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

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725 Holiday homes

(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 £110 / night

£370 - £780 / week

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Responds fast!
avg. 2 hours 31 minutes

from £110 / 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 £110 / night

£330 - £495 / week

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from £110 / 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 £100 / night

£595 / week

Book View

Responds fast!
avg. 20 minutes

from £100 / 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 £179 / night

£899 - £1,599 / week

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from £179 / night

(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 £90 / night

£350 - £585 / week

Book View

Responds fast!
avg. 2 hours 31 minutes

from £90 / 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 £75 / night

£525 - £950 / week

Book View

Responds fast!
avg. 1 hour 46 minutes

from £75 / 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 

17

Holiday home in Upwey

Weymouth / Upwey

3 6 3 nights min

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

from £69 / night

£489 - £1,805 / week

Enquire View

from £69 / 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 - £1,310 / week

Enquire View

from £62 / 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 - £1,170 / week

Enquire View

from £57 / 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 - £1,310 / week

Enquire View

from £62 / 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 £56 / night

£394 - £1,204 / week

Enquire View

from £56 / 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 - £1,824 / week

Enquire View

from £69 / night

Great rentals within 20 miles that match your search

Distance approx 19.44 miles from Upwey

(9) Excellent 

9

Sherborne holiday cottage rental

Dorset / Sherborne

1 2 min stay varies

  • 1 bedroom
  • sleeps 2
  • min stay varies
  • Nearest beach 37 km
  • Car not necessary

from £43 / night

£295 - £570 / week

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from £43 / night

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 £200 / night

£1,200 - £1,550 / week

Book View

Responds fast!
avg. 2 hours 0 minutes

from £200 / night

Distance approx 3.8 miles from Upwey Show on Map

(12) Very Good 

21

Chickerell holiday caravan/mobile home rental

Weymouth / Chickerell

3 8 2 nights min

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

from £60 / night

£560 - £895 / week

Book View

Responds fast!
avg. 2 hours 16 minutes

from £60 / night

Distance approx 3.73 miles from Upwey Show on Map

15

Cottage rental in Abbotsbury

Weymouth / Abbotsbury

2 5 7 nights min

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

from £86 / night

£600 / week

Enquire View

from £86 / night

Distance approx 10.05 miles from Upwey

(1) Excellent 

5

Holiday home in Tolpuddle

Dorchester / Tolpuddle

1 2 min stay varies

  • 1 bedroom
  • sleeps 2
  • min stay varies
  • Nearest beach 25 km
  • Private garden

from £84 / night

£425 - £500 / week

Book View

Responds fast!
avg. 2 hours 58 minutes

from £84 / night

Distance approx 8.18 miles from Upwey

(46) Excellent 

Certificate of Excellence

12

Holiday apartment in Piddlehinton

Dorchester / Piddlehinton

1 4 min stay varies

  • 1 bedroom
  • sleeps 4
  • min stay varies
  • Nearest beach 21 km
  • Child friendly
  • Private garden

Certificate of Excellence

from £60 / night

£320 - £620 / week

Book View

Responds fast!
avg. 3 hours 3 minutes

from £60 / night

Distance approx 4.91 miles from Upwey

(2) Excellent 

26

Holiday home in Weymouth

Dorset / Weymouth

3 6 3 nights min

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

from £130 / night

£600 - £1,100 / week

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from £130 / night

Distance approx 19.58 miles from Upwey

(8) Excellent 

16

East Coker holiday home rental

Somerset / East Coker

2 4 7 nights min

  • 2 bedrooms
  • sleeps 4
  • 7 nights min
  • Nearest beach 50 km
  • Swimming pool
  • Child friendly

from £150 / night

£1,050 / week

Book View

Responds fast!
avg. 28 minutes

from £150 / 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 min stay varies

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

Certificate of Excellence

from £55 / night

£350 - £500 / week

Book View

Responds fast!
avg. 1 hour 44 minutes

from £55 / night

Distance approx 15.46 miles from Upwey

(1) Excellent 

15

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 £575 / night

£1,080 - £2,145 / week

Book View

from £575 / 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 £60 / night

£420 - £670 / week

Book View

from £60 / night

Distance approx 8.68 miles from Upwey

(3) Very Good 

18

Isle of Portland holiday home rental

Dorset / Isle of Portland

4 8 min stay varies

  • 4 bedrooms
  • sleeps 8
  • min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0.2 km
  • Suitable for children age 5+

from £100 / night

£700 - £1,350 / week

Enquire View

from £100 / 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 £180 / night

£550 - £1,170 / week

Book View

from £180 / night

Distance approx 15.69 miles from Upwey

(26) Very Good 

27

Holiday farmhouse with indoor pool in Moorbath

Bridport / Moorbath

9 17 min stay varies

  • 9 bedrooms
  • sleeps 17
  • min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly

from £150 / night

£1,800 - £5,400 / week

Book View

from £150 / night

Distance approx 2.79 miles from Upwey Show on Map

(9) Excellent 

26

Holiday caravan/mobile home in Preston, Dorset

Weymouth / Preston, Dorset

3 8 min stay varies

  • 3 bedrooms
  • sleeps 8
  • min stay varies
  • Nearest beach 0.5 km
  • Swimming pool
  • Child friendly

from £115 / night

£700 - £1,100 / week

Book View

Responds fast!
avg. 1 hour 21 minutes

from £115 / night

Distance approx 15.38 miles from Upwey

(2) Excellent 

18

Holiday cottage in Melbury Osmond

Dorset / Melbury Osmond

3 5 1 night min

  • 3 bedrooms
  • sleeps 5
  • 1 night min
  • Nearest beach 31 km
  • Child friendly
  • Pet friendly

from £130 / night

£750 - £900 / week

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from £130 / night

Distance approx 13.33 miles from Upwey

(10) Excellent 

5

Holiday yurt in Bridport

Dorset / Bridport

1 2 2 nights min

  • 1 bedroom
  • sleeps 2
  • 2 nights min
  • Nearest beach 7 km
  • Child friendly
  • Private garden

from £120 / night

£840 / week

Book View

from £120 / night

Distance approx 18.52 miles from Upwey

(9) Very Good 

25

Holiday cottage in Corfe Castle

Isle of Purbeck / Corfe Castle

2 5 min stay varies

  • 2 bedrooms
  • sleeps 5
  • min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 5 km
  • Child friendly

from £129 / night

£495 - £958 / week

Enquire View

from £129 / night

Distance approx 6.08 miles from Upwey

40

Ski lodge to rent in Weymouth

Dorset / Weymouth

3 6 min stay varies

  • 3 bedrooms
  • sleeps 6
  • min stay varies
  • Swimming pool
  • Ski
  • Child friendly

from £110 / night

£900 - £1,500 / week

Book View

Responds fast!
avg. 33 minutes

from £110 / night

Distance approx 13.14 miles from Upwey

(1) Excellent 

12

Dorchester holiday cottage rental

Dorset / Dorchester

2 4 7 nights min

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

from £125 / night

£700 / week

Book View

Responds fast!
avg. 3 hours 20 minutes

from £125 / 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 19.01 miles from Upwey

(23) Excellent 

15

Holiday barn in Corfe Castle

Corfe Castle / Kingston, Dorset

3 6 min stay varies

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

Pricing unknown

Enquire View

Pricing unknown

Distance approx 14.89 miles from Upwey

(1) Very Good 

30

Holiday caravan/mobile home with shared pool in Poole Harbour

Poole / Poole Harbour

3 6 min stay varies

  • 3 bedrooms
  • sleeps 6
  • min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0 km
  • Swimming pool

from £55 / night

£300 - £1,050 / week

Book View

from £55 / night

Distance approx 3.6 miles from Upwey Show on Map

13

Weymouth holiday apartment rental

Dorset / Weymouth

2 6 min stay varies

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

from £37 / night

£255 - £895 / week

Book View

from £37 / night

Distance approx 7.91 miles from Upwey

9

Home rental in Bridport

Dorset / Bridport

3 6 2 nights min

  • 3 bedrooms
  • sleeps 6
  • 2 nights min
  • Child friendly
  • Pet friendly

from £135 / night

£945 / week

Book View

Responds fast!
avg. 3 hours 34 minutes

from £135 / night

Distance approx 4.94 miles from Upwey Show on Map

(1) Excellent 

9

Holiday b&b in Abbotsbury

Weymouth / Abbotsbury

2 4 2 nights min

  • 2 bedrooms
  • sleeps 4
  • 2 nights min
  • Beach / lakeside relaxation
  • Nearest beach 3 km
  • Child friendly

from £195 / night

£1,320 / week

Book View

from £195 / night

Distance approx 13.18 miles from Upwey

(1) Excellent 

7

Holiday home in West Bay

Bridport / West Bay

2 4 3 nights min

  • 2 bedrooms
  • sleeps 4
  • 3 nights min
  • Nearest beach 2 km
  • Child friendly
  • Car not necessary

from £60 / night

£700 / week

Book View

Responds fast!
avg. 3 hours 16 minutes

from £60 / 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