Vacation Rentals & Cottages in Winchester

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338 Houses

(4) Excellent 

21

South House - In the centre of Winchester

Hampshire / Winchester

Winchester house

3 6 2 nights min

  • 3 bedrooms
  • sleeps 6
  • 2 nights min
  • Child Friendly

Price per night from

$281

Responds fast!
avg. 1 hour 9 minutes

Price per night from

$281

(35) Excellent 

Certificate of Excellence

16

Hang Your Hat - classy hideaway in Winchester

Hampshire / Winchester

Winchester cottage

1 3 2 nights min

  • 1 bedroom
  • sleeps 3
  • 2 nights min
  • Car not necessary
  • Private garden
“A peaceful haven close to the centre” Generous English gentleman host gave us a taste of classy eccentric hospitality in unusual setting. Simply marvellous.
…see more

Certificate of Excellence

Price per night from

$215

Responds fast!
avg. 1 hour 30 minutes

Price per night from

$215

(12) Very Good 

11

HARDY HOUSE, WINCHESTER

Hampshire / Winchester

Winchester b and b

1 2 1 night min

  • 1 bedroom
  • sleeps 2
  • 1 night min
  • Nearest beach 45 mi
  • Car not necessary
  • Air conditioning

Price per night from

$119

Responds fast!
avg. 3 hours 30 minutes

Price per night from

$119

4

Exec Spec Apartments

Hampshire / Winchester

Winchester apartment

1 4 1 night min

  • 1 bedroom
  • sleeps 4
  • 1 night min
  • Child Friendly

Price per night from

$222

Price per night from

$222

(2) Very Good 

7

Sunnyside

Hampshire / Winchester

Winchester apartment

1 2 2 nights min

  • 1 bedroom
  • sleeps 2
  • 2 nights min
  • Child Friendly
  • Pet Friendly

Price per night from

$134

Responds fast!
avg. 1 hour 58 minutes

Price per night from

$134

25

Bereweeke Coach House

Hampshire / Winchester

Winchester house

3 5 1 night min

  • 3 bedrooms
  • sleeps 5
  • 1 night min
  • Child Friendly

Price per night from

$170

Price per night from

$170

12

43193 Cottage situated in Winchester

Hampshire / Winchester

Winchester house

2 3 7 nights min

  • 2 bedrooms
  • sleeps 3
  • 7 nights min
  • Child Friendly
  • Pet Friendly
  • Private garden

Price per night from

$93

Price per night from

$93

(10) Excellent 

22

The Hayloft, Crabwood Cottages

Hampshire / Winchester

Winchester guest house

1 2 1 night min

  • 1 bedroom
  • sleeps 2
  • 1 night min
  • Nearest beach 25 mi
  • Pet Friendly

Price per night from

$126

Responds fast!
avg. 1 hour 29 minutes

Price per night from

$126

(9) Excellent 

15

Charming apartment, 1 bed, easy walk to Cathedral and restaurants, lovely views

Hampshire / Winchester

Winchester apartment

1 2 2 nights min

  • 1 bedroom
  • sleeps 2
  • 2 nights min
  • Car not necessary

Price per night from

$134

Responds fast!
avg. 2 hours 25 minutes

Price per night from

$134

20

Station Cottage

Hampshire / Winchester

Winchester cottage

3 6 min stay varies

  • 3 bedrooms
  • sleeps 6
  • min stay varies
  • Child Friendly
  • Private garden

Price per night from

$463

Price per night from

$463

(6) Very Good 

41

Willow Cottage - The Old Barns

Hampshire / Winchester

Winchester barn

1 2 2 nights min

  • 1 bedroom
  • sleeps 2
  • 2 nights min
  • Child Friendly
  • Pet Friendly

Price per night from

$207

Price per night from

$207

(14) Excellent 

Certificate of Excellence

18

Self Contained Garden Annexe

Hampshire / Winchester

Winchester log cabin

1 2 2 nights min

  • 1 bedroom
  • sleeps 2
  • 2 nights min
  • Child Friendly
  • Car not necessary

Certificate of Excellence

Price per night from

$89

Responds fast!
avg. 2 hours 59 minutes

Price per night from

$89

(3) Very Good 

21

Luxury 3 Bedroom, Scandinavian Lodge with HOT TUB

Hampshire / Winchester

Winchester lodge

3 6 min stay varies

  • 3 bedrooms
  • sleeps 6
  • min stay varies
  • Child Friendly
  • Pet Friendly

Price per night from

$212

Price per night from

$212

(11) Very Good 

Certificate of Excellence

14

The Granary Annex at Worthy Barn

Hampshire / Winchester

Winchester house

2 4 2 nights min

  • 2 bedrooms
  • sleeps 4
  • 2 nights min
  • Child Friendly

Certificate of Excellence

Price per night from

$151

Price per night from

$151

7

Family home in beautiful Hampshire countryside

Hampshire / Winchester

Winchester house

5 10 2 nights min

  • 5 bedrooms
  • sleeps 10
  • 2 nights min
  • Swimming pool
  • Child Friendly
  • Pet Friendly

Price per night from

$1,036

Responds fast!
avg. 3 hours 1 minutes

Price per night from

$1,036

(18) Very Good 

16

Garden Apartment in Winchester

Hampshire / Winchester

Winchester apartment

1 4 min stay varies

  • 1 bedroom
  • sleeps 4
  • min stay varies
  • Child Friendly
  • Car not necessary

Price per night from

$163

Price per night from

$163

(8) Very Good 

11

The Loft Winchester

Hampshire / Winchester

Winchester apartment

3 5 2 nights min

  • 3 bedrooms
  • sleeps 5
  • 2 nights min
  • Child Friendly

Price per night from

$230

Price per night from

$230

(2) Excellent 

21

Luxury 2 Bedroom Scandinavian Lodge with HOT TUB

Hampshire / Winchester

Winchester lodge

2 4 min stay varies

  • 2 bedrooms
  • sleeps 4
  • min stay varies
  • Nearest beach 20 mi
  • Child Friendly
  • Pet Friendly

Price per night from

$182

Price per night from

$182

(9) Excellent 

17

Stylish House in Winchester

Hampshire / Winchester

Winchester house

2 6 min stay varies

  • 2 bedrooms
  • sleeps 6
  • min stay varies
  • Child Friendly
  • Car not necessary

Price per night from

$259

Price per night from

$259

(21) Excellent 

Certificate of Excellence

31

The Old Tractor Barn, Crabwood Cottages

Winchester / Pitt

Winchester cottage

3 5 min stay varies

  • 3 bedrooms
  • sleeps 5
  • min stay varies
  • Nearest beach 30 mi
  • Child Friendly
  • Pet Friendly

Certificate of Excellence

Price per night from

$129

Responds fast!
avg. 1 hour 29 minutes

Price per night from

$129

(21) Excellent 

16

The Sky Penthouse

Hampshire / Winchester

Winchester penthouse

2 6 2 nights min

  • 2 bedrooms
  • sleeps 6
  • 2 nights min
  • Car not necessary

Price per night from

$370

Responds fast!
avg. 2 hours 8 minutes

Price per night from

$370

(9) Excellent 

15

The Down House Cottage

Hampshire / Winchester

Winchester cottage

1 2 3 nights min

  • 1 bedroom
  • sleeps 2
  • 3 nights min
  • Ask about children
  • Car not necessary
  • Private garden

Price per night from

$134

Price per night from

$134

(11) Excellent 

7

Idyllic Hampshire Hideaway - The Orchard Studio

Hampshire / Winchester

Winchester b and b

1 2 1 night min

  • 1 bedroom
  • sleeps 2
  • 1 night min
  • Child Friendly
  • Pet Friendly
  • Private garden

Price per night from

$111

Responds fast!
avg. 2 hours 39 minutes

Price per night from

$111

(11) Very Good 

18

Cosy character cottage in central Winchester

Hampshire / Winchester

Winchester cottage

2 4 min stay varies

  • 2 bedrooms
  • sleeps 4
  • min stay varies
  • Child Friendly
  • Car not necessary
  • Private garden

Price per night from

$222

Price per night from

$222

(9) Excellent 

20

Luxury 3 bedroom Scandinavian Lodge

Hampshire / Winchester

Winchester log cabin

3 6 min stay varies

  • 3 bedrooms
  • sleeps 6
  • min stay varies
  • Nearest beach 20 mi
  • Child Friendly
  • Pet Friendly

Price per night from

$182

Price per night from

$182

29

No. 01 St Swithuns Court

Hampshire / Winchester

Winchester townhouse

3 6 7 nights min

  • 3 bedrooms
  • sleeps 6
  • 7 nights min
  • Child Friendly
  • Private garden

Price per night from

$250

Price per night from

$250

(8) Excellent 

17

South House Winchester

Hampshire / Winchester

Winchester house

3 6 2 nights min

  • 3 bedrooms
  • sleeps 6
  • 2 nights min
  • Child Friendly
  • Car not necessary

Price per night from

$281

Responds fast!
avg. 1 hour 35 minutes

Price per night from

$281

17

No. 01b 1 Clifton Terrace

Hampshire / Winchester

Winchester apartment

1 4 7 nights min

  • 1 bedroom
  • sleeps 4
  • 7 nights min

Price per night from

$236

Price per night from

$236

(8) Excellent 

13

Luxury 2 Bedroom Scandinavian Lodge

Hampshire / Winchester

Winchester log cabin

2 4 min stay varies

  • 2 bedrooms
  • sleeps 4
  • min stay varies
  • Nearest beach 20 mi
  • Child Friendly
  • Pet Friendly

Price per night from

$215

Price per night from

$215

47

No. 11 Cossack Lane House

Hampshire / Winchester

Winchester apartment

2 4 7 nights min

  • 2 bedrooms
  • sleeps 4
  • 7 nights min
  • Ask about children

Price per night from

$182

Price per night from

$182

11

No. 79 Tower Street

Hampshire / Winchester

Winchester house

2 7 7 nights min

  • 2 bedrooms
  • sleeps 7
  • 7 nights min
  • Child Friendly

Price per night from

$275

Price per night from

$275

14

Westgate View

Hampshire / Winchester

Winchester house

3 5 7 nights min

  • 3 bedrooms
  • sleeps 5
  • 7 nights min
  • Child Friendly

Price per night from

$166

Price per night from

$166

20

Pemberly

Hampshire / Winchester

Winchester house

2 4 min stay varies

  • 2 bedrooms
  • sleeps 4
  • min stay varies
  • Child Friendly

Price per night from

$293

Price per night from

$293

13

Panoramic view of Winchester Cathedral

Hampshire / Winchester

Winchester apartment

1 2 3 nights min

  • 1 bedroom
  • sleeps 2
  • 3 nights min
  • Nearest beach 40 mi
  • Car not necessary

Price per night from

$185

Price per night from

$185

19

Westgate Winchester

Hampshire / Winchester

Winchester house

2 4 3 nights min

  • 2 bedrooms
  • sleeps 4
  • 3 nights min
  • Child Friendly

Price per night from

$199

Price per night from

$199

25

Blackbird Cottage

Hampshire / Winchester

Winchester house

2 4 3 nights min

  • 2 bedrooms
  • sleeps 4
  • 3 nights min
  • Child Friendly

Price per night from

$663

Price per night from

$663

15

Dashwood Terrace

Hampshire / Winchester

Winchester house

2 5 min stay varies

  • 2 bedrooms
  • sleeps 5
  • min stay varies
  • Child Friendly

Price per night from

$188

Price per night from

$188

11

City Centre Home With Private Off Road Parking

Hampshire / Winchester

Winchester house

2 4 2 nights min

  • 2 bedrooms
  • sleeps 4
  • 2 nights min
  • Child Friendly

Price per night from

$148

Price per night from

$148