Holiday Cottages in Portland

holiday cottages in portlandDorset Cottage Holidays of Portland make it very easy to find a self catering holiday cottage on Portland.  Choose from our large selection of holiday cottages, from those that are ideal for couples to large, family homes.  We have handpicked these cottages to offer the very best quality accommodation.  All of our holiday cottages are independently graded by Visit Britain.  So whether you love to visit Portland Bill or want to visit the Sailing Academy, we have a cottage to suit your requirements.

Scroll through our list of cottages to make your choice.  We are based locally in Weymouth, so always on hand to answer any of your queries.

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75 Results

Purbeck Escape

£420 - £1,155

*Per week

Ref:562141

Location: Swanage & Studland

  • 6 Sleeps
  • 3 Bedrooms
  • 2 Bathrooms

Harbour Reach

£400 - £860

*Per week

Ref:562821

Location: Weymouth & Portland

  • 4 Sleeps
  • 2 Bedrooms
  • 1 Bathrooms

Pier View

£490 - £710

*Per week

Ref:562139

Location: Swanage & Studland

  • 2 Sleeps
  • 1 Bedrooms
  • 1 Bathrooms

Cricket Cottage

£355 - £590

*Per week

Ref:562142

Location: Swanage & Studland

  • 2 Sleeps
  • 1 Bedrooms
  • 1 Bathrooms

Malvern Apartment

£305 - £585

*Per week

Ref:562137

Location: Swanage & Studland

  • 2 Sleeps
  • 1 Bedrooms
  • 1 Bathrooms

Saxon Mews

£345 - £845

*Per week

Ref:562150

Location: Corfe Castle & Wareham

  • 4 Sleeps
  • 2 Bedrooms
  • 2 Bathrooms

Apple Tree Cottage

£510 - £1,000

*Per week

Ref:562805

Location: Dorchester & Surrounding

  • 6 Sleeps
  • 3 Bedrooms
  • 3 Bathrooms
  • 2 Pets

Magnolia Cottage

£395 - £1,150

*Per week

Ref:570757

Location: Weymouth & Portland

  • 6 Sleeps
  • 3 Bedrooms
  • 2 Bathrooms

Middle Cottage

£425 - £1,220

*Per week

Ref:562161

Location: Purbeck Villages

  • 5 Sleeps
  • 2 Bedrooms
  • 2 Bathrooms

Church View

£580 - £900

*Per week

Ref:562167

Location: Weymouth & Portland

  • 4 Sleeps
  • 3 Bedrooms
  • 1 Bathrooms
  • 1 Pets

Heathlands

£460 - £1,110

*Per week

Ref:562180

Location: Swanage & Studland

  • 6 Sleeps
  • 3 Bedrooms
  • 1 Bathrooms

Cherry Tree Cottage

£360 - £785

*Per week

Ref:562178

Location: Corfe Castle & Wareham

  • 4 Sleeps
  • 2 Bedrooms
  • 1 Bathrooms
  • 1 Pets

Anchor Cottage

£325 - £850

*Per week

Ref:562816

Location: Weymouth & Portland

  • 7 Sleeps
  • 3 Bedrooms
  • 2 Bathrooms

Cranborne Apartment

£395 - £935

*Per week

Ref:562127

Location: Swanage & Studland

  • 4 Sleeps
  • 2 Bedrooms
  • 2 Bathrooms

Homeground

£440 - £1,095

*Per week

Ref:562170

Location: Lulworth & Surrounding

  • 6 Sleeps
  • 2 Bedrooms
  • 2 Bathrooms
  • 2 Pets

The Old Rectory

£1,035 - £2,535

*Per week

Ref:562802

Location: Corfe Castle & Wareham

  • 9 Sleeps
  • 5 Bedrooms
  • 3 Bathrooms
  • 2 Pets

Forest Edge

£360 - £850

*Per week

Ref:561640

Location: Corfe Castle & Wareham

  • 4 Sleeps
  • 2 Bedrooms
  • 2 Bathrooms
  • 2 Pets

The Old Bakehouse

£395 - £1,010

*Per week

Ref:562138

Location: Swanage & Studland

  • 6 Sleeps
  • 3 Bedrooms
  • 2 Bathrooms

Denbur Cottage

£330 - £885

*Per week

Ref:562126

Location: Poole & Bournemouth

  • 4 Sleeps
  • 2 Bedrooms
  • 2 Bathrooms

Winspit View

£440 - £1,345

*Per week

Ref:562153

Location: Purbeck Villages

  • 6 Sleeps
  • 3 Bedrooms
  • 2 Bathrooms
  • 1 Pets

The Cow Byre

£955 - £1,930

*Per week

Ref:562819

Location: Weymouth & Portland

  • 6 Sleeps
  • 3 Bedrooms
  • 2 Bathrooms
  • 1 Pets

Froxfield Cottage

£405 - £1,020

*Per week

Ref:562159

Location: Purbeck Villages

  • 6 Sleeps
  • 3 Bedrooms
  • 1 Bathrooms
  • 2 Pets

The Lawns

£335 - £845

*Per week

Ref:562164

Location: Rural Dorset

  • 4 Sleeps
  • 2 Bedrooms
  • 1 Bathrooms
  • 1 Pets

Newton Manor Grange

£400 - £1,125

*Per week

Ref:562176

Location: Swanage & Studland

  • 6 Sleeps
  • 3 Bedrooms
  • 2 Bathrooms

Piona

£375 - £950

*Per week

Ref:562185

Location: Swanage & Studland

  • 6 Sleeps
  • 3 Bedrooms
  • 2 Bathrooms

The Grain Store

£575 - £1,530

*Per week

Ref:562820

Location: Weymouth & Portland

  • 6 Sleeps
  • 3 Bedrooms
  • 2 Bathrooms
  • 2 Pets

East View Barn

Ref:562806

Location: Dorchester & Surrounding

  • 5 Sleeps
  • 3 Bedrooms
  • 2 Bathrooms
  • 1 Pets

Little Westport

£415 - £1,345

*Per week

Ref:562151

Location: Corfe Castle & Wareham

  • 8 Sleeps
  • 4 Bedrooms
  • 2 Bathrooms

Swans

£320 - £1,010

*Per week

Ref:562169

Location: Weymouth & Portland

  • 6 Sleeps
  • 3 Bedrooms
  • 3 Bathrooms

Elm Villa

£360 - £980

*Per week

Ref:562149

Location: Corfe Castle & Wareham

  • 6 Sleeps
  • 3 Bedrooms
  • 1 Bathrooms

Stone Quay Cottage

£390 - £660

*Per week

Ref:562814

Location: Swanage & Studland

  • 3 Sleeps
  • 2 Bedrooms
  • 1 Bathrooms
  • 2 Pets

Windjammer

£290 - £795

*Per week

Ref:562134

Location: Swanage & Studland

  • 5 Sleeps
  • 2 Bedrooms
  • 1 Bathrooms
  • 2 Pets

Lavender Cottage

£360 - £950

*Per week

Ref:562187

Location: Weymouth & Portland

  • 6 Sleeps
  • 3 Bedrooms
  • 2 Bathrooms

The Stables

£840 - £1,995

*Per week

Ref:562822

Location: Weymouth & Portland

  • 8 Sleeps
  • 4 Bedrooms
  • 3 Bathrooms
  • 2 Pets

Beach Approach

£315 - £780

*Per week

Ref:562813

Location: Swanage & Studland

  • 4 Sleeps
  • 2 Bedrooms
  • 1 Bathrooms

Greenhayes

£380 - £955

*Per week

Ref:562160

Location: Purbeck Villages

  • 4 Sleeps
  • 2 Bedrooms
  • 1 Bathrooms
  • 2 Pets

White Sands

£870 - £2,295

*Per week

Ref:562140

Location: Swanage & Studland

  • 9 Sleeps
  • 4 Bedrooms
  • 2 Bathrooms
  • 2 Pets

Coach House

£460 - £1,620

*Per week

Ref:562824

Location: Corfe Castle & Wareham

  • 6 Sleeps
  • 3 Bedrooms
  • 1 Bathrooms
  • 2 Pets

Balcony Apartment

£420 - £1,130

*Per week

Ref:562179

Location: Swanage & Studland

  • 4 Sleeps
  • 2 Bedrooms
  • 1 Bathrooms

Lulwind

£535 - £1,305

*Per week

Ref:562175

Location: Lulworth & Surrounding

  • 5 Sleeps
  • 3 Bedrooms
  • 2 Bathrooms
  • 2 Pets

Seacombe

£665 - £1,820

*Per week

Ref:562808

Location: Purbeck Villages

  • 8 Sleeps
  • 4 Bedrooms
  • 3 Bathrooms
  • 1 Pets

Daisy's

£420 - £1,145

*Per week

Ref:562182

Location: Swanage & Studland

  • 6 Sleeps
  • 3 Bedrooms
  • 3 Bathrooms

Wessex

£740 - £1,865

*Per week

Ref:562157

Location: Purbeck Villages

  • 10 Sleeps
  • 5 Bedrooms
  • 3 Bathrooms
  • 2 Pets

Foxglove Cottage

£380 - £1,005

*Per week

Ref:562804

Location: Corfe Castle & Wareham

  • 4 Sleeps
  • 2 Bedrooms
  • 1 Bathrooms

Clayhanger Lodge

Ref:562818

Location: Weymouth & Portland

  • 6 Sleeps
  • 3 Bedrooms
  • 3 Bathrooms
  • 2 Pets

Lizards Rest

£460 - £1,660

*Per week

Ref:562129

Location: Swanage & Studland

  • 9 Sleeps
  • 4 Bedrooms
  • 2 Bathrooms

Tilshead

£670 - £1,820

*Per week

Ref:562154

Location: Purbeck Villages

  • 8 Sleeps
  • 4 Bedrooms
  • 3 Bathrooms
  • 2 Pets

Rosemount

£470 - £1,065

*Per week

Ref:562174

Location: Corfe Castle & Wareham

  • 4 Sleeps
  • 2 Bedrooms
  • 2 Bathrooms

Seagulls Rest

£440 - £1,125

*Per week

Ref:562131

Location: Swanage & Studland

  • 6 Sleeps
  • 3 Bedrooms
  • 2 Bathrooms

Canaan

£770 - £1,935

*Per week

Ref:562152

Location: Purbeck Villages

  • 8 Sleeps
  • 4 Bedrooms
  • 3 Bathrooms
  • 2 Pets

Russett Cottage

£700 - £1,665

*Per week

Ref:562803

Location: Corfe Castle & Wareham

  • 6 Sleeps
  • 3 Bedrooms
  • 2 Bathrooms
  • 1 Pets

Bronte Cottage

£375 - £975

*Per week

Ref:562145

Location: Corfe Castle & Wareham

  • 4 Sleeps
  • 3 Bedrooms
  • 2 Bathrooms
  • 1 Pets

Ailwood Cottage

£340 - £590

*Per week

Ref:562144

Location: Corfe Castle & Wareham

  • 2 Sleeps
  • 1 Bedrooms
  • 1 Bathrooms
  • 1 Pets

Brambles

£560 - £1,125

*Per week

Ref:562158

Location: Purbeck Villages

  • 6 Sleeps
  • 3 Bedrooms
  • 2 Bathrooms

Angel Cottage

£350 - £630

*Per week

Ref:562811

Location: Swanage & Studland

  • 2 Sleeps
  • 1 Bedrooms
  • 1 Bathrooms
  • 2 Pets

The Stone Barn

£1,510 - £2,880

*Per week

Ref:562825

Location: Lulworth & Surrounding

  • 12 Sleeps
  • 5 Bedrooms
  • 4 Bathrooms
  • 2 Pets

Glebe Cottage

£900 - £1,785

*Per week

Ref:562143

Location: Swanage & Studland

  • 5 Sleeps
  • 3 Bedrooms
  • 2 Bathrooms

Woodland Falls

£430 - £1,375

*Per week

Ref:562125

Location: Poole & Bournemouth

  • 6 Sleeps
  • 3 Bedrooms
  • 2 Bathrooms

The Old Butcher's Cottage

£410 - £1,085

*Per week

Ref:562801

Location: Corfe Castle & Wareham

  • 6 Sleeps
  • 3 Bedrooms
  • 2 Bathrooms
  • 2 Pets

Pebbles

£400 - £1,125

*Per week

Ref:562186

Location: Swanage & Studland

  • 5 Sleeps
  • 3 Bedrooms
  • 2 Bathrooms

Le Beeche

£365 - £755

*Per week

Ref:562183

Location: Weymouth & Portland

  • 5 Sleeps
  • 2 Bedrooms
  • 1 Bathrooms

Miller Cottage

£410 - £900

*Per week

Ref:562172

Location: Lulworth & Surrounding

  • 4 Sleeps
  • 2 Bedrooms
  • 1 Bathrooms
  • 2 Pets

Gable Cottage

£420 - £1,105

*Per week

Ref:562147

Location: Corfe Castle & Wareham

  • 6 Sleeps
  • 3 Bedrooms
  • 2 Bathrooms

Bluebell Cottage

£365 - £890

*Per week

Ref:562823

Location: Weymouth & Portland

  • 6 Sleeps
  • 3 Bedrooms
  • 2 Bathrooms
  • 2 Pets

Brook Cottage

£510 - £1,325

*Per week

Ref:566861

Location: Corfe Castle & Wareham

  • 6 Sleeps
  • 3 Bedrooms
  • 3 Bathrooms

Westport Cottage

£380 - £985

*Per week

Ref:562146

Location: Corfe Castle & Wareham

  • 5 Sleeps
  • 3 Bedrooms
  • 2 Bathrooms

Sea Reach

£390 - £930

*Per week

Ref:562173

Location: Swanage & Studland

  • 4 Sleeps
  • 2 Bedrooms
  • 1 Bathrooms

Daisy Cottage

£500 - £1,095

*Per week

Ref:562800

Location: Corfe Castle & Wareham

  • 4 Sleeps
  • 2 Bedrooms
  • 1 Bathrooms
  • 1 Pets

Cheesemans Cottage

£335 - £875

*Per week

Ref:562163

Location: Dorchester & Surrounding

  • 5 Sleeps
  • 2 Bedrooms
  • 1 Bathrooms
  • 3 Pets

Elizabeth Cottage

£375 - £925

*Per week

Ref:562171

Location: Lulworth & Surrounding

  • 4 Sleeps
  • 2 Bedrooms
  • 2 Bathrooms

Coastguard Cottage

£420 - £1,420

*Per week

Ref:562807

Location: Purbeck Villages

  • 8 Sleeps
  • 4 Bedrooms
  • 3 Bathrooms

Tanglewood

£395 - £1,000

*Per week

Ref:562132

Location: Swanage & Studland

  • 5 Sleeps
  • 2 Bedrooms
  • 1 Bathrooms

Stable Cottage

£355 - £750

*Per week

Ref:562177

Location: Dorchester & Surrounding

  • 2 Sleeps
  • 1 Bedrooms
  • 1 Bathrooms
  • 1 Pets

West Lodge

£770 - £1,935

*Per week

Ref:562148

Location: Corfe Castle & Wareham

  • 10 Sleeps
  • 5 Bedrooms
  • 3 Bathrooms

Newton House

£390 - £1,115

*Per week

Ref:562130

Location: Swanage & Studland

  • 6 Sleeps
  • 3 Bedrooms
  • 2 Bathrooms
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