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
£479 total
Show price breakdown
£479 total
,
·
4.86 out of 5 average rating, 92 reviews
4.86 (92)
Photo 1 of 13
Guest favourite
Guest favourite
Cabin in Winchester
The Ironclad Mountain Retreat
2 bedrooms
2 bedrooms
,
·
2 beds
2 beds
,
·
1 bathroom
1 bathroom
4–9 Oct
4–9 Oct
£862 total
Show price breakdown
£862 total
4.84 out of 5 average rating, 61 reviews
4.84 (61)
Photo 1 of 29
Guest favourite
Guest favourite
Chalet in Winchester
Chalet Sonsie: A Sweetwater Stay
2 bedrooms
2 bedrooms
,
·
3 beds
3 beds
,
·
1.5 bathrooms
1.5 bathrooms
3–8 Nov
3–8 Nov
£775 total
Show price breakdown
£775 total
4.85 out of 5 average rating, 167 reviews
4.85 (167)
Photo 1 of 29
Guest favourite
Guest favourite
Cottage in Winchester
The Humblebee Cottage
2 bedrooms
2 bedrooms
,
·
3 beds
3 beds
,
·
1 bathroom
1 bathroom
17–22 Oct
17–22 Oct
£809 total
Show price breakdown
£809 total
4.9 out of 5 average rating, 10 reviews
4.9 (10)
Photo 1 of 29
Guest favourite
Guest favourite
Home in Richmond
Porcupine Hill Farm
6 bedrooms
6 bedrooms
,
·
8 beds
8 beds
,
·
2 bathrooms
2 bathrooms
1–6 Oct
1–6 Oct
£1,902
£1,598 total
Show price breakdown
Free cancellation
5.0 out of 5 average rating, 9 reviews
5.0 (9)
Photo 1 of 28
Home in Chesterfield
Large Vacation Rental Nestled in 400 Acres
7 bedrooms
7 bedrooms
,
·
14 single beds
14 single beds
,
·
4 bathrooms
4 bathrooms
1–6 Oct
1–6 Oct
£4,794
£3,896 total
Show price breakdown
Free cancellation
New place to stay
New
Photo 1 of 13
Top guest favourite
Guest favourite
Flat in Vernon
Farm land view.
1 bedroom
1 bedroom
,
·
1 queen bed
1 queen bed
,
·
1 bathroom
1 bathroom
1–6 Oct
1–6 Oct
£481 total
Show price breakdown
£481 total
Free cancellation
4.95 out of 5 average rating, 196 reviews
4.95 (196)
Photo 1 of 29
Superhost
Superhost
Home in Chesterfield
Peaceful and Private Farmhouse Retreat
3 bedrooms
3 bedrooms
,
·
4 beds
4 beds
,
·
2 bathrooms
2 bathrooms
21–26 Oct
21–26 Oct
£1,783 total
Show price breakdown
£1,783 total
5.0 out of 5 average rating, 3 reviews
5.0 (3)
Photo 1 of 14
Camper van/Motorhome in Chesterfield
Vintage Cruiser on Spofford Lake
1 bedroom
1 bedroom
,
·
2 beds
2 beds
,
·
1 bathroom
1 bathroom
4–9 Oct
4–9 Oct
£405 total
Show price breakdown
£405 total
Free cancellation
Photo 1 of 29
Guest favourite
Guest favourite
Home in Guilford
Vermont Mirror House
1 bedroom
1 bedroom
,
·
2 beds
2 beds
,
·
1 bathroom
1 bathroom
13–18 Nov
13–18 Nov
£1,861
£1,666 total
Show price breakdown
4.95 out of 5 average rating, 161 reviews
4.95 (161)
Photo 1 of 29
Guest favourite
Guest favourite
Treehouse in Stoddard
Handcrafted Treehouse · 2hr Boston · Fire + Stars
1 bedroom
1 bedroom
,
·
1 bathroom
1 bathroom
12–17 Oct
12–17 Oct
£1,208
£1,093 total
Show price breakdown
Free cancellation
4.92 out of 5 average rating, 133 reviews
4.92 (133)
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
,
·
1 bathroom
1 bathroom
19–24 Oct
19–24 Oct
£1,585
£1,413 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
Flat in Vernon
Deck, Mountain Views: Colorful Retreat in Vernon!
2 bedrooms
2 bedrooms
,
·
3 beds
3 beds
,
·
2 bathrooms
2 bathrooms
25–30 Oct
25–30 Oct
£600 total
Show price breakdown
£600 total
4.86 out of 5 average rating, 35 reviews
4.86 (35)
Photo 1 of 17
Guest favourite
Guest favourite
Tiny home in Chesterfield
Cozy Cottage on Spofford Lake
1 bedroom
1 bedroom
,
·
2 beds
2 beds
,
·
1 bathroom
1 bathroom
4–9 Oct
4–9 Oct
£635 total
Show price breakdown
£635 total
5.0 out of 5 average rating, 7 reviews
5.0 (7)
Photo 1 of 29
Guest favourite
Guest favourite
Flat in Greenfield
Treetop Haven
2 bedrooms
2 bedrooms
,
·
3 beds
3 beds
,
·
1 bathroom
1 bathroom
25–30 Oct
25–30 Oct
£811
£723 total
Show price breakdown
Free cancellation
4.91 out of 5 average rating, 54 reviews
4.91 (54)
Photo 1 of 29
Top guest favourite
Guest favourite
Treehouse in Putney
Treehouse Haven in Putney-All Seasons
2 beds
2 beds
,
·
1 bathroom
1 bathroom
18–23 Oct
18–23 Oct
£927
£826 total
Show price breakdown
Free cancellation
4.97 out of 5 average rating, 202 reviews
4.97 (202)
Photo 1 of 6
Guest favourite
Guest favourite
Room in Chesterfield
Waterfront Paradise - 1.3 mile to Brattleboro
2 beds
2 beds
,
·
1 bathroom
1 bathroom
4–9 Oct
4–9 Oct
£598 total
Show price breakdown
£598 total
Free cancellation
4.93 out of 5 average rating, 69 reviews
4.93 (69)
Photo 1 of 12
Guest favourite
Guest favourite
Flat in Hinsdale
Welcome to the Kilburn House!
6 beds
6 beds
,
·
1 bathroom
1 bathroom
20–25 Oct
20–25 Oct
£483 total
Show price breakdown
£483 total
5.0 out of 5 average rating, 6 reviews
5.0 (6)
Photo 1 of 16
Top guest favourite
Guest favourite
Place to stay in Chesterfield
The Ultimate Romantic Getaway
1 bed
1 bed
,
·
1 bathroom
1 bathroom
1–6 Oct
1–6 Oct
£832 total
Show price breakdown
£832 total
Free cancellation
5.0 out of 5 average rating, 67 reviews
5.0 (67)
1
2
3
4
…
15