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Holiday Lettings
> Europe
> United Kingdom
> England
> Dorset
> Weymouth
> Houses and Chalets in Upwey

Holiday Rentals in Upwey - Holiday Lettings - Villas

Price per night

£1 £750 -

Bedrooms

Property rating (out of 5)
  • 5
  • 4 and above
  • 3 and above
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Filtered properties are rated either by Tripadvisor Vacation Rentals users, or by Vrbo users. Both rating systems are separate, and are depicted differently as shown in the key above. Tripadvisor performs checks on its reviews. Holiday Lettings and companies under Tripadvisor Group do not check Vrbo reviews.
Property type
  • Cottage (1)
  • House (3)
  • Chalet (1)
  • Farmhouse (1)

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1 Holiday homes

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Great rentals within 20 miles that match your search

Holiday cottage in Symondsbury

Symondsbury cottage

  • 3 bedrooms
  • 1 bathroom
  • sleeps 5
29 reviews

from £304 / night

£1,140 / week

1 / 6

Great rentals within 20 miles that match your search

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Holiday cottage in Weymouth

Weymouth cottage

  • 3 bedrooms
  • 1 bathroom
  • sleeps 6

1 filter does not match: Beach or lakeside relaxation

5 reviews

from £115 / night

£802 - £1,684 / week

1 / 28

Great rentals within 20 miles that match your search

Holiday cottage in Langton Herring

Langton Herring cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

1 filter does not match: Beach or lakeside relaxation

1 review

from £139 / night

£974 / week

1 / 40

Great rentals within 20 miles that match your search

Holiday cottage in West Milton

West Milton cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

1 filter does not match: Beach or lakeside relaxation

18 reviews

from £109 / night

£831 - £1,031 / week

1 / 13

Great rentals within 20 miles that match your search

Holiday cottage with golf nearby in Burton Bradstock

Burton Bradstock cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

1 filter does not match: Beach or lakeside relaxation

45 reviews

from £92 / night

£802 - £1,031 / week

1 / 15

Great rentals within 20 miles that match your search

Holiday cottage in Symondsbury

Symondsbury cottage

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

1 filter does not match: Beach or lakeside relaxation

45 reviews

from £227 / night

£911 / week

1 / 8

Great rentals within 20 miles that match your search

Holiday cottage with golf nearby in East Burton

East Burton cottage

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

1 filter does not match: Beach or lakeside relaxation

5 reviews

from £287 / night

£2,004 / week

1 / 0

Great rentals within 20 miles that match your search

Holiday home with golf nearby in Wareham

Wareham house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 10

1 filter does not match: Property type

5 reviews

from £287 / night

£2,004 / week

1 / 15

Great rentals within 20 miles that match your search

Holiday home in Wareham

Wareham house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 10

1 filter does not match: Property type

11 reviews

from £287 / night

£2,004 / week

1 / 16

Great rentals within 20 miles that match your search

Chideock holiday cottage rental

Chideock cottage

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 filter does not match: Beach or lakeside relaxation

30 reviews

from £172 / night

£654 - £1,634 / week

1 / 36

Great rentals within 20 miles that match your search

Holiday cottage in Lulworth Cove

Lulworth Cove cottage

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 filter does not match: Beach or lakeside relaxation

26 reviews

from £195 / night

£1,363 / week

1 / 23

Great rentals within 20 miles that match your search

Isle of Portland holiday cottage rental

Isle of Portland cottage

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

1 filter does not match: Beach or lakeside relaxation

32 reviews

from £126 / night

£745 - £1,546 / week

1 / 44

Great rentals within 20 miles that match your search

Holiday chalet in Eype

Eype chalet

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

1 filter does not match: Property type

35 reviews

from £296 / night

£1,060 / week

1 / 5

Great rentals within 20 miles that match your search

Holiday cottage rental

Osmington Mills cottage

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

1 filter does not match: Beach or lakeside relaxation

20 reviews

from £184 / night

£1,283 / week

1 / 17

Great rentals within 20 miles that match your search

Holiday cottage in Lulworth Cove

Lulworth Cove cottage

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 10

1 filter does not match: Beach or lakeside relaxation

36 reviews

from £269 / night

£1,603 / week

1 / 21

Great rentals within 20 miles that match your search

Holiday cottage in Chideock

Chideock cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

1 filter does not match: Beach or lakeside relaxation

6 reviews

from £121 / night

£596 - £1,203 / week

1 / 56

Great rentals within 20 miles that match your search

Holiday cottage in Symondsbury

Symondsbury cottage

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

1 filter does not match: Beach or lakeside relaxation

39 reviews

from £410 / night

£1,712 / week

1 / 8

Great rentals within 20 miles that match your search

Holiday cottage in Isle of Portland

Isle of Portland cottage

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 filter does not match: Beach or lakeside relaxation

30 reviews

from £155 / night

£573 - £1,489 / week

1 / 35

Great rentals within 20 miles that match your search

Holiday cottage in Symondsbury

Symondsbury cottage

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 7

1 filter does not match: Beach or lakeside relaxation

33 reviews

from £495 / night

£1,941 / week

1 / 10

Great rentals within 20 miles that match your search

Holiday farmhouse with indoor pool in Symondsbury

Symondsbury farmhouse

  • 8 bedrooms
  • 5 bathrooms
  • sleeps 17

1 filter does not match: Property type

28 reviews

from £1,792 / night

£6,292 / week

1 / 16

Great rentals within 20 miles that match your search

Holiday cottage in Piddlehinton

Piddlehinton cottage

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 filter does not match: Beach or lakeside relaxation

7 reviews

from £197 / night

£1,374 / week

1 / 11

Great rentals within 20 miles that match your search

Langton Herring holiday cottage rental

Langton Herring cottage

  • 1 bedroom
  • 2 bathrooms
  • sleeps 2

1 filter does not match: Beach or lakeside relaxation

32 reviews

from £172 / night

£1,203 / week

1 / 21

Great rentals within 20 miles that match your search

Swyre holiday cottage rental

Swyre cottage

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

1 filter does not match: Beach or lakeside relaxation

14 reviews

from £338 / night

£2,365 / week

1 / 24

Great rentals within 20 miles that match your search

Melplash holiday cottage rental

Melplash cottage

  • 3 bedrooms
  • 1 bathroom
  • sleeps 5

1 filter does not match: Beach or lakeside relaxation

37 reviews

from £211 / night

£873 - £1,449 / week

1 / 41

Great rentals within 20 miles that match your search

Holiday cottage in Maiden Newton

Maiden Newton cottage

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 filter does not match: Beach or lakeside relaxation

61 reviews

from £83 / night

£576 - £1,156 / week

1 / 20

Great rentals within 20 miles that match your search

Holiday cottage in Whitchurch Canonicorum

Whitchurch Canonicorum cottage

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 11

1 filter does not match: Beach or lakeside relaxation

1 review

from £292 / night

£927 - £3,741 / week

1 / 55

Great rentals within 20 miles that match your search

Weymouth holiday cottage rental

Weymouth cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

1 filter does not match: Beach or lakeside relaxation

59 reviews

from £81 / night

£561 / week

1 / 21

Great rentals within 20 miles that match your search

Weymouth holiday cottage rental

Weymouth cottage

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 5

1 filter does not match: Beach or lakeside relaxation

10 reviews

from £178 / night

£1,243 / week

1 / 38

Great rentals within 20 miles that match your search

Bere Regis holiday cottage rental

Bere Regis cottage

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 filter does not match: Beach or lakeside relaxation

1 review

from £204 / night

£612 - £2,298 / week

1 / 29

Great rentals within 20 miles that match your search

East Stoke holiday home rental

East Stoke house

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 18

1 filter does not match: Property type

from £287 / night

£2,004 / week

1 / 16

Great rentals within 20 miles that match your search

Weymouth holiday cottage rental

Weymouth cottage

  • 12 bedrooms
  • 6 bathrooms
  • sleeps 12

1 filter does not match: Beach or lakeside relaxation

from £356 / night

£1,357 - £4,559 / week

1 / 19

Great rentals within 20 miles that match your search

Cottage rental in Chideock with golf nearby

Chideock cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

1 filter does not match: Beach or lakeside relaxation

1 review

from £318 / night

£1,363 / week

1 / 30

Great rentals within 20 miles that match your search

Weymouth holiday cottage rental

Weymouth cottage

  • 5 bedrooms
  • 6 bathrooms
  • sleeps 10

1 filter does not match: Beach or lakeside relaxation

3 reviews

from £479 / night

£1,621 - £4,990 / week

1 / 31

Great rentals within 20 miles that match your search

Cottage rental in Weymouth

Weymouth cottage

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 7

1 filter does not match: Beach or lakeside relaxation

from £268 / night

£804 - £2,404 / week

1 / 38

Great rentals within 20 miles that match your search

Holiday cottage in Weymouth

Weymouth cottage

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 5

1 filter does not match: Beach or lakeside relaxation

from £202 / night

£690 - £1,721 / week

1 / 26

Great rentals within 20 miles that match your search

Cottage rental in Weymouth

Weymouth cottage

  • 5 bedrooms
  • 7 bathrooms
  • sleeps 10

1 filter does not match: Beach or lakeside relaxation

3 reviews

from £479 / night

£1,621 - £4,901 / week

1 / 40

Great rentals within 20 miles that match your search

Holiday cottage in East Knighton

East Knighton cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

1 filter does not match: Beach or lakeside relaxation

1 review

from £169 / night

£505 - £1,642 / week

1 / 32

Great rentals within 20 miles that match your search

Weymouth holiday cottage rental

Weymouth cottage

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 filter does not match: Beach or lakeside relaxation

from £242 / night

£745 - £2,302 / week

1 / 34

Great rentals within 20 miles that match your search

Holiday cottage in Weston

Weston cottage

  • 9 bedrooms
  • 11 bathrooms
  • sleeps 20

1 filter does not match: Beach or lakeside relaxation

from £5,454 / night

£25,010 / week

1 / 70

Great rentals within 20 miles that match your search

Bridport holiday cottage rental

Bridport cottage

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 filter does not match: Beach or lakeside relaxation

1 review

from £266 / night

£1,060 / week

1 / 6

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