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

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729 Holiday homes

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.

31 reviews

from £132 / night

£544 - £1,718 / week

1 / 41

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.

28 reviews

from £109 / night

£516 - £1,432 / week

1 / 34

Holiday home in Isle of Portland

Isle of Portland house

3 bedrooms • 2 bathrooms • sleeps 5

10 reviews

from £184 / night

£831 / week

1 / 9

Holiday bungalow in Isle of Portland

Isle of Portland bungalow

2 bedrooms • 1 bathroom • sleeps 4

13 reviews

from £98 / night

£682 / week

1 / 16

Holiday home in Isle of Portland

Isle of Portland house

3 bedrooms • 3 bathrooms • sleeps 7

12 reviews

from £149 / night

£723 / week

1 / 11

Cottage rental in Isle of Portland

Isle of Portland cottage

1 bedroom • 1 bathroom • sleeps 2

16 reviews

from £69 / night

£458 / week

1 / 8

Holiday home in Isle of Portland

Isle of Portland house

2 bedrooms • 1 bathroom • sleeps 4

2 reviews

from £115 / night

£556 - £1,374 / week

1 / 37

Isle of Portland holiday apartment accommodation

Isle of Portland apartment

3 bedrooms • 2 bathrooms • sleeps 6

4 reviews

from £168 / night

£812 - £1,363 / week

1 / 23

Holiday cottage in Isle of Portland

Isle of Portland cottage

2 bedrooms • 1 bathroom • sleeps 4

7 reviews

from £92 / night

£453 - £859 / week

1 / 14

Isle of Portland holiday cottage rental

Isle of Portland cottage

3 bedrooms • 2 bathrooms • sleeps 5

4 reviews

from £101 / night

£493 - £916 / week

1 / 20

Isle of Portland holiday cottage rental

Isle of Portland cottage

3 bedrooms • 2 bathrooms • sleeps 6

1 review

from £227 / night

£607 - £1,134 / week

1 / 8

Cottage letting in Isle of Portland

Isle of Portland cottage

4 bedrooms • 2 bathrooms • sleeps 8

11 reviews

from £148 / night

£739 - £1,449 / week

1 / 22

Holiday bungalow rental

Isle of Portland bungalow

3 bedrooms • 4 bathrooms • sleeps 6

3 reviews

from £155 / night

£687 - £1,987 / week

1 / 49

Home rental in Isle of Portland

Isle of Portland house

2 bedrooms • 2 bathrooms • sleeps 4

6 reviews

from £109 / night

£458 - £1,145 / week

1 / 44

Home rental in Isle of Portland

Isle of Portland house

4 bedrooms • 2 bathrooms • sleeps 8

4 reviews

from £236 / night

£1,180 / week

1 / 18

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

4 bedrooms • 2 bathrooms • sleeps 8

2 reviews

from £144 / night

£1,002 / week

1 / 15

Holiday home in Isle of Portland

Isle of Portland house

2 bedrooms • 2 bathrooms • sleeps 6

1 review

from £146 / night

£1,018 / week

1 / 27

Holiday cottage in Isle of Portland

Isle of Portland cottage

3 bedrooms • 1 bathroom • sleeps 6

8 reviews

from £106 / night

£521 - £1,002 / week

1 / 9

Holiday home in Isle of Portland

Isle of Portland house

2 bedrooms • 1 bathroom • sleeps 4

from £98 / night

£458 - £974 / week

1 / 30

Holiday home with swimming pool in Isle of Portland

Isle of Portland house

2 bedrooms • 1 bathroom • sleeps 4

10 reviews

from £224 / night

£684 - £2,267 / week

1 / 17

Isle of Portland holiday home rental

Isle of Portland house

2 bedrooms • 1 bathroom • sleeps 4

3 reviews

from £218 / night

£652 - £2,369 / week

1 / 26

Holiday cottage rental

Castletown cottage

3 bedrooms • 2 bathrooms • sleeps 6

1 review

from £240 / night

£732 - £2,088 / week

1 / 22

Castletown holiday cottage accommodation

Castletown cottage

4 bedrooms • 2 bathrooms • sleeps 8

from £298 / night

£909 - £3,020 / week

1 / 29

Holiday cottage in Castletown

Castletown cottage

4 bedrooms • 2 bathrooms • sleeps 8

1 review

from £287 / night

£884 - £2,526 / week

1 / 23

Holiday cottage in Weston

Weston cottage

9 bedrooms • 11 bathrooms • sleeps 20

from £3,840 / night

£11,847 - £34,769 / week

1 / 70

Holiday cottage in Weston

Weston cottage

2 bedrooms • 1 bathroom • sleeps 4

3 reviews

from £153 / night

£457 - £1,451 / week

1 / 22

Cottage rental in Weston

Weston cottage

3 bedrooms • 1 bathroom • sleeps 5

from £191 / night

£573 - £1,685 / week

1 / 14

Holiday cottage in Castletown

Castletown cottage

1 bedroom • 1 bathroom • sleeps 2

from £131 / night

£391 - £1,099 / week

1 / 30

Weston holiday apartment rental

Weston apartment

3 bedrooms • 2 bathrooms • sleeps 6

1 review

from £199 / night

£606 - £1,828 / week

1 / 29

Holiday cottage in Castletown

Castletown cottage

2 bedrooms • 1 bathroom • sleeps 4

from £188 / night

£573 - £1,657 / week

1 / 21

Holiday cottage in Castletown

Castletown cottage

4 bedrooms • 4 bathrooms • sleeps 8

from £373 / night

£1,139 - £3,395 / week

1 / 33

Holiday apartment in Castletown

Castletown apartment

2 bedrooms • 2 bathrooms • sleeps 4

1 review

from £169 / night

£513 - £1,512 / week

1 / 22

Holiday cottage rental

Castletown cottage

3 bedrooms • 2 bathrooms • sleeps 6

from £199 / night

£602 - £1,826 / week

1 / 27

Holiday bungalow in Weston

Weston bungalow

1 bedroom • 1 bathroom • sleeps 2

from £188 / night

£573 - £1,614 / week

1 / 20

Holiday cottage in Weston

Weston cottage

3 bedrooms • 1 bathroom • sleeps 6

from £199 / night

£606 - £1,770 / week

1 / 25

Holiday bungalow in Weston

Weston bungalow

2 bedrooms • 1 bathroom • sleeps 3

from £150 / night

£456 - £1,299 / week

1 / 16

Castletown holiday cottage rental

Castletown cottage

3 bedrooms • 2 bathrooms • sleeps 5

from £199 / night

£606 - £1,726 / week

1 / 28

Holiday apartment in Castletown

Castletown apartment

1 bedroom • 1 bathroom • sleeps 2

7 reviews

from £134 / night

£403 - £1,129 / week

1 / 12

Castletown holiday cottage rental

Castletown cottage

2 bedrooms • 2 bathrooms • sleeps 4

from £176 / night

£527 - £1,534 / week

1 / 19

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Top Destination reviews

Tompot Cottage - Character cottage by the sea
What a pleasure!

Yes, we all like a foreign holiday, but deep inside we know you can’t beat going to the English coast. Fish and chips, stony beaches, waves, pubs, chip shops, need I go on? This this recent experience happens to have taken place in Portland, Dorset. We stayed at Vickie and Paul’s beautiful cottage and had a ball. What would I rather? A holiday in Mauritius - with my dog unhappy in a kennel - or going to the beautiful south coast and taking my lovely canine for a run along an English beach. And what’s more I could can tire him out so that I could have a pint at the Cove Inn - literally opposite to the cottage. This scenario would have been my parents’ worst nightmare when I was a child. But fortunately I’m now grown up and I can do what I like! And I love great pubs. Life is about what is real. It’s what you have on your doorstep. Going to the other side of the world does not solve anything. But staying local and being with family and friends and enjoying the Chesil chippy maybe does? It certainly saves you the credit card bills Tomtop cottage is on your doorstep. It’s on my doorstep. It was just brilliant…. Thank you Vickie and Paul.see more
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
Bay View Apartment
Portland apartment

The apartment was clean and contained everything needed for a self catering stay. View from the balcony in lounge over the castle and marina was great. We enjoyed watching helicopters land and take off from the balcony. Nothing was very far away on the island and only a short drive to Weymouth. Only negatives were being overlooked from bedroom patio doors and outside and communal areas a little rundown, but as this is a very large block that is maybe to be expected. Would be a great location for water sports, walking or cycling.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
Sea View
really lovely house, great location

Really lovely 3 bed roomed house. Great Facilities, comfortable beds, the front bedroom is delightful. lovely kitchen and bathrooms, all mod cons. sun on the back patio in morning and evening, sun in the front decking in the evening. parking is terrible, but you get used to this, and can park nearby on the top road. The bus drops off, and picks up really near, and the service runs through to the late night into Weymouth and back would love to returnsee 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

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