Cottages in Upton St Leonards and Houses – Holiday Lettings - Holiday Rentals Upton St Leonards

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1,141 Holiday homes

(15) Excellent 

24

Upton St Leonards holiday cottage rental

Gloucester / Upton St Leonards

3 5 min stay varies

  • 3 bedrooms
  • sleeps 5
  • min stay varies
  • Nearest beach 50 km
  • Child friendly
  • Ask about pets

from £48 / night

£335 - £670 / week

Enquire View

from £48 / night

(1) Very Good 

30

Holiday cottage in Upton St Leonards

Gloucester / Upton St Leonards

2 4 7 nights min

  • 2 bedrooms
  • sleeps 4
  • 7 nights min
  • Child friendly

from £68 / night

£475 / week

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from £68 / night

20

Upton St Leonards holiday cottage accommodation

Gloucester / Upton St Leonards

1 2 7 nights min

  • 1 bedroom
  • sleeps 2
  • 7 nights min
  • Child friendly
  • Car not necessary

from £54 / night

£375 / week

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from £54 / night

(1)  

14

Holiday home in Upton St Leonards

Gloucester / Upton St Leonards

1 2 7 nights min

  • 1 bedroom
  • sleeps 2
  • 7 nights min
  • Child friendly
  • Pet friendly

from £39 / night

£268 - £450 / week

Enquire View

from £39 / night

11

Holiday home letting

Gloucester / Upton St Leonards

3 5 3 nights min

  • 3 bedrooms
  • sleeps 5
  • 3 nights min
  • Child friendly
  • Private garden

from £51 / night

£362 - £1,035 / week

Enquire View

from £51 / night

Great rentals within 20 miles that match your search

Distance approx 15.41 miles from Upton St Leonards

(38) Excellent 

23

Holiday cottage in Ampney Crucis

Cotswolds / Ampney Crucis

2 4 3 nights min

  • 2 bedrooms
  • sleeps 4
  • 3 nights min
  • Child friendly
  • Private garden

from £89 / night

£425 - £600 / week

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from £89 / night

Distance approx 6.66 miles from Upton St Leonards

(7) Excellent 

9

Holiday cottage with golf nearby in Cheltenham

Cheltenham / Cheltenham

1 2 min stay varies

  • 1 bedroom
  • sleeps 2
  • min stay varies
  • Child friendly

from £60 / night

£300 - £550 / week

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from £60 / night

Distance approx 16.11 miles from Upton St Leonards

(17) Excellent 

Certificate of Excellence

16

Holiday barn accommodation

Herefordshire / Ross-on-Wye

2 4 min stay varies

  • 2 bedrooms
  • sleeps 4
  • min stay varies
  • Child friendly
  • Private garden

Certificate of Excellence

from £110 / night

£770 / week

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Responds fast!
avg. 1 hour 45 minutes

from £110 / night

Distance approx 7.3 miles from Upton St Leonards

(10) Excellent 

20

Holiday cottage with golf nearby in Charlton Kings

Cheltenham / Charlton Kings

3 6 min stay varies

  • 3 bedrooms
  • sleeps 6
  • min stay varies
  • Child friendly

from £100 / night

£550 - £630 / week

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Responds fast!
avg. 2 hours 37 minutes

from £100 / night

Distance approx 16.78 miles from Upton St Leonards

(15) Excellent 

Certificate of Excellence

49

Holiday lodge in South Cerney

Cotswolds / South Cerney

3 6 min stay varies

  • 3 bedrooms
  • sleeps 6
  • min stay varies
  • Beach / lakeside relaxation
  • Child friendly
  • Car not necessary

Certificate of Excellence

from £110 / night

£650 - £970 / week

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from £110 / night

Distance approx 15.46 miles from Upton St Leonards

13

Castlemorton holiday b&b rental

Malvern Hills / Castlemorton

1 3 2 nights min

  • 1 bedroom
  • sleeps 3
  • 2 nights min
  • Private garden

from £90 / night

£490 - £560 / week

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from £90 / night

Distance approx 17.7 miles from Upton St Leonards

8

Holiday apartment rental

Ross-on-Wye / Goodrich

2 4 min stay varies

  • 2 bedrooms
  • sleeps 4
  • min stay varies
  • Child friendly
  • Pet friendly

from £96 / night

£410 - £684 / week

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from £96 / night

Distance approx 16.54 miles from Upton St Leonards

29

Holiday home in Lydbrook

Forest of Dean / Lydbrook

8 16 min stay varies

  • 8 bedrooms
  • sleeps 16
  • min stay varies
  • Child friendly
  • Pet friendly
  • Private garden

from £550 / night

£1,700 - £3,942 / week

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from £550 / night

Distance approx 17.49 miles from Upton St Leonards

(5) Very Good 

21

Home rental in Kerne Bridge

Ross-on-Wye / Kerne Bridge

2 4 min stay varies

  • 2 bedrooms
  • sleeps 4
  • min stay varies
  • Child friendly
  • Private garden

from £58 / night

£291 - £495 / week

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Responds fast!
avg. 1 hour 54 minutes

from £58 / night

Distance approx 6.95 miles from Upton St Leonards

(5) Very Good 

6

Holiday barn in Cheltenham

Cheltenham / Cheltenham

1 2 2 nights min

  • 1 bedroom
  • sleeps 2
  • 2 nights min

from £80 / night

£350 / week

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Responds fast!
avg. 3 hours 5 minutes

from £80 / night

Distance approx 17.26 miles from Upton St Leonards

(5) Excellent 

28

Holiday home in Ledbury

Herefordshire / Ledbury

4 8 min stay varies

  • 4 bedrooms
  • sleeps 8
  • min stay varies
  • Child friendly
  • Pet friendly
  • Private garden

from £125 / night

£794 - £1,442 / week

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from £125 / night

Distance approx 6.93 miles from Upton St Leonards

(41) Excellent 

Certificate of Excellence

25

Holiday barn letting

Cotswolds / Gloucester

2 4 3 nights min

  • 2 bedrooms
  • sleeps 4
  • 3 nights min
  • Child friendly
  • Pet friendly
  • Private garden

Certificate of Excellence

from £80 / night

£300 - £650 / week

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Responds fast!
avg. 1 hour 29 minutes

from £80 / night

Distance approx 11.5 miles from Upton St Leonards

(28) Excellent 

Certificate of Excellence

22

Holiday cottage in Longhope

Gloucestershire / Longhope

2 6 min stay varies

  • 2 bedrooms
  • sleeps 6
  • min stay varies
  • Nearest beach 67 km
  • Child friendly
  • Pet friendly

Certificate of Excellence

from £150 / night

£495 - £1,005 / week

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Responds fast!
avg. 3 hours 12 minutes

from £150 / night

Distance approx 19.56 miles from Upton St Leonards

(55) Excellent 

36

Holiday apartment in Bourton-on-the-Water

Cotswolds / Bourton-on-the-Water

1 2 min stay varies

  • 1 bedroom
  • sleeps 2
  • min stay varies
  • Child friendly

from £65 / night

£450 - £500 / week

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Responds fast!
avg. 2 hours 13 minutes

from £65 / night

Distance approx 14.74 miles from Upton St Leonards

(2) Very Good 

12

South Cerney holiday home rental

Cotswolds / South Cerney

4 8 3 nights min

  • 4 bedrooms
  • sleeps 8
  • 3 nights min
  • Nearest beach 8 km
  • Child friendly

from £135 / night

£945 - £1,400 / week

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Responds fast!
avg. 29 minutes

from £135 / night

Distance approx 17.98 miles from Upton St Leonards

(30) Excellent 

19

Home rental in Christchurch, Gloucestershire

Forest of Dean / Christchurch, Gloucestershire

3 6 min stay varies

  • 3 bedrooms
  • sleeps 6
  • min stay varies
  • Child friendly
  • Pet friendly
  • Private garden

from £102 / night

£582 - £1,248 / week

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Responds fast!
avg. 3 hours 19 minutes

from £102 / night

Distance approx 7.53 miles from Upton St Leonards

(16) Excellent 

Certificate of Excellence

9

Holiday lodge in Chalford

Stroud / Chalford

1 2 3 nights min

  • 1 bedroom
  • sleeps 2
  • 3 nights min

Certificate of Excellence

from £55 / night

£385 / week

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Responds fast!
avg. 1 hour 8 minutes

from £55 / night

Distance approx 4.3 miles from Upton St Leonards

(5) Excellent 

11

Holiday apartment in Cranham

Gloucester / Cranham

1 4 2 nights min

  • 1 bedroom
  • sleeps 4
  • 2 nights min

from £90 / night

£450 / week

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from £90 / night

Distance approx 6 miles from Upton St Leonards

18

Holiday apartment rental

Stroud District / Stroud

3 9 1 night min

  • 3 bedrooms
  • sleeps 9
  • 1 night min
  • Child friendly

from £250 / night

£1,750 / week

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from £250 / night

Distance approx 18.63 miles from Upton St Leonards

(21) Excellent 

23

Holiday barn in Lydney

Forest of Dean / Lydney

1 3 7 nights min

  • 1 bedroom
  • sleeps 3
  • 7 nights min
  • Nearest beach 58 km
  • Child friendly

from £75 / night

£525 / week

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Responds fast!
avg. 1 hour 34 minutes

from £75 / night

Distance approx 16.11 miles from Upton St Leonards

(37) Excellent 

Certificate of Excellence

20

Holiday studio rental

Herefordshire / Ross-on-Wye

Studio 2 2 nights min

  • Studio
  • sleeps 2
  • 2 nights min
  • Pet friendly
  • Private garden

Certificate of Excellence

from £60 / night

£420 / week

Book View

Responds fast!
avg. 2 hours 17 minutes

from £60 / night

Distance approx 5.96 miles from Upton St Leonards

(1) Excellent 

45

Holiday home in Cheltenham

Cotswolds / Cheltenham

7 20 min stay varies

  • 7 bedrooms
  • sleeps 20
  • min stay varies
  • Child friendly
  • Private garden

from £1,300 / night

£4,000 - £11,800 / week

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from £1,300 / night

Distance approx 13.29 miles from Upton St Leonards

(5) Average 

22

Holiday cottage in Blakeney

Forest of Dean / Blakeney

1 6 1 night min

  • 1 bedroom
  • sleeps 6
  • 1 night min
  • Ask owner if suitable for children
  • Pet friendly
  • Private garden

from £150 / night

£1,050 / week

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from £150 / night

Distance approx 16.29 miles from Upton St Leonards

(18) Excellent 

24

Holiday villa with shared pool in Lower Mill

Cirencester / Lower Mill

5 9 min stay varies

  • 5 bedrooms
  • sleeps 9
  • min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly

from £400 / night

£2,200 / week

Book View

Responds fast!
avg. 1 hour 33 minutes

from £400 / night

Distance approx 19.2 miles from Upton St Leonards

(14) Excellent 

19

Holiday cottage in Bourton-on-the-Water

Cotswolds / Bourton-on-the-Water

2 5 min stay varies

  • 2 bedrooms
  • sleeps 5
  • min stay varies
  • Child friendly
  • Pet friendly
  • Private garden

from £120 / night

£545 - £995 / week

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Responds fast!
avg. 3 hours 34 minutes

from £120 / night

Distance approx 3.21 miles from Upton St Leonards

(3) Excellent 

30

Painswick holiday manor house rental

Stroud District / Painswick

14 24 2 nights min

  • 14 bedrooms
  • sleeps 24
  • 2 nights min
  • Swimming pool
  • Child friendly
  • Private garden

from £3,000 / night

£12,000 - £54,000 / week

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from £3,000 / night

Distance approx 5.96 miles from Upton St Leonards

(14) Very Good 

22

Apartment rental in Stroud

Stroud District / Stroud

3 8 min stay varies

  • 3 bedrooms
  • sleeps 8
  • min stay varies
  • Child friendly
  • Car not necessary
  • Pet friendly

from £100 / night

£760 - £1,675 / week

Enquire View

from £100 / night

Distance approx 14.24 miles from Upton St Leonards

12

Holiday caravan/mobile home in Dymock

Forest of Dean / Dymock

1 4 3 nights min

  • 1 bedroom
  • sleeps 4
  • 3 nights min
  • Child friendly

from £49 / night

£343 / week

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from £49 / night

Distance approx 2.8 miles from Upton St Leonards

(2) Average 

8

Holiday apartment letting

Cotswolds / Gloucester

1 2 min stay varies

  • 1 bedroom
  • sleeps 2
  • min stay varies
  • Child friendly
  • Car not necessary

from £125 / night

£700 / week

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from £125 / night

Distance approx 17.06 miles from Upton St Leonards

38

Holiday apartment in Cirencester

Cotswolds / Cirencester

2 4 min stay varies

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

from £142 / night

£998 - £1,383 / week

Enquire View

from £142 / night

Distance approx 14.64 miles from Upton St Leonards

(11) Excellent 

35

Holiday cottage rental

Cirencester / Barnsley

4 8 min stay varies

  • 4 bedrooms
  • sleeps 8
  • min stay varies
  • Child friendly
  • Private garden

from £189 / night

£1,323 - £3,149 / week

Book View

Responds fast!
avg. 49 minutes

from £189 / night

Distance approx 9.27 miles from Upton St Leonards

13

Nailsworth holiday cottage rental

Stroud District / Nailsworth

1 2 2 nights min

  • 1 bedroom
  • sleeps 2
  • 2 nights min
  • Child friendly
  • Pet friendly
  • Private garden

from £163 / night

£600 / week

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from £163 / night

Distance approx 15.54 miles from Upton St Leonards

8

Home rental in Lydbrook

Forest of Dean / Lydbrook

3 7 2 nights min

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

from £70 / night

£490 / week

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from £70 / night

Distance approx 9.27 miles from Upton St Leonards

(1) Excellent 

9

Holiday cottage rental

Stroud District / Nailsworth

1 2 2 nights min

  • 1 bedroom
  • sleeps 2
  • 2 nights min
  • Child friendly
  • Pet friendly
  • Private garden

from £190 / night

£650 / week

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from £190 / night

Distance approx 15.85 miles from Upton St Leonards

4

Whitecroft holiday home rental

Lydney / Whitecroft

2 4 7 nights min

  • 2 bedrooms
  • sleeps 4
  • 7 nights min
  • Child friendly
  • Private garden

from £572 / night

£4,000 / week

Book View

from £572 / night

Top Destination reviews

Bondend Holiday Cottage
Perfect!

A former Gloucestershire resident I travelled back to visit friends from the area. I stayed for one week and the cottage was everything I had hoped for. It gave me a great base for getting around and also allowed me the opportunity to have friends visit me. The cottage itself was ideal, well maintained, clean and fresh. A fresh Flower arrangement was my welcome - a seriously nice touch. Attention to detail by the owners went a long way to making my stay Perfect. One caution - if booking from overseas or even Scotland get the banking arranged in good time. I was in Scotland when I booked and the banks there could not do the booking transfer for me in good enough time. Once across the border it was fine.Again though throughout the process the owners were a delight to deal with.see more
1 Little Court Cottages
Kids felt safe

My daughters said that they felt safe here, protected by a very high perimeter wall and a sold remote-controlled gate, my wife and I agree with them. Good location, close to the city of Gloucester, and the postcard town of Painswick. It's a cozy small place, and was perfect for our family of four. The owner went beyond the call of duty to ensure our stay was void of any hassle, even though we arrived rather late at night on Christmas Eve.see more