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from £72 / night

£500 / week

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(3) Very Good 4.5/5 

1 / 9

Portland holiday home rental

Isle of Portland / Portland

House / 3 Bedrooms / sleeps 6

  • Beach / lakeside relaxation
  • Nearest beach 1 km
  • Great for children of all ages
  • Car not necessary

Very Good 4.5/5 

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from £72 / night

£500 / week

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Pebbles view cottages is the perfect holiday destination whether you just want to get away from it all exploring the Isle of Portland or beaches of Weymouth or a more active holiday with fantastic sailing,diving rock climbing cycling and walking, portland has it all.  …see more

from £40 / night

£280 - £690 / week

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(8) Very Good 4.5/5 

1 / 14

Holiday cottage in Portland

Isle of Portland / Portland

Cottage / 3 Bedrooms / sleeps 4

  • Beach / lakeside relaxation
  • Nearest beach 0 km
  • Suitable for children over 5
  • Car advised

Very Good 4.5/5 

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from £40 / night

£280 - £690 / week

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Cottage newly decorated in good order dog friendly with sea views also from south facing patio looking over Chesil beach In quiet street close to all amenities buses pubs restaurant. Lovely walks along sea front and beach ideal fishing water sports dogs and swimming. Portland was the choice for the Olympic sailing venue chosen from all the places in the UK.  …see more

from £45 / night

£315 - £393 / week

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1 / 17

Holiday studio in Portland

Isle of Portland / Portland

Studio / sleeps 2

  • Nearest beach 3 km
  • Suitable for children over 5
  • Car advised
  • No pets allowed

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from £45 / night

£315 - £393 / week

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Portland is at the heart of the 95 mile long 'Jurassic Coast', designated by UNESCO as England's first Natural World Heritage Site, as it provides a geological' walk through 185 millions years of earth's history'. Portland is the mecca for sporting activities such as windsurfing, sailing, rock climbing and leisure diving  …see more

Featured properties

from £43 / night

£295 - £360 / week

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(14) Very Good 4.5/5 

1 / 31

Holiday studio in Portland

Isle of Portland / Portland

Studio / sleeps 2

  • Beach / lakeside relaxation
  • Nearest beach 2 km
  • Not suitable for children
  • Car advised

Very Good 4.5/5 

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from £43 / night

£295 - £360 / week

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Weymouth, Portland, Dorset. Jurassic coast, sea view, beach, cliff walks, sailing, water sports, kayaking, wind surfing, snorkelling, bathing, fishing, golf, rock climbing, horse riding, bird watching, on-site creche, peaceful quiet location, kite & seafood festivals. This modern apartment is situated in a stunning setting overlooking the ocean at Portland Bill.  …see more

from £50 / night

£350 - £690 / week

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(12) Very Good 4.5/5 

1 / 14

Holiday cottage accommodation

Isle of Portland / Portland

Cottage / 2 Bedrooms / sleeps 5

  • Beach / lakeside relaxation
  • Great for children of all ages
  • Car advised
  • No pets allowed

Very Good 4.5/5 

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from £50 / night

£350 - £690 / week

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Situated in a quiet location at the southern end of the island with stunning sea views just a stone's throw away from beautiful coastal walks and scenery - near Portland Bill lighthouse and the Lobster Pot restaurant.  …see more

from £50 / night

£350 - £895 / week

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(6) Very Good 4.5/5 

1 / 20

Portland holiday cottage rental

Isle of Portland / Portland

Cottage / 3 Bedrooms / sleeps 6

  • Beach / lakeside relaxation
  • Nearest beach 12 km
  • Great for children of all ages
  • Car advised

Very Good 4.5/5 

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from £50 / night

£350 - £895 / week

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Fishermans Cottage is a charming detached 18th century cottage on the edge of Southwell, with excellent sea views. Ideal for Sailing academy, bird watching or just a quiet getaway. The ideal location for the 2012 Olympic Sailing whether supporting, taking part or just for the atmosphere.  …see more

from £50 / night

£350 - £695 / week

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(5) Very Good 4.5/5 

1 / 21

Holiday cottage letting

Isle of Portland / Portland

Cottage / 2 Bedrooms / sleeps 5

  • Beach / lakeside relaxation
  • Nearest beach 1 km
  • Great for children of all ages
  • No pets allowed

Very Good 4.5/5 

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from £50 / night

£350 - £695 / week

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Seagull Cottage is a lovely holiday house ideal for sailing, beach, and outdoor activity holidays in Portland. It is located a mile from the WPNSA National Sailing Academy, the 2012 Olympic Sailing venue, and just a few minutes walk from the world famous Chesil Beach. The well-equpped cottage offers comfortable, superior two bedroom accommodation in a convenient location.  …see more

from £47 / night

£325 - £795 / week

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(7) Very Good 4.5/5 

1 / 20

Holiday cottage in Portland

Isle of Portland / Portland

Cottage / 3 Bedrooms / sleeps 6

  • Beach / lakeside relaxation
  • Nearest beach 0 km
  • Great for children of all ages
  • Car advised

Very Good 4.5/5 

Add to shortlist

from £47 / night

£325 - £795 / week

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Pebble Reef is a traditional Quarryman's Cottage, full of character but lovingly renovated to include all the modern comforts you need. Now has WiFi.  …see more

from £60 / night

£420 - £1540 / week

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(27) Very Good 4.5/5 

1 / 17

Holiday home letting

Isle of Portland / Portland

House / 4 Bedrooms / sleeps 10

  • Beach / lakeside relaxation
  • Great for children of all ages
  • Car not necessary
  • Some pets are welcome - please contact the owner

Very Good 4.5/5 

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from £60 / night

£420 - £1540 / week

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Ideal for small groups, couples and families - fabulous sea & rural views. Sleeps up to 8 +2 people comfortably. 4 bedrooms - 3 double/twin, bunk bedroom & sofa bed. Secure gated parking for several cars. There is a generous 50% discount for just 2 people staying. Situated very near to Weymouth & Portland National Sailing Academy & in centre of Dorset's Jurassic Coast  …see more

from £50 / night

£350 - £1330 / week

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(22) Excellent 5/5 

1 / 16

Home rental in Portland

Isle of Portland / Portland

House / 3 Bedrooms / sleeps 8

  • Beach / lakeside relaxation
  • Nearest beach 0 km
  • Great for children of all ages
  • Car not necessary

Excellent 5/5 

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from £50 / night

£350 - £1330 / week

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Ideal for small groups, couples and families - extensive sea views. Sleeps up to 6 +2 people comfortably. 3 bedrooms with either single/twin or king-size beds and a sofa bed in the lounge. Off road parking. There is a generous 50% discount for just 2 people staying. Situated very near to Weymouth & Portland National Sailing Academy & in centre of Dorset's Jurassic Coast  …see more

from £61 / night

£425 - £625 / week

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(4) Excellent 5/5 

1 / 20

Holiday home in Portland

Isle of Portland / Portland

House / 3 Bedrooms / sleeps 6

  • Nearest beach 0 km
  • Great for children of all ages
  • Car advised
  • No pets allowed

Excellent 5/5 

Add to shortlist

from £61 / night

£425 - £625 / week

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Within sound of the breaking surf, take breakfast on the balcony and enjoy stunning views of Chesil Beach. Situated in a quiet area of Fortuneswell yet only a short walk from Shops, Restaurants, Pubs and Beach and 5 minutes from the Olympic Sailing Venue.  …see more

from £53 / night

£366 - £433 / week

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(1) Good 3/5 

1 / 16

Portland holiday studio rental

Isle of Portland / Portland

Studio / sleeps 2

  • Beach / lakeside relaxation
  • Nearest beach 3 km
  • Suitable for children over 5
  • Car advised

Good 3/5 

Add to shortlist

from £53 / night

£366 - £433 / week

View

Portland is at the heart of the 95 mile long 'Jurassic Coast', designated by UNESCO as England's first Natural World Heritage Site, as it provides a geological' walk through 185 millions years of earth's history'. Portland is the mecca for sporting activities such as windsurfing, sailing, rock climbing and leisure diving  …see more

from £48 / night

£333 - £399 / week

View

1 / 16

Holiday studio rental

Isle of Portland / Portland

Studio / sleeps 2

  • Suitable for children over 5
  • No pets allowed

Add to shortlist

from £48 / night

£333 - £399 / week

View

Portland is at the heart of the 95 mile long 'Jurassic Coast', designated by UNESCO as England's first Natural World Heritage Site, as it provides a geological' walk through 185 millions years of earth's history'. Portland is the Mecca for sporting activities such as windsurfing, sailing, rock climbing and leisure diving  …see more

from £48 / night

£333 - £399 / week

View

1 / 10

Portland holiday studio accommodation

Isle of Portland / Portland

Studio / sleeps 2

  • Nearest beach 3 km
  • Suitable for children over 5
  • Car advised
  • No pets allowed

Add to shortlist

from £48 / night

£333 - £399 / week

View

Portland is at the heart of the 95 mile long 'Jurassic Coast', designated by UNESCO as England's first Natural World Heritage Site, as it provides a geological' walk through 185 millions years of earth's history'. Portland is the Mecca for sporting activities such as windsurfing, sailing, rock climbing and leisure diving  …see more

from £72 / night

£500 - £720 / week

View

(1) Very Good 4/5 

1 / 8

Holiday cottage rental

Isle of Portland / Portland

Cottage / 3 Bedrooms / sleeps 4

  • Beach / lakeside relaxation
  • Nearest beach 1 km
  • Suitable for children over 5
  • Car advised

Very Good 4/5 

Add to shortlist

Not on the map

from £72 / night

£500 - £720 / week

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A charming cottage in this pretty road, a short walk down to Chesil Beach and Cove and easy going of the National Sailing Academy at Portland Harbour.  …see more

from £47 / night

£325 - £395 / week

View

(23) Very Good 4.5/5 

1 / 24

Holiday studio in Portland

Isle of Portland / Portland

Studio / sleeps 2

  • Beach / lakeside relaxation
  • Nearest beach 0 km
  • Not suitable for children
  • Car not necessary

Very Good 4.5/5 

Add to shortlist

from £47 / night

£325 - £395 / week

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Open all year. Tranquil, warm retreat above Church Ope Cove. Self catering Studio for 2 set on the cliff path a 7 minute walk from the nearest village and major amenities. Comfy four poster bed (new pics coming soon) Wet room, Wifi, Woodburner, Ipod dock. Pet welcome. Suits romance and retreat, sail, walk, climb, work or study with Wifi, Pets and walkers Welcome Awards.  …see more

from £89 / night

£620 - £632 / week

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(4) Excellent 5/5 

1 / 22

Holiday home in Portland

Isle of Portland / Portland

House / 2 Bedrooms / sleeps 5

  • Beach / lakeside relaxation
  • Nearest beach 0 km
  • Great for children of all ages
  • Car advised

Excellent 5/5 

Add to shortlist

from £89 / night

£620 - £632 / week

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Stunning location with probably the best uninterrupted sea views on Portland. Attractive 2 bedroom house with gardens and easy parking.Close to shops, pubs, restaurants and beaches but right on the edge of open hillside. Only 5 minutes from the National Sailing Academy. Ideal situation for exploring Portland's natural heritage.  …see more

from £86 / night

£600 - £850 / week

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(2) Very Good 4/5 

1 / 8

Holiday cottage in Portland

Isle of Portland / Portland

Cottage / 4 Bedrooms / sleeps 8

  • Beach / lakeside relaxation
  • Nearest beach 1 km
  • Great for children of all ages
  • Car advised

Very Good 4/5 

Add to shortlist

Not on the map

from £86 / night

£600 - £850 / week

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Mallams Cottage is a beautifully finished period cottage, well located for Chesil Beach, Portland Harbour and the National Sailing Academy. Close to the best sailing waters in Europe.  …see more

from £86 / night

£600 - £850 / week

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1 / 8

Portland holiday cottage rental

Isle of Portland / Portland

Cottage / 3 Bedrooms / sleeps 6

  • Beach / lakeside relaxation
  • Nearest beach 1 km
  • Great for children of all ages
  • Car advised

Add to shortlist

Not on the map

from £86 / night

£600 - £850 / week

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4 Sea View offers the best of modern comforts with period character in a cottage just a short walk from the splendors of Chesil Beach & Cove on the Isle of Portland Dorset. Offering a fabulous kitchen and comfortable accommodation.  …see more

from £65 / night

£450 - £650 / week

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1 / 5

Portland holiday cottage rental

Isle of Portland / Portland

Cottage / 2 Bedrooms / sleeps 4

  • Beach / lakeside relaxation
  • Nearest beach 1 km
  • Suitable for children over 5
  • Car not necessary

Add to shortlist

from £65 / night

£450 - £650 / week

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If you were much closer you would be in the sea!!  …see more

from £72 / night

£500 - £720 / week

View

1 / 8

Holiday cottage letting

Isle of Portland / Portland

Cottage / 3 Bedrooms / sleeps 7

  • Beach / lakeside relaxation
  • Nearest beach 0 km
  • Great for children of all ages
  • Car advised

Add to shortlist

Not on the map

from £72 / night

£500 - £720 / week

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Character cottage over three floors, sleeps seven comfortably. A short walk from Chesil Beach and the local amenities, the National Sailing Academy and Portland Harbour. The harbour is found within a short drive or leisurely walk from the property. At the centre of the Jurassic Coast, Portland is an ideal base for water sports, walking & exploring Dorset.  …see more

from £86 / night

£600 - £900 / week

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1 / 8

Holiday home in Portland

Isle of Portland / Portland

House / 4 Bedrooms / sleeps 10

  • Beach / lakeside relaxation
  • Great for children of all ages
  • Car advised
  • No pets allowed

Add to shortlist

Not on the map

from £86 / night

£600 - £900 / week

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Whether you are looking for that relaxing break, or here to sail or just time with the family this charming cottage would suit your needs. Nestled off Wakeham, you will agree this cottage is a real find. This deceptive very comfortable house offers home from home facilities with everything to entertain a family  …see more

from £86 / night

£600 - £850 / week

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1 / 10

Apartment rental in Portland with shared pool

Isle of Portland / Portland

Apartment / 2 Bedrooms / sleeps 4

  • Beach / lakeside relaxation
  • Nearest beach 1 km
  • Swimming pool
  • Great for children of all ages

Add to shortlist

from £86 / night

£600 - £850 / week

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Frigate Apartment is a stunning holiday apartment with sea views situated in the eye-catching Ocean Views development, close to Portland Harbour and the National Sailing Academy. The development boasts a state-of-the-art health and fitness centre complete with an indoor swimming pool.  …see more
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