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

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384 Holiday homes

(4) Average 

8

Holiday home in Isle of Portland

Dorset / Isle of Portland

3 5 min stay varies

  • 3 bedrooms
  • sleeps 5
  • min stay varies
  • Nearest beach 0 km
  • Child friendly
  • Pet friendly

from £80 / night

£425 / week

Book View

from £80 / night

(11) Very Good 

Certificate of Excellence

8

Cottage rental in Isle of Portland

Dorset / Isle of Portland

1 2 3 nights min

  • 1 bedroom
  • sleeps 2
  • 3 nights min
  • Nearest beach 3 km
  • Car not necessary
  • Air conditioning

Certificate of Excellence

from £50 / night

£325 - £425 / week

Book View

Responds fast!
avg. 1 hour 25 minutes

from £50 / night

(9) Excellent 

17

Holiday home in Isle of Portland

Dorset / Isle of Portland

3 7 min stay varies

  • 3 bedrooms
  • sleeps 7
  • min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 1 km
  • Child friendly

from £110 / night

£530 - £1,035 / week

Book View

from £110 / night

(27) Very Good 

Certificate of Excellence

42

Isle of Portland holiday cottage rental

Dorset / Isle of Portland

3 6 min stay varies

  • 3 bedrooms
  • sleeps 6
  • min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 12 km
  • Child friendly
“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.

Certificate of Excellence

from £95 / night

£375 - £1,045 / week

Book View

Responds fast!
avg. 29 minutes

from £95 / night

(13) Excellent 

8

Holiday bungalow in Isle of Portland

Dorset / Isle of Portland

2 4 2 nights min

  • 2 bedrooms
  • sleeps 4
  • 2 nights min
  • Child friendly

from £80 / night

£560 / week

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Responds fast!
avg. 33 minutes

from £80 / night

(4) Very Good 

14

Chalet rental in Isle of Portland

Dorset / Isle of Portland

2 4 min stay varies

  • 2 bedrooms
  • sleeps 4
  • min stay varies
  • Child friendly
  • Pet friendly

from £85 / night

£406 - £787 / week

Book View

from £85 / night

(3) Very Good 

Certificate of Excellence

22

Home rental in Isle of Portland

Dorset / Isle of Portland

2 4 min stay varies

  • 2 bedrooms
  • sleeps 4
  • min stay varies
  • Child friendly
  • Pet friendly
  • Private garden

Certificate of Excellence

from £70 / night

£300 - £600 / week

Book View

Responds fast!
avg. 29 minutes

from £70 / night

(21) Very Good 

9

Holiday cottage in Isle of Portland

Dorset / Isle of Portland

3 4 7 nights min

  • 3 bedrooms
  • sleeps 4
  • 7 nights min
  • Beach / lakeside relaxation
  • Nearest beach 0.2 km
  • Suitable for children age 5+

from £40 / night

£280 - £770 / week

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from £40 / night

(21) Very Good 

9

Isle of Portland holiday home rental

Dorset / Isle of Portland

3 6 4 nights min

  • 3 bedrooms
  • sleeps 6
  • 4 nights min
  • Beach / lakeside relaxation
  • Nearest beach 1 km
  • Child friendly

from £90 / night

£650 / week

Book View

from £90 / night

(38) Excellent 

Certificate of Excellence

19

Home rental in Isle of Portland

Dorset / Isle of Portland

3 7 min stay varies

  • 3 bedrooms
  • sleeps 7
  • min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0 km
  • Child friendly

Certificate of Excellence

from £100 / night

£700 - £950 / week

Book View

Responds fast!
avg. 15 minutes

from £100 / night

(24) Excellent 

Certificate of Excellence

21

Holiday cottage in Isle of Portland

Dorset / Isle of Portland

3 6 min stay varies

  • 3 bedrooms
  • sleeps 6
  • min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0.5 km
  • Child friendly

Certificate of Excellence

from £85 / night

£350 - £950 / week

Book View

Responds fast!
avg. 29 minutes

from £85 / night

(3) Very Good 

22

Holiday home in Isle of Portland

Dorset / Isle of Portland

4 8 min stay varies

  • 4 bedrooms
  • sleeps 8
  • min stay varies
  • Child friendly
  • Car not necessary
  • Pet friendly

from £175 / night

£1,225 / week

Book View

Responds fast!
avg. 1 hour 34 minutes

from £175 / night

(34) Very Good 

31

Holiday studio in Isle of Portland

Dorset / Isle of Portland

Studio 2 min stay varies

  • Studio
  • sleeps 2
  • min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 2 km
“gorgeous views, lovely clean inviting appartment” was a lovely stay and will defiantly be returning, some stunning sights and lovely rural walks fantastic

from £47 / night

£295 - £350 / week

Book View

Responds fast!
avg. 1 hour 38 minutes

from £47 / night

(1) Very Good 

11

Home rental in Isle of Portland

Dorset / Isle of Portland

4 8 min stay varies

  • 4 bedrooms
  • sleeps 8
  • min stay varies
  • Child friendly
  • Pet friendly
  • Private garden

from £107 / night

£517 - £1,009 / week

Book View

from £107 / night

37

Holiday home in Isle of Portland

Dorset / Isle of Portland

2 4 min stay varies

  • 2 bedrooms
  • sleeps 4
  • min stay varies
  • Nearest beach 3 km
  • Child friendly

from £90 / night

£374 - £1,020 / week

Book View

Responds fast!
avg. 29 minutes

from £90 / night

(3) Very Good 

20

Isle of Portland holiday cottage rental

Dorset / Isle of Portland

3 5 min stay varies

  • 3 bedrooms
  • sleeps 5
  • min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 1 km
  • Child friendly

from £88 / night

£369 - £813 / week

Book View

from £88 / night

(2) Excellent 

18

Isle of Portland holiday apartment accommodation

Dorset / Isle of Portland

3 6 min stay varies

  • 3 bedrooms
  • sleeps 6
  • min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 1 km
  • Swimming pool

from £123 / night

£595 - £1,165 / week

Book View

from £123 / night

(10) Very Good 

22

Holiday studio in Isle of Portland

Dorset / Isle of Portland

Studio 2 min stay varies

  • Studio
  • sleeps 2
  • min stay varies
  • Nearest beach 3 km
  • Suitable for children age 5+

from £45 / night

£300 / week

Book View

Responds fast!
avg. 12 minutes

from £45 / night

(1) Excellent 

6

Penthouse rental in Isle of Portland with shared pool

Dorset / Isle of Portland

2 4 3 nights min

  • 2 bedrooms
  • sleeps 4
  • 3 nights min
  • Beach / lakeside relaxation
  • Swimming pool

from £125 / night

£600 - £1,400 / week

Book View

Responds fast!
avg. 3 hours 42 minutes

from £125 / night

(5) Excellent 

22

Holiday home in Isle of Portland

Dorset / Isle of Portland

2 5 7 nights min

  • 2 bedrooms
  • sleeps 5
  • 7 nights min
  • Beach / lakeside relaxation
  • Nearest beach 0.5 km
  • Child friendly

from £86 / night

£600 / week

Book View

from £86 / night

11

Holiday home in Isle of Portland

Dorset / Isle of Portland

3 6 3 nights min

  • 3 bedrooms
  • sleeps 6
  • 3 nights min
  • Child friendly
  • Private garden

from £120 / night

£840 / week

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from £120 / night

8

Isle of Portland holiday cottage rental

Dorset / Isle of Portland

3 6 7 nights min

  • 3 bedrooms
  • sleeps 6
  • 7 nights min
  • Beach / lakeside relaxation
  • Nearest beach 1 km
  • Child friendly

from £100 / night

£478 - £932 / week

Book View

from £100 / night

(1) Excellent 

8

Holiday home in Isle of Portland

Dorset / Isle of Portland

4 10 min stay varies

  • 4 bedrooms
  • sleeps 10
  • min stay varies
  • Beach / lakeside relaxation
  • Child friendly
  • Private garden

from £115 / night

£556 - £1,087 / week

Book View

from £115 / night

(2) Average 

15

Holiday cottage in Isle of Portland

Dorset / Isle of Portland

2 4 min stay varies

  • 2 bedrooms
  • sleeps 4
  • min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 1 km
  • Child friendly

from £60 / night

£300 - £699 / week

Book View

from £60 / night

22

Holiday home letting

Dorset / Isle of Portland

3 9 min stay varies

  • 3 bedrooms
  • sleeps 9
  • min stay varies
  • Nearest beach 6 km
  • Child friendly
  • Pet friendly

from £85 / night

£500 - £875 / week

Book View

Responds fast!
avg. 2 hours 15 minutes

from £85 / night

(9) Excellent 

12

Cottage letting in Isle of Portland

Dorset / Isle of Portland

4 8 min stay varies

  • 4 bedrooms
  • sleeps 8
  • min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 1 km
  • Child friendly

from £114 / night

£555 - £1,215 / week

Book View

from £114 / night

(3) Very Good 

18

Isle of Portland holiday home rental

Dorset / Isle of Portland

4 8 min stay varies

  • 4 bedrooms
  • sleeps 8
  • min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0.2 km
  • Suitable for children age 5+

from £100 / night

£700 - £1,350 / week

Enquire View

from £100 / night

(34) Very Good 

Certificate of Excellence

30

Holiday cottage letting

Dorset / Isle of Portland

3 5 min stay varies

  • 3 bedrooms
  • sleeps 5
  • min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0.2 km
  • Child friendly
“A character cottage” The cottage was warm, cosy and well furnished. The living areas were spacious with a warm sunny patio garden at the back. We loved the log burner. The location was great; just two minutes walk from the coastal path, several good restaurants and at least two pubs with live music - what a delight! We will definitely be back next year. Julie Evans

Certificate of Excellence

from £85 / night

£550 - £880 / week

Book View

Responds fast!
avg. 2 hours 39 minutes

from £85 / night

(4) Very Good 

12

Holiday cottage in Isle of Portland

Dorset / Isle of Portland

2 4 min stay varies

  • 2 bedrooms
  • sleeps 4
  • min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 1 km
  • Child friendly

from £79 / night

£375 - £724 / week

Book View

from £79 / night

(57) Excellent 

Certificate of Excellence

17

Holiday home letting

Dorset / Isle of Portland

4 10 min stay varies

  • 4 bedrooms
  • sleeps 10
  • min stay varies
  • Beach / lakeside relaxation
  • Child friendly
  • Pet friendly

Certificate of Excellence

from £120 / night

£800 - £1,090 / week

Book View

Responds fast!
avg. 15 minutes

from £120 / night

(9) Very Good 

46

Holiday cottage in Isle of Portland

Dorset / Isle of Portland

3 6 min stay varies

  • 3 bedrooms
  • sleeps 6
  • min stay varies
  • Child friendly
  • Pet friendly

from £60 / night

£400 - £1,000 / week

Book View

from £60 / night

(2)  

8

Holiday apartment in Isle of Portland

Dorset / Isle of Portland

1 2 min stay varies

  • 1 bedroom
  • sleeps 2
  • min stay varies
  • Child friendly
  • Ask about pets

from £49 / night

£300 / week

Book View

Responds fast!
avg. 12 minutes

from £49 / night

(1) Average 

15

Isle of Portland holiday studio accommodation

Dorset / Isle of Portland

Studio 2 2 nights min

  • Studio
  • sleeps 2
  • 2 nights min
  • Nearest beach 3 km
  • Suitable for children age 5+

from £69 / night

£399 - £525 / week

Book View

Responds fast!
avg. 12 minutes

from £69 / night

(2) Very Good 

11

Isle of Portland holiday home accommodation

Dorset / Isle of Portland

3 6 min stay varies

  • 3 bedrooms
  • sleeps 6
  • min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 5 km
  • Child friendly

from £100 / night

£500 - £740 / week

Book View

Responds fast!
avg. 57 minutes

from £100 / night

(19) Very Good 

Certificate of Excellence

20

Holiday cottage letting

Dorset / Isle of Portland

2 4 min stay varies

  • 2 bedrooms
  • sleeps 4
  • min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 1 km
  • Child friendly
“Excellent property and location” We stayed in Seagull Cottage for 5 nights to attend a training camp at the WPNSA Sailing Academy. The cottage was ideally located for us as it was walking distance to the academy (or 2 minutes in the car). A nice view out the back lets you judge the weather before you set off for excursions. It's close to the local shops, so very handy indeed. The house itself was lovely and comfortable. The kitchen is well-equipped the living room spacious and homely. Entertainment and wifi is also provided. Our group consisted of 4 teenage girls and one adult. The girls all slept comfortably in the big bedroom which had a double, a single and a guest bed. They found it big enough and enjoyed it. As the only adult I enjoyed the peace in the other room (which has 2 single beds). The little area round the back would probably be really nice to sit in the summer. Parking in Fortuneswell seems to be a bit of an issue at times but it's no problem either across the road in the big car park or 2 minutes down the hill next to the school (could possibly be an issue for drivers with restricted mobility as the whole village is on a hill). To drop off and pick up people and things at the house was fine though as there's enough space right in front. David the owner was a pleasure to deal with. If I have the need for accommodation in Portland in the future I would definitely try to book the cottage again.

Certificate of Excellence

from £90 / night

£610 - £740 / week

Book View

Responds fast!
avg. 1 hour 42 minutes

from £90 / night

13

Holiday home rental

Dorset / Isle of Portland

2 4 min stay varies

  • 2 bedrooms
  • sleeps 4
  • min stay varies
  • Child friendly
  • Pet friendly

from £92 / night

£440 - £854 / week

Book View

from £92 / night

8

Isle of Portland holiday cottage rental

Dorset / Isle of Portland

3 5 min stay varies

  • 3 bedrooms
  • sleeps 5
  • min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 1 km
  • Child friendly

from £87 / night

£414 - £802 / week

Book View

from £87 / night

9

Holiday bungalow in Isle of Portland

Dorset / Isle of Portland

2 4 min stay varies

  • 2 bedrooms
  • sleeps 4
  • min stay varies
  • Child friendly

from £85 / night

£406 - £787 / week

Book View

from £85 / night

49

Holiday bungalow rental

Dorset / Isle of Portland

3 6 min stay varies

  • 3 bedrooms
  • sleeps 6
  • min stay varies
  • Nearest beach 3 km
  • Child friendly

from £100 / night

£450 - £1,550 / week

Book View

Responds fast!
avg. 29 minutes

from £100 / night

29

Holiday home in Isle of Portland

Dorset / Isle of Portland

2 4 min stay varies

  • 2 bedrooms
  • sleeps 4
  • min stay varies
  • Child friendly
  • Private garden

from £85 / night

£350 - £800 / week

Book View

Responds fast!
avg. 29 minutes

from £85 / night

Top Destination reviews

Shearwater located in Portland, Dorset
Special birthday

My partner & our dog the house was beautiful we would recomend it ever one made our holiday perfect … see more
Quarries Reach, rural & sea views Portland, Dorset
Mrs

Had a fantastic stay in this beautiful property. Equipped with everything you need. Clean and comfortable. It's a brilliant base to explore the surrounding area. This was our first visit to Portland as we normally stay in a hotel on Weymouth seafront when visiting family whom live in the area. So glad we decided to stay here instead. Beautiful sea views throughout the house. Couldn't fault it and we're already planning our next stay.see more
Fishermans Cottage
,Great place, many extras, comfy beds, nice hot tub.

Conveniently located property of good size, nice walking areas nearby, good sea view. Plenty of good food and drink venues to walk or drive to. loved the hot tub. So many extras provided, even milk and flowers. Good value for money. … see more
Rosa Cottage
Lovely well equipped cottage

Rosa cottage is a warm, spacious character cottage within easy walking distance of Chesil Beach and the coast path. It was very clean and tidy and the welcome items left were appreciated. We returned to the house at various times and found parking right outside on all occasions. Karin also made the booking process very easy. A lovely few days away.see more
Schooner Cottage - At Christmas
Good spot to tour south coast

Schooner Cottage itself is outstandingly cheerful, warm, hospitable and comfortable. It has been decorated in a delightfully bright manner to provide an individual, high quality feeling of being at home. The stairs inside are steep and difficult, especially for the aged and disabled, although the rope banister adds lots of character. The rear decking, although another considered feature, is smaller than appears on the photographs and was of little use to us. The cottage would benefit from additional clothes hanging spaces and a shelf in the shower room. We all loved the place and the exceptional high quality of its design and decoration. Perhaps next year additional leaflets on more local attractions could be provided, especially dog friendly pubs. We only found two, the Cove Inn and the Little Ship, but the Cove only allowed dogs in the very small bar and there was always a waiting list of those waiting to get food for the two tables available. It is a cosy Inn whereas the Little Ship is very basic. Food could be very good or bad in both. I think it worthwhile emphasising the approach, the street is very narrow, exceptionally tight turn into it, made more difficult by pipes down the walls. And its steepness should be recognised, None of us expected Portland to be so up and down and to walk back to the cottage from the local pubs was difficult.see more
Pebble Reef
Lovely place to stay enjoyed by us all

It was a brilliant place with plenty of room. Unfortunately the en-suite bathroom shower leaked water into the ceiling below. We reported it to the owner but their attempted fix was not successful. The washer/dryer washed well but the dryer did not appear to work. It wold have been helpful to have instructions!! Despite these minor issues we would definitely stay again and would also recommend it to friends. Thank you.see more

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