Cottages in Upwey and Houses – Holiday Lettings - Holiday Rentals Upwey

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933 Holiday homes

(3) Very Good 

12

Holiday cottage in Upwey

Weymouth / Upwey

1 2 min stay varies

  • 1 bedroom
  • sleeps 2
  • min stay varies
  • Beach / lakeside relaxation
  • Child friendly
  • Pet friendly

from £103 / night

£401 - £670 / week

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Responds fast!
avg. 2 hours 47 minutes

from £103 / night

(3) Excellent 

12

Holiday cottage in Upwey

Weymouth / Upwey

2 4 min stay varies

  • 2 bedrooms
  • sleeps 4
  • min stay varies
  • Beach / lakeside relaxation
  • Child friendly
  • Pet friendly

from £115 / night

£424 - £894 / week

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Responds fast!
avg. 2 hours 47 minutes

from £115 / night

(2) Excellent 

12

Cottage rental in Upwey

Weymouth / Upwey

1 4 3 nights min

  • 1 bedroom
  • sleeps 4
  • 3 nights min
  • Beach / lakeside relaxation
  • Nearest beach 8 km
  • Child friendly

from £115 / night

£682 / week

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Responds fast!
avg. 19 minutes

from £115 / night

(11) Excellent 

57

Holiday cottage in Upwey

Weymouth / Upwey

4 8 min stay varies

  • 4 bedrooms
  • sleeps 8
  • min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 4 km
  • Child friendly

from £252 / night

£1,831 / week

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from £252 / night

(19) Very Good 

21

Upwey holiday cottage rental

Weymouth / Upwey

2 4 2 nights min

  • 2 bedrooms
  • sleeps 4
  • 2 nights min
  • Beach / lakeside relaxation
  • Nearest beach 4 km
  • Child friendly
“The most idyllic holiday cottage” This is the second time that I have visited this gorgeous cottage. It is compact but has everything you could need for a short break. The garden is sweet and my children aged 11 and 6, love the cottage and found plenty to do in the area and have already requested to go again. Even washing up is a pleasure here - when you look out the window at the calm, rural view. Thoroughly recommend it.

from £126 / night

£378 - £796 / week

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from £126 / night

(2) Excellent 

32

Holiday cottage in Upwey

Weymouth / Upwey

3 6 min stay varies

  • 3 bedrooms
  • sleeps 6
  • min stay varies
  • Nearest beach 5 km
  • Child friendly
  • Pet friendly

from £103 / night

£642 - £1,088 / week

Book View

Responds fast!
avg. 1 hour 32 minutes

from £103 / night

(2) Excellent 

20

Holiday home letting

Weymouth / Upwey

3 6 3 nights min

  • 3 bedrooms
  • sleeps 6
  • 3 nights min
  • Child friendly
  • Pet friendly
  • Private garden

from £69 / night

£489 - £1,934 / week

Enquire View

from £69 / night

17

Holiday home in Upwey

Weymouth / Upwey

1 2 3 nights min

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

from £44 / night

£308 - £615 / week

Enquire View

from £44 / night

(1) Excellent 

15

Holiday home accommodation

Weymouth / Upwey

2 4 3 nights min

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

from £57 / night

£401 - £1,393 / week

Enquire View

from £57 / night

(2) Excellent 

19

Holiday home rental

Weymouth / Upwey

2 4 3 nights min

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

from £62 / night

£438 - £1,440 / week

Enquire View

from £62 / night

18

Holiday home rental

Weymouth / Upwey

2 4 3 nights min

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

from £62 / night

£438 - £1,510 / week

Enquire View

from £62 / night

(1) Excellent 

17

Holiday home in Upwey

Weymouth / Upwey

3 6 3 nights min

  • 3 bedrooms
  • sleeps 6
  • 3 nights min
  • Child friendly
  • Private garden

from £70 / night

£495 - £1,805 / week

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from £70 / night

18

Holiday cottage in Upwey

Weymouth / Upwey

1 2 3 nights min

  • 1 bedroom
  • sleeps 2
  • 3 nights min

from £56 / night

£396 - £745 / week

Enquire View

from £56 / night

13

Upwey holiday cottage rental

Weymouth / Upwey

2 4 3 nights min

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

from £59 / night

£417 - £860 / week

Enquire View

from £59 / night

(5) Excellent 

31

Holiday home in Upwey

Weymouth / Upwey

2 4 3 nights min

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

from £57 / night

£403 - £1,382 / week

Enquire View

from £57 / night

Great rentals within 20 miles that match your search

Distance approx 3.14 miles from Upwey Show on Map

(14) Very Good 

38

Holiday home in Greenhill

Weymouth / Greenhill

4 6 2 nights min

  • 4 bedrooms
  • sleeps 6
  • 2 nights min
  • Beach / lakeside relaxation
  • Child friendly
  • Car not necessary

from £229 / night

£1,374 - £1,775 / week

Book View

Responds fast!
avg. 2 hours 7 minutes

from £229 / night

Distance approx 15.44 miles from Upwey

12

Holiday lodge with shared pool in Woolland

Blandford Forum / Woolland

2 4 min stay varies

  • 2 bedrooms
  • sleeps 4
  • min stay varies
  • Nearest beach 40 km
  • Swimming pool
  • Child friendly

from £115 / night

£573 - £1,117 / week

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from £115 / night

Distance approx 15.45 miles from Upwey

(1) Excellent 

16

Cottage rental in Woolland with shared pool

Blandford Forum / Woolland

3 7 min stay varies

  • 3 bedrooms
  • sleeps 7
  • min stay varies
  • Nearest beach 40 km
  • Swimming pool
  • Child friendly

from £228 / night

£1,140 - £2,405 / week

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from £228 / night

Distance approx 17.43 miles from Upwey

(31) Excellent 

13

Holiday cottage in Sturminster Newton

Dorset / Sturminster Newton

2 4 7 nights min

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

from £69 / night

£481 - £768 / week

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from £69 / night

Distance approx 11.8 miles from Upwey

(25) Very Good 

Certificate of Excellence

32

Holiday home in West Lulworth

Dorset / West Lulworth

3 8 min stay varies

  • 3 bedrooms
  • sleeps 8
  • min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 3 km
  • Child friendly

Certificate of Excellence

from £201 / night

£911 - £1,924 / week

Book View

Responds fast!
avg. 3 hours 29 minutes

from £201 / night

Distance approx 15.45 miles from Upwey

(2) Very Good 

18

Holiday home rental

Blandford Forum / Woolland

4 8 min stay varies

  • 4 bedrooms
  • sleeps 8
  • min stay varies
  • Nearest beach 40 km
  • Swimming pool
  • Child friendly

from £457 / night

£1,065 - £2,285 / week

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from £457 / night

Distance approx 4.03 miles from Upwey Show on Map

(22) Excellent 

Certificate of Excellence

10

Holiday caravan/mobile home with shared pool in Littlesea Holiday Park

Weymouth / Littlesea Holiday Park

3 8 3 nights min

  • 3 bedrooms
  • sleeps 8
  • 3 nights min
  • Beach / lakeside relaxation
  • Nearest beach 3 km
  • Swimming pool

Certificate of Excellence

from £63 / night

£401 / week

Book View

Responds fast!
avg. 1 hour 34 minutes

from £63 / night

Distance approx 12.26 miles from Upwey

(8) Excellent 

17

Holiday cottage in Cerne Abbas

Dorset / Cerne Abbas

4 9 min stay varies

  • 4 bedrooms
  • sleeps 9
  • min stay varies
  • Nearest beach 30 km
  • Child friendly
  • Pet friendly

from £155 / night

£773 - £1,701 / week

Book View

Responds fast!
avg. 1 hour 37 minutes

from £155 / night

Distance approx 14.72 miles from Upwey

(23) Excellent 

27

Bridport holiday home rental

Dorset / Bridport

11 30 2 nights min

  • 11 bedrooms
  • sleeps 30
  • 2 nights min
  • Beach / lakeside relaxation
  • Nearest beach 2 km
  • Child friendly

from £1,603 / night

£5,153 / week

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from £1,603 / night

Distance approx 6.7 miles from Upwey

(2) Excellent 

18

Isle of Portland holiday apartment accommodation

Dorset / Isle of Portland

3 6 min stay varies

  • 3 bedrooms
  • sleeps 6
  • min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 1 km
  • Swimming pool

from £134 / night

£622 - £1,334 / week

Book View

Responds fast!
avg. 3 hours 27 minutes

from £134 / night

Distance approx 16.18 miles from Upwey

(11) Excellent 

22

Holiday cottage in Sturminster Newton

Dorset / Sturminster Newton

2 6 min stay varies

  • 2 bedrooms
  • sleeps 6
  • min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 46 km
  • Child friendly

from £98 / night

£401 - £742 / week

Book View

Responds fast!
avg. 3 hours 44 minutes

from £98 / night

Distance approx 2.82 miles from Upwey Show on Map

(71) Excellent 

Certificate of Excellence

24

Holiday b&b in Preston, Dorset

Weymouth / Preston, Dorset

1 2 2 nights min

  • 1 bedroom
  • sleeps 2
  • 2 nights min
  • Beach / lakeside relaxation
  • Nearest beach 2 km
  • Car not necessary

Certificate of Excellence

from £92 / night

£722 - £802 / week

Book View

Responds fast!
avg. 1 hour 6 minutes

from £92 / night

Distance approx 11.29 miles from Upwey

6

Holiday home in Shipton Gorge

Bridport / Shipton Gorge

3 8 14 nights min

  • 3 bedrooms
  • sleeps 8
  • 14 nights min
  • Child friendly
  • Private garden

from £144 / night

£1,002 / week

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from £144 / night

Distance approx 9.3 miles from Upwey

(34) Very Good 

31

Holiday studio in Isle of Portland

Dorset / Isle of Portland

Studio 2 min stay varies

  • Studio
  • sleeps 2
  • min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 2 km

from £54 / night

£338 - £401 / week

Book View

Responds fast!
avg. 1 hour 38 minutes

from £54 / night

Distance approx 4.62 miles from Upwey

(30) Excellent 

21

Weymouth holiday townhouse rental

Dorset / Weymouth

2 4 min stay varies

  • 2 bedrooms
  • sleeps 4
  • min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0.1 km
  • Child friendly

from £60 / night

£300 - £1,050 / week

Enquire View

from £60 / night

Distance approx 10.21 miles from Upwey

(21) Excellent 

23

Holiday cottage in Lulworth Cove

Wareham / Lulworth Cove

3 6 min stay varies

  • 3 bedrooms
  • sleeps 6
  • min stay varies
  • Beach / lakeside relaxation
  • Child friendly
  • Private garden

from £130 / night

£470 - £995 / week

Enquire View

from £130 / night

Distance approx 2.84 miles from Upwey Show on Map

(10) Very Good 

24

Cottage rental in Preston, Dorset

Weymouth / Preston, Dorset

2 7 3 nights min

  • 2 bedrooms
  • sleeps 7
  • 3 nights min
  • Beach / lakeside relaxation
  • Nearest beach 0 km
  • Child friendly

from £287 / night

£859 - £1,340 / week

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from £287 / night

Distance approx 14.48 miles from Upwey

(20) Excellent 

14

Holiday farmhouse with indoor pool in Symondsbury

Bridport / Symondsbury

8 17 min stay varies

  • 8 bedrooms
  • sleeps 17
  • min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 5 km
  • Swimming pool

from £499 / night

£3,495 - £6,400 / week

Enquire View

from £499 / night

Distance approx 6.9 miles from Upwey

(5) Excellent 

22

Holiday home in Isle of Portland

Dorset / Isle of Portland

2 5 7 nights min

  • 2 bedrooms
  • sleeps 5
  • 7 nights min
  • Beach / lakeside relaxation
  • Nearest beach 0.5 km
  • Child friendly

from £99 / night

£687 / week

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from £99 / night

Distance approx 17 miles from Upwey

(5) Very Good 

13

Holiday home in Ibberton

Dorset / Ibberton

2 4 3 nights min

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

from £50 / night

£350 - £1,026 / week

Enquire View

from £50 / night

Distance approx 17.38 miles from Upwey

(2) Excellent 

21

Ibberton holiday home rental

Dorset / Ibberton

2 4 3 nights min

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

from £49 / night

£346 - £887 / week

Enquire View

from £49 / night

Distance approx 14.76 miles from Upwey

8

Holiday home in East Chelborough

Dorset / East Chelborough

1 4 3 nights min

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

from £42 / night

£295 - £638 / week

Enquire View

from £42 / night

Distance approx 8.69 miles from Upwey

(2) Excellent 

19

Holiday home in Weymouth

Dorset / Weymouth

4 8 3 nights min

  • 4 bedrooms
  • sleeps 8
  • 3 nights min
  • Child friendly
  • Pet friendly
  • Private garden

from £75 / night

£531 - £1,957 / week

Enquire View

from £75 / night

Distance approx 18.4 miles from Upwey

16

Wootton Fitzpaine holiday cottage rental

Bridport / Wootton Fitzpaine

1 2 3 nights min

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

from £50 / night

£354 - £780 / week

Enquire View

from £50 / night

Distance approx 2.53 miles from Upwey Show on Map

10

Holiday home in Osmington Mills

Dorset / Osmington Mills

3 5 3 nights min

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

from £48 / night

£341 - £1,074 / week

Enquire View

from £48 / night

Top Destination reviews

The Brambles
Lovely cottage

The brambles is a lovely cottage in a lovely location, & easy to get to different places would recamend to friends … see more
Upwey Cottage - Weymouth
Cosy and comfortable

Enjoyed a great weekend away in this cosy and comfortable cottage, which had everything we needed for our stay. Lovely views from the windows over local countryside. Garden was quiet and secure. … see more
Vitality Cottage
Lovely cottage in quiet village close to Dorchester and Weymouth

We stayed for a week with teenage daughters and an elderly parent, and had a wonderful time. Very quiet (apart from Saturday night when a private party at the nearby pub continued into the small hours). We ate twice in the pub, but otherwise cooked at the cottage (after shopping at supermarkets in Dorchester and Weymouth, or the local shop at Broadwey), and found everything we needed in the well-equipped kitchen. Lovely to sit outside in the gravelled garden. Bedrooms clean and attractive, with a loft bedroom where our teenage daughters could establish their own space! Lovely location, with a footpath leading up to the top of the Ridgeway and splendid views both north over Dorchester and south towards Portland. A gentle walk down Elwell Street leads to the Wishing Well and lovely tea rooms. We were in Upwey without a car, but there is an excellent local bus service (every ten minutes for much of the day). The house was immaculate when we arrived, and the owners friendly and helpful.see more

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