20 Best Vacation Rentals in Winchcombe - Holiday Lettings - Cabins

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1,241 Vacation rentals

(47) Very Good 

10

Vacation cottage in Winchcombe

Cotswolds / Winchcombe

1 2 2 nights min

  • 1 bedroom
  • Sleeps 2
  • 2 nights min
Anvil Cottage is a lovely one bedroom self-catering holiday cottage located in the heart of Winchcombe. This quirky holiday cottage makes a great base for a short break or longer holiday whilst exploring the Cotswolds. The cottage is well equipped - we hope to offer eve …see more

from $86 / night

$572 - $715 / week

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avg. 3 hours 59 minutes

from $86 / night

(65) Excellent 

Certificate of Excellence

19

Winchcombe Vacation cottage accommodation

Cotswolds / Winchcombe

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Child friendly
“The Cottage” is a charming honey coloured stone cottage situated in Winchcombes most picturesque street which leads to the historic Sudeley Castle. The property has Gas central heating. Downstairs – The front door opens into the beautiful living room with exposed be …see more

Certificate of Excellence

from $101 / night

$1,716 / week

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Responds fast!
avg. 7 minutes

from $101 / night

(27) Excellent 

Certificate of Excellence

17

Winchcombe Vacation shepherds hut rental

Cotswolds / Winchcombe

1 2 2 nights min

  • 1 bedroom
  • Sleeps 2
  • 2 nights min
Pinnock Wood Farm Shepherds Hut is located in a quiet rural setting on a working livestock farm in the North Cotswolds. Situated close to the historic town of Winchcombe. The Shepherds Hut is fully serviced with a Double bed, fully fitted kitchen, bathroom with heatin …see more

Certificate of Excellence

from $86 / night

$568 / week

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Responds fast!
avg. 1 hour 27 minutes

from $86 / night

(1) Excellent 

25

Vacation home in Winchcombe

Cotswolds / Winchcombe

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Child friendly
  • Private garden
A delightful riverside retreat in the heart of historic Winchcombe, perfect for groups who can’t get enough of the great outdoors. Families and groups in search of a true home away from home need look no further than Kingfisher Cottage; a modern, spacious cottage jam- …see more

from $391 / night

$1,775 - $4,260 / week

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Responds fast!
avg. 1 hour 3 minutes

from $391 / night

(3) Very Good 

27

Vacation home in Winchcombe

Cotswolds / Winchcombe

2 4 3 nights min

  • 2 bedrooms
  • Sleeps 4
  • 3 nights min
  • Child friendly
  • Pet friendly
Mad Molly's is as unique in name as it is unique inside! Tucked down a little lane and within seconds of some superb restaurants and bars, this cute cottage is the epitome of all things romantic and relaxing. Walking devotees will adore it here, the paths offer some o …see more

from $208 / night

$825 - $1,829 / week

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from $208 / night

(80) Excellent 

15

Winchcombe Vacation log cabin rental

Cotswolds / Winchcombe

1 2 3 nights min

  • 1 bedroom
  • Sleeps 2
  • 3 nights min
  • Pet friendly
  • Private garden
Situated in the unspoilt village of Brockhampton in the heart of the Cotswolds Area of Outstanding Natural Beauty yet close to Regency Cheltenham, Coomb Cottage is a luxury log cabin with wide-ranging views out across our magnificent limestone uplands. Coomb Cottage ha …see more

from $128 / night

$852 / week

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Responds fast!
avg. 3 hours 56 minutes

from $128 / night

(7) Excellent 

5

Winchcombe Vacation cottage rental

Cotswolds / Winchcombe

2 4 2 nights min

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min
  • Child friendly
  • Private garden
This modern Cotswold stone cottage lies close to the heart of the delightful town of Winchcombe. Adjoining another property, it is set along a quiet lane, 2 minutes' walk from an excellent range of shops, historic pubs, restaurants and beautiful Sudeley Castle (once hom …see more

from $114 / night

$709 - $908 / week

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from $114 / night

(3) Excellent 

17

Vacation apartment in Winchcombe

Cotswolds / Winchcombe

2 5 2 nights min

  • 2 bedrooms
  • Sleeps 5
  • 2 nights min
  • Suitable for children age 5+
  • Ask about pets
The apartment is in the centre of the delightful Cotswold town of Winchcombe. It is housed in an old Cotswold stone building on the first and second floors. The ground floor houses a chic ladies' shop. It is open plan with plenty of windows so is spacious, light and ai …see more

from $135 / night

$923 - $1,023 / week

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from $135 / night

(2) Excellent 

37

Vacation castle in Winchcombe

Cotswolds / Winchcombe

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Child friendly
  • Pet friendly
  • Private garden
The Gatehouse to Sudeley Castle is now available as a holiday home! Situated on the edge of the Sudeley Estate, the gatehouse structure consisting of two large towers that support the gate are considered the strongest defensive positions in the castle. Within walking di …see more

from $171 / night

$888 - $1,775 / week

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Responds fast!
avg. 1 hour 3 minutes

from $171 / night

(2) Very Good 

73

Vacation farmhouse accommodation

Cotswolds / Winchcombe

7 14 Min stay varies

  • 7 bedrooms
  • Sleeps 14
  • Min stay varies
  • Child friendly
  • Pet friendly
  • Private garden
Unpretentious and very welcoming, there is a great sense of style about this recently refurbished 18th century farmhouse. Situated on the edge of the Sudeley Estate, the farmhouse is within walking distance of the village known as the "The Jewel of the Cotswolds", Winch …see more

from $497 / night

$2,521 - $5,112 / week

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Responds fast!
avg. 1 hour 3 minutes

from $497 / night

(7) Excellent 

Certificate of Excellence

13

Vacation home in Winchcombe

Cotswolds / Winchcombe

2 3 Min stay varies

  • 2 bedrooms
  • Sleeps 3
  • Min stay varies
  • Child friendly
  • Car not necessary
  • Private garden
No 61 comfortably sleeps 3, plus an infant, and is situated on a quaint residential road just outside the Cotswold town of Winchcombe. The cottage has two comfy bedrooms and a wood burning stove. There is private parking for one car and a landscaped garden with decking …see more

Certificate of Excellence

from $142 / night

$845 - $1,065 / week

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Responds fast!
avg. 32 minutes

from $142 / night

19

Home rental in Winchcombe

Cotswolds / Winchcombe

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Suitable for children age 5+
  • Pet friendly
  • Private garden
TRADITONAL STONE BUILT COTTAGE IN AN IDYLIC SETTING REGRET NO CHILDREN UNDER THE AGE OF 6 BABES IN ARMS ONLY SHORT BREAKS AVAILABLE - 3 NIGHTS TO START ON A FRIDAY OR 4 NIGHTS TO START ON A MONDAY  The property is peacefully tucked within a wooded h …see more

from $185 / night

$1,295 - $1,716 / week

Inquire View

from $185 / night

17

Vacation home in Winchcombe

Cotswolds / Winchcombe

6 16 2 nights min

  • 6 bedrooms
  • Sleeps 16
  • 2 nights min
  • Child friendly
  • Pet friendly
Milestone, aka the Big Cotswold Cottage, is an affordable, large, luxury home in a beautiful location. Perfect for friend and family reunions, hen parties and corporate team gatherings. Note: If you are booking for 7 days, please get in touch for a custom quote as we …see more

from $533 / night

$3,728 / week

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from $533 / night

(18) Very Good 

Certificate of Excellence

10

Vacation cottage in Winchcombe

Cotswolds / Winchcombe

3 6 3 nights min

  • 3 bedrooms
  • Sleeps 6
  • 3 nights min
  • Nearest beach 0 mi
  • Child friendly
  • Ask about pets
Our comfortable cosy Cotswold cottage on the ground floor has a fitted kitchen which includes a dishwasher, cooker, hob, microwave and fridge.A Washer dryer is situated in the under stairs cupboard.The kitchen leads to a dining room with a large pine table and six comfo …see more

Certificate of Excellence

from $142 / night

$1,122 / week

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Responds fast!
avg. 59 minutes

from $142 / night

42

Cottage rental in Winchcombe

Cotswolds / Winchcombe

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Child friendly
The private guest cottage of the owners Sudeley Castle, is now available for rent. The Guest Cottage has been completely renovated to the highest standard and contains many items of furniture and pictures from the Castle's private collection. Upstairs, the accommodation …see more

from $206 / night

$1,136 - $2,343 / week

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Responds fast!
avg. 1 hour 3 minutes

from $206 / night

20

Vacation cottage in Winchcombe

Cotswolds / Winchcombe

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Child friendly
St. Kenelm is an apartment that was restored from a paper mill to make spectacular accommodation with exposed stone walls and original beams. It is named after St Kenelm, who was a member of the royal family of Mercia, a boy king and martyr, who was murdered by an ambi …see more

from $142 / night

$746 - $1,207 / week

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Responds fast!
avg. 1 hour 3 minutes

from $142 / night

21

Vacation cottage in Winchcombe

Cotswolds / Winchcombe

2 3 Min stay varies

  • 2 bedrooms
  • Sleeps 3
  • Min stay varies
  • Child friendly
  • Pet friendly
Completely refurbished in November 2017, this apartment, which sleeps 3 people, is converted from the old forge. It is named in memory of Prince Rupert, who was a nephew of Charles I and commanded the Royalist cavalry during the English Civil War, made Sudeley his headq …see more

from $142 / night

$746 - $1,207 / week

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Responds fast!
avg. 1 hour 3 minutes

from $142 / night

28

Cottage rental in Winchcombe

Cotswolds / Winchcombe

2 3 Min stay varies

  • 2 bedrooms
  • Sleeps 3
  • Min stay varies
  • Child friendly
  • Pet friendly
This apartment, which sleeps 3 people, is converted from the old forge. It is named in memory of Charles I, who took refuge at Sudeley Castle after his failed siege of Gloucester during the English Civil War. Guests staying at Charles I enjoy complimentary entrance to …see more

from $142 / night

$746 - $1,207 / week

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Responds fast!
avg. 1 hour 3 minutes

from $142 / night

(19) Very Good 

13

Cottage rental in Winchcombe

Cotswolds / Winchcombe

2 4 3 nights min

  • 2 bedrooms
  • Sleeps 4
  • 3 nights min
  • Suitable for children age 5+
  • Car not necessary
  • Pet friendly
ARRIVAL DAYS - FRIDAYS for 3 or 7 nights, MONDAYS for 4 or 7 nights. Coates Mill Cottage is a 200-year-old Cotswold stone property with large private garden. It lies in a quiet position at the end of a terrace, in a wooded hollow with a mill stream opposite . The proper …see more

from $212 / night

$1,257 - $1,413 / week

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Responds fast!
avg. 1 hour 54 minutes

from $212 / night

22

Cottage rental in Winchcombe

Cotswolds / Winchcombe

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Child friendly
  • Pet friendly
  • Private garden
Welcome to Millers Cottage, brought to you exclusively by Character Cottages, local specialists in stylish, Cotswold holiday rentals Millers Cottage is one of a row of traditional Cotswold stone cottages in the heart of Winchcombe, an ancient Saxon town situated on the …see more

from $169 / night

$675 - $1,511 / week

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Responds fast!
avg. 46 minutes

from $169 / night