Vacation Rentals & Cottages in Upwey

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518 Houses

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Casterbridge, Upwey

Upwey house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Garden

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Price per night from

$273

Match: Garden

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Price per night from

$239

Bramshurst, Upwey

Upwey house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Match: Garden

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Price per night from

$239

Match: Garden

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Price per night from

$239

Match: Garden

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Price per night from

$273

The Swallows

Upwey cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

Match: Garden

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Price per night from

$174

The Brambles

Upwey cottage

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Match: Garden

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Price per night from

$154

The Kiln House, Weymouth

Upwey cottage

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Match: Garden

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Price per night from

$167

Little Brook, Weymouth

Upwey cottage

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Match: Garden

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Price per night from

$214

Wren rests in Upwey, in Dorset

Upwey cottage

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Match: Garden

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Price per night from

$200

Great rentals within 20 miles that match your search

Seaside Retreat in Rural Dorset

Ringstead house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Garden

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Price per night from

$329

Cogden cottages - Ketch Cottage

Burton Bradstock apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

Responds fast! avg. 2 hours 54 minutes

Match: Garden

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Price per night from

$130

Three Little Pigs Luxury Cottage

Milton Abbas cottage

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Garden

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Price per night from

$546

Character cottage originally part of the barracks

West Bay house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

Match: Garden

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Price per night from

$115

Cogden Cottages

Bridport apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

Match: Garden

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Price per night from

$130

Dorset Cottage near coast (Puncknowle, Dorchester)

Puncknowle house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 9

Match: Garden

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Price per night from

$180

Sky Cabin, Rustic forest getaway.

Wareham barn

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Match: Garden

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Price per night from

$202

Russet Yurt at Walnut Farm Glamping

Bridport yurt

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Match: Garden

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Price per night from

$237

Apple Tree Cottage, Shillingstone

Shillingstone house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

Match: Garden

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Price per night from

$158

The Stables, Hazelbury Bryan

Ibberton house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

“Wonderful cottage, wonderful area...just wonderful!” Arrived to find cupcakes, tea bags, milk and sugar waiting for us! The cottage, gardens, views are fabulous and the surrounding area is so peaceful and quiet.

Match: Garden

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Price per night from

$177

The Old Stables, Winterborne Stickland

Winterborne Stickland house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Garden

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Price per night from

$169

CORNER BARN, single-storey pet-friendly cottage with en-suites, woodburner

Winterborne Stickland house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Match: Garden

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Price per night from

$147

NEW BARN, single-storey pet-friendly cottage with wwodburner, en-suite

Winterborne Stickland house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Match: Garden

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Price per night from

$147

The Old Cart Shed, Winterborne Stickland

Winterborne Stickland house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Garden

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Price per night from

$170

KEEPERS COTTAGE, pet-friendly single-storey cottage with en-suite, woodburner

Winterborne Stickland house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Match: Garden

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Price per night from

$147

Match: Garden

All filters match

Price per night from

$170

1 Cowdea Farm, Bettiscombe

Marshwood house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 3

Match: Garden

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Price per night from

$182

Cogden Cottages - Brigantine

Burton Bradstock cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

Responds fast! avg. 2 hours 54 minutes

Match: Garden

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Price per night from

$115

THE BARN detached, single-storey, woodburning stove on a working farm in

Chedington house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

Match: Garden

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Price per night from

$142

Sika lodge

Wareham log cabin

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Match: Garden

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Price per night from

$288

Welcome back on the July 4th 2020

East Burton house

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 24

Responds fast! avg. 4 minutes

Match: Garden

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Price per night from

$719

Welcome back on the July 4th 2020

East Burton cottage

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

Responds fast! avg. 4 minutes

Match: Garden

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Price per night from

$360

Two bedroom caravan in Rockley park with sea views. Sleeps 6. Parking & garden

Hamworthy caravan/mobile home

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

Match: Garden

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Price per night from

$316

Netherway Farmhouse Thatched Cottage (also Farmhouse+Barn sleeps 12)

Okeford Fitzpaine cottage

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

Match: Garden

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Price per night from

$246

Match: Garden

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Price per night from

$161

Sycamores Cottage

Langton Herring cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

Match: Garden

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Price per night from

$174

Ocean House 80 yds from beach 4 Bed, 4 Bath, 4star

Weymouth house

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 10

Match: Garden

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Price per night from

$431

Match: Garden

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Price per night from

$123

Viewing 38 of 518
rentals in Upwey

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