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Cottages in Isle of Portland and Houses – Holiday Lettings - Holiday Rentals Isle of Portland

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812 Holiday homes

Holiday cottage in Isle of Portland

Isle of Portland cottage

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

“Great Cottage would rent again” Fully met with our expectations, would rent again, all info and details sent in advance and everything explained well.

from £126 / night

£573 - £1,260 / week

1 / 34

Holiday home in Isle of Portland

Isle of Portland house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 5

from £195 / night

£945 / week

1 / 9

Holiday home in Isle of Portland

Isle of Portland house

  • 3 bedrooms
  • 1 bathroom
  • sleeps 5

from £166 / night

£1,160 / week

1 / 18

Isle of Portland holiday cottage rental

Isle of Portland cottage

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

“Perfect Weekend Away” We have just returned from a lovely long weekend in this perfect cottage. It's very well equipped with everything you need. It was a great base for all the attractions and we were blessed with amazing weather. We enjoyed a coastal walk to Portland lighthouse which is on the doorstep of Fishermans Cottage and the views from the bedroom were idyllic. The hot tub was a great way to start and end the day! I can not fault it and we were sad to leave.

from £138 / night

£573 - £1,546 / week

1 / 42

Isle of Portland holiday studio rental

Isle of Portland studio

  • Studio
  • 1 bathroom
  • sleeps 3

from £132 / night

£894 - £1,014 / week

1 / 24

Home rental in Isle of Portland

Isle of Portland house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from £115 / night

£516 - £1,145 / week

1 / 45

Home rental in Isle of Portland

Isle of Portland house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

from £146 / night

£1,018 / week

1 / 15

Holiday bungalow in Isle of Portland

Isle of Portland bungalow

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

from £103 / night

£722 / week

1 / 16

Holiday bungalow rental

Isle of Portland bungalow

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

from £103 / night

£630 - £1,031 / week

1 / 17

Isle of Portland holiday home rental

Isle of Portland house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from £103 / night

£802 - £1,260 / week

1 / 19

Holiday cottage in Easton

Easton cottage

  • 3 bedrooms
  • 1 bathroom
  • sleeps 6

from £171 / night

£512 - £1,616 / week

1 / 25

Weston holiday home rental

Weston house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

from £159 / night

£557 - £1,824 / week

1 / 26

Holiday cottage in Fortuneswell

Fortuneswell cottage

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 5

from £167 / night

£499 - £1,486 / week

1 / 20

Holiday home in Isle of Portland

Isle of Portland house

  • 3 bedrooms
  • 1 bathroom
  • sleeps 5

from £132 / night

£745 - £974 / week

1 / 25

Holiday bungalow in Weston

Weston bungalow

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

from £172 / night

£588 - £1,614 / week

1 / 20

Holiday cottage rental

Fortuneswell cottage

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from £189 / night

£565 - £1,666 / week

1 / 27

Apartment letting in Weston

Weston apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

from £99 / night

£313 - £992 / week

1 / 21

Holiday cottage with golf nearby in Castletown

Castletown cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

from £124 / night

£395 - £1,307 / week

1 / 15

Holiday cottage with golf nearby in Weston

Weston cottage

  • 3 bedrooms
  • 1 bathroom
  • sleeps 5

from £138 / night

£422 - £1,542 / week

1 / 34

Holiday home rental

Isle of Portland house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from £213 / night

£1,491 / week

1 / 37

Holiday cottage rental

Castletown cottage

  • 3 bedrooms
  • 1 bathroom
  • sleeps 5

from £167 / night

£499 - £1,450 / week

1 / 20

Holiday home in Isle of Portland

Isle of Portland house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from £146 / night

£1,018 / week

1 / 27

Weston holiday cottage rental

Weston cottage

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 5

from £189 / night

£565 - £1,616 / week

1 / 28

Holiday home with golf nearby in Castletown

Castletown house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 7

from £184 / night

£640 - £2,211 / week

1 / 42

Home letting in Easton

Easton house

  • 3 bedrooms
  • 1 bathroom
  • sleeps 5

from £114 / night

£359 - £1,292 / week

1 / 25

Holiday cottage in Weston

Weston cottage

  • 9 bedrooms
  • 11 bathrooms
  • sleeps 20

from £2,142 / night

£12,200 - £34,769 / week

1 / 70

Fortuneswell holiday apartment accommodation

Fortuneswell apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

from £115 / night

£802 / week

1 / 21

Holiday cottage in Fortuneswell

Fortuneswell cottage

  • 3 bedrooms
  • 1 bathroom
  • sleeps 8

from £157 / night

£469 - £1,677 / week

1 / 38

Holiday home with golf nearby in Fortuneswell

Fortuneswell house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

from £344 / night

£1,031 - £2,804 / week

1 / 41

Holiday cottage rental

Castletown cottage

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 5

from £193 / night

£578 - £1,686 / week

1 / 30

Holiday cottage in Castletown

Castletown cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

from £175 / night

£525 - £1,542 / week

1 / 21

Castletown holiday cottage rental

Castletown cottage

  • 3 bedrooms
  • 1 bathroom
  • sleeps 5

from £163 / night

£558 - £1,738 / week

1 / 27

Holiday cottage rental

Fortuneswell cottage

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from £228 / night

£682 - £1,967 / week

1 / 22

Holiday home with golf nearby in Weston

Weston house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

from £175 / night

£524 - £1,614 / week

1 / 41

Holiday cottage in Castletown

Castletown cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

from £192 / night

£610 - £1,741 / week

1 / 25

Cottage rental in Castletown with golf nearby

Castletown cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

from £175 / night

£524 - £1,542 / week

1 / 20

Holiday home with swimming pool in Weston

Weston house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

from £166 / night

£591 - £1,859 / week

1 / 17

Cottage rental in Easton

Easton cottage

  • 3 bedrooms
  • 1 bathroom
  • sleeps 5

from £175 / night

£525 - £1,542 / week

1 / 14

Castletown holiday apartment rental

Castletown apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

from £126 / night

£377 - £1,163 / week

1 / 22

Fortuneswell holiday cottage rental

Fortuneswell cottage

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from £173 / night

£518 - £1,553 / week

1 / 19

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Top Destination reviews

Fishermans Cottage, Hot Tub and sea views
Cottage

Lovely cottage, comfortable and homely. The sun room was a lovely reading and chatting area. Lots of local walks … see more
Hecla House
A fantastic stay!

Quite simply the perfect place to stay for our week away! Clean, great size and well located. A nice beach cove in walkable distance with some lovely local pubs most notably the Punchbowl (especially if you are a sports fan!) If we are ever to stay in Portland again we would be straight back here! … see more
1 The Old Police Station
1 police station

The house is beautiful overlooking the beach It has lovely character prison cell door windows It has everything you can think of washing machine Dishwasher lots of pans pots classes ect Plenty of towels tea towels very well equipped It also has a barbecue which we used, but had to clean it first as it was left dirty Did miss not having a bath but that’s personal choice Outside area barbecue ect was lovely we had good weather so we ate outside I must admit I’m a bit ocd on windows and they was dirty I think 4 o’clock getting in was late My opinion 2 pm we was there early and the cleaners left at 1.30 ( we was waiting on the park opposite ) I asked holiday Lettings if we could go in early and they said no Beautiful walks Chip shop is lovely but very expensive I didn’t think it was worth £11.00 for fish chips and peas Chinese is lovely and reasonable priced It’s about 15 minutes in a car to Weymouth Overall we absolutely loved it Would we go back ……. Yeahsee more
House at Chesil Beach
Fabulous house in the perfect location

We have just returned from 5 nights staying at this gorgeous house which is perfectly located for exploring Portland and the surrounding area. The house has a lovely big front garden with a comfy seating area where we enjoyed our morning coffee soaking up the sun. Inside the house, the living area is cosy with plenty of sofa seating space. The kitchen is small but wonderfully equipped with everything you might need to eat in, or pack a picnic for the day. The beds all have gorgeous bedding and plenty of storage space in each. There is only one bathroom, which was fine for us, the shower is a great size and there was always plenty of hot water for the four of us. All of the equipment, kitchenware, towels, bedding etc are really high quality which all helped to make this feel like a luxurious break. The house is located just minutes from Chesil beach. There we watched amazing sunsets from the New Cove Inn which serves great quality pub food. We also had a great breakfast at Quiddles on the beach, we ate amazing shellfish at the Crab House Cafe and enjoyed fish and chips on the beach from the nearby Chesil Chippie. We explored all over the island which is easily done on foot or by car. Further afield we visited Durdle Door and in the other diresction we went fossil hunting at Charmouth beach. Portland is a beautiful part of the world, and the house is a fantastic gem to stay in - I would highly recommend.see more
Pebble Reef
Pebble Reef Review

Pebble Reef Cottage is ideally located on Portland, access to all parts of the island is only a short drive away. The cottage is well suited for a family of 4+ with good size bedrooms and bathrooms. The cottage has all you need for a short or long stay. The kitchen is a good size with ample dining space for the family. Internet and media facilities are good. The owner was very responsive to questions or resolving minor issues. This was our second stay at the cottage and would highly recommend it.see more
Brand new contemporary Eco accommodation located on the Isle of Portland, Dorset
Brilliant!

Awesome little cabin. Has everything you could need, whilst being compact and cosy. Central to everything in Portland, and a short wander over to Weymouth. The owner is lovely, and the whole place is so beautifully styled in the most lovely, artistic way. 10/10! … see more

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