Skip to content
We’re sorry, some parts of the Airbnb website don’t work properly without JavaScript enabled.
Homes
Homes
Experiences
Experiences
Services
Services
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
Gift cards
Log in or sign up
filters
Filters
Price
Price filter
Type of place
Type of place filter
Show map
Search results; Over 1,000 homes in Winchester
Over 1,000 homes in Winchester
Photo 1 of 15
Superhost
Superhost
Guest house in Winchester
The Higgle House: A Sweetwater Farm Stay
2 bedrooms
,
·
2 beds
,
·
1 private bathroom
1–6 Nov
1–6 Nov
£474 total
Show price breakdown
£474 total
,
·
4.86 out of 5 average rating, 92 reviews
4.86 (92)
Photo 1 of 29
Guest favourite
Guest favourite
Cottage in Winchester
The Humblebee Cottage
2 bedrooms
2 bedrooms
,
·
3 beds
3 beds
27 Sept – 2 Oct
27 Sept – 2 Oct
£865
£793 total
Show price breakdown
4.9 out of 5 average rating, 10 reviews
4.9 (10)
Photo 1 of 13
Guest favourite
Guest favourite
Cabin in Winchester
The Ironclad Mountain Retreat
2 bedrooms
2 bedrooms
,
·
2 beds
2 beds
4–9 Oct
4–9 Oct
£860 total
Show price breakdown
£860 total
4.83 out of 5 average rating, 60 reviews
4.83 (60)
Photo 1 of 29
Guest favourite
Guest favourite
Home in Richmond
Porcupine Hill Farm
6 bedrooms
6 bedrooms
,
·
8 beds
8 beds
29 Sept – 4 Oct
29 Sept – 4 Oct
£1,898
£1,595 total
Show price breakdown
Free cancellation
5.0 out of 5 average rating, 9 reviews
5.0 (9)
Photo 1 of 27
Top guest favourite
Guest favourite
Home in Putney
Charming Putney Village Home!
4 bedrooms
4 bedrooms
,
·
7 beds
7 beds
26 Sept – 1 Oct
26 Sept – 1 Oct
£1,385
£1,222 total
Show price breakdown
4.95 out of 5 average rating, 21 reviews
4.95 (21)
Photo 1 of 29
Home in Royalston
Historic Home w/ Modern Updates on < 4 Acres
4 bedrooms
4 bedrooms
,
·
5 beds
5 beds
27 Sept – 2 Oct
27 Sept – 2 Oct
£1,703 total
Show price breakdown
£1,703 total
4.94 out of 5 average rating, 77 reviews
4.94 (77)
Photo 1 of 28
Top guest favourite
Guest favourite
Home in Keene
The Brick House on Washington Street
3 bedrooms
3 bedrooms
,
·
4 beds
4 beds
19–24 Oct
19–24 Oct
£1,582
£1,416 total
Show price breakdown
Free cancellation
4.93 out of 5 average rating, 251 reviews
4.93 (251)
Photo 1 of 29
Guest favourite
Guest favourite
Home in West Brattleboro
Private Brookside Farmhouse
3 bedrooms
3 bedrooms
,
·
4 beds
4 beds
26 Sept – 1 Oct
26 Sept – 1 Oct
£974
£873 total
Show price breakdown
4.93 out of 5 average rating, 88 reviews
4.93 (88)
Photo 1 of 29
Top guest favourite
Guest favourite
Cabin in West Brattleboro
Hidden Forest Cabin: Kitchen, Deck, Babbling Brook
3 bedrooms
3 bedrooms
,
·
6 beds
6 beds
27 Sept – 2 Oct
27 Sept – 2 Oct
£1,445
£1,099 total
Show price breakdown
4.98 out of 5 average rating, 46 reviews
4.98 (46)
Photo 1 of 29
Guest favourite
Guest favourite
Home in Chesterfield
Governer's Brook Camp - 2 Bedroom
2 bedrooms
2 bedrooms
,
·
3 beds
3 beds
21–26 Sept
21–26 Sept
£685
£610 total
Show price breakdown
4.9 out of 5 average rating, 146 reviews
4.9 (146)
Photo 1 of 29
Guest favourite
Guest favourite
Home in Brattleboro
Bright, spacious country home
4 bedrooms
4 bedrooms
,
·
5 beds
5 beds
18–23 Oct
18–23 Oct
£1,358 total
Show price breakdown
£1,358 total
4.91 out of 5 average rating, 67 reviews
4.91 (67)
Photo 1 of 18
Top guest favourite
Guest favourite
Flat in Brattleboro
Charming 2BR Vermont Home • Porch • Full Kitchen
2 bedrooms
2 bedrooms
,
·
3 beds
3 beds
25–30 Oct
25–30 Oct
£1,015 total
Show price breakdown
£1,015 total
Free cancellation
5.0 out of 5 average rating, 17 reviews
5.0 (17)
Photo 1 of 12
Guest favourite
Guest favourite
Flat in Swanzey
Swanzey Retreat-serene yet close to Keene
2 bedrooms
2 bedrooms
,
·
2 beds
2 beds
26–31 Oct
26–31 Oct
£598 total
Show price breakdown
£598 total
Free cancellation
4.88 out of 5 average rating, 17 reviews
4.88 (17)
Photo 1 of 29
Guest favourite
Guest favourite
Home in Dummerston
Dutton Farmhouse
4 bedrooms
4 bedrooms
,
·
6 beds
6 beds
2–7 Nov
2–7 Nov
£1,966 total
Show price breakdown
£1,966 total
4.97 out of 5 average rating, 58 reviews
4.97 (58)
Photo 1 of 29
Guest favourite
Guest favourite
Cottage in Orange
The Film Shack: A Sweetwater Stay
5 bedrooms
5 bedrooms
,
·
6 beds
6 beds
26 Sept – 1 Oct
26 Sept – 1 Oct
£939 total
Show price breakdown
£939 total
4.9 out of 5 average rating, 156 reviews
4.9 (156)
Photo 1 of 29
Top guest favourite
Guest favourite
Treehouse in Guilford
Cozy tent in the trees on organic flower farm
1 bedroom
1 bedroom
,
·
1 king bed
1 king bed
27 Sept – 2 Oct
27 Sept – 2 Oct
£647 total
Show price breakdown
£647 total
Free cancellation
4.99 out of 5 average rating, 209 reviews
4.99 (209)
Photo 1 of 29
Top guest favourite
Guest favourite
Yurt in Dover
Mount Snow Yurt: Hot Tub~Wood Stove~WiFi~EVcharger
3 bedrooms
3 bedrooms
,
·
4 beds
4 beds
26 Sept – 1 Oct
26 Sept – 1 Oct
£4,798
£3,411 total
Show price breakdown
4.93 out of 5 average rating, 137 reviews
4.93 (137)
Photo 1 of 25
Top guest favourite
Guest favourite
Cottage in Orange
Lake House with view of mountain
2 bedrooms
2 bedrooms
,
·
3 beds
3 beds
20–25 May
20–25 May
£1,168 total
Show price breakdown
£1,168 total
Free cancellation
4.99 out of 5 average rating, 96 reviews
4.99 (96)
Photo 1 of 29
Guest favourite
Guest favourite
Home in Chesterfield
Beautiful Home near the sand at Spofford Lake!
2 bedrooms
2 bedrooms
,
·
6 beds
6 beds
6–11 Oct
6–11 Oct
£2,158 total
Show price breakdown
£2,158 total
5.0 out of 5 average rating, 19 reviews
5.0 (19)
1
2
3
4
…
15