Updating

Tell us your dates, and we will find the most accurate rates and availability for you

Updating

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

All filters

Filters

77 Holiday homes

Holiday home in Isle of Portland

Isle of Portland house

  • 3 bedrooms
  • 1 bathroom
  • sleeps 4

from £98 / night

£802 / week

1 / 27

Holiday apartment with shared pool in Isle of Portland

Isle of Portland apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from £184 / night

£1,283 / week

1 / 14

Holiday home in Isle of Portland

Isle of Portland house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 5

from £218 / night

£1,002 / week

1 / 9

Holiday home with swimming pool in Weston

Weston house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

from £164 / night

£661 - £2,038 / week

1 / 17

Holiday cottage in Castletown

Castletown cottage

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

from £231 / night

£692 - £2,037 / week

1 / 27

Holiday bungalow rental

Isle of Portland bungalow

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

from £207 / night

£1,443 / week

1 / 17

Holiday cottage rental

Fortuneswell cottage

  • 4 bedrooms
  • 1 bathroom
  • sleeps 6

from £180 / night

£714 - £2,180 / week

1 / 55

Holiday bungalow in Weston

Weston bungalow

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

from £329 / night

£1,371 / week

1 / 20

Weston holiday home rental

Weston house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

from £164 / night

£619 - £2,000 / week

1 / 26

Holiday apartment in Isle of Portland

Isle of Portland apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from £172 / night

£1,203 / week

1 / 9

Holiday cottage rental

Fortuneswell cottage

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from £203 / night

£608 - £1,761 / week

1 / 27

Apartment letting in Weston

Weston apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

from £105 / night

£330 - £990 / week

1 / 26

Fortuneswell holiday cottage accommodation

Fortuneswell cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

from £128 / night

£468 - £1,499 / week

1 / 32

Holiday cottage with golf nearby in Castletown

Castletown cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

from £131 / night

£424 - £1,415 / week

1 / 15

Holiday cottage with golf nearby in Weston

Weston cottage

  • 3 bedrooms
  • 1 bathroom
  • sleeps 5

from £292 / night

£1,256 / week

1 / 34

Holiday apartment with shared pool in Isle of Portland

Isle of Portland apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from £161 / night

£1,123 / week

1 / 10

Holiday apartment with shared pool in Isle of Portland

Isle of Portland apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from £161 / night

£1,123 / week

1 / 11

Isle of Portland holiday home let

Isle of Portland house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from £161 / night

£1,123 / week

1 / 10

Holiday cottage in Castletown

Castletown cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

from £192 / night

£577 - £1,701 / week

1 / 21

Holiday home with golf nearby in Weston

Weston house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

from £178 / night

£604 - £1,845 / week

1 / 35

Castletown holiday cottage rental

Castletown cottage

  • 3 bedrooms
  • 1 bathroom
  • sleeps 5

from £175 / night

£622 - £1,901 / week

1 / 27

Weston holiday cottage rental

Weston cottage

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 5

from £204 / night

£612 - £1,460 / week

1 / 28

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 £138 / night

£573 - £1,489 / week

1 / 33

Holiday apartment in Castletown

Castletown apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from £149 / night

£471 - £1,644 / week

1 / 31

Castletown holiday apartment rental

Castletown apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from £173 / night

£519 - £1,644 / week

1 / 34

Holiday home with golf nearby in Castletown

Castletown house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 7

from £170 / night

£557 - £2,904 / week

1 / 42

Holiday cottage in Weston

Weston cottage

  • 9 bedrooms
  • 11 bathrooms
  • sleeps 20

from £5,454 / night

£25,010 / week

1 / 70

Cottage rental in Fortuneswell

Fortuneswell cottage

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 7

from £178 / night

£604 - £1,845 / week

1 / 29

Easton holiday home rental

Easton house

  • 3 bedrooms
  • 1 bathroom
  • sleeps 6

from £184 / night

£1,283 / week

1 / 11

Holiday apartment in Castletown

Castletown apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from £158 / night

£472 - £1,432 / week

1 / 50

Holiday cottage with golf nearby in Fortuneswell

Fortuneswell cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

from £195 / night

£585 - £1,799 / week

1 / 25

Holiday home rental

Castletown house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

from £318 / night

£952 - £3,535 / week

1 / 22

Holiday apartment with shared pool in Castletown

Castletown apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from £163 / night

£526 - £1,708 / week

1 / 22

Holiday home with golf nearby in Fortuneswell

Fortuneswell house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

from £248 / night

£934 - £3,031 / week

1 / 41

Holiday cottage in Easton

Easton cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

from £161 / night

£482 - £1,449 / week

1 / 19

Holiday cottage in Fortuneswell

Fortuneswell cottage

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 5

from £180 / night

£550 - £1,629 / week

1 / 20

Holiday cottage in Castletown

Castletown cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

from £377 / night

£1,587 / week

1 / 25

Weston holiday cottage let

Weston cottage

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from £245 / night

£734 - £2,198 / week

1 / 23

Holiday home in Fortuneswell

Fortuneswell house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

from £241 / night

£1,708 - £3,658 / week

1 / 65

Holiday home with golf nearby in Fortuneswell

Fortuneswell house

  • 6 bedrooms
  • 2 bathrooms
  • sleeps 12

from £489 / night

£1,465 - £4,310 / week

1 / 43

×

Top Destination reviews

Cliff House
Cliff House June 2021

We enjoyed our stay, yes the accommodation is quite basic but had all we needed. Pool table was a great addition and was enjoyed by us all every evening. The house has excellent transport links with a selection of small supermarkets and takeaways or cafes within easy walking distance. We would certainly stay again and recommend to those that are looking for a back to basics break. Cliff House' host, Peter was both friendly and available to help if required, will definitely be staying again. Portland is a great place to visit and Cliff House a great place to stay.see more
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
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
Lloyds Cottage, stunning views over English Channel and lighthouse
Lloyds cottage ❤️

Really great place. Nice accommodation with amazing views! Lovely hot tub! The more extreme the weather the more amazing the coast!! Will defo return!! … see more

Also consider