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

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671 Holiday homes

(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 £103 / night

£430 - £1,088 / week

Book View

Responds fast!
avg. 33 minutes

from £103 / night

(29) 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

Certificate of Excellence

from £109 / night

£457 - £1,226 / week

Book View

Responds fast!
avg. 33 minutes

from £109 / night

(4) Average 

8

Holiday home in Isle of Portland

Dorset / Isle of Portland

3 5 2 nights min

  • 3 bedrooms
  • sleeps 5
  • 2 nights min
  • Nearest beach 0 km
  • Child friendly
  • Pet friendly

from £115 / night

£802 / week

Book View

from £115 / 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 £98 / night

£465 - £902 / week

Book View

Responds fast!
avg. 3 hours 28 minutes

from £98 / 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 £92 / night

£642 / week

Book View

Responds fast!
avg. 31 minutes

from £92 / night

(9) Excellent 

40

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 £126 / night

£607 - £1,185 / week

Book View

Responds fast!
avg. 3 hours 28 minutes

from £126 / 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 £58 / night

£373 - £487 / week

Book View

Responds fast!
avg. 1 hour 24 minutes

from £58 / night

(9) Very Good 

43

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 £75 / night

£481 - £1,145 / week

Book View

Responds fast!
avg. 3 hours 28 minutes

from £75 / 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

Certificate of Excellence

from £109 / night

£630 - £1,008 / week

Book View

Responds fast!
avg. 2 hours 37 minutes

from £109 / night

(1) Excellent 

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 £103 / night

£429 - £1,168 / week

Book View

Responds fast!
avg. 33 minutes

from £103 / 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 £132 / night

£637 - £1,245 / week

Book View

Responds fast!
avg. 3 hours 28 minutes

from £132 / night

(11) Very Good 

22

Holiday studio in Isle of Portland

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 £52 / night

£344 / week

Book View

Responds fast!
avg. 38 minutes

from £52 / night

(38) Excellent 

Certificate of Excellence

19

Home rental in Isle of Portland

Dorset / Isle of Portland

3 7 2 nights min

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

Certificate of Excellence

from £115 / night

£802 - £916 / week

Book View

Responds fast!
avg. 14 minutes

from £115 / 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 £91 / night

£430 - £829 / week

Book View

Responds fast!
avg. 3 hours 28 minutes

from £91 / 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 £141 / night

£682 - £1,334 / week

Book View

Responds fast!
avg. 3 hours 12 minutes

from £141 / 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

from £54 / night

£338 - £401 / week

Book View

Responds fast!
avg. 1 hour 38 minutes

from £54 / night

(3) Very Good 

37

Holiday home in Isle of Portland

Dorset / Isle of Portland

4 9 min stay varies

  • 4 bedrooms
  • sleeps 9
  • min stay varies
  • Child friendly
  • Car not necessary
  • Pet friendly

from £252 / night

£1,764 / week

Book View

Responds fast!
avg. 1 hour 34 minutes

from £252 / 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 £101 / night

£423 - £874 / week

Book View

Responds fast!
avg. 3 hours 12 minutes

from £101 / night

11

Holiday home in Isle of Portland

Dorset / Isle of Portland

3 6 min stay varies

  • 3 bedrooms
  • sleeps 6
  • min stay varies
  • Child friendly
  • Private garden

from £138 / night

£962 / week

Book View

Responds fast!
avg. 3 hours 28 minutes

from £138 / 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 £136 / night

£548 - £1,068 / week

Book View

Responds fast!
avg. 3 hours 28 minutes

from £136 / night

(58) Excellent 

Certificate of Excellence

17

Holiday home letting

Dorset / Isle of Portland

4 10 2 nights min

  • 4 bedrooms
  • sleeps 10
  • 2 nights min
  • Beach / lakeside relaxation
  • Child friendly
  • Pet friendly

Certificate of Excellence

from £115 / night

£916 - £1,191 / week

Book View

Responds fast!
avg. 15 minutes

from £115 / night

(1) Excellent 

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 £144 / night

£602 - £1,775 / week

Book View

Responds fast!
avg. 33 minutes

from £144 / 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 £75 / night

£287 - £687 / week

Book View

Responds fast!
avg. 33 minutes

from £75 / 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 £79 / night

£457 / week

Book View

Responds fast!
avg. 12 minutes

from £79 / night

(2)  

8

Holiday apartment in Isle of Portland

Dorset / Isle of Portland

1 2 2 nights min

  • 1 bedroom
  • sleeps 2
  • 2 nights min
  • Child friendly
  • Ask about pets

from £57 / night

£344 / week

Book View

Responds fast!
avg. 12 minutes

from £57 / night

(2) 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 £123 / night

£592 - £1,156 / week

Book View

Responds fast!
avg. 3 hours 28 minutes

from £123 / 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

Certificate of Excellence

from £103 / night

£699 - £848 / week

Book View

Responds fast!
avg. 1 hour 28 minutes

from £103 / 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 £109 / night

£739 - £1,392 / week

Book View

Responds fast!
avg. 3 hours 12 minutes

from £109 / 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 £229 / night

£1,603 / week

Book View

Responds fast!
avg. 3 hours 42 minutes

from £229 / 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 £98 / night

£465 - £902 / week

Book View

Responds fast!
avg. 3 hours 12 minutes

from £98 / night

(4) Excellent 

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 - £1,200 / week

Enquire View

from £100 / 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 £115 / night

£573 - £848 / week

Book View

Responds fast!
avg. 56 minutes

from £115 / 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 £106 / night

£504 - £978 / week

Book View

Responds fast!
avg. 3 hours 12 minutes

from £106 / night

32

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 £75 / night

£516 - £974 / week

Book View

Responds fast!
avg. 3 hours 28 minutes

from £75 / night

13

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 £98 / night

£573 - £1,002 / week

Book View

Responds fast!
avg. 2 hours 18 minutes

from £98 / 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 £100 / night

£474 - £919 / week

Book View

Responds fast!
avg. 3 hours 12 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 £98 / night

£401 - £916 / week

Book View

Responds fast!
avg. 33 minutes

from £98 / night

(3) Very Good 

20

Isle of Portland holiday home rental

Dorset / Isle of Portland

2 4 3 nights min

  • 2 bedrooms
  • sleeps 4
  • 3 nights min
  • Swimming pool
  • Child friendly

from £83 / night

£583 - £1,869 / week

Enquire View

from £83 / night

(8) Very Good 

16

Holiday home with shared pool in Isle of Portland

Dorset / Isle of Portland

2 4 3 nights min

  • 2 bedrooms
  • sleeps 4
  • 3 nights min
  • Swimming pool
  • Child friendly

from £81 / night

£571 - £1,860 / week

Enquire View

from £81 / night

20

Holiday cottage in Castletown

Isle of Portland / Castletown

3 5 1 night min

  • 3 bedrooms
  • sleeps 5
  • 1 night min
  • Child friendly
  • Pet friendly

from £61 / night

£427 / week

Enquire View

from £61 / night

Top Destination reviews

Ocean Studio Apartments OSA11A-Southwell, Portland
Outstanding views

Very clean, well kept apartment, outstanding views of the sea and Portland Bill Lighthouse although the building can be off putting on approach until you get in would defiantly stay at this apartment again for a lovely quiet, relaxing holiday. … see more
Spacious 3 bedroom house large balcony magnificent sea views & secure parking
Perfect place !

We - 6 french people and 10 others staying in the neighbourhoods - really enjoyed the warm, cosy, neat house of Deborah with its magnificent view. Everything is easy ! I definitively recommand it if you come by Portland ! … 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
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 ** New 2018 **
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 spacious cottage

Home from home, all you need and more. Spacious cottage with all you need for a relaxing holiday. Would recommend and not hesitate to return. … see more
BEAUTIFUL STUDIO APARTMENT - OCEAN VIEWS,PORTLAND
Clean, well appointed, comfortable, stunning views

Lovely situation for a 'get away from it all' break. fantastic views, great cliff walking, good regular bus service to Weymouth. Nice clean flat, comfy beds, everything you need for a relaxing stay. Interesting quirky building. Friendly locals make you welcome. Hotel adjacent, staff helpful, we didn't use as out all day but menu looked good.see more
Seagull Cottage
Very Comfortable cottage, well equipped and good position

My husband and I with our 2 grown up boys stayed here to celebrate my youngest's 30th birthday. It was a perfect location for us to discover the island on our bikes and also the Jurassic coast. … see more
Fishermans Cottage
Lovely

The cottage is smashing and the hot tub is great and a lovely location short walk to the pub with great food shops close by we are having a lovely time … see more
Two bedroom holiday bungalow
ecellent could not wish for anything better .

made very wellcome on arrival by the owner lesley rose,spotlasley clean .everything you could wish for even roses on the table.no problems . … see more
Chiswell Cottage
Mr

Really nice house, well equipped and spotlessly clean. The location was great, everything necessary is within walking distance and the beach is no distance away – would happily book to stay again … see more
Portland Hideaway
Mrs

Absolutely wonderful. Full of light and everything you could want for a quiet break. Near to good pub and The Bill with fantastic walks. Will definitely try to go back again. … see more

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