative to Hotel Living
4 queen beds
4 queen beds
Apr. 7 – 12
Apr. 7 – 12
$548 CAD
$406 CAD
night
$406 CAD per night, originally $548 CAD
·
$2,028 CAD total
$2,028 CAD total
Show price breakdown
4.86 out of 5 average rating, 99 reviews
4.86 (99)
Superhost
Superhost
4
Reviews
5.0
Rating
2
Years hosting
Room in Winchester
Stay with Qingde
Stay with Qingde
Dream room with working space
Apr. 6 – 11
Apr. 6 – 11
$113 CAD
night
$113 CAD per night
·
$563 CAD total
$563 CAD total
Show price breakdown
5.0 out of 5 average rating, 4 reviews
5.0 (4)
Superhost
Superhost
Room in Medford
Stay with Ivone
Stay with Ivone
Hosting for 5 years
,
·
Hosting for 5 years
Small space room
Mar. 25 – 30
Mar. 25 – 30
$115 CAD
night
$115 CAD per night
·
$576 CAD total
$576 CAD total
Show price breakdown
New place to stay
New
Apartment in Woburn
Renovated Clean Quiet 1.5 Bed
2 beds
2 beds
Mar. 22 – 27
Mar. 22 – 27
$280 CAD
$226 CAD
night
$226 CAD per night, originally $280 CAD
·
$1,129 CAD total
$1,129 CAD total
Show price breakdown
4.73 out of 5 average rating, 22 reviews
4.73 (22)
Superhost
Superhost
Place to stay in Medford
$PEND @ dAy in B🙄ST⚾N
2 queen beds
2 queen beds
Mar. 19 – 24
Mar. 19 – 24
$122 CAD
$111 CAD
night
$111 CAD per night, originally $122 CAD
·
$556 CAD total
$556 CAD total
Show price breakdown
4.66 out of 5 average rating, 38 reviews
4.66 (38)
Superhost
Superhost
Guesthouse in Lexington
Unique Loft/ Studio Guesthouse (super convenient)
2 beds
2 beds
Mar. 31 – Apr. 5
Mar. 31 – Apr. 5
$189 CAD
night
$189 CAD per night
·
$943 CAD total
$943 CAD total
Show price breakdown
4.71 out of 5 average rating, 180 reviews
4.71 (180)
1
2
3
4
…
15