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 / Check out
Any week
Guests
Add guests
Stays
Experiences
Online Experiences
Where
Search by region
I’m flexible
I’m flexible
Europe
Europe
Canada
Canada
Caribbean
Caribbean
Italy
Italy
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
Countryside
Lake
Beachfront
Skiing
Trending
Chef's kitchens
Bed & breakfasts
Play
Vineyards
Cabins
Lakefront
Farms
New
Design
Tiny homes
Grand pianos
Houseboats
Surfing
Golfing
Boats
Barns
Camping
Ski-in/out
Mansions
Off-the-grid
Beach
Filters
0
Show map
Search results; Over 1,000 places in Winchester
Over 1,000 places in Winchester
Guest favourite
Guest favourite
Flat in Woburn
Charming 1 BR private entrance apt commuters dream
1 bed
1 bed
3–8 Jun
3–8 Jun
£156
night
£156 per night
·
£779 total
£779 total
Show price breakdown
5.0 out of 5 average rating, 96 reviews
5.0 (96)
Superhost
Superhost
Flat in Arlington
#1 Completely Remodeled 3Br Arlington Heights Unit
3 beds
3 beds
21–26 Apr
21–26 Apr
£244
night
£244 per night
·
£1,219 total
£1,219 total
Show price breakdown
4.8 out of 5 average rating, 15 reviews
4.8 (15)
Flat in Woburn
Renovated Enormous 3 Bedroom
Professional Host
Professional Host
27 Apr – 2 May
27 Apr – 2 May
£219
£156
night
£156 per night, originally £219
·
£779 total
£779 total
Show price breakdown
4.65 out of 5 average rating, 26 reviews
4.65 (26)
Guest favourite
Guest favourite
Flat in Woburn
Comfy-Spacious-private 1BR conveniently located
2 beds
2 beds
22–27 Apr
22–27 Apr
£148
night
£148 per night
·
£736 total
£736 total
Show price breakdown
4.96 out of 5 average rating, 105 reviews
4.96 (105)
Guest favourite
Guest favourite
Flat in Woburn
Your Cozy 1 BR Apt & Relaxing Retreat
Individual Host
Individual Host
28 Apr – 3 May
28 Apr – 3 May
£251
£227
night
£227 per night, originally £251
·
£1,133 total
£1,133 total
Show price breakdown
4.94 out of 5 average rating, 66 reviews
4.94 (66)
Flat in Woburn
Renovated Clean Quiet 1.5 Bed
Professional Host
Professional Host
1–6 May
1–6 May
£205
£158
night
£158 per night, originally £205
·
£790 total
£790 total
Show price breakdown
4.74 out of 5 average rating, 23 reviews
4.74 (23)
Guest favourite
Guest favourite
Flat in Stoneham
Entire guest suite in Stoneham
1 queen bed
1 queen bed
14–19 Aug
14–19 Aug
£85
night
£85 per night
·
£421 total
£421 total
Show price breakdown
4.88 out of 5 average rating, 135 reviews
4.88 (135)
Guest favourite
Guest favourite
Flat in Medford
Garden Apartment for Vacation & Business Travelers
Individual Host
Individual Host
2–7 Jun
2–7 Jun
£160
night
£160 per night
·
£798 total
£798 total
Show price breakdown
4.92 out of 5 average rating, 258 reviews
4.92 (258)
Superhost
Superhost
Flat in Arlington
Spotless and Modern Apt w/2Ba,W/D,King Bed,Parking
20–25 Apr
20–25 Apr
£233
night
£233 per night
·
£1,164 total
£1,164 total
Show price breakdown
New place to stay
New
Guest favourite
Guest favourite
Flat in Arlington
Lakeside apartment, patio, hot tub, outside shower
Individual Host
Individual Host
16–21 Jul
16–21 Jul
£193
night
£193 per night
·
£965 total
£965 total
Show price breakdown
4.98 out of 5 average rating, 174 reviews
4.98 (174)
Guest favourite
Guest favourite
Flat in Burlington
The Robins Nest
Individual Host
Individual Host
21–26 May
21–26 May
£175
night
£175 per night
·
£873 total
£873 total
Show price breakdown
4.99 out of 5 average rating, 94 reviews
4.99 (94)
Guest favourite
Guest favourite
Flat in Stoneham
Cozy Basement Apartment-Stoneham
Individual Host
Individual Host
6–11 Jun
6–11 Jun
£114
night
£114 per night
·
£566 total
£566 total
Show price breakdown
4.99 out of 5 average rating, 91 reviews
4.99 (91)
Guest favourite
Guest favourite
Flat in Lexington
Warm home in Lexington, walk to town, nature trail
Individual Host
Individual Host
12–17 Jun
12–17 Jun
£228
night
£228 per night
·
£1,136 total
£1,136 total
Show price breakdown
4.94 out of 5 average rating, 337 reviews
4.94 (337)
Guest favourite
Guest favourite
Flat in Woburn
New Construction En-suite
Individual Host
Individual Host
21–26 Apr
21–26 Apr
£174
£158
night
£158 per night, originally £174
·
£790 total
£790 total
Show price breakdown
5.0 out of 5 average rating, 26 reviews
5.0 (26)
Guest favourite
Guest favourite
Flat in Wakefield
Walk to train, lake and downtown - pets welcome
3 beds
3 beds
19–24 Apr
19–24 Apr
£215
night
£215 per night
·
£1,075 total
£1,075 total
Show price breakdown
5.0 out of 5 average rating, 69 reviews
5.0 (69)
Guest favourite
Guest favourite
Flat in Woburn
Apartment in the Heart of Woburn|Pool|Balcony|Gym
2 queen beds
2 queen beds
20–25 Apr
20–25 Apr
£383
£303
night
£303 per night, originally £383
·
£1,513 total
£1,513 total
Show price breakdown
5.0 out of 5 average rating, 10 reviews
5.0 (10)
Guest favourite
Guest favourite
Flat in Waltham
Just Renovated, Private & Quiet 2 Bedroom Unit
2 beds
2 beds
28 Apr – 3 May
28 Apr – 3 May
£227
night
£227 per night
·
£1,135 total
£1,135 total
Show price breakdown
4.96 out of 5 average rating, 25 reviews
4.96 (25)
Guest favourite
Guest favourite
Flat in Medford
Charming Colonial Two Bedroom Basement Apartment
2 queen beds
2 queen beds
8–13 Aug
8–13 Aug
£202
night
£202 per night
·
£1,007 total
£1,007 total
Show price breakdown
4.98 out of 5 average rating, 199 reviews
4.98 (199)
1
2
3
4
…
15